|
Back to products
Browse products
Approved anticancer agents
Anticancer agents in trials
Anticancer agents
in preclinical trials
Anticancer molecular libraries
Other drug agents
Drug intermediates
Bio-reagents and biochemicals
|
MedKoo product information:
Patupilone
Desciprtion of Patupilone (Epothilone B): Epothilone B is a
compound isolated from the myxobacterium Sorangium cellulosum. Similar
to paclitaxel, epothilone B induces microtubule polymerization and
stabilizes microtubules against depolymerization conditions. In addition
to promoting tubulin polymerization and stabilization of microtubules,
this agent is cytotoxic for cells overexpressing P-glycoprotein, a
characteristic that distinguishes it from the taxanes. Epothilone B may
cause complete cell-cycle arrest. Check for
active clinical trials or
closed clinical trials using this agent. (NCI
Thesaurus).
Current developer:
Novartis Pharma AG.
|
MedKoo Code#: 202160
|
|
Name: Patupilone
|
|
CAS#: 152044-54-7
Synonym: (-)-Epothilone
B; patupilone. Code name: EPO906.
IUPAC/Chemical name:
(1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
|
|
Chemical structure |
Theoretical analysis
|
|
.gif)
|
MedKoo Code#: 202160
Name: Patupilone
CAS#: 152044-54-7
Chemical Formula: C27H41NO6S
Exact Mass: 507.26546
Molecular Weight: 507.68
Elemental Analysis: C, 63.88; H, 8.14; N,
2.76; O, 18.91; S, 6.32
|
|
Availability and price:
Patupilone (Epothilone B) is in
stock, estimated delivery time 7-9 business days.
10 mg / $290.00 (minimum order)
25 mg / $550.00
50 mg / $950.00
100mg / $1,650.00
200mg / $2,950.00
Grams in stock at low price.
(YYPharma, TZCB)
To inquire quotation and lead time or to ask questions, please send email to
sales@medkoo.com to describe your needs. A representative
will respond your email shortly. We offer big discount for orders of bulk quantities.
|
|
Information about this agent
|
1: Hortobagyi GN, Gomez HL, Li RK, Chung HC,
Fein LE, Chan VF, Jassem J, Lerzo GL, Pivot XB, Hurtado de Mendoza F, Xu
B, Vahdat LT, Peck RA, Mukhopadhyay P, Roché HH. Analysis of overall
survival from a phase III study of ixabepilone plus capecitabine versus
capecitabine in patients with MBC resistant to anthracyclines and
taxanes. Breast Cancer Res Treat. 2010 Jul;122(2):409-18. Epub 2010 May
8. PubMed PMID: 20454927.
2: Rivera E. Implications of anthracycline-resistant and taxane-resistant
metastatic breast cancer and new therapeutic options. Breast J. 2010
May-Jun;16(3):252-63. Epub 2010 Apr 12. PubMed PMID: 20408828.
3: Chuang E, Wiener N, Christos P, Kessler R, Cobham M, Donovan D,
Goldberg GL, Caputo T, Doyle A, Vahdat L, Sparano JA. Phase I trial of
ixabepilone plus pegylated liposomal doxorubicin in patients with
adenocarcinoma of breast or ovary. Ann Oncol. 2010 Mar 31. [Epub ahead
of print] PubMed PMID: 20357034.
4: Stalder MW, Anthony CT, Woltering EA. Metronomic Dosing Enhances The
Anti-Angiogenic Effect of Epothilone B. J Surg Res. 2009 Dec 30. [Epub
ahead of print] PubMed PMID: 20338584.
5: Yang CP, Liu L, Ikui AE, Horwitz SB. The interaction between mitotic
checkpoint proteins, CENP-E and BubR1, is diminished in epothilone
B-resistant A549 cells. Cell Cycle. 2010 Mar 4;9(6). [Epub ahead of
print] PubMed PMID: 20237434.
6: Perez EA, Patel T, Moreno-Aspitia A. Efficacy of ixabepilone in
ER/PR/HER2-negative (triple-negative) breast cancer. Breast Cancer Res
Treat. 2010 Jun;121(2):261-71. Epub 2010 Mar 13. PubMed PMID: 20229176.
7: Huang H, Menefee M, Edgerly M, Zhuang S, Kotz H, Poruchynsky M, Huff
LM, Bates S, Fojo T. A phase II clinical trial of ixabepilone (Ixempra;
BMS-247550; NSC 710428), an epothilone B analog, in patients with
metastatic renal cell carcinoma. Clin Cancer Res. 2010 Mar
1;16(5):1634-41. Epub 2010 Feb 23. PubMed PMID: 20179242.
8: Chan A, Andreae PM, Northcote PT, Miller JH. Peloruside A inhibits
microtubule dynamics in a breast cancer cell line MCF7. Invest New
Drugs. 2010 Feb 20. [Epub ahead of print] PubMed PMID: 20169398.
9: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp
Clin Pharmacol. 2009 Dec;31(10):661-700. PubMed PMID: 20140276.
10: Yardley DA. Visceral disease in patients with metastatic breast
cancer: efficacy and safety of treatment with ixabepilone and other
chemotherapeutic agents. Clin Breast Cancer. 2010 Feb;10(1):64-73.
Review. PubMed PMID: 20133261.
11: Ott PA, Hamilton A, Jones A, Haas N, Shore T, Liddell S, Christos
PJ, Doyle LA, Millward M, Muggia FM, Pavlick AC. A phase II trial of the
epothilone B analog ixabepilone (BMS-247550) in patients with metastatic
melanoma. PLoS One. 2010 Jan 20;5(1):e8714. PubMed PMID: 20098694;
PubMed Central PMCID: PMC2808339.
12: Guarneri V, Piacentini F, Barbieri E, Conte PF. Achievements and
unmet needs in the management of advanced ovarian cancer. Gynecol Oncol.
2010 May;117(2):152-8. Epub 2010 Jan 6. Review. PubMed PMID: 20056266.
13: Harichand-Herdt S, O'Regan RM. Identifying Subsets of Metastatic
Breast Cancer Patients Likely to Benefit From Treatment With the
Epothilone B Analog Ixabepilone. Am J Clin Oncol. 2010 Jan 4. [Epub
ahead of print] PubMed PMID: 20051810.
14: Cömezoğlu SN, Ly VT, Zhang D, Humphreys WG, Bonacorsi SJ, Everett
DW, Cohen MB, Gan J, Beumer JH, Beijnen JH, Schellens HM, Lappin G.
Biotransformation profiling of [(14)C]ixabepilone in human plasma, urine
and feces samples using accelerator mass spectrometry (AMS). Drug Metab
Pharmacokinet. 2009;24(6):511-22. PubMed PMID: 20045986.
15: Toppmeyer DL, Goodin S. Ixabepilone, a New Treatment Option for
Metastatic Breast Cancer. Am J Clin Oncol. 2009 Dec 17. [Epub ahead of
print] PubMed PMID: 20023567.
16: Shen S, Kepp O, Martins I, Vitale I, Souquère S, Castedo M, Pierron
G, Kroemer G. Defective autophagy associated with LC3 puncta in
epothilone-resistant cancer cells. Cell Cycle. 2010 Jan 15;9(2):377-83.
Epub 2010 Jan 29. PubMed PMID: 20023420.
17: Moulder S, Li H, Wang M, Gradishar WJ, Perez EA, Sparano JA, Pins M,
Yang X, Sledge GW. A phase II trial of trastuzumab plus weekly
ixabepilone and carboplatin in patients with HER2-positive metastatic
breast cancer: an Eastern Cooperative Oncology Group Trial. Breast
Cancer Res Treat. 2010 Feb;119(3):663-71. PubMed PMID: 20012354.
18: Lazo JS, Reese CE, Vogt A, Vollmer LL, Kitchens CA, Günther E,
Graham TH, Hopkins CD, Wipf P. Identifying a resistance determinant for
the antimitotic natural products disorazole C1 and A1. J Pharmacol Exp
Ther. 2010 Mar;332(3):906-11. Epub 2009 Dec 15. PubMed PMID: 20008956;
PubMed Central PMCID: PMC2835430.
19: McSheehy PM, Weidensteiner C, Cannet C, Ferretti S, Laurent D, Ruetz
S, Stumm M, Allegrini PR. Quantified tumor t1 is a generic
early-response imaging biomarker for chemotherapy reflecting cell
viability. Clin Cancer Res. 2010 Jan 1;16(1):212-25. Epub 2009 Dec 15.
PubMed PMID: 20008843.
20: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp
Clin Pharmacol. 2009 Oct;31(8):541-57. PubMed PMID: 19967103.
21: Reiff EA, Nair SK, Henri JT, Greiner JF, Reddy BS, Chakrasali R,
David SA, Chiu TL, Amin EA, Himes RH, Vander Velde DG, Georg GI. Total
synthesis and evaluation of C26-hydroxyepothilone D derivatives for
photoaffinity labeling of beta-tubulin. J Org Chem. 2010 Jan
1;75(1):86-94. PubMed PMID: 19954175; PubMed Central PMCID: PMC2798899.
22: Galmarini CM. Sagopilone, a microtubule stabilizer for the potential
treatment of cancer. Curr Opin Investig Drugs. 2009 Dec;10(12):1359-71.
Review. PubMed PMID: 19943207.
23: Gradishar W. Management of advanced breast cancer with the
epothilone B analog, ixabepilone. Drug Des Devel Ther. 2009 Sep
21;3:163-71. PubMed PMID: 19920932; PubMed Central PMCID: PMC2769224.
24: De Geest K, Blessing JA, Morris RT, Yamada SD, Monk BJ, Zweizig SL,
Matei D, Muller CY, Richards WE. Phase II clinical trial of ixabepilone
in patients with recurrent or persistent platinum- and taxane-resistant
ovarian or primary peritoneal cancer: a gynecologic oncology group
study. J Clin Oncol. 2010 Jan 1;28(1):149-53. Epub 2009 Nov 16. PubMed
PMID: 19917861; PubMed Central PMCID: PMC2799230.
25: Kelly WK. Epothilones in prostate cancer. Urol Oncol. 2009 Nov 12. [Epub
ahead of print] PubMed PMID: 19914096.
26: Forli S, Manetti F, Altmann KH, Botta M. Evaluation of novel
epothilone analogues by means of a common pharmacophore and a QSAR
pseudoreceptor model for taxanes and epothilones. ChemMedChem. 2010
Jan;5(1):35-40. PubMed PMID: 19904799.
27: Po'uha ST, Shum MS, Goebel A, Bernard O, Kavallaris M. LIM-kinase 2,
a regulator of actin dynamics, is involved in mitotic spindle integrity
and sensitivity to microtubule-destabilizing drugs. Oncogene. 2010 Jan
28;29(4):597-607. Epub 2009 Nov 2. PubMed PMID: 19881550.
28: Fogh S, Machtay M, Werner-Wasik M, Curran WJ Jr, Bonanni R, Axelrod
R, Andrews D, Dicker AP. Phase I trial using patupilone (epothilone B)
and concurrent radiotherapy for central nervous system malignancies. Int
J Radiat Oncol Biol Phys. 2010 Jul 15;77(4):1009-16. Epub 2009 Oct 30.
PubMed PMID: 19879067.
29: Stein WD, Huang H, Menefee M, Edgerly M, Kotz H, Dwyer A, Yang J,
Bates SE. Other paradigms: growth rate constants and tumor burden
determined using computed tomography data correlate strongly with the
overall survival of patients with renal cell carcinoma. Cancer J. 2009
Sep-Oct;15(5):441-7. Review. PubMed PMID: 19826366.
30: Ferretti S, Allegrini PR, Becquet MM, McSheehy PM. Tumor
interstitial fluid pressure as an early-response marker for anticancer
therapeutics. Neoplasia. 2009 Sep;11(9):874-81. PubMed PMID: 19724681;
PubMed Central PMCID: PMC2735799.
31: Cheng KL, Bradley T, Budman DR. Novel microtubule-targeting agents -
the epothilones. Biologics. 2008 Dec;2(4):789-811. PubMed PMID:
19707459; PubMed Central PMCID: PMC2727900.
32: Puhalla S, Brufsky A. Ixabepilone: a new chemotherapeutic option for
refractory metastatic breast cancer. Biologics. 2008 Sep;2(3):505-15.
PubMed PMID: 19707381; PubMed Central PMCID: PMC2721395.
33: Dietrich SA, Lindauer R, Stierlin C, Gertsch J, Matesanz R,
Notararigo S, Díaz JF, Altmann KH. Epothilone analogues with
benzimidazole and quinoline side chains: chemical synthesis,
antiproliferative activity, and interactions with tubulin. Chemistry.
2009 Oct 5;15(39):10144-57. PubMed PMID: 19697384.
34: Shivanna M, Srinivas SP. Microtubule stabilization opposes the
(TNF-alpha)-induced loss in the barrier integrity of corneal
endothelium. Exp Eye Res. 2009 Dec;89(6):950-9. Epub 2009 Aug 18. PubMed
PMID: 19695246; PubMed Central PMCID: PMC2784278.
35: Pivot XB, Li RK, Thomas ES, Chung HC, Fein LE, Chan VF, Jassem J, de
Mendoza FH, Mukhopadyay P, Roché HH. Activity of ixabepilone in
oestrogen receptor-negative and oestrogen receptor-progesterone
receptor-human epidermal growth factor receptor 2-negative metastatic
breast cancer. Eur J Cancer. 2009 Nov;45(17):2940-6. Epub 2009 Aug 13.
PubMed PMID: 19683429.
36: Nimeiri HS, Singh DA, Kasza K, Taber DA, Ansari RH, Vokes EE,
Kindler HL. The epothilone B analogue ixabepilone in patients with
advanced hepatobiliary cancers: a trial of the University of Chicago
Phase II Consortium. Invest New Drugs. 2009 Aug 11. [Epub ahead of
print] PubMed PMID: 19669700.
37: Moen MD. Ixabepilone: in locally advanced or metastatic breast
cancer. Drugs. 2009 Jul 30;69(11):1471-81. doi:
10.2165/00003495-200969110-00006. Review. PubMed PMID: 19634925.
38: Michaud LB. The epothilones: how pharmacology relates to clinical
utility. Ann Pharmacother. 2009 Jul;43(7):1294-309. Epub 2009 Jul 7.
Review. PubMed PMID: 19584389.
39: Wang J, Zhang H, Ying L, Wang C, Jiang N, Zhou Y, Wang H, Bai H.
Five new epothilone metabolites from Sorangium cellulosum strain
So0157-2. J Antibiot (Tokyo). 2009 Sep;62(9):483-7. Epub 2009 Jul 3.
PubMed PMID: 19575038.
40: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp
Clin Pharmacol. 2009 Apr;31(3):183-226. PubMed PMID: 19536362.
41: Bekier ME, Fischbach R, Lee J, Taylor WR. Length of mitotic arrest
induced by microtubule-stabilizing drugs determines cell death after
mitotic exit. Mol Cancer Ther. 2009 Jun;8(6):1646-54. Epub 2009 Jun 9.
PubMed PMID: 19509263.
42: Chiorazzi A, Nicolini G, Canta A, Oggioni N, Rigolio R, Cossa G,
Lombardi R, Roglio I, Cervellini I, Lauria G, Melcangi RC, Bianchi R,
Crippa D, Cavaletti G. Experimental epothilone B neurotoxicity: results
of in vitro and in vivo studies. Neurobiol Dis. 2009 Aug;35(2):270-7.
Epub 2009 May 21. PubMed PMID: 19464369.
43: Ebenhan T, Honer M, Ametamey SM, Schubiger PA, Becquet M, Ferretti
S, Cannet C, Rausch M, McSheehy PM. Comparison of [18F]-tracers in
various experimental tumor models by PET imaging and identification of
an early response biomarker for the novel microtubule stabilizer
patupilone. Mol Imaging Biol. 2009 Sep-Oct;11(5):308-21. Epub 2009 May
22. Erratum in: Mol Imaging Biol. 2009 Sep-Oct;11(5):379-80. PubMed
PMID: 19462209.
44: Ten Bokkel Huinink WW, Sufliarsky J, Smit WM, Spanik S, Wagnerova M,
Hirte HW, Kaye S, Johri AR, Oza AM. Safety and efficacy of patupilone in
patients with advanced ovarian, primary fallopian, or primary peritoneal
cancer: a phase I, open-label, dose-escalation study. J Clin Oncol. 2009
Jul 1;27(19):3097-103. Epub 2009 May 18. PubMed PMID: 19451434.
45: Villanueva C, Vuillemin AT, Demarchi M, Bazan F, Chaigneau L, Pivot
X. Ixabepilone: a new active chemotherapy in the treatment of breast
cancer. Womens Health (Lond Engl). 2009 Mar;5(2):115-21. Review. PubMed
PMID: 19245349.
46: Gupta D, Mani S. The efficacy and safety of ixabepilone monotherapy
in the treatment of breast and gynecologic malignancies. Expert Opin
Drug Saf. 2009 Jan;8(1):81-8. Review. PubMed PMID: 19236220.
47: Bley CR, Jochum W, Orlowski K, Furmanova P, Vuong V, McSheehy PM,
Pruschy M. Role of the microenvironment for radiosensitization by
patupilone. Clin Cancer Res. 2009 Feb 15;15(4):1335-42. PubMed PMID:
19228735.
48: Cigler T, Vahdat L. Integrating epothilones into the treatment of
patients with metastatic breast cancer: clinical perspectives on
incorporating recent data in the practice setting. Clin Breast Cancer.
2008 Dec;8 Suppl 4:S166-70. Review. PubMed PMID: 19158037.
49: Nayeem A, Chiang SJ, Liu SW, Sun Y, You L, Basch J. Engineering
enzymes for improved catalytic efficiency: a computational study of site
mutagenesis in epothilone-B hydroxylase. Protein Eng Des Sel. 2009
Apr;22(4):257-66. Epub 2009 Jan 28. PubMed PMID: 19179341.
50: Hunt JT. Discovery of ixabepilone. Mol Cancer Ther. 2009
Feb;8(2):275-81. Epub 2009 Jan 27. Review. PubMed PMID: 19174552.
51: Boehnke Michaud L. The optimal therapeutic use of ixabepilone in
patients with locally advanced or metastatic breast cancer. J Oncol
Pharm Pract. 2009 Jun;15(2):95-106. Epub 2009 Jan 26. Review. PubMed
PMID: 19171553.
52: Dumontet C, Jordan MA, Lee FF. Ixabepilone: targeting
betaIII-tubulin expression in taxane-resistant malignancies. Mol Cancer
Ther. 2009 Jan;8(1):17-25. Review. PubMed PMID: 19139109.
53: Hopper-Borge E, Xu X, Shen T, Shi Z, Chen ZS, Kruh GD. Human
multidrug resistance protein 7 (ABCC10) is a resistance factor for
nucleoside analogues and epothilone B. Cancer Res. 2009 Jan
1;69(1):178-84. PubMed PMID: 19118001; PubMed Central PMCID: PMC2745904.
54: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp
Clin Pharmacol. 2008 Oct;30(8):643-72. PubMed PMID: 19088949.
55: Rivera E, Lee J, Davies A. Clinical development of ixabepilone and
other epothilones in patients with advanced solid tumors. Oncologist.
2008 Dec;13(12):1207-23. Epub 2008 Dec 16. Review. PubMed PMID:
19088324.
56: Hussain A, DiPaola RS, Baron AD, Higano CS, Tchekmedyian NS, Johri
AR. Phase II trial of weekly patupilone in patients with
castration-resistant prostate cancer. Ann Oncol. 2009 Mar;20(3):492-7.
Epub 2008 Dec 15. PubMed PMID: 19087985.
57: Mozzetti S, Iantomasi R, De Maria I, Prislei S, Mariani M,
Camperchioli A, Bartollino S, Gallo D, Scambia G, Ferlini C. Molecular
mechanisms of patupilone resistance. Cancer Res. 2008 Dec
15;68(24):10197-204. PubMed PMID: 19074887.
58: Gertsch J, Meier S, Müller M, Altmann KH. Differential effects of
natural product microtubule stabilizers on microtubule assembly: single
agent and combination studies with taxol, epothilone B, and
discodermolide. Chembiochem. 2009 Jan 5;10(1):166-75. PubMed PMID:
19058273.
59: Lee JJ, Kelly WK. Epothilones: tubulin polymerization as a novel
target for prostate cancer therapy. Nat Clin Pract Oncol. 2009
Feb;6(2):85-92. Epub 2008 Dec 2. Review. PubMed PMID: 19048010.
60: Keck GE, Giles RL, Cee VJ, Wager CA, Yu T, Kraft MB. Total synthesis
of epothilones B and D: stannane equivalents for beta-keto ester
dianions. J Org Chem. 2008 Dec 19;73(24):9675-91. PubMed PMID: 18991385;
PubMed Central PMCID: PMC2736362.
61: Risinger AL, Jackson EM, Polin LA, Helms GL, LeBoeuf DA, Joe PA,
Hopper-Borge E, Ludueña RF, Kruh GD, Mooberry SL. The taccalonolides:
microtubule stabilizers that circumvent clinically relevant taxane
resistance mechanisms. Cancer Res. 2008 Nov 1;68(21):8881-8. PubMed
PMID: 18974132; PubMed Central PMCID: PMC2727482.
62: Goodin S. Ixabepilone: a novel microtubule-stabilizing agent for the
treatment of metastatic breast cancer. Am J Health Syst Pharm. 2008 Nov
1;65(21):2017-26. Review. PubMed PMID: 18945860.
63: Klar U, Hoffmann J, Giurescu M. Sagopilone (ZK-EPO): from a natural
product to a fully synthetic clinical development candidate. Expert Opin
Investig Drugs. 2008 Nov;17(11):1735-48. Review. PubMed PMID: 18922109.
64: Liaw TY, Salam NK, McKay MJ, Cunningham AM, Hibbs DE, Kavallaris M.
Class I beta-tubulin mutations in 2-methoxyestradiol-resistant acute
lymphoblastic leukemia cells: implications for drug-target interactions.
Mol Cancer Ther. 2008 Oct;7(10):3150-9. PubMed PMID: 18852118.
65: Halterman PA. Lapatinib and ixabepilone for the treatment of
metastatic breast cancer. Pharmacotherapy. 2008 Oct;28(10):1255-66.
Review. PubMed PMID: 18823221.
66: Quick QA. Epothilone B induces glioblastoma cell death via survivin
down-regulation. Exp Oncol. 2008 Sep;30(3):195-201. PubMed PMID:
18806741.
67: Park SR, Park JW, Jung WS, Han AR, Ban YH, Kim EJ, Sohng JK, Sim SJ,
Yoon YJ. Heterologous production of epothilones B and D in Streptomyces
venezuelae. Appl Microbiol Biotechnol. 2008 Nov;81(1):109-17. Epub 2008
Sep 4. PubMed PMID: 18769916.
68: Liberatore AM, Coulomb H, Pons D, Dutruel O, Kasprzyk PG, Carlson M,
Nelson AS, Newman SP, Stengel C, Auvray P, Hesry V, Foll B, Narboux N,
Morlais D, Le Moing M, Bernetiere S, Dellile R, Camara J, Ferrandis E,
Bigg DC, Prévost GP. IRC-083927 is a new tubulin binder that inhibits
growth of human tumor cells resistant to standard tubulin-binding
agents. Mol Cancer Ther. 2008 Aug;7(8):2426-34. Erratum in: Mol Cancer
Ther. 2009 Jan;8(1):274. PubMed PMID: 18723488.
69: Beardsley EK, Chi KN. Systemic therapy after first-line docetaxel in
metastatic castration-resistant prostate cancer. Curr Opin Support
Palliat Care. 2008 Sep;2(3):161-6. Review. PubMed PMID: 18685415.
70: Trivedi M, Budihardjo I, Loureiro K, Reid TR, Ma JD. Epothilones: a
novel class of microtubule-stabilizing drugs for the treatment of
cancer. Future Oncol. 2008 Aug;4(4):483-500. Review. PubMed PMID:
18684060.
71: Kuppens IE. Current state of the art of new tubulin inhibitors in
the clinic. Curr Clin Pharmacol. 2006 Jan;1(1):57-70. Review. PubMed
PMID: 18666378.
72: Bunnell C, Vahdat L, Schwartzberg L, Gralow J, Klimovsky J, Poulart
V, Peck R, Thomas E. Phase I/II study of ixabepilone plus capecitabine
in anthracycline-pretreated/resistant and taxane-resistant metastatic
breast cancer. Clin Breast Cancer. 2008 Jun;8(3):234-41. PubMed PMID:
18650153.
73: Goel S, Goldberg GL, Kuo DY, Muggia F, Arezzo J, Mani S. Novel
neurosensory testing in cancer patients treated with the epothilone B
analog, ixabepilone. Ann Oncol. 2008 Dec;19(12):2048-52. Epub 2008 Jul
21. PubMed PMID: 18644829; PubMed Central PMCID: PMC2733111.
74: Bijman MN, van Berkel MP, van Nieuw Amerongen GP, Boven E.
Interference with actin dynamics is superior to disturbance of
microtubule function in the inhibition of human ovarian cancer cell
motility. Biochem Pharmacol. 2008 Sep 15;76(6):707-16. Epub 2008 Jul 2.
PubMed PMID: 18644348.
75: Buzdar AU. Clinical experience with epothilones in patients with
breast cancer. Clin Breast Cancer. 2008 Mar;8 Suppl 2:S71-8. Review.
PubMed PMID: 18637402.
76: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp
Clin Pharmacol. 2008 Apr;30(3):231-51. PubMed PMID: 18597009.
77: Hoffmann J, Vitale I, Buchmann B, Galluzzi L, Schwede W, Senovilla
L, Skuballa W, Vivet S, Lichtner RB, Vicencio JM, Panaretakis T,
Siemeister G, Lage H, Nanty L, Hammer S, Mittelstaedt K, Winsel S,
Eschenbrenner J, Castedo M, Demarche C, Klar U, Kroemer G. Improved
cellular pharmacokinetics and pharmacodynamics underlie the wide
anticancer activity of sagopilone. Cancer Res. 2008 Jul 1;68(13):5301-8.
PubMed PMID: 18593931.
78: Khawaja NR, Carré M, Kovacic H, Estève MA, Braguer D. Patupilone-induced
apoptosis is mediated by mitochondrial reactive oxygen species through
Bim relocalization to mitochondria. Mol Pharmacol. 2008
Oct;74(4):1072-83. Epub 2008 Jul 1. PubMed PMID: 18593821.
79: Swain SM, Arezzo JC. Neuropathy associated with microtubule
inhibitors: diagnosis, incidence, and management. Clin Adv Hematol Oncol.
2008 Jun;6(6):455-67. Review. PubMed PMID: 18567992.
80: Moulder SL. Ixabepilone for the treatment of taxane-refractory
breast cancer. Future Oncol. 2008 Jun;4(3):333-40. Review. PubMed PMID:
18518758.
81: Goodin S. Novel cytotoxic agents: epothilones. Am J Health Syst
Pharm. 2008 May 15;65(10 Suppl 3):S10-5. Review. PubMed PMID: 18463327.
82: Donovan D, Vahdat LT. Epothilones: clinical update and future
directions. Oncology (Williston Park). 2008 Apr 15;22(4):408-16;
discussion 416, 421, 424 passim. Review. PubMed PMID: 18472615.
83: Goel S, Cohen M, Cömezoglu SN, Perrin L, André F, Jayabalan D,
Iacono L, Comprelli A, Ly VT, Zhang D, Xu C, Humphreys WG, McDaid H,
Goldberg G, Horwitz SB, Mani S. The effect of ketoconazole on the
pharmacokinetics and pharmacodynamics of ixabepilone: a first in class
epothilone B analogue in late-phase clinical development. Clin Cancer
Res. 2008 May 1;14(9):2701-9. PubMed PMID: 18451235.
84: Vahdat LT. Clinical studies with epothilones for the treatment of
metastatic breast cancer. Semin Oncol. 2008 Apr;35(2 Suppl 2):S22-30;
quiz S40. Review. PubMed PMID: 18410796.
85: Burris HA 3rd. Preclinical investigations with epothilones in breast
cancer models. Semin Oncol. 2008 Apr;35(2 Suppl 2):S15-21; quiz S39.
Review. PubMed PMID: 18410795.
86: Altmann KH, Memmert K. Epothilones as lead structures for new
anticancer drugs--pharmacology, fermentation, and
structure-activity-relationships. Prog Drug Res. 2008;66:273, 275-334.
Review. PubMed PMID: 18416309.
87: Vahdat L. Ixabepilone: a novel antineoplastic agent with low
susceptibility to multiple tumor resistance mechanisms. Oncologist. 2008
Mar;13(3):214-21. Review. PubMed PMID: 18378531.
88: Pivot X, Villanueva C, Chaigneau L, Nguyen T, Demarchi M, Maurina T,
Stein U, Borg C. Ixabepilone, a novel epothilone analog in the treatment
of breast cancer. Expert Opin Investig Drugs. 2008 Apr;17(4):593-9.
Review. PubMed PMID: 18363523.
89: Harrison M, Swanton C. Epothilones and new analogues of the
microtubule modulators in taxane-resistant disease. Expert Opin Investig
Drugs. 2008 Apr;17(4):523-46. Review. PubMed PMID: 18363517.
90: Lee FY, Smykla R, Johnston K, Menard K, McGlinchey K, Peterson RW,
Wiebesiek A, Vite G, Fairchild CR, Kramer R. Preclinical efficacy
spectrum and pharmacokinetics of ixabepilone. Cancer Chemother Pharmacol.
2009 Jan;63(2):201-12. Epub 2008 Mar 19. PubMed PMID: 18350296.
91: Lee FY, Borzilleri R, Fairchild CR, Kamath A, Smykla R, Kramer R,
Vite G. Preclinical discovery of ixabepilone, a highly active
antineoplastic agent. Cancer Chemother Pharmacol. 2008 Dec;63(1):157-66.
Epub 2008 Mar 18. Review. PubMed PMID: 18347795.
92: Lee JJ, Swain SM. The epothilones: translating from the laboratory
to the clinic. Clin Cancer Res. 2008 Mar 15;14(6):1618-24. Review.
PubMed PMID: 18347162.
93: Dinh P, Harnett P, Piccart-Gebhart MJ, Awada A. New therapies for
ovarian cancer: cytotoxics and molecularly targeted agents. Crit Rev
Oncol Hematol. 2008 Aug;67(2):103-12. Epub 2008 Mar 14. Review. PubMed
PMID: 18342536.
94: Denduluri N, Swain SM. Ixabepilone for the treatment of solid
tumors: a review of clinical data. Expert Opin Investig Drugs. 2008
Mar;17(3):423-35. Review. PubMed PMID: 18321240.
95: Villanueva C, Dufresne A, Pivot X, Viel E. [Efficacy and safety of
ixabepilone (BMS-247550), a novel epothilone B analogue]. Bull Cancer.
2008 Feb;95(2):197-204. Review. French. PubMed PMID: 18304905.
96: O'Reilly T, Wartmann M, Brueggen J, Allegrini PR, Floersheimer A,
Maira M, McSheehy PM. Pharmacokinetic profile of the microtubule
stabilizer patupilone in tumor-bearing rodents and comparison of
anti-cancer activity with other MTS in vitro and in vivo. Cancer
Chemother Pharmacol. 2008 Nov;62(6):1045-54. Epub 2008 Feb 27. PubMed
PMID: 18301895.
97: Han SJ, Park SW, Park BW, Sim SJ. Selective production of epothilone
B by heterologous expression of propionyl-CoA synthetase in Sorangium
cellulosum. J Microbiol Biotechnol. 2008 Jan;18(1):135-7. PubMed PMID:
18239430.
98: Sakaushi S, Nishida K, Fukada T, Senda-Murata K, Oka S, Sugimoto K.
Differential responses of mitotic spindle pole formation to
microtubule-stabilizing agents epothilones A and B at low
concentrations. Cell Cycle. 2008 Feb 15;7(4):477-83. Epub 2007 Nov 9.
PubMed PMID: 18235240.
99: Pronzato P. New therapeutic options for chemotherapy-resistant
metastatic breast cancer: the epothilones. Drugs. 2008;68(2):139-46.
Review. PubMed PMID: 18197722.
100: Schelman W, Morgan-Meadows S, Bailey H, Holen K, Thomas JP,
Eickhoff J, Brandon H, Oliver K, Alberti D, Wilding G. A phase I trial
of gemcitabine in combination with patupilone in patients with advanced
solid tumors. Cancer Chemother Pharmacol. 2008 Sep;62(4):727-33. Epub
2008 Jan 3. PubMed PMID: 18172649.
101: Reichenbach H, Höfle G. Discovery and development of the
epothilones : a novel class of antineoplastic drugs. Drugs R D.
2008;9(1):1-10. Review. PubMed PMID: 18095749.
102: Guo WJ, Tao GJ, Tao WY, Cui FJ, Jin XC, Bi F, Xu ZH, Ao ZH. A
myxobacterium strain Sorangium cellulosum AHB125 producing epothilone B
and other anticancer substances. Nat Prod Res. 2007 Dec;21(14):1256-65.
PubMed PMID: 18075888.
103: Raccor BS, Vogt A, Sikorski RP, Madiraju C, Balachandran R,
Montgomery K, Shin Y, Fukui Y, Jung WH, Curran DP, Day BW. Cell-based
and biochemical structure-activity analyses of analogs of the
microtubule stabilizer dictyostatin. Mol Pharmacol. 2008
Mar;73(3):718-26. Epub 2007 Dec 11. PubMed PMID: 18073274.
104: Park WS, Park SJ, Han SJ, Lee J, Kim DS, Kim JH, Kim BW, Lee J, Sim
SJ. Repeated batch production of epothilone B by immobilized Sorangium
cellulosum. J Microbiol Biotechnol. 2007 Jul;17(7):1208-12. PubMed PMID:
18051335.
105: Fornier MN. Ixabepilone, first in a new class of antineoplastic
agents: the natural epothilones and their analogues. Clin Breast Cancer.
2007 Oct;7(10):757-63. Review. PubMed PMID: 18021476.
106: Lee SH, Son SM, Son DJ, Kim SM, Kim TJ, Song S, Moon DC, Lee HW,
Ryu JC, Yoon DY, Hong JT. Epothilones induce human colon cancer SW620
cell apoptosis via the tubulin polymerization independent activation of
the nuclear factor-kappaB/IkappaB kinase signal pathway. Mol Cancer Ther.
2007 Oct;6(10):2786-97. PubMed PMID: 17938270.
107: Fumoleau P, Coudert B, Isambert N, Ferrant E. Novel tubulin-targeting
agents: anticancer activity and pharmacologic profile of epothilones and
related analogues. Ann Oncol. 2007 Jul;18 Suppl 5:v9-15. Review. PubMed
PMID: 17656562.
108: Larkin JM, Kaye SB. Potential clinical applications of epothilones:
a review of phase II studies. Ann Oncol. 2007 Jul;18 Suppl 5:v28-34.
Review. PubMed PMID: 17656559.
109: Dawson NA. Epothilones in prostate cancer: review of clinical
experience. Ann Oncol. 2007 Jul;18 Suppl 5:v22-7. Review. PubMed PMID:
17656558.
110: Sessa C, Perotti A, Lladò A, Cresta S, Capri G, Voi M, Marsoni S,
Corradino I, Gianni L. Phase I clinical study of the novel epothilone B
analogue BMS-310705 given on a weekly schedule. Ann Oncol. 2007
Sep;18(9):1548-53. PubMed PMID: 17761711.
111: Mok TS, Choi E, Yau D, Johri A, Yeo W, Chan AT, Wong C. Effects of
patupilone (epothilone B; EPO906), a novel chemotherapeutic agent, in
hepatocellular carcinoma: an in vitro study. Oncology.
2006;71(3-4):292-6. Epub 2007 Jul 26. PubMed PMID: 17657173.
112: Gong GL, Sun X, Liu XL, Hu W, Cao WR, Liu H, Liu WF, Li YZ.
Mutation and a high-throughput screening method for improving the
production of Epothilones of Sorangium. J Ind Microbiol Biotechnol. 2007
Sep;34(9):615-23. Epub 2007 Jul 24. PubMed PMID: 17647035.
113: Forster M, Kaye S, Oza A, Sklenar I, Johri A, Cheung W, Zaknoen S,
Gore M. A phase Ib and pharmacokinetic trial of patupilone combined with
carboplatin in patients with advanced cancer. Clin Cancer Res. 2007 Jul
15;13(14):4178-84. PubMed PMID: 17634546.
114: Thomas E, Tabernero J, Fornier M, Conté P, Fumoleau P, Lluch A,
Vahdat LT, Bunnell CA, Burris HA, Viens P, Baselga J, Rivera E, Guarneri
V, Poulart V, Klimovsky J, Lebwohl D, Martin M. Phase II clinical trial
of ixabepilone (BMS-247550), an epothilone B analog, in patients with
taxane-resistant metastatic breast cancer. J Clin Oncol. 2007 Aug
10;25(23):3399-406. Epub 2007 Jul 2. PubMed PMID: 17606975.
115: Vansteenkiste J, Lara PN Jr, Le Chevalier T, Breton JL, Bonomi P,
Sandler AB, Socinski MA, Delbaldo C, McHenry B, Lebwohl D, Peck R,
Edelman MJ. Phase II clinical trial of the epothilone B analog,
ixabepilone, in patients with non small-cell lung cancer whose tumors
have failed first-line platinum-based chemotherapy. J Clin Oncol. 2007
Aug 10;25(23):3448-55. Epub 2007 Jul 2. Erratum in: J Clin Oncol. 2007
Nov 20;25(33):5339. Edelman, Mark [corrected to Edelman, Martin J].
PubMed PMID: 17606973.
116: Roché H, Yelle L, Cognetti F, Mauriac L, Bunnell C, Sparano J,
Kerbrat P, Delord JP, Vahdat L, Peck R, Lebwohl D, Ezzeddine R, Curé H.
Phase II clinical trial of ixabepilone (BMS-247550), an epothilone B
analog, as first-line therapy in patients with metastatic breast cancer
previously treated with anthracycline chemotherapy. J Clin Oncol. 2007
Aug 10;25(23):3415-20. Epub 2007 Jul 2. PubMed PMID: 17606972.
117: Denduluri N, Low JA, Lee JJ, Berman AW, Walshe JM, Vatas U, Chow
CK, Steinberg SM, Yang SX, Swain SM. Phase II trial of ixabepilone, an
epothilone B analog, in patients with metastatic breast cancer
previously untreated with taxanes. J Clin Oncol. 2007 Aug
10;25(23):3421-7. Epub 2007 Jul 2. PubMed PMID: 17606971.
118: Gianni L. Ixabepilone and the narrow path to developing new
cytotoxic drugs. J Clin Oncol. 2007 Aug 10;25(23):3389-91. Epub 2007 Jul
2. PubMed PMID: 17606970.
119: Dreicer R, Li S, Manola J, Haas NB, Roth BJ, Wilding G; Eastern
Cooperative Oncology Group. Phase 2 trial of epothilone B analog
BMS-247550 (ixabepilone) in advanced carcinoma of the urothelium
(E3800): a trial of the Eastern Cooperative Oncology Group. Cancer. 2007
Aug 15;110(4):759-63. PubMed PMID: 17594721.
120: Shimizu T, Yamamoto N, Yamada Y, Fujisaka Y, Yamada K, Fujiwara Y,
Takayama K, Tokudome T, Klimovsky J, Tamura T. Phase I clinical and
pharmacokinetic study of 3-weekly, 3-h infusion of ixabepilone
(BMS-247550), an epothilone B analog, in Japanese patients with
refractory solid tumors. Cancer Chemother Pharmacol. 2008
Apr;61(5):751-8. Epub 2007 Jun 27. PubMed PMID: 17594093.
121: Grewal RP. Axonal neuropathy caused by epothilone B. Neurol India.
2007 Apr-Jun;55(2):178-9. PubMed PMID: 17558132.
122: Posadas EM, Undevia S, Manchen E, Wade JL, Colevas AD, Karrison T,
Vokes EE, Stadler WM. A phase II study of ixabepilone (BMS-247550) in
metastatic renal-cell carcinoma. Cancer Biol Ther. 2007 Apr;6(4):490-3.
PubMed PMID: 17457044.
123: Cortes J, Baselga J. Targeting the microtubules in breast cancer
beyond taxanes: the epothilones. Oncologist. 2007 Mar;12(3):271-80.
Review. PubMed PMID: 17405891.
124: Beumer JH, Garner RC, Cohen MB, Galbraith S, Duncan GF, Griffin T,
Beijnen JH, Schellens JH. Human mass balance study of the novel
anticancer agent ixabepilone using accelerator mass spectrometry. Invest
New Drugs. 2007 Aug;25(4):327-34. Epub 2007 Mar 9. PubMed PMID:
17347871; PubMed Central PMCID: PMC1915607.
125: Lange A, Schupp T, Petersen F, Carlomagno T, Baldus M.
High-resolution solid-state NMR structure of an anticancer agent.
ChemMedChem. 2007 Apr;2(4):522-7. PubMed PMID: 17315255.
126: Failly M, Korur S, Egler V, Boulay JL, Lino MM, Imber R, Merlo A.
Combination of sublethal concentrations of epidermal growth factor
receptor inhibitor and microtubule stabilizer induces apoptosis of
glioblastoma cells. Mol Cancer Ther. 2007 Feb;6(2):773-81. PubMed PMID:
17308073.
127: Lim Y, Kim TJ, Jin YR, Kim DW, Kwon JS, Son JH, Jung JC, Avery MA,
Son DJ, Hong JT, Yun YP. Epothilone B inhibits neointimal formation
after rat carotid injury through the regulation of cell cycle-related
proteins. J Pharmacol Exp Ther. 2007 May;321(2):648-55. Epub 2007 Feb 8.
PubMed PMID: 17289837.
128: Hartmann JT. Systemic treatment options for patients with
refractory adult-type sarcoma beyond anthracyclines. Anticancer Drugs.
2007 Mar;18(3):245-54. Review. PubMed PMID: 17264755.
129: Buey RM, Calvo E, Barasoain I, Pineda O, Edler MC, Matesanz R,
Cerezo G, Vanderwal CD, Day BW, Sorensen EJ, López JA, Andreu JM, Hamel
E, Díaz JF. Cyclostreptin binds covalently to microtubule pores and
lumenal taxoid binding sites. Nat Chem Biol. 2007 Feb;3(2):117-25. Epub
2007 Jan 7. PubMed PMID: 17206139.
130: End N, Furet P, van Campenhout N, Wartmann M, Altmann KH. Total
synthesis and biological evaluation of a C(10)/C(12)-phenylene-bridged
analog of epothilone D. Chem Biodivers. 2004 Nov;1(11):1771-84. PubMed
PMID: 17191815.
131: Verrills NM, Po'uha ST, Liu ML, Liaw TY, Larsen MR, Ivery MT,
Marshall GM, Gunning PW, Kavallaris M. Alterations in gamma-actin and
tubulin-targeted drug resistance in childhood leukemia. J Natl Cancer
Inst. 2006 Oct 4;98(19):1363-74. PubMed PMID: 17018783.
132: Mani S, McDaid HM, Grossman A, Muggia F, Goel S, Griffin T, Colevas
D, Horwitz SB, Egorin MJ. Peripheral blood mononuclear and tumor cell
pharmacodynamics of the novel epothilone B analogue, ixabepilone. Ann
Oncol. 2007 Jan;18(1):190-5. Epub 2006 Oct 3. PubMed PMID: 17018704.
133: Ryoo S, Lemmon CA, Soucy KG, Gupta G, White AR, Nyhan D, Shoukas A,
Romer LH, Berkowitz DE. Oxidized low-density lipoprotein-dependent
endothelial arginase II activation contributes to impaired nitric oxide
signaling. Circ Res. 2006 Oct 27;99(9):951-60. Epub 2006 Sep 28. PubMed
PMID: 17008605.
134: Petrylak DP. Hormone-refractory prostate cancer: new horizons. Rev
Urol. 2003;5 Suppl 6:S54-8. PubMed PMID: 16985978; PubMed Central PMCID:
PMC1502368.
135: Bijman MN, van Nieuw Amerongen GP, Laurens N, van Hinsbergh VW,
Boven E. Microtubule-targeting agents inhibit angiogenesis at subtoxic
concentrations, a process associated with inhibition of Rac1 and Cdc42
activity and changes in the endothelial cytoskeleton. Mol Cancer Ther.
2006 Sep;5(9):2348-57. PubMed PMID: 16985069.
136: Basch J, Chiang SJ. Cloning and expression of a cytochrome P450
hydroxylase gene from Amycolatopsis orientalis: hydroxylation of
epothilone B for the production of epothilone F. J Ind Microbiol
Biotechnol. 2007 Feb;34(2):171-6. Epub 2006 Sep 14. Erratum in: J Ind
Microbiol Biotechnol. 2007 Feb;34(2):177. PubMed PMID: 16972046.
137: Denduluri N, Lee JJ, Walshe J, Berman AW, Vatas U, Chow CK,
Steinberg SM, Cox MC, Low JA, Swain SM. Phase II trial of ixabepilone,
an epothilone B analog, given daily for three days every three weeks, in
metastatic breast cancer. Invest New Drugs. 2007 Feb;25(1):63-7. Epub
2006 Aug 25. PubMed PMID: 16933153.
138: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials.
Methods Find Exp Clin Pharmacol. 2006 May;28(4):233-77. PubMed PMID:
16801985.
139: Larkin JM, Kaye SB. Epothilones in the treatment of cancer. Expert
Opin Investig Drugs. 2006 Jun;15(6):691-702. Review. PubMed PMID:
16732719.
140: Whitehead RP, McCoy S, Rivkin SE, Gross HM, Conrad ME, Doolittle
GC, Wolff RA, Goodwin JW, Dakhil SR, Abbruzzese JL. A Phase II trial of
epothilone B analogue BMS-247550 (NSC #710428) ixabepilone, in patients
with advanced pancreas cancer: a Southwest Oncology Group study. Invest
New Drugs. 2006 Nov;24(6):515-20. PubMed PMID: 16699973.
141: Lee JJ, Swain SM. Peripheral neuropathy induced by
microtubule-stabilizing agents. J Clin Oncol. 2006 Apr 1;24(10):1633-42.
Review. PubMed PMID: 16575015.
142: Hari M, Loganzo F, Annable T, Tan X, Musto S, Morilla DB, Nettles
JH, Snyder JP, Greenberger LM. Paclitaxel-resistant cells have a
mutation in the paclitaxel-binding region of beta-tubulin (Asp26Glu) and
less stable microtubules. Mol Cancer Ther. 2006 Feb;5(2):270-8. PubMed
PMID: 16505100.
143: Khalil MW, Sasse F, Lünsdorf H, Elnakady YA, Reichenbach H.
Mechanism of action of tubulysin, an antimitotic peptide from
myxobacteria. Chembiochem. 2006 Apr;7(4):678-83. PubMed PMID: 16491500.
144: Sonnenschein RN, Johnson TA, Tenney K, Valeriote FA, Crews P. A
reassignment of (-)-mycothiazole and the isolation of a related diol. J
Nat Prod. 2006 Jan;69(1):145-7. PubMed PMID: 16441088; PubMed Central
PMCID: PMC2031212.
145: Lee JJ, Swain SM. Development of novel chemotherapeutic agents to
evade the mechanisms of multidrug resistance (MDR). Semin Oncol. 2005
Dec;32(6 Suppl 7):S22-6. Review. PubMed PMID: 16360719.
146: Rosenberg JE, Galsky MD, Rohs NC, Weinberg VK, Oh WK, Kelly WK,
Small EJ. A retrospective evaluation of second-line chemotherapy
response in hormone-refractory prostate carcinoma: second line taxane-based
therapy after first-line epothilone-B analog ixabepilone (BMS-247550)
therapy. Cancer. 2006 Jan 1;106(1):58-62. PubMed PMID: 16329138.
147: Hussain M, Tangen CM, Lara PN Jr, Vaishampayan UN, Petrylak DP,
Colevas AD, Sakr WA, Crawford ED; Southwest Oncology Group. Ixabepilone
(epothilone B analogue BMS-247550) is active in chemotherapy-naive
patients with hormone-refractory prostate cancer: a Southwest Oncology
Group trial S0111. J Clin Oncol. 2005 Dec 1;23(34):8724-9. PubMed PMID:
16314632.
148: Rubin EH, Rothermel J, Tesfaye F, Chen T, Hubert M, Ho YY, Hsu CH,
Oza AM. Phase I dose-finding study of weekly single-agent patupilone in
patients with advanced solid tumors. J Clin Oncol. 2005 Dec
20;23(36):9120-9. Epub 2005 Nov 21. PubMed PMID: 16301595.
149: Ferretti S, Allegrini PR, O'Reilly T, Schnell C, Stumm M, Wartmann
M, Wood J, McSheehy PM. Patupilone induced vascular disruption in
orthotopic rodent tumor models detected by magnetic resonance imaging
and interstitial fluid pressure. Clin Cancer Res. 2005 Nov
1;11(21):7773-84. PubMed PMID: 16278399.
150: Madiraju C, Edler MC, Hamel E, Raccor BS, Balachandran R, Zhu G,
Giuliano KA, Vogt A, Shin Y, Fournier JH, Fukui Y, Brückner AM, Curran
DP, Day BW. Tubulin assembly, taxoid site binding, and cellular effects
of the microtubule-stabilizing agent dictyostatin. Biochemistry. 2005
Nov 15;44(45):15053-63. PubMed PMID: 16274252.
151: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials.
Methods Find Exp Clin Pharmacol. 2005 Oct;27(8):569-612. PubMed PMID:
16273137.
152: Chou TC, Dong H, Zhang X, Tong WP, Danishefsky SJ. Therapeutic cure
against human tumor xenografts in nude mice by a microtubule
stabilization agent, fludelone, via parenteral or oral route. Cancer
Res. 2005 Oct 15;65(20):9445-54. PubMed PMID: 16230408.
153: Gökmen-Polar Y, Escuin D, Walls CD, Soule SE, Wang Y, Sanders KL,
Lavallee TM, Wang M, Guenther BD, Giannakakou P, Sledge GW Jr. beta-Tubulin
mutations are associated with resistance to 2-methoxyestradiol in
MDA-MB-435 cancer cells. Cancer Res. 2005 Oct 15;65(20):9406-14. PubMed
PMID: 16230404.
154: Escuin D, Kline ER, Giannakakou P. Both microtubule-stabilizing and
microtubule-destabilizing drugs inhibit hypoxia-inducible factor-1alpha
accumulation and activity by disrupting microtubule function. Cancer
Res. 2005 Oct 1;65(19):9021-8. PubMed PMID: 16204076.
155: Peterson JK, Tucker C, Favours E, Cheshire PJ, Creech J, Billups
CA, Smykla R, Lee FY, Houghton PJ. In vivo evaluation of ixabepilone
(BMS247550), a novel epothilone B derivative, against pediatric cancer
models. Clin Cancer Res. 2005 Oct 1;11(19 Pt 1):6950-8. PubMed PMID:
16203787.
156: Wakelee HA, Sikic BI. Activity of novel cytotoxic agents in lung
cancer: epothilones and topoisomerase I inhibitors. Clin Lung Cancer.
2005 Sep;7 Suppl 1:S6-12. Review. PubMed PMID: 16159420.
157: Mani S, Huang H, Sundarababu S, Liu W, Kalpana G, Smith AB, Horwitz
SB. Activation of the steroid and xenobiotic receptor (human pregnane X
receptor) by nontaxane microtubule-stabilizing agents. Clin Cancer Res.
2005 Sep 1;11(17):6359-69. PubMed PMID: 16144941.
158: Gadgeel SM, Wozniak A, Boinpally RR, Wiegand R, Heilbrun LK, Jain
V, Parchment R, Colevas D, Cohen MB, LoRusso PM. Phase I clinical trial
of BMS-247550, a derivative of epothilone B, using accelerated titration
2B design. Clin Cancer Res. 2005 Sep 1;11(17):6233-9. PubMed PMID:
16144926.
159: Harvey A. Natural Products in Drug Discovery and Development. 27-28
June 2005, London, UK. IDrugs. 2005 Sep;8(9):719-21. PubMed PMID:
16118691.
160: Bhandari MS, Hussain M. Epothilones and the next generation of
phase III trials for prostate cancer. BJU Int. 2005 Aug;96(3):296-302.
Review. PubMed PMID: 16042717.
161: Ross RW, Manola J, Hennessy K, Galsky M, Scher H, Small E, Kelly
WK, Kantoff PW. Prognostic significance of baseline reverse
transcriptase-PCR for prostate-specific antigen in men with
hormone-refractory prostate cancer treated with chemotherapy. Clin
Cancer Res. 2005 Jul 15;11(14):5195-8. PubMed PMID: 16033836.
162: Yang CP, Verdier-Pinard P, Wang F, Lippaine-Horvath E, He L, Li D,
Höfle G, Ojima I, Orr GA, Horwitz SB. A highly epothilone B-resistant
A549 cell line with mutations in tubulin that confer drug dependence.
Mol Cancer Ther. 2005 Jun;4(6):987-95. PubMed PMID: 15956256.
163: O'Reilly T, McSheehy PM, Wenger F, Hattenberger M, Muller M,
Vaxelaire J, Altmann KH, Wartmann M. Patupilone (epothilone B, EPO906)
inhibits growth and metastasis of experimental prostate tumors in vivo.
Prostate. 2005 Nov 1;65(3):231-40. PubMed PMID: 15948135.
164: Altmann KH. Recent developments in the chemical biology of
epothilones. Curr Pharm Des. 2005;11(13):1595-613. Review. PubMed PMID:
15892665.
165: Okuno S, Maples WJ, Mahoney MR, Fitch T, Stewart J, Fracasso PM,
Kraut M, Ettinger DS, Dawkins F, Erlichman C. Evaluation of epothilone B
analog in advanced soft tissue sarcoma: a phase II study of the phase II
consortium. J Clin Oncol. 2005 May 1;23(13):3069-73. PubMed PMID:
15860865.
166: Low JA, Wedam SB, Lee JJ, Berman AW, Brufsky A, Yang SX,
Poruchynsky MS, Steinberg SM, Mannan N, Fojo T, Swain SM. Phase II
clinical trial of ixabepilone (BMS-247550), an epothilone B analog, in
metastatic and locally advanced breast cancer. J Clin Oncol. 2005 Apr
20;23(12):2726-34. PubMed PMID: 15837987.
167: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials.
Methods Find Exp Clin Pharmacol. 2005 Jan-Feb;27(1):49-77. PubMed PMID:
15834459.
168: Kamath AV, Chang M, Lee FY, Zhang Y, Marathe PH. Preclinical
pharmacokinetics and oral bioavailability of BMS-310705, a novel
epothilone B analog. Cancer Chemother Pharmacol. 2005 Aug;56(2):145-53.
Epub 2005 Apr 14. PubMed PMID: 15830240.
169: Zhuang SH, Agrawal M, Edgerly M, Bakke S, Kotz H, Thambi P, Rutt A,
Balis FM, Bates S, Fojo T. A Phase I clinical trial of ixabepilone
(BMS-247550), an epothilone B analog, administered intravenously on a
daily schedule for 3 days. Cancer. 2005 May 1;103(9):1932-8. PubMed
PMID: 15800893.
170: Gaich T, Mulzer J. Synthesis of epothilones via a silicon-tethered
RCM reaction. Org Lett. 2005 Mar 31;7(7):1311-3. PubMed PMID: 15787494.
171: Azzabi A, Hughes AN, Calvert PM, Plummer ER, Todd R, Griffin MJ,
Lind MJ, Maraveyas A, Kelly C, Fishwick K, Calvert AH, Boddy AV. Phase I
study of temozolomide plus paclitaxel in patients with advanced
malignant melanoma and associated in vitro investigations. Br J Cancer.
2005 Mar 28;92(6):1006-12. PubMed PMID: 15756276; PubMed Central PMCID:
PMC2361941.
172: Hofstetter B, Vuong V, Broggini-Tenzer A, Bodis S, Ciernik IF,
Fabbro D, Wartmann M, Folkers G, Pruschy M. Patupilone acts as
radiosensitizing agent in multidrug-resistant cancer cells in vitro and
in vivo. Clin Cancer Res. 2005 Feb 15;11(4):1588-96. PubMed PMID:
15746064.
173: Galsky MD, Small EJ, Oh WK, Chen I, Smith DC, Colevas AD, Martone
L, Curley T, Delacruz A, Scher HI, Kelly WK. Multi-institutional
randomized phase II trial of the epothilone B analog ixabepilone
(BMS-247550) with or without estramustine phosphate in patients with
progressive castrate metastatic prostate cancer. J Clin Oncol. 2005 Mar
1;23(7):1439-46. PubMed PMID: 15735119.
174: O'Reilly T, Wartmann M, Maira SM, Hattenberger M, Vaxelaire J,
Muller M, Ferretti S, Buchdunger E, Altmann KH, McSheehy PM. Patupilone
(epothilone B, EPO906) and imatinib (STI571, Glivec) in combination
display enhanced antitumour activity in vivo against experimental rat C6
glioma. Cancer Chemother Pharmacol. 2005 Apr;55(4):307-17. Epub 2004 Oct
26. PubMed PMID: 15723258.
175: Heinz DW, Schubert WD, Höfle G. Much anticipated--the bioactive
conformation of epothilone and its binding to tubulin. Angew Chem Int Ed
Engl. 2005 Feb 18;44(9):1298-301. PubMed PMID: 15714588.
176: Caponigro F, Basile M, de Rosa V, Normanno N. New drugs in cancer
therapy, National Tumor Institute, Naples, 17-18 June 2004. Anticancer
Drugs. 2005 Feb;16(2):211-21. PubMed PMID: 15655420.
177: Ferguson RE, Jackson SM, Stanley AJ, Joyce AD, Harnden P, Morrison
EE, Patel PM, Phillips RM, Selby PJ, Banks RE. Intrinsic chemotherapy
resistance to the tubulin-binding antimitotic agents in renal cell
carcinoma. Int J Cancer. 2005 May 20;115(1):155-63. PubMed PMID:
15645438.
178: Jung JC, Kache R, Vines KK, Zheng YS, Bijoy P, Valluri M, Avery MA.
Total syntheses of epothilones B and d. J Org Chem. 2004 Dec
24;69(26):9269-84. PubMed PMID: 15609966.
179: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials.
Methods Find Exp Clin Pharmacol. 2004 Oct;26(8):639-63. PubMed PMID:
15605126.
180: Liu F, Garneau S, Walsh CT. Hybrid nonribosomal peptide-polyketide
interfaces in epothilone biosynthesis: minimal requirements at N and C
termini of EpoB for elongation. Chem Biol. 2004 Nov;11(11):1533-42.
PubMed PMID: 15556004.
181: Ogura H, Nishida CR, Hoch UR, Perera R, Dawson JH, Ortiz de
Montellano PR. EpoK, a cytochrome P450 involved in biosynthesis of the
anticancer agents epothilones A and B. Substrate-mediated rescue of a
P450 enzyme. Biochemistry. 2004 Nov 23;43(46):14712-21. PubMed PMID:
15544342.
182: Souquet PJ. [Second-line chemotherapy in non-small cell lung
cancer]. Rev Pneumol Clin. 2004 Nov;60(5 Pt 2):3S57-9. Review. French.
PubMed PMID: 15536355.
183: Lee D. Activity of epothilone B analogues ixabepilone and
patupilone in hormone-refractory prostate cancer. Clin Prostate Cancer.
2004 Sep;3(2):80-2. Review. PubMed PMID: 15479489.
184: Lin B, Catley L, LeBlanc R, Mitsiades C, Burger R, Tai YT, Podar K,
Wartmann M, Chauhan D, Griffin JD, Anderson KC. Patupilone (epothilone
B) inhibits growth and survival of multiple myeloma cells in vitro and
in vivo. Blood. 2005 Jan 1;105(1):350-7. Epub 2004 Sep 14. PubMed PMID:
15367426.
185: Yamaguchi H, Chen J, Bhalla K, Wang HG. Regulation of Bax
activation and apoptotic response to microtubule-damaging agents by p53
transcription-dependent and -independent pathways. J Biol Chem. 2004 Sep
17;279(38):39431-7. Epub 2004 Jul 19. PubMed PMID: 15262986.
186: Kolman A. Epothilone D (Kosan/Roche). Curr Opin Investig Drugs.
2004 Jun;5(6):657-67. Review. PubMed PMID: 15242255.
187: Eng C, Kindler HL, Nattam S, Ansari RH, Kasza K, Wade-Oliver K,
Vokes EE. A phase II trial of the epothilone B analog, BMS-247550, in
patients with previously treated advanced colorectal cancer. Ann Oncol.
2004 Jun;15(6):928-32. PubMed PMID: 15151950.
188: Kingston DG. What makes epothilones stick? Chem Biol. 2004
Feb;11(2):153-5. PubMed PMID: 15123274.
189: Hayakawa Y. [Structure-activity relationship analysis]. Gan To
Kagaku Ryoho. 2004 Apr;31(4):526-8. Japanese. PubMed PMID: 15114695.
190: Dabydeen DA, Florence GJ, Paterson I, Hamel E. A quantitative
evaluation of the effects of inhibitors of tubulin assembly on
polymerization induced by discodermolide, epothilone B, and paclitaxel.
Cancer Chemother Pharmacol. 2004 May;53(5):397-403. Epub 2004 Jan 22.
PubMed PMID: 15060743.
191: Khabele D, Lopez-Jones M, Yang W, Arango D, Gross SJ, Augenlicht
LH, Goldberg GL. Tumor necrosis factor-alpha related gene response to
Epothilone B in ovarian cancer. Gynecol Oncol. 2004 Apr;93(1):19-26.
PubMed PMID: 15047209.
192: Tyagi P, Klem J, D'Orazio A. Highlights from the 39th Annual
meeting of the American Society of Clinical Oncology Chicago, Illinois.
Clin Prostate Cancer. 2003 Sep;2(2):73-9. PubMed PMID: 15040866.
193: Altmann KH, Flörsheimer A, O'Reilly T, Wartmann M. 4. The natural
products epothilones A and B as lead structures for anticancer drug
discovery: chemistry, biology, and SAR studies. Prog Med Chem.
2004;42:171-205. Review. PubMed PMID: 15003721.
194: Mani S, McDaid H, Hamilton A, Hochster H, Cohen MB, Khabelle D,
Griffin T, Lebwohl DE, Liebes L, Muggia F, Horwitz SB. Phase I clinical
and pharmacokinetic study of BMS-247550, a novel derivative of
epothilone B, in solid tumors. Clin Cancer Res. 2004 Feb
15;10(4):1289-98. PubMed PMID: 14977827.
195: Mulzer J, Martin HJ. Lessons learned from macrolide synthesis. Chem
Rec. 2004;3(5):258-70. Review. PubMed PMID: 14762826.
196: Bröker LE, Huisman C, Span SW, Rodriguez JA, Kruyt FA, Giaccone G.
Cathepsin B mediates caspase-independent cell death induced by
microtubule stabilizing agents in non-small cell lung cancer cells.
Cancer Res. 2004 Jan 1;64(1):27-30. PubMed PMID: 14729603.
197: Honore S, Kamath K, Braguer D, Wilson L, Briand C, Jordan MA.
Suppression of microtubule dynamics by discodermolide by a novel
mechanism is associated with mitotic arrest and inhibition of tumor cell
proliferation. Mol Cancer Ther. 2003 Dec;2(12):1303-11. PubMed PMID:
14707271.
198: Galmarini CM, Dumontet C. EPO-906 (Novartis). IDrugs. 2003
Dec;6(12):1182-7. Review. PubMed PMID: 14666430.
199: Chen JG, Yang CP, Cammer M, Horwitz SB. Gene expression and mitotic
exit induced by microtubule-stabilizing drugs. Cancer Res. 2003 Nov
15;63(22):7891-9. PubMed PMID: 14633718.
200: Fuino L, Bali P, Wittmann S, Donapaty S, Guo F, Yamaguchi H, Wang
HG, Atadja P, Bhalla K. Histone deacetylase inhibitor LAQ824
down-regulates Her-2 and sensitizes human breast cancer cells to
trastuzumab, taxotere, gemcitabine, and epothilone B. Mol Cancer Ther.
2003 Oct;2(10):971-84. PubMed PMID: 14578462.
201: Uyar D, Takigawa N, Mekhail T, Grabowski D, Markman M, Lee F,
Canetta R, Peck R, Bukowski R, Ganapathi R. Apoptotic pathways of
epothilone BMS 310705. Gynecol Oncol. 2003 Oct;91(1):173-8. PubMed PMID:
14529678.
202: Kamath K, Jordan MA. Suppression of microtubule dynamics by
epothilone B is associated with mitotic arrest. Cancer Res. 2003 Sep
15;63(18):6026-31. PubMed PMID: 14522931.
203: Pietras K, Stumm M, Hubert M, Buchdunger E, Rubin K, Heldin CH,
McSheehy P, Wartmann M, Ostman A. STI571 enhances the therapeutic index
of epothilone B by a tumor-selective increase of drug uptake. Clin
Cancer Res. 2003 Sep 1;9(10 Pt 1):3779-87. PubMed PMID: 14506171.
204: Smaletz O, Galsky M, Scher HI, DeLaCruz A, Slovin SF, Morris MJ,
Solit DB, Davar U, Schwartz L, Kelly WK. Pilot study of epothilone B
analog (BMS-247550) and estramustine phosphate in patients with
progressive metastatic prostate cancer following castration. Ann Oncol.
2003 Oct;14(10):1518-24. PubMed PMID: 14504052.
205: Kim JC, Kim JS, Saha D, Cao Q, Shyr Y, Choy H. Potential
radiation-sensitizing effect of semisynthetic epothilone B in human lung
cancer cells. Radiother Oncol. 2003 Sep;68(3):305-13. PubMed PMID:
13129641.
206: Nagano S, Li H, Shimizu H, Nishida C, Ogura H, Ortiz de Montellano
PR, Poulos TL. Crystal structures of epothilone D-bound, epothilone
B-bound, and substrate-free forms of cytochrome P450epoK. J Biol Chem.
2003 Nov 7;278(45):44886-93. Epub 2003 Aug 21. PubMed PMID: 12933799.
207: Nicolaou KC, Sasmal PK, Rassias G, Reddy MV, Altmann KH, Wartmann
M, O'Brate A, Giannakakou P. Design, synthesis, and biological
properties of highly potent epothilone B analogues. Angew Chem Int Ed
Engl. 2003 Aug 4;42(30):3515-20. PubMed PMID: 12900969.
208: Agrawal M, Edgerly M, Fojo T, Kotz H. Treatment of recurrent
cervical adenocarcinoma with BMS-247550, an epothilone B analog. Gynecol
Oncol. 2003 Jul;90(1):96-9. PubMed PMID: 12821348.
209: Rothermel J, Wartmann M, Chen T, Hohneker J. EPO906 (epothilone B):
a promising novel microtubule stabilizer. Semin Oncol. 2003 Jun;30(3
Suppl 6):51-5. Review. PubMed PMID: 12802795.
210: Yoshimura F, Rivkin A, Gabarda AE, Chou TC, Dong H, Sukenick G,
Morel FF, Taylor RE, Danishefsky SJ. Synthesis and conformational
analysis of (E)-9,10-dehydroepothilone B: a suggestive link between the
chemistry and biology of epothilones. Angew Chem Int Ed Engl. 2003 Jun
6;42(22):2518-21. PubMed PMID: 12800175.
211: Woltering EA, Lewis JM, Maxwell PJ 4th, Frey DJ, Wang YZ, Rothermel
J, Anthony CT, Balster DA, O'Leary JP, Harrison LH. Development of a
novel in vitro human tissue-based angiogenesis assay to evaluate the
effect of antiangiogenic drugs. Ann Surg. 2003 Jun;237(6):790-8;
discussion 798-800. PubMed PMID: 12796575; PubMed Central PMCID:
PMC1514676.
212: Abraham J, Agrawal M, Bakke S, Rutt A, Edgerly M, Balis FM,
Widemann B, Davis L, Damle B, Sonnichsen D, Lebwohl D, Bates S, Kotz H,
Fojo T. Phase I trial and pharmacokinetic study of BMS-247550, an
epothilone B analog, administered intravenously on a daily schedule for
five days. J Clin Oncol. 2003 May 1;21(9):1866-73. PubMed PMID:
12721265.
213: Walsh CT, O'Connor SE, Schneider TL. Polyketide-nonribosomal
peptide epothilone antitumor agents: the EpoA, B, C subunits. J Ind
Microbiol Biotechnol. 2003 Aug;30(8):448-55. Epub 2003 Apr 18. Review.
PubMed PMID: 12707798.
214: Petrache I, Birukova A, Ramirez SI, Garcia JG, Verin AD. The role
of the microtubules in tumor necrosis factor-alpha-induced endothelial
cell permeability. Am J Respir Cell Mol Biol. 2003 May;28(5):574-81.
PubMed PMID: 12707013.
215: Griffin D, Wittmann S, Guo F, Nimmanapalli R, Bali P, Wang HG,
Bhalla K. Molecular determinants of epothilone B derivative (BMS 247550)
and Apo-2L/TRAIL-induced apoptosis of human ovarian cancer cells.
Gynecol Oncol. 2003 Apr;89(1):37-47. PubMed PMID: 12694652.
216: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials.
Methods Find Exp Clin Pharmacol. 2003 Jan-Feb;25(1):53-76. PubMed PMID:
12690708.
217: Ahmed A, Hoegenauer EK, Enev VS, Hanbauer M, Kaehlig H, Ohler E,
Mulzer J. Total synthesis of the microtubule stabilizing antitumor agent
laulimalide and some nonnatural analogues: the power of Sharpless'
asymmetric epoxidation. J Org Chem. 2003 Apr 18;68(8):3026-42. PubMed
PMID: 12688769.
218: Wartmann M, Altmann KH. The biology and medicinal chemistry of
epothilones. Curr Med Chem Anticancer Agents. 2002 Jan;2(1):123-48.
Review. PubMed PMID: 12678754.
219: Tang L, Qiu RG, Li Y, Katz L. Generation of novel epothilone
analogs with cytotoxic activity by biotransformation. J Antibiot
(Tokyo). 2003 Jan;56(1):16-23. PubMed PMID: 12670045.
220: Bayés M, Rabasseda X, Prous JR. Gateways to clinical trials.
Methods Find Exp Clin Pharmacol. 2002 Nov;24(9):615-43. PubMed PMID:
12616707.
221: Regueiro-Ren A, Leavitt K, Kim SH, Höfle G, Kiffe M, Gougoutas JZ,
DiMarco JD, Lee FY, Fairchild CR, Long BH, Vite GD. SAR and pH stability
of cyano-substituted epothilones. Org Lett. 2002 Oct 31;4(22):3815-8.
PubMed PMID: 12599466.
222: Koch G, Loiseleur O, Fuentes D, Jantsch A, Altmann KH.
Diastereoselective titanium enolate aldol reaction for the total
synthesis of epothilones. Org Lett. 2002 Oct 31;4(22):3811-4. PubMed
PMID: 12599465.
223: Altmann KH. Epothilone B and its analogs - a new family of
anticancer agents. Mini Rev Med Chem. 2003 Mar;3(2):149-58. Review.
PubMed PMID: 12570848.
224: Wittmann S, Bali P, Donapaty S, Nimmanapalli R, Guo F, Yamaguchi H,
Huang M, Jove R, Wang HG, Bhalla K. Flavopiridol down-regulates
antiapoptotic proteins and sensitizes human breast cancer cells to
epothilone B-induced apoptosis. Cancer Res. 2003 Jan 1;63(1):93-9.
PubMed PMID: 12517783.
225: Taylor RE, Chen Y, Beatty A, Myles DC, Zhou Y.
Conformation-activity relationships in polyketide natural products: a
new perspective on the rational design of epothilone analogues. J Am
Chem Soc. 2003 Jan 8;125(1):26-7. PubMed PMID: 12515494.
226: Bocci G, Nicolaou KC, Kerbel RS. Protracted low-dose effects on
human endothelial cell proliferation and survival in vitro reveal a
selective antiangiogenic window for various chemotherapeutic drugs.
Cancer Res. 2002 Dec 1;62(23):6938-43. PubMed PMID: 12460910.
227: Rivkin A, Biswas K, Chou TC, Danishefsky SJ. On the introduction of
a trifluoromethyl substituent in the epothilone setting: chemical issues
related to ring forming olefin metathesis and earliest biological
findings. Org Lett. 2002 Nov 14;4(23):4081-4. PubMed PMID: 12423091.
228: Julien B, Shah S. Heterologous expression of epothilone
biosynthetic genes in Myxococcus xanthus. Antimicrob Agents Chemother.
2002 Sep;46(9):2772-8. PubMed PMID: 12183227; PubMed Central PMCID:
PMC127399.
229: Altaha R, Fojo T, Reed E, Abraham J. Epothilones: a novel class of
non-taxane microtubule-stabilizing agents. Curr Pharm Des.
2002;8(19):1707-12. Review. PubMed PMID: 12171542.
230: Giannakakou P, Nakano M, Nicolaou KC, O'Brate A, Yu J, Blagosklonny
MV, Greber UF, Fojo T. Enhanced microtubule-dependent trafficking and
p53 nuclear accumulation by suppression of microtubule dynamics. Proc
Natl Acad Sci U S A. 2002 Aug 6;99(16):10855-60. Epub 2002 Jul 26.
PubMed PMID: 12145320; PubMed Central PMCID: PMC125062.
231: Bröker LE, Huisman C, Ferreira CG, Rodriguez JA, Kruyt FA, Giaccone
G. Late activation of apoptotic pathways plays a negligible role in
mediating the cytotoxic effects of discodermolide and epothilone B in
non-small cell lung cancer cells. Cancer Res. 2002 Jul 15;62(14):4081-8.
PubMed PMID: 12124345.
232: McDaid HM, Mani S, Shen HJ, Muggia F, Sonnichsen D, Horwitz SB.
Validation of the pharmacodynamics of BMS-247550, an analogue of
epothilone B, during a phase I clinical study. Clin Cancer Res. 2002
Jul;8(7):2035-43. PubMed PMID: 12114401.
233: Hood KA, West LM, Rouwé B, Northcote PT, Berridge MV, Wakefield SJ,
Miller JH. Peloruside A, a novel antimitotic agent with paclitaxel-like
microtubule- stabilizing activity. Cancer Res. 2002 Jun
15;62(12):3356-60. PubMed PMID: 12067973.
234: Lavelle F. [New taxanes and epothilone derivatives in clinical
trials]. Bull Cancer. 2002 Apr;89(4):343-50. Review. French. PubMed
PMID: 12016034.
235: Atadja P, Yan-Neale Y, Towbin H, Buxton F, Cohen D. Gene expression
profiling of epothilone A-resistant cells. Novartis Found Symp.
2002;243:119-32; discussion 132-6, 180-5. PubMed PMID: 11990772.
236: O'Connor SE, Chen H, Walsh CT. Enzymatic assembly of epothilones:
the EpoC subunit and reconstitution of the EpoA-ACP/B/C polyketide and
nonribosomal peptide interfaces. Biochemistry. 2002 Apr
30;41(17):5685-94. PubMed PMID: 11969430.
237: Guo F, Nimmanapalli R, Paranawithana S, Wittman S, Griffin D, Bali
P, O'Bryan E, Fumero C, Wang HG, Bhalla K. Ectopic overexpression of
second mitochondria-derived activator of caspases (Smac/DIABLO) or
cotreatment with N-terminus of Smac/DIABLO peptide potentiates
epothilone B derivative-(BMS 247550) and Apo-2L/TRAIL-induced apoptosis.
Blood. 2002 May 1;99(9):3419-26. PubMed PMID: 11964312.
238: Chen JG, Horwitz SB. Differential mitotic responses to
microtubule-stabilizing and -destabilizing drugs. Cancer Res. 2002 Apr
1;62(7):1935-8. PubMed PMID: 11929805.
239: Gerth K, Steinmetz H, Höflel G, Reichenbach H. Studies on the
biosynthesis of epothilones: hydroxylation of Epo A and B to epothilones
E and F. J Antibiot (Tokyo). 2002 Jan;55(1):41-5. PubMed PMID: 11918064.
240: Bode CJ, Gupta ML Jr, Reiff EA, Suprenant KA, Georg GI, Himes RH.
Epothilone and paclitaxel: unexpected differences in promoting the
assembly and stabilization of yeast microtubules. Biochemistry. 2002 Mar
26;41(12):3870-4. Erratum in: Biochemistry 2002 Jun 18;41(24):7858.
PubMed PMID: 11900528.
241: Hertweck C. The multiplasmid approach: a new perspective for
combinatorial biosynthesis. Chembiochem. 2000 Aug 18;1(2):103-6. Review.
PubMed PMID: 11828403.
242: Schinzer D, Altmann KH, Stuhlmann F, Bauer A, Wartmann M. Synthesis
and biological evaluation of aza-epothilones. Chembiochem. 2000 Jul
3;1(1):67-70. PubMed PMID: 11828400.
243: Yamaguchi H, Paranawithana SR, Lee MW, Huang Z, Bhalla KN, Wang HG.
Epothilone B analogue (BMS-247550)-mediated cytotoxicity through
induction of Bax conformational change in human breast cancer cells.
Cancer Res. 2002 Jan 15;62(2):466-71. PubMed PMID: 11809697.
244: Newman RA, Yang J, Raymond M, Finlay V, Cabral F, Vourloumis D,
Stephens LC, Troncoso P, Wu X, Logothetis CJ, Nicolaou KC, Navone NM.
Antitumor efficacy of 26-fluoroepothilone B against human prostate
cancer xenografts. Cancer Chemother Pharmacol. 2001 Oct;48(4):319-26.
PubMed PMID: 11710633.
245: Valluri M, Hindupur RM, Bijoy P, Labadie G, Jung JC, Avery MA.
Total synthesis of epothilone B. Org Lett. 2001 Nov 15;3(23):3607-9.
PubMed PMID: 11700093.
246: White JD, Carter RG, Sundermann KF. A Highly Stereoselective
Synthesis of Epothilone B. J Org Chem. 1999 Feb 5;64(3):684-685. PubMed
PMID: 11674127.
247: Colevas AD, West PJ, Cheson BD. Clinical trials referral resource.
Current clinical trials of epothilone B analog (BMS-247550). Oncology
(Williston Park). 2001 Sep;15(9):1168-9, 1172-5. PubMed PMID: 11589064.
248: Chen H, O'Connor S, Cane DE, Walsh CT. Epothilone biosynthesis:
assembly of the methylthiazolylcarboxy starter unit on the EpoB subunit.
Chem Biol. 2001 Sep;8(9):899-912. PubMed PMID: 11564558.
249: Lichtner RB, Rotgeri A, Bunte T, Buchmann B, Hoffmann J, Schwede W,
Skuballa W, Klar U. Subcellular distribution of epothilones in human
tumor cells. Proc Natl Acad Sci U S A. 2001 Sep 25;98(20):11743-8. Epub
2001 Sep 18. PubMed PMID: 11562452; PubMed Central PMCID: PMC58800.
250: Nicolaou KC, Namoto K, Ritzén A, Ulven T, Shoji M, Li J, D'Amico G,
Liotta D, French CT, Wartmann M, Altmann KH, Giannakakou P. Chemical
synthesis and biological evaluation of cis- and trans-12,13-cyclopropyl
and 12,13-cyclobutyl epothilones and related pyridine side chain
analogues. J Am Chem Soc. 2001 Sep 26;123(38):9313-23. PubMed PMID:
11562214.
251: Bode JW, Carreira EM. Stereoselective syntheses of epothilones A
and B via nitrile oxide cycloadditions and related studies. J Org Chem.
2001 Sep 21;66(19):6410-24. PubMed PMID: 11559194.
252: Seiden MV. Ovarian cancer. Oncologist. 2001;6(4):327-32. Review.
PubMed PMID: 11524550.
253: Crabtree DV, Ojima I, Geng X, Adler AJ. Tubulins in the primate
retina: evidence that xanthophylls may be endogenous ligands for the
paclitaxel-binding site. Bioorg Med Chem. 2001 Aug;9(8):1967-76. PubMed
PMID: 11504633.
254: Hardt IH, Steinmetz H, Gerth K, Sasse F, Reichenbach H, Höfle G.
New natural epothilones from Sorangium cellulosum, strains So ce90/B2
and So ce90/D13: isolation, structure elucidation, and SAR studies. J
Nat Prod. 2001 Jul;64(7):847-56. PubMed PMID: 11473410.
255: Stachel SJ, Biswas K, Danishefsky SJ. The epothilones,
eleutherobins, and related types of molecules. Curr Pharm Des. 2001
Sep;7(13):1277-90. Review. PubMed PMID: 11472267.
256: Bode JW, Carreira EM. Stereoselective syntheses of epothilones A
and B via directed nitrile oxide cycloaddition. J Am Chem Soc. 2001 Apr
18;123(15):3611-2. PubMed PMID: 11472140.
257: Taylor RE, Chen Y. Total synthesis of epothilones B and D. Org Lett.
2001 Jul 12;3(14):2221-4. PubMed PMID: 11440584.
258: Meurer-Grob P, Kasparian J, Wade RH. Microtubule structure at
improved resolution. Biochemistry. 2001 Jul 10;40(27):8000-8. PubMed
PMID: 11434769.
259: Blagosklonny MV. Treatment with inhibitors of caspases, that are
substrates of drug transporters, selectively permits
chemotherapy-induced apoptosis in multidrug-resistant cells but protects
normal cells. Leukemia. 2001 Jun;15(6):936-41. PubMed PMID: 11417480.
260: Martin HJ, Pojarliev P, Kählig H, Mulzer J. The 12,13-diol
cyclization approach for a truly stereocontrolled total synthesis of
epothilone B and the synthesis of a conformationally restrained
analogue. Chemistry. 2001 May 18;7(10):2261-71. PubMed PMID: 11411998.
261: Stachel SJ, Lee CB, Spassova M, Chappell MD, Bornmann WG,
Danishefsky SJ, Chou TC, Guan Y. On the interactivity of complex
synthesis and tumor pharmacology in the drug discovery process: total
synthesis and comparative in vivo evaluations of the 15-aza epothilones.
J Org Chem. 2001 Jun 15;66(12):4369-78. PubMed PMID: 11397179.
262: White JD, Carter RG, Sundermann KF, Wartmann M. Total synthesis of
epothilone B, epothilone D, and cis- and trans-9,10-dehydroepothilone D.
J Am Chem Soc. 2001 Jun 13;123(23):5407-13. Erratum in: J Am Chem Soc.
2003 M ar 12;125(10):3190.. PubMed PMID: 11389619.
263: Lee FY, Borzilleri R, Fairchild CR, Kim SH, Long BH, Reventos-Suarez
C, Vite GD, Rose WC, Kramer RA. BMS-247550: a novel epothilone analog
with a mode of action similar to paclitaxel but possessing superior
antitumor efficacy. Clin Cancer Res. 2001 May;7(5):1429-37. PubMed PMID:
11350914.
264: Sinha SC, Sun J, Miller GP, Wartmann M, Lerner RA. Catalytic
antibody route to the naturally occurring epothilones: total synthesis
of epothilones A-F. Chemistry. 2001 Apr 17;7(8):1691-702. PubMed PMID:
11349910.
265: Gerth K, Steinmetz H, Höfle G, Reichenbach H. Studies on the
biosynthesis of epothilones: the PKS and Epothilone C/D monooxygenase. J
Antibiot (Tokyo). 2001 Feb;54(2):144-8. PubMed PMID: 11302486.
266: Blum W, Aichholz R, Ramstein P, Kühnöl J, Brüggen J, O'Reilly T,
Flörsheimer A. In vivo metabolism of epothilone B in tumor-bearing nude
mice: identification of three new epothilone B metabolites by capillary
high-pressure liquid chromatography/mass spectrometry/tandem mass
spectrometry. Rapid Commun Mass Spectrom. 2001;15(1):41-9. PubMed PMID:
11135423.
267: Altmann KH, Bold G, Caravatti G, Flörsheimer A, Guagnano V,
Wartmann M. Synthesis and biological evaluation of highly potent
analogues of epothilones B and D. Bioorg Med Chem Lett. 2000 Dec
18;10(24):2765-8. PubMed PMID: 11133086.
268: Mulzer J, Mantoulidis A, Ohler E. Total syntheses of epothilones B
and D. J Org Chem. 2000 Nov 3;65(22):7456-67. PubMed PMID: 11076603.
269: Nicolaou KC, Scarpelli R, Bollbuck B, Werschkun B, Pereira MM,
Wartmann M, Altmann KH, Zaharevitz D, Gussio R, Giannakakou P. Chemical
synthesis and biological properties of pyridine epothilones. Chem Biol.
2000 Aug;7(8):593-9. PubMed PMID: 11048950.
270: Nicolaou KC, Hepworth D, King NP, Finlay MR, Scarpelli R, Pereira
MM, Bollbuck B, Bigot A, Werschkun B, Winssinger N. Total synthesis of
16-desmethylepothilone B, epothilone B10, epothilone F, and related side
chain modified epothilone B analogues. Chemistry. 2000 Aug
4;6(15):2783-800. PubMed PMID: 10985727.
271: Stachel SJ, Chappell MD, Lee CB, Danishefsky SJ, Chou TC, He L,
Horwitz SB. On the total synthesis and preliminary biological
evaluations of 15(R) and 15(S) aza-dEpoB: a Mitsunobu inversion at C15
in pre-epothilone fragments. Org Lett. 2000 Jun 1;2(11):1637-9. PubMed
PMID: 10841498.
272: Chappell MD, Stachel SJ, Lee CB, Danishefsky SJ. En route to a
plant scale synthesis of the promising antitumor agent
12,13-desoxyepothilone B. Org Lett. 2000 Jun 1;2(11):1633-6. PubMed
PMID: 10841497.
273: Johnson J, Kim SH, Bifano M, DiMarco J, Fairchild C, Gougoutas J,
Lee F, Long B, Tokarski J, Vite G. Synthesis, structure proof, and
biological activity of epothilone cyclopropanes. Org Lett. 2000 Jun
1;2(11):1537-40. PubMed PMID: 10841473.
274: Julien B, Shah S, Ziermann R, Goldman R, Katz L, Khosla C.
Isolation and characterization of the epothilone biosynthetic gene
cluster from Sorangium cellulosum. Gene. 2000 May 16;249(1-2):153-60.
PubMed PMID: 10831849.
275: White JD, Sundermann KF, Carter RG. Improved synthesis of
epothilone B employing alkylation of an alkyne for assembly of subunits.
Org Lett. 1999 Nov 4;1(9):1431-4. PubMed PMID: 10825989.
276: Wang M, Xia X, Kim Y, Hwang D, Jansen JM, Botta M, Liotta DC,
Snyder JP. A unified and quantitative receptor model for the microtubule
binding of paclitaxel and epothilone. Org Lett. 1999 Jul 15;1(1):43-6.
PubMed PMID: 10822530.
277: Martello LA, McDaid HM, Regl DL, Yang CP, Meng D, Pettus TR,
Kaufman MD, Arimoto H, Danishefsky SJ, Smith AB 3rd, Horwitz SB. Taxol
and discodermolide represent a synergistic drug combination in human
carcinoma cell lines. Clin Cancer Res. 2000 May;6(5):1978-87. PubMed
PMID: 10815923.
278: Altmann KH, Wartmann M, O'Reilly T. Epothilones and related
structures--a new class of microtubule inhibitors with potent in vivo
antitumor activity. Biochim Biophys Acta. 2000 May 17;1470(3):M79-91.
Review. PubMed PMID: 10799747.
279: Santi DV, Siani MA, Julien B, Kupfer D, Roe B. An approach for
obtaining perfect hybridization probes for unknown polyketide synthase
genes: a search for the epothilone gene cluster. Gene. 2000 Apr
18;247(1-2):97-102. PubMed PMID: 10773448.
280: Giannakakou P, Gussio R, Nogales E, Downing KH, Zaharevitz D,
Bollbuck B, Poy G, Sackett D, Nicolaou KC, Fojo T. A common
pharmacophore for epothilone and taxanes: molecular basis for drug
resistance conferred by tubulin mutations in human cancer cells. Proc
Natl Acad Sci U S A. 2000 Mar 14;97(6):2904-9. PubMed PMID: 10688884;
PubMed Central PMCID: PMC16028.
281: Martin HJ, Drescher M, Mulzer J. How Stable Are Epoxides? A Novel
Synthesis of Epothilone B. Angew Chem Int Ed Engl. 2000
Feb;39(3):581-583. PubMed PMID: 10671265.
282: Molnár I, Schupp T, Ono M, Zirkle R, Milnamow M, Nowak-Thompson B,
Engel N, Toupet C, Stratmann A, Cyr DD, Gorlach J, Mayo JM, Hu A, Goff
S, Schmid J, Ligon JM. The biosynthetic gene cluster for the
microtubule-stabilizing agents epothilones A and B from Sorangium
cellulosum So ce90. Chem Biol. 2000 Feb;7(2):97-109. PubMed PMID:
10662695.
283: Tang L, Shah S, Chung L, Carney J, Katz L, Khosla C, Julien B.
Cloning and heterologous expression of the epothilone gene cluster.
Science. 2000 Jan 28;287(5453):640-2. PubMed PMID: 10649995.
284: Nicolaou KC, King NP, Finlay MR, He Y, Roschangar F, Vourloumis D,
Vallberg H, Sarabia F, Ninkovic S, Hepworth D. Total synthesis of
epothilone E and related side-chain modified analogues via a Stille
coupling based strategy. Bioorg Med Chem. 1999 May;7(5):665-97. PubMed
PMID: 10400321.
285: Ojima I, Chakravarty S, Inoue T, Lin S, He L, Horwitz SB, Kuduk SD,
Danishefsky SJ. A common pharmacophore for cytotoxic natural products
that stabilize microtubules. Proc Natl Acad Sci U S A. 1999 Apr
13;96(8):4256-61. PubMed PMID: 10200249; PubMed Central PMCID: PMC16319.
286: Sefkow M, Kiffe M, Höfle G. Derivatization of the C12-C13
functional groups of epothilones A, B and C. Bioorg Med Chem Lett. 1998
Nov 3;8(21):3031-6. PubMed PMID: 9873670.
287: Yang CP, Galbiati F, Volonte D, Horwitz SB, Lisanti MP.
Upregulation of caveolin-1 and caveolae organelles in Taxol-resistant
A549 cells. FEBS Lett. 1998 Nov 20;439(3):368-72. PubMed PMID: 9845355.
288: Chou TC, Zhang XG, Balog A, Su DS, Meng D, Savin K, Bertino JR,
Danishefsky SJ. Desoxyepothilone B: an efficacious microtubule-targeted
antitumor agent with a promising in vivo profile relative to epothilone
B. Proc Natl Acad Sci U S A. 1998 Aug 4;95(16):9642-7. PubMed PMID:
9689134; PubMed Central PMCID: PMC21392.
289: Muhlradt PF, Sasse F. Epothilone B stabilizes microtubuli of
macrophages like taxol without showing taxol-like endotoxin activity.
Cancer Res. 1997 Aug 15;57(16):3344-6. PubMed PMID: 9269992.
290: Giannakakou P, Sackett DL, Kang YK, Zhan Z, Buters JT, Fojo T,
Poruchynsky MS. Paclitaxel-resistant human ovarian cancer cells have
mutant beta-tubulins that exhibit impaired paclitaxel-driven
polymerization. J Biol Chem. 1997 Jul 4;272(27):17118-25. PubMed PMID:
9202030.
291: Nicolaou KC, Winssinger N, Pastor J, Ninkovic S, Sarabia F, He Y,
Vourloumis D, Yang Z, Li T, Giannakakou P, Hamel E. Synthesis of
epothilones A and B in solid and solution phase. Nature. 1997 May
15;387(6630):268-72. Erratum in: Nature 1997 Nov 6;390(6655):100. PubMed
PMID: 9153390.
292: Cowden CJ, Paterson I. Synthetic chemistry. Cancer drugs better
than taxol? Nature. 1997 May 15;387(6630):238-9. PubMed PMID: 9153384.
293: Kowalski RJ, Giannakakou P, Hamel E. Activities of the
microtubule-stabilizing agents epothilones A and B with purified tubulin
and in cells resistant to paclitaxel (Taxol(R)). J Biol Chem. 1997 Jan
24;272(4):2534-41. PubMed PMID: 8999970.
294: Gerth K, Bedorf N, Höfle G, Irschik H, Reichenbach H. Epothilons A
and B: antifungal and cytotoxic compounds from Sorangium cellulosum (Myxobacteria).
Production, physico-chemical and biological properties. J Antibiot
(Tokyo). 1996 Jun;49(6):560-3. PubMed PMID: 8698639.
295: Bollag DM, McQueney PA, Zhu J, Hensens O, Koupal L, Liesch J, Goetz
M, Lazarides E, Woods CM. Epothilones, a new class of
microtubule-stabilizing agents with a taxol-like mechanism of action.
Cancer Res. 1995 Jun 1;55(11):2325-33. PubMed PMID: 7757983.
|
Contact MedKoo:
Email:
sales@medkoo.com
(Keyword; CAS#; MedKoo code#)
|