Maitansine

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 123213

CAS#: 35846-53-8

Description: Maitansine, also known as maytansine and NSC153858, is a cytotoxic agent. It inhibits the assembly of microtubules by binding to tubulin at the rhizoxin binding site. It is a macrolide of the ansamycin type and can be isolated from plants of the genus Maytenus. An ansamycin antibiotic originally isolated from the Ethiopian shrub Maytenus serrata. Maytansine binds to tubulin at the rhizoxin binding site, thereby inhibiting microtubule assembly, inducing microtubule disassembly, and disrupting mitosis. Maytansine exhibits cytotoxicity against many tumor cell lines and may inhibit tumor growth in vivo.


Price and Availability

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1g
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2g
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Size
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5g
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Maitansine, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 123213
Name: Maitansine
CAS#: 35846-53-8
Chemical Formula: C34H46ClN3O10
Exact Mass: 691.28717
Molecular Weight: 692.2
Elemental Analysis: C, 59.00; H, 6.70; Cl, 5.12; N, 6.07; O, 23.11


Synonym: NSC153858; NSC 153858; NSC-153858; maytansine; Maitansine; Maitansina; Maitansinum; DM-1; Mertansine.

IUPAC/Chemical Name: (14S,16S,32S,33S,2R,4S,10E,12E,14R)-86-chloro-14-hydroxy-85,14-dimethoxy-33,2,7,10-tetramethyl-12,6-dioxo-7-aza-1(6,4)-oxazinana-3(2,3)-oxirana-8(1,3)-benzenacyclotetradecaphane-10,12-dien-4-yl N-acetyl-N-methyl-L-alaninate

InChi Key: WKPWGQKGSOKKOO-RSFHAFMBSA-N

InChi Code: InChI=1S/C34H46ClN3O10/c1-18-11-10-12-26(45-9)34(43)17-25(46-32(42)36-34)19(2)30-33(5,48-30)27(47-31(41)20(3)37(6)21(4)39)16-28(40)38(7)23-14-22(13-18)15-24(44-8)29(23)35/h10-12,14-15,19-20,25-27,30,43H,13,16-17H2,1-9H3,(H,36,42)/b12-10+,18-11+/t19-,20+,25+,26-,27+,30+,33+,34+/m1/s1

SMILES Code: C[C@@H]1[C@@H]2C[C@]([C@@H](/C=C/C=C(/CC3=CC(=C(C(=C3)OC)Cl)N(C(=O)C[C@@H]([C@]4([C@H]1O4)C)OC(=O)[C@H](C)N(C)C(=O)C)C)\C)OC)(NC(=O)O2)O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


References

1: Kusari S, Lamshöft M, Kusari P, Gottfried S, Zühlke S, Louven K, Hentschel U, Kayser O, Spiteller M. Endophytes are hidden producers of maytansine in Putterlickia roots. J Nat Prod. 2014 Dec 26;77(12):2577-84. doi: 10.1021/np500219a. Epub 2014 Dec 5. PubMed PMID: 25478947.

2: Tang X, Dai H, Zhu Y, Tian Y, Zhang R, Mei R, Li D. Maytansine-loaded star-shaped folate-core PLA-TPGS nanoparticles enhancing anticancer activity. Am J Transl Res. 2014 Oct 11;6(5):528-37. eCollection 2014. PubMed PMID: 25360217; PubMed Central PMCID: PMC4212927.

3: Wings S, Müller H, Berg G, Lamshöft M, Leistner E. A study of the bacterial community in the root system of the maytansine containing plant Putterlickia verrucosa. Phytochemistry. 2013 Jul;91:158-64. doi: 10.1016/j.phytochem.2012.06.016. Epub 2012 Jul 14. PubMed PMID: 22795602.

4: Lopus M, Oroudjev E, Wilson L, Wilhelm S, Widdison W, Chari R, Jordan MA. Maytansine and cellular metabolites of antibody-maytansinoid conjugates strongly suppress microtubule dynamics by binding to microtubules. Mol Cancer Ther. 2010 Oct;9(10):2689-99. doi: 10.1158/1535-7163.MCT-10-0644. PubMed PMID: 20937594; PubMed Central PMCID: PMC2954514.

5: Widdison WC, Wilhelm SD, Cavanagh EE, Whiteman KR, Leece BA, Kovtun Y, Goldmacher VS, Xie H, Steeves RM, Lutz RJ, Zhao R, Wang L, Blättler WA, Chari RV. Semisynthetic maytansine analogues for the targeted treatment of cancer. J Med Chem. 2006 Jul 13;49(14):4392-408. PubMed PMID: 16821799.

6: Liu Z, Floss HG, Cassady JM, Chan KK. Metabolism studies of the anti-tumor agent maytansine and its analog ansamitocin P-3 using liquid chromatography/tandem mass spectrometry. J Mass Spectrom. 2005 Mar;40(3):389-99. PubMed PMID: 15674857.

7: Tassone P, Gozzini A, Goldmacher V, Shammas MA, Whiteman KR, Carrasco DR, Li C, Allam CK, Venuta S, Anderson KC, Munshi NC. In vitro and in vivo activity of the maytansinoid immunoconjugate huN901-N2'-deacetyl-N2'-(3-mercapto-1-oxopropyl)-maytansine against CD56+ multiple myeloma cells. Cancer Res. 2004 Jul 1;64(13):4629-36. PubMed PMID: 15231675.

8: Iwasaki S. [Inhibitors of tubulin assembly: specially on rhizoxin-maytansine site ligands]. Tanpakushitsu Kakusan Koso. 1993 Aug;38(11):1742-52. Review. Japanese. PubMed PMID: 8210422.

9: Sawada T, Kato Y, Kobayashi H, Hashimoto Y, Watanabe T, Sugiyama Y, Iwasaki S. A fluorescent probe and a photoaffinity labeling reagent to study the binding site of maytansine and rhizoxin on tubulin. Bioconjug Chem. 1993 Jul-Aug;4(4):284-9. PubMed PMID: 8218485.

10: Hamel E. Natural products which interact with tubulin in the vinca domain: maytansine, rhizoxin, phomopsin A, dolastatins 10 and 15 and halichondrin B. Pharmacol Ther. 1992;55(1):31-51. Review. PubMed PMID: 1287674.

11: Takahashi M, Iwasaki S, Kobayashi H, Okuda S, Murai T, Sato Y. Rhizoxin binding to tubulin at the maytansine-binding site. Biochim Biophys Acta. 1987 Dec 7;926(3):215-23. PubMed PMID: 3120782.

12: Suchocki JA, Sneden AT. Characterization of decomposition products of maytansine. J Pharm Sci. 1987 Sep;76(9):738-43. PubMed PMID: 11002812.

13: Luduena RF, Anderson WH, Prasad V, Jordan MA, Ferrigni KC, Roach MC, Horowitz PM, Murphy DB, Fellous A. Interactions of vinblastine and maytansine with tubulin. Ann N Y Acad Sci. 1986;466:718-32. PubMed PMID: 3460446.

14: Fellous A, Ludueña RF, Prasad V, Jordan MA, Anderson W, Ohayon R, Smith PT. Effects of Tau and MAP2 on the interaction of maytansine with tubulin: inhibitory effect of maytansine on vinblastine-induced aggregation of tubulin. Cancer Res. 1985 Oct;45(10):5004-10. PubMed PMID: 3928146.

15: Schibler MJ, Cabral FR. Maytansine-resistant mutants of Chinese hamster ovary cells with an alteration in alpha-tubulin. Can J Biochem Cell Biol. 1985 Jun;63(6):503-10. PubMed PMID: 4041962.

16: Huang AB, Lin CM, Hamel E. Maytansine inhibits nucleotide binding at the exchangeable site of tubulin. Biochem Biophys Res Commun. 1985 May 16;128(3):1239-46. PubMed PMID: 4004859.

17: Ravry MJ, Omura GA, Birch R. Phase II evaluation of maytansine (NSC 153858) in advanced cancer. A Southeastern Cancer Study Group trial. Am J Clin Oncol. 1985 Apr;8(2):148-50. PubMed PMID: 3834790.

18: Phase II trials of maytansine, low-dose chlorozotocin, and high-dose chlorozotocin as single agents against advanced measurable adenocarcinoma of the pancreas. Gastrointestinal Tumor Study Group. Cancer Treat Rep. 1985 Apr;69(4):417-20. PubMed PMID: 2859924.

19: Fan YJ, Zhou J, Li M. [Effect of maytansine on the cell cycle of Ehrlich ascites carcinoma cells in mice]. Zhongguo Yao Li Xue Bao. 1985 Mar;6(1):63-7. Chinese. PubMed PMID: 3158164.

20: Rebert CS, Pryor GT, Frick MS. Effects of vincristine, maytansine, and cis-platinum on behavioral and electrophysiological indices of neurotoxicity in the rat. J Appl Toxicol. 1984 Dec;4(6):330-8. PubMed PMID: 6542922.