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MedKoo product information:
Tretazicar
Description of Tretazicar: Tretazicar (CB1954) is a dinitrobenzamide prodrug
that is converted in the presence of the enzyme NQO2 and co-substrate
caricotamide (EP-0152R) (EP) into a potent cytotoxic bifunctional alkylating agent.
Descritpion of caricotamide/tretazicar: caricotamide/tretazicar
is a combination therapy consisting of the prodrug tretazicar and the
enzyme co-substrate caricotamide with potential antineoplastic activity.
In the presence of separately and simultaneously administered
caricotamide, tretazicar is converted to the short-lived cytotoxic DNA
cross-linking agent dinitrobenzamide by NAD(P)H quinine oxidoreductase 2
(NQO2), resulting in the inhibition of DNA replication and the induction
of apoptosis. NQO2 has been found to be elevated in certain cancers such
as hepatocellular carcinoma (HCC). Check for
active clinical trials or
closed clinical trials using this agent. (NCI
Thesaurus).
Current developer:
Protherics PLC.
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MedKoo Code#: 202980
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Name:
Tretazicar
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CAS#:
21919-05-1
Synonym: CB1954;Lopac-C-2235;Lopac0_000200;2,4-Dinitroethyleneiminobenzamide;C2235_SIGMA;CB
1954;5-Aziridino-2,4-dinitrobenzamide;CCRIS
1631;2,4-Dinitro-5-ethyleneiminobenzamide;5-(1-Aziridinyl)-2,4-dinitrobenzamide;5-Aziridinyl-2,4-dinitrobenzamide;
Prolarix™。
IUPAC/Chemical name:
5-(aziridin-1-yl)-2,4-dinitrobenzamide
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Chemical structure: |
Theoretical analysis
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MedKoo Code#: 202980
Name: Tretazicar
CAS#: 21919-05-1
Chemical Formula: C9H8N4O5
Exact Mass: 252.04947
Molecular Weight: 252.18
Elemental Analysis: C, 42.86; H, 3.20; N,
22.22; O, 31.72
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Availability and price:
This agent is not in stock, which may be available through custom synthesis.
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.
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Quality control
data:
Product will be shipped with
supporting analytical data.
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Information about this agent
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1: Dachs GU, Hunt MA, Syddall S, Singleton DC,
Patterson AV. Bystander or no bystander for gene directed enzyme prodrug
therapy. Molecules. 2009 Nov 10;14(11):4517-45. Review. PubMed PMID:
19924084.
2: Prosser GA, Copp JN, Syddall SP, Williams EM, Smaill JB, Wilson WR,
Patterson AV, Ackerley DF. Discovery and evaluation of Escherichia coli
nitroreductases that activate the anti-cancer prodrug CB1954. Biochem
Pharmacol. 2010 Mar 1;79(5):678-87. Epub 2009 Oct 21. PubMed PMID:
19852945.
3: Grohmann M, Paulmann N, Fleischhauer S, Vowinckel J, Priller J,
Walther DJ. A mammalianized synthetic nitroreductase gene for high-level
expression. BMC Cancer. 2009 Aug 27;9:301. PubMed PMID: 19712451.
4: Jarrom D, Jaberipour M, Guise CP, Daff S, White SA, Searle PF, Hyde
EI. Steady-state and stopped-flow kinetic studies of three Escherichia
coli NfsB mutants with enhanced activity for the prodrug CB1954.
Biochemistry. 2009 Aug 18;48(32):7665-72. PubMed PMID: 19580253.
5: Braidwood L, Dunn PD, Hardy S, Evans TR, Brown SM. Antitumor activity
of a selectively replication competent herpes simplex virus (HSV) with
enzyme prodrug therapy. Anticancer Res. 2009 Jun;29(6):2159-66. PubMed
PMID: 19528476.
6: Vass SO, Jarrom D, Wilson WR, Hyde EI, Searle PF. E. coli NfsA: an
alternative nitroreductase for prodrug activation gene therapy in
combination with CB1954. Br J Cancer. 2009 Jun 16;100(12):1903-11. Epub
2009 May 19. PubMed PMID: 19455141; PubMed Central PMCID: PMC2690450.
7: Patel P, Young JG, Mautner V, Ashdown D, Bonney S, Pineda RG, Collins
SI, Searle PF, Hull D, Peers E, Chester J, Wallace DM, Doherty A, Leung
H, Young LS, James ND. A phase I/II clinical trial in localized prostate
cancer of an adenovirus expressing nitroreductase with CB1954
[correction of CB1984]. Mol Ther. 2009 Jul;17(7):1292-9. Epub 2009 Apr
14. Erratum in: Mol Ther. 2009 Jul;17(7):1302. PubMed PMID: 19367257;
PubMed Central PMCID: PMC2835198.
8: Christofferson A, Wilkie J. Mechanism of CB1954 reduction by
Escherichia coli nitroreductase. Biochem Soc Trans. 2009 Apr;37(Pt
2):413-8. Review. PubMed PMID: 19290872.
9: Mitchell DJ, Minchin RF. E. coli nitroreductase/CB1954 gene-directed
enzyme prodrug therapy: role of arylamine N-acetlytransferase 2. Cancer
Gene Ther. 2008 Nov;15(11):758-64. Epub 2008 Jul 4. PubMed PMID:
18600257.
10: White CL, Menghistu T, Twigger KR, Searle PF, Bhide SA, Vile RG,
Melcher AA, Pandha HS, Harrington KJ. Escherichia coli nitroreductase
plus CB1954 enhances the effect of radiotherapy in vitro and in vivo.
Gene Ther. 2008 Mar;15(6):424-33. Epub 2007 Dec 13. PubMed PMID:
18079753.
11: Ludwig C, Michiels PJ, Wu X, Kavanagh KL, Pilka E, Jansson A,
Oppermann U, Günther UL. SALMON: solvent accessibility, ligand binding,
and mapping of ligand orientation by NMR spectroscopy. J Med Chem. 2008
Jan 10;51(1):1-3. Epub 2007 Dec 7. PubMed PMID: 18062662.
12: Singleton DC, Li D, Bai SY, Syddall SP, Smaill JB, Shen Y, Denny WA,
Wilson WR, Patterson AV. The nitroreductase prodrug SN 28343 enhances
the potency of systemically administered armed oncolytic adenovirus
ONYX-411(NTR). Cancer Gene Ther. 2007 Dec;14(12):953-67. Epub 2007 Nov
2. PubMed PMID: 17975564.
13: Young JG, Green NK, Mautner V, Searle PF, Young LS, James ND.
Combining gene and immunotherapy for prostate cancer. Prostate Cancer
Prostatic Dis. 2008;11(2):187-93. Epub 2007 Aug 28. PubMed PMID:
17726452.
14: Race PR, Lovering AL, White SA, Grove JI, Searle PF, Wrighton CW,
Hyde EI. Kinetic and structural characterisation of Escherichia coli
nitroreductase mutants showing improved efficacy for the prodrug
substrate CB1954. J Mol Biol. 2007 Apr 27;368(2):481-92. Epub 2007 Feb
11. PubMed PMID: 17350040.
15: Jamieson D, Wilson K, Pridgeon S, Margetts JP, Edmondson RJ, Leung
HY, Knox R, Boddy AV. NAD(P)H:quinone oxidoreductase 1 and nrh:quinone
oxidoreductase 2 activity and expression in bladder and ovarian cancer
and lower NRH:quinone oxidoreductase 2 activity associated with an NQO2
exon 3 single-nucleotide polymorphism. Clin Cancer Res. 2007 Mar
1;13(5):1584-90. PubMed PMID: 17332305.
16: Guise CP, Grove JI, Hyde EI, Searle PF. Direct positive selection
for improved nitroreductase variants using SOS triggering of
bacteriophage lambda lytic cycle. Gene Ther. 2007 Apr;14(8):690-8. Epub
2007 Feb 15. PubMed PMID: 17301844.
17: Jamieson D, Tung AT, Knox RJ, Boddy AV. Reduction of mitomycin C is
catalysed by human recombinant NRH:quinone oxidoreductase 2 using
reduced nicotinamide adenine dinucleotide as an electron donating
co-factor. Br J Cancer. 2006 Nov 6;95(9):1229-33. Epub 2006 Oct 10.
PubMed PMID: 17031400; PubMed Central PMCID: PMC2360572.
18: Theys J, Pennington O, Dubois L, Anlezark G, Vaughan T, Mengesha A,
Landuyt W, Anné J, Burke PJ, Dûrre P, Wouters BG, Minton NP, Lambin P.
Repeated cycles of Clostridium-directed enzyme prodrug therapy result in
sustained antitumour effects in vivo. Br J Cancer. 2006 Nov
6;95(9):1212-9. Epub 2006 Oct 3. PubMed PMID: 17024128; PubMed Central
PMCID: PMC2360559.
19: Berne C, Betancor L, Luckarift HR, Spain JC. Application of a
microfluidic reactor for screening cancer prodrug activation using
silica-immobilized nitrobenzene nitroreductase. Biomacromolecules. 2006
Sep;7(9):2631-6. PubMed PMID: 16961327.
20: Boyle RG, Travers S. Hypoxia: targeting the tumour. Anticancer
Agents Med Chem. 2006 Jul;6(4):281-6. Review. PubMed PMID: 16842231.
21: Barak Y, Thorne SH, Ackerley DF, Lynch SV, Contag CH, Matin A. New
enzyme for reductive cancer chemotherapy, YieF, and its improvement by
directed evolution. Mol Cancer Ther. 2006 Jan;5(1):97-103. PubMed PMID:
16432167.
22: Benouchan M, Do Nascimento F, Perret GY, Colombo BM. Delivery of the
bacterial nitroreductase gene into endothelial cells prolongs the
survival of tumour-bearing mice by bystander mechanisms. Int J Oncol.
2006 Feb;28(2):457-62. PubMed PMID: 16391801.
23: Lukashev AN, Fuerer C, Chen MJ, Searle P, Iggo R. Late expression of
nitroreductase in an oncolytic adenovirus sensitizes colon cancer cells
to the prodrug CB1954. Hum Gene Ther. 2005 Dec;16(12):1473-83. PubMed
PMID: 16390278.
24: Fu Y, Buryanovskyy L, Zhang Z. Crystal structure of quinone
reductase 2 in complex with cancer prodrug CB1954. Biochem Biophys Res
Commun. 2005 Oct 14;336(1):332-8. PubMed PMID: 16129418.
25: Lipinski KS, Pelech S, Mountain A, Irvine AS, Kraaij R, Bangma CH,
Mills KH, Todryk SM. Nitroreductase-based therapy of prostate cancer,
enhanced by raising expression of heat shock protein 70, acts through
increased anti-tumour immunity. Cancer Immunol Immunother. 2006
Mar;55(3):347-54. Epub 2005 Jun 17. PubMed PMID: 16075195.
26: Palmer DH, Chen MJ, Searle PF, Kerr DJ, Young LS. Inhibition of NF-kappaB
enhances the cytotoxicity of virus-directed enzyme prodrug therapy and
oncolytic adenovirus cancer gene therapy. Gene Ther. 2005
Aug;12(15):1187-97. PubMed PMID: 15800660.
27: Djeha HA, Todryk SM, Pelech S, Wrighton CJ, Irvine AS, Mountain A,
Lipinski KS. Antitumor immune responses mediated by adenoviral GDEPT
using nitroreductase/CB1954 is enhanced by high-level coexpression of
heat shock protein 70. Cancer Gene Ther. 2005 Jun;12(6):560-71. PubMed
PMID: 15665820.
28: Searle PF, Chen MJ, Hu L, Race PR, Lovering AL, Grove JI, Guise C,
Jaberipour M, James ND, Mautner V, Young LS, Kerr DJ, Mountain A, White
SA, Hyde EI. Nitroreductase: a prodrug-activating enzyme for cancer gene
therapy. Clin Exp Pharmacol Physiol. 2004 Nov;31(11):811-6. Review.
PubMed PMID: 15566399.
29: Chen MJ, Green NK, Reynolds GM, Flavell JR, Mautner V, Kerr DJ,
Young LS, Searle PF. Enhanced efficacy of Escherichia coli
nitroreductase/CB1954 prodrug activation gene therapy using an
E1B-55K-deleted oncolytic adenovirus vector. Gene Ther. 2004
Jul;11(14):1126-36. PubMed PMID: 15164095.
30: Palmer DH, Mautner V, Mirza D, Oliff S, Gerritsen W, van der Sijp
JR, Hubscher S, Reynolds G, Bonney S, Rajaratnam R, Hull D, Horne M,
Ellis J, Mountain A, Hill S, Harris PA, Searle PF, Young LS, James ND,
Kerr DJ. Virus-directed enzyme prodrug therapy: intratumoral
administration of a replication-deficient adenovirus encoding
nitroreductase to patients with resectable liver cancer. J Clin Oncol.
2004 May 1;22(9):1546-52. Epub 2004 Mar 29. PubMed PMID: 15051757.
31: Sausville EA. Genes in the service of therapeutic index: progress
for virus-directed enzyme prodrug therapy. J Clin Oncol. 2004 May
1;22(9):1535-7. Epub 2004 Mar 29. PubMed PMID: 15051753.
32: Minton NP. Clostridia in cancer therapy. Nat Rev Microbiol. 2003
Dec;1(3):237-42. Review. PubMed PMID: 15035028.
33: Helsby NA, Ferry DM, Patterson AV, Pullen SM, Wilson WR. 2-Amino
metabolites are key mediators of CB 1954 and SN 23862 bystander effects
in nitroreductase GDEPT. Br J Cancer. 2004 Mar 8;90(5):1084-92. PubMed
PMID: 14997211; PubMed Central PMCID: PMC2409616.
34: Green NK, Kerr DJ, Mautner V, Harris PA, Searle PF. The
nitroreductase/CB1954 enzyme-prodrug system. Methods Mol Med.
2004;90:459-77. PubMed PMID: 14657579.
35: Schepelmann S, Spooner R, Friedlos F, Marais R. Methods to improve
efficacy in suicide gene therapy approaches: targeting prodrug-activating
enzymes carboxypeptidase G2 and nitroreductase to different subcellular
compartments. Methods Mol Med. 2004;90:279-301. PubMed PMID: 14657569.
36: Benouchan M, Do Nascimento F, Sebbah-Louriki M, Salzmann JL, Crépin
M, Perret GY, Colombo BM. Bystander cell killing spreading from
endothelial to tumor cells in a three-dimensional multicellular nodule
model after Escherichia coli nitroreductase gene delivery. Biochem
Biophys Res Commun. 2003 Nov 28;311(4):822-8. PubMed PMID: 14623255.
37: Knox RJ, Burke PJ, Chen S, Kerr DJ. CB 1954: from the Walker tumor
to NQO2 and VDEPT. Curr Pharm Des. 2003;9(26):2091-104. Review. PubMed
PMID: 14529407.
38: Grove JI, Lovering AL, Guise C, Race PR, Wrighton CJ, White SA, Hyde
EI, Searle PF. Generation of Escherichia coli nitroreductase mutants
conferring improved cell sensitization to the prodrug CB1954. Cancer
Res. 2003 Sep 1;63(17):5532-7. PubMed PMID: 14500391.
39: Johansson E, Parkinson GN, Denny WA, Neidle S. Studies on the
nitroreductase prodrug-activating system. Crystal structures of
complexes with the inhibitor dicoumarol and dinitrobenzamide prodrugs
and of the enzyme active form. J Med Chem. 2003 Sep 11;46(19):4009-20.
PubMed PMID: 12954054.
40: Palmer DH, Milner AE, Kerr DJ, Young LS. Mechanism of cell death
induced by the novel enzyme-prodrug combination, nitroreductase/CB1954,
and identification of synergism with 5-fluorouracil. Br J Cancer. 2003
Sep 1;89(5):944-50. PubMed PMID: 12942130; PubMed Central PMCID:
PMC2394473.
41: Helsby NA, Wheeler SJ, Pruijn FB, Palmer BD, Yang S, Denny WA,
Wilson WR. Effect of nitroreduction on the alkylating reactivity and
cytotoxicity of the 2,4-dinitrobenzamide-5-aziridine CB 1954 and the
corresponding nitrogen mustard SN 23862: distinct mechanisms of
bioreductive activation. Chem Res Toxicol. 2003 Apr;16(4):469-78. PubMed
PMID: 12703963.
42: Sato N, Masai M. [The trends in new drugs for the prostate cancer].
Nippon Rinsho. 2002 Dec;60 Suppl 11:278-83. Review. Japanese. PubMed
PMID: 12599585.
43: Bilsland AE, Anderson CJ, Fletcher-Monaghan AJ, McGregor F, Evans
TR, Ganly I, Knox RJ, Plumb JA, Keith WN. Selective ablation of human
cancer cells by telomerase-specific adenoviral suicide gene therapy
vectors expressing bacterial nitroreductase. Oncogene. 2003 Jan
23;22(3):370-80. PubMed PMID: 12545158.
44: Green NK, McNeish IA, Doshi R, Searle PF, Kerr DJ, Young LS. Immune
enhancement of nitroreductase-induced cytotoxicity: studies using a
bicistronic adenovirus vector. Int J Cancer. 2003 Mar 10;104(1):104-12.
PubMed PMID: 12532426.
45: Hull D, Chester M. Gene therapy trials: a patient pathway. Nurs
Stand. 2002 Oct 2-8;17(3):39-42. PubMed PMID: 12382486.
46: Denny WA. Nitroreductase-based GDEPT. Curr Pharm Des.
2002;8(15):1349-61. Review. PubMed PMID: 12052212.
47: Yazawa K, Fisher WE, Brunicardi FC. Current progress in suicide gene
therapy for cancer. World J Surg. 2002 Jul;26(7):783-9. Epub 2002 Apr
15. Review. PubMed PMID: 11948367.
48: Shibata T, Giaccia AJ, Brown JM. Hypoxia-inducible regulation of a
prodrug-activating enzyme for tumor-specific gene therapy. Neoplasia.
2002 Jan-Feb;4(1):40-8. PubMed PMID: 11922390; PubMed Central PMCID:
PMC1503309.
49: Wilson WR, Pullen SM, Hogg A, Helsby NA, Hicks KO, Denny WA.
Quantitation of bystander effects in nitroreductase suicide gene therapy
using three-dimensional cell cultures. Cancer Res. 2002 Mar
1;62(5):1425-32. PubMed PMID: 11888915.
50: Cui W, Gusterson BA, Clark AJ. Inhibition of myc-dependent breast
tumor formation in transgenic mice. Breast Cancer Res Treat. 2002
Jan;71(1):9-20. PubMed PMID: 11859878.
51: Plumb JA, Bilsland A, Kakani R, Zhao J, Glasspool RM, Knox RJ, Evans
TR, Keith WN. Telomerase-specific suicide gene therapy vectors
expressing bacterial nitroreductase sensitize human cancer cells to the
pro-drug CB1954. Oncogene. 2001 Nov 22;20(53):7797-803. PubMed PMID:
11753658.
52: Lipinski KS, Djeha AH, Ismail T, Mountain A, Young LS, Wrighton CJ.
High-level, beta-catenin/TCF-dependent transgene expression in secondary
colorectal cancer tissue. Mol Ther. 2001 Oct;4(4):365-71. PubMed PMID:
11592840.
53: Chung-Faye G, Palmer D, Anderson D, Clark J, Downes M, Baddeley J,
Hussain S, Murray PI, Searle P, Seymour L, Harris PA, Ferry D, Kerr DJ.
Virus-directed, enzyme prodrug therapy with nitroimidazole reductase: a
phase I and pharmacokinetic study of its prodrug, CB1954. Clin Cancer
Res. 2001 Sep;7(9):2662-8. PubMed PMID: 11555577.
54: Chen MJ, Chung-Faye GA, Searle PF, Young LS, Kerr DJ. Gene therapy
for colorectal cancer: therapeutic potential. BioDrugs.
2001;15(6):357-67. Review. PubMed PMID: 11520247.
55: Spooner RA, Maycroft KA, Paterson H, Friedlos F, Springer CJ, Marais
R. Appropriate subcellular localisation of prodrug-activating enzymes
has important consequences for suicide gene therapy. Int J Cancer. 2001
Jul 1;93(1):123-30. PubMed PMID: 11391631.
56: Wu K, Eng E, Knox R, Chen S. Demonstration of the activation of
prodrug CB 1954 using human DT-diaphorase mutant Q104Y-transfected
MDA-MB-231 cells and mouse xenograft model. Arch Biochem Biophys. 2001
Jan 1;385(1):203-8. PubMed PMID: 11361019.
57: Blackwood L, O'Shaughnessy PJ, Reid SW, Argyle DJ. E. coli
nitroreductase/CB1954: in vitro studies into a potential system for
feline cancer gene therapy. Vet J. 2001 May;161(3):269-79. PubMed PMID:
11352484.
58: Djeha AH, Thomson TA, Leung H, Searle PF, Young LS, Kerr DJ, Harris
PA, Mountain A, Wrighton CJ. Combined adenovirus-mediated nitroreductase
gene delivery and CB1954 treatment: a well-tolerated therapy for
established solid tumors. Mol Ther. 2001 Feb;3(2):233-40. PubMed PMID:
11237680.
59: Kestell P, Pruijn FB, Siim BG, Palmer BD, Wilson WR.
Pharmacokinetics and metabolism of the nitrogen mustard bioreductive
drug 5. Cancer Chemother Pharmacol. 2000;46(5):365-74. PubMed PMID:
11127940.
60: Weedon SJ, Green NK, McNeish IA, Gilligan MG, Mautner V, Wrighton
CJ, Mountain A, Young LS, Kerr DJ, Searle PF. Sensitisation of human
carcinoma cells to the prodrug CB1954 by adenovirus vector-mediated
expression of E. coli nitroreductase. Int J Cancer. 2000 Jun
15;86(6):848-54. PubMed PMID: 10842200.
61: Grove JI, Searle PF, Weedon SJ, Green NK, McNeish IA, Kerr DJ.
Virus-directed enzyme prodrug therapy using CB1954. Anticancer Drug Des.
1999 Dec;14(6):461-72. Review. PubMed PMID: 10834268.
62: Djeha AH, Hulme A, Dexter MT, Mountain A, Young LS, Searle PF, Kerr
DJ, Wrighton CJ. Expression of Escherichia coli B nitroreductase in
established human tumor xenografts in mice results in potent antitumoral
and bystander effects upon systemic administration of the prodrug
CB1954. Cancer Gene Ther. 2000 May;7(5):721-31. PubMed PMID: 10830719.
63: Westphal EM, Ge J, Catchpole JR, Ford M, Kenney SC. The
nitroreductase/CB1954 combination in Epstein-Barr virus-positive B-cell
lines: induction of bystander killing in vitro and in vivo. Cancer Gene
Ther. 2000 Jan;7(1):97-106. PubMed PMID: 10678362.
64: Latham JP, Searle PF, Mautner V, James ND. Prostate-specific antigen
promoter/enhancer driven gene therapy for prostate cancer: construction
and testing of a tissue-specific adenovirus vector. Cancer Res. 2000 Jan
15;60(2):334-41. PubMed PMID: 10667585.
65: Skelly JV, Sanderson MR, Suter DA, Baumann U, Read MA, Gregory DS,
Bennett M, Hobbs SM, Neidle S. Crystal structure of human DT-diaphorase:
a model for interaction with the cytotoxic prodrug
5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954). J Med Chem. 1999 Oct
21;42(21):4325-30. PubMed PMID: 10543876.
66: Anderson D, Ferry DR, Knox RJ, Andrews SJ, Downes AJ, Kerr DJ,
Seymour LW. High-performance liquid chromatographic method for sensitive
determination of the alkylating agent CB1954 in human plasma. J
Chromatogr B Biomed Sci Appl. 1999 Aug 20;731(2):293-8. PubMed PMID:
10510783.
67: Bagshawe KD, Sharma SK, Burke PJ, Melton RG, Knox RJ. Developments
with targeted enzymes in cancer therapy. Curr Opin Immunol. 1999
Oct;11(5):579-83. Review. PubMed PMID: 10508703.
68: Cui W, Gusterson B, Clark AJ. Nitroreductase-mediated cell ablation
is very rapid and mediated by a p53-independent apoptotic pathway. Gene
Ther. 1999 May;6(5):764-70. PubMed PMID: 10505099.
69: McNeish IA, Green NK, Gilligan MG, Ford MJ, Mautner V, Young LS,
Kerr DJ, Searle PF. Virus directed enzyme prodrug therapy for ovarian
and pancreatic cancer using retrovirally delivered E. coli
nitroreductase and CB1954. Gene Ther. 1998 Aug;5(8):1061-9. PubMed PMID:
10326029.
70: Searle PF, Weedon SJ, McNeish IA, Gilligan MG, Ford MJ, Friedlos F,
Springer CJ, Young LS, Kerr DJ. Sensitisation of human ovarian cancer
cells to killing by the prodrug CB1954 following retroviral or
adenoviral transfer of the E. coli nitroreductase gene. Adv Exp Med
Biol. 1998;451:107-13. PubMed PMID: 10026858.
71: Rauth AM, Melo T, Misra V. Bioreductive therapies: an overview of
drugs and their mechanisms of action. Int J Radiat Oncol Biol Phys. 1998
Nov 1;42(4):755-62. PubMed PMID: 9845091.
72: Nishihara E, Nagayama Y, Narimatsu M, Namba H, Watanabe M, Niwa M,
Yamashita S. Treatment of thyroid carcinoma cells with four different
suicide gene/prodrug combinations in vitro. Anticancer Res. 1998
May-Jun;18(3A):1521-5. PubMed PMID: 9673364.
73: Friedlos F, Court S, Ford M, Denny WA, Springer C. Gene-directed
enzyme prodrug therapy: quantitative bystander cytotoxicity and DNA
damage induced by CB1954 in cells expressing bacterial nitroreductase.
Gene Ther. 1998 Jan;5(1):105-12. PubMed PMID: 9536271.
74: Lemmon MJ, van Zijl P, Fox ME, Mauchline ML, Giaccia AJ, Minton NP,
Brown JM. Anaerobic bacteria as a gene delivery system that is
controlled by the tumor microenvironment. Gene Ther. 1997
Aug;4(8):791-6. PubMed PMID: 9338007.
75: Green NK, Youngs DJ, Neoptolemos JP, Friedlos F, Knox RJ, Springer
CJ, Anlezark GM, Michael NP, Melton RG, Ford MJ, Young LS, Kerr DJ,
Searle PF. Sensitization of colorectal and pancreatic cancer cell lines
to the prodrug 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954) by
retroviral transduction and expression of the E. coli nitroreductase
gene. Cancer Gene Ther. 1997 Jul-Aug;4(4):229-38. PubMed PMID: 9253508.
76: Bridgewater JA, Knox RJ, Pitts JD, Collins MK, Springer CJ. The
bystander effect of the nitroreductase/CB1954 enzyme/prodrug system is
due to a cell-permeable metabolite. Hum Gene Ther. 1997 Apr
10;8(6):709-17. PubMed PMID: 9113510.
77: Bailey SM, Hart IR. Nitroreductase activation of CB1954--an
alternative 'suicide' gene system. Gene Ther. 1997 Feb;4(2):80-1. PubMed
PMID: 9081709.
78: Bailey SM, Knox RJ, Hobbs SM, Jenkins TC, Mauger AB, Melton RG,
Burke PJ, Connors TA, Hart IR. Investigation of alternative prodrugs for
use with E. coli nitroreductase in 'suicide gene' approaches to cancer
therapy. Gene Ther. 1996 Dec;3(12):1143-50. PubMed PMID: 8986441.
79: Minton NP, Mauchline ML, Lemmon MJ, Brehm JK, Fox M, Michael NP,
Giaccia A, Brown JM. Chemotherapeutic tumour targeting using clostridial
spores. FEMS Microbiol Rev. 1995 Oct;17(3):357-64. Review. PubMed PMID:
7576773.
80: Knox RJ, Friedlos F, Jarman M, Davies LC, Goddard P, Anlezark GM,
Melton RG, Sherwood RF. Virtual cofactors for an Escherichia coli
nitroreductase enzyme: relevance to reductively activated prodrugs in
antibody directed enzyme prodrug therapy (ADEPT). Biochem Pharmacol.
1995 May 26;49(11):1641-7. PubMed PMID: 7786305.
81: Knox RJ, Friedlos F, Biggs PJ, Flitter WD, Gaskell M, Goddard P,
Davies L, Jarman M. Identification, synthesis and properties of
5-(aziridin-1-yl)-2-nitro-4-nitrosobenzamide, a novel DNA crosslinking
agent derived from CB1954. Biochem Pharmacol. 1993 Sep 1;46(5):797-803.
PubMed PMID: 8373433.
82: Knox RJ, Friedlos F, Boland MP. The bioactivation of CB 1954 and its
use as a prodrug in antibody-directed enzyme prodrug therapy (ADEPT).
Cancer Metastasis Rev. 1993 Jun;12(2):195-212. Review. PubMed PMID:
8375021.
83: Knox RJ, Friedlos F, Sherwood RF, Melton RG, Anlezark GM. The
bioactivation of 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954)--II. A
comparison of an Escherichia coli nitroreductase and Walker DT
diaphorase. Biochem Pharmacol. 1992 Dec 15;44(12):2297-301. PubMed PMID:
1472095.
84: Friedlos F, Biggs PJ, Abrahamson JA, Knox RJ. Potentiation of CB
1954 cytotoxicity by reduced pyridine nucleotides in human tumour cells
by stimulation of DT diaphorase activity. Biochem Pharmacol. 1992 Nov
3;44(9):1739-43. PubMed PMID: 1449531.
85: Friedlos F, Knox RJ. Metabolism of NAD(P)H by blood components.
Relevance to bioreductively activated prodrugs in a targeted enzyme
therapy system. Biochem Pharmacol. 1992 Aug 18;44(4):631-5. PubMed PMID:
1387314.
86: Friedlos F, Jarman M, Davies LC, Boland MP, Knox RJ. Identification
of novel reduced pyridinium derivatives as synthetic co-factors for the
enzyme DT diaphorase (NAD(P)H dehydrogenase (quinone), EC 1.6.99.2).
Biochem Pharmacol. 1992 Jul 7;44(1):25-31. PubMed PMID: 1385952.
87: Riley RJ, Workman P. DT-diaphorase and cancer chemotherapy. Biochem
Pharmacol. 1992 Apr 15;43(8):1657-69. Review. PubMed PMID: 1575764.
88: Friedlos F, Quinn J, Knox RJ, Roberts JJ. The properties of total
adducts and interstrand crosslinks in the DNA of cells treated with CB
1954. Exceptional frequency and stability of the crosslink. Biochem
Pharmacol. 1992 Mar 17;43(6):1249-54. PubMed PMID: 1562278.
89: Walton MI, Sugget N, Workman P. The role of human and rodent DT-diaphorase
in the reductive metabolism of hypoxic cell cytotoxins. Int J Radiat
Oncol Biol Phys. 1992;22(4):643-7. PubMed PMID: 1544831.
90: Knox RJ, Friedlos F, Marchbank T, Roberts JJ. Bioactivation of CB
1954: reaction of the active 4-hydroxylamino derivative with thioesters
to form the ultimate DNA-DNA interstrand crosslinking species. Biochem
Pharmacol. 1991 Oct 9;42(9):1691-7. PubMed PMID: 1930294.
91: Sunters A, Baer J, Bagshawe KD. Cytotoxicity and activation of
CB1954 in a human tumour cell line. Biochem Pharmacol. 1991 May
1;41(9):1293-8. PubMed PMID: 2018561.
92: Boland MP, Knox RJ, Roberts JJ. The differences in kinetics of rat
and human DT diaphorase result in a differential sensitivity of derived
cell lines to CB 1954 (5-(aziridin-1-yl)-2,4-dinitrobenzamide). Biochem
Pharmacol. 1991 Mar 15-Apr 1;41(6-7):867-75. Erratum in: Biochem
Pharmacol 1991 Dec 11;42 Suppl:S229. PubMed PMID: 1901207.
93: Roberts JJ, Marchbank T, Kotsaki-Kovatsi VP, Boland MP, Friedlos F,
Knox RJ. Caffeine, aminoimidazolecarboxamide and dicoumarol, inhibitors
of NAD(P)H dehydrogenase (quinone) (DT diaphorase), prevent both the
cytotoxicity and DNA interstrand crosslinking produced by
5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) in Walker cells.
Biochem Pharmacol. 1989 Nov 15;38(22):4137-43. PubMed PMID: 2480794.
94: Chaplin DJ. Hydralazine-induced tumor hypoxia: a potential target
for cancer chemotherapy. J Natl Cancer Inst. 1989 Apr 19;81(8):618-22.
PubMed PMID: 2704051.
95: Walton MI, Wolf CR, Workman P. Molecular enzymology of the reductive
bioactivation of hypoxic cell cytotoxins. Int J Radiat Oncol Biol Phys.
1989 Apr;16(4):983-6. PubMed PMID: 2703406.
96: Knox RJ, Friedlos F, Jarman M, Roberts JJ. A new cytotoxic, DNA
interstrand crosslinking agent,
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide, is formed from
5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) by a nitroreductase
enzyme in Walker carcinoma cells. Biochem Pharmacol. 1988 Dec
15;37(24):4661-9. PubMed PMID: 3202902.
97: Knox RJ, Boland MP, Friedlos F, Coles B, Southan C, Roberts JJ. The
nitroreductase enzyme in Walker cells that activates
5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB 1954) to
5-(aziridin-1-yl)-4-hydroxylamino-2-nitrobenzamide is a form of NAD(P)H
dehydrogenase (quinone) (EC 1.6.99.2). Biochem Pharmacol. 1988 Dec
15;37(24):4671-7. PubMed PMID: 3144286.
98: Venitt S, Crofton-Sleigh C. The toxicity and mutagenicity of the
anti-tumour drug 5-aziridino-2,4-dinitrobenzamide (CB1954) is greatly
reduced in a nitroreductase-deficient strain of E. coli. Mutagenesis.
1987 Sep;2(5):375-81. PubMed PMID: 3325769.
99: Roberts JJ, Friedlos F, Knox RJ. CB 1954 (2,4-dinitro-5-aziridinyl
benzamide) becomes a DNA interstrand crosslinking agent in Walker tumour
cells. Biochem Biophys Res Commun. 1986 Nov 14;140(3):1073-8. PubMed
PMID: 3778483.
100: Workman P, Morgan JE, Talbot K, Wright KA, Donaldson J, Twentyman
PR. CB 1954 revisited. II. Toxicity and antitumour activity. Cancer
Chemother Pharmacol. 1986;16(1):9-14. PubMed PMID: 3940225.
101: Workman P, White RA, Talbot K. CB 1954 revisited. I. Disposition
kinetics and metabolism. Cancer Chemother Pharmacol. 1986;16(1):1-8.
PubMed PMID: 3940216.
102: Workman P, Walton MI. Pharmacology of the mixed-function radio- and
chemosensitizers CB 1954 and RSU 1069. Int J Radiat Oncol Biol Phys.
1984 Aug;10(8):1307-10. PubMed PMID: 6547936.
103: Adams GE. Radiosensitizers: a conference preview. Int J Radiat
Oncol Biol Phys. 1984 Aug;10(8):1181-4. PubMed PMID: 6236183.
104: Tisdale MJ, Habberfield AD. Selective inhibition of ribonucleotide
reductase by the monofunctional alkylating agent
5(1-aziridinyl)-2,4-dinitrobenzamide (CB 1954). Biochem Pharmacol. 1980
Oct 15;29(20):2845-53. PubMed PMID: 7002161.
105: Tisdale MJ, Phillips BJ. Guanosine 3',5'-monophosphate and the
action of alkylating agents. Chem Biol Interact. 1977 Dec;19(3):375-81.
PubMed PMID: 202413.
106: Jarman M, Melzack DH, Ross WC. The metabolism of the anti-tumour
agent 5-(1-aziridinyl)-2,4-dinitrobenzamide (CB 1954). Biochem Pharmacol.
1976 Nov 15;25(22):2475-8. PubMed PMID: 985569.
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