Maytansine

• CAT Number: R014876
• CAS Number: 35846-53-8
• Molecular Formula: C₃₄H₄₆ClN₃O₁₀
• Molecular Weight: 692.2
• Purity: ≥95%
• Target: microtubule inhibitor
• Storage: -20°C
• InChI: 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+,2
• InChIKey: WKPWGQKGSOKKOO-RSFHAFMBSA-N
• SMILES: 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

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.

Reference

1:Spatial profiling of maytansine during the germination process of Maytenus senegalensis seeds. Eckelmann D, Kusari S, Spiteller M.Fitoterapia. 2017 Apr 3;119:51-56. doi: 10.1016/j.fitote.2017.03.014. [Epub ahead of print] PMID: 28385670 2:SLC46A3 Is Required to Transport Catabolites of Noncleavable Antibody Maytansine Conjugates from the Lysosome to the Cytoplasm. Hamblett KJ, Jacob AP, Gurgel JL, Tometsko ME, Rock BM, Patel SK, Milburn RR, Siu S, Ragan SP, Rock DA, Borths CJ, O/’Neill JW, Chang WS, Weidner MF, Bio MM, Quon KC, Fanslow WC.Cancer Res. 2015 Dec 15;75(24):5329-40. doi: 10.1158/0008-5472.CAN-15-1610. Epub 2015 Dec 2. PMID: 26631267 Free Article3:Endophytes are hidden producers of maytansine in Putterlickia roots. Kusari S, Lamshöft M, Kusari P, Gottfried S, Zühlke S, Louven K, Hentschel U, Kayser O, Spiteller M.J Nat Prod. 2014 Dec 26;77(12):2577-84. doi: 10.1021/np500219a. Epub 2014 Dec 5. PMID: 25478947 4:Maytansine-loaded star-shaped folate-core PLA-TPGS nanoparticles enhancing anticancer activity. Tang X, Dai H, Zhu Y, Tian Y, Zhang R, Mei R, Li D.Am J Transl Res. 2014 Oct 11;6(5):528-37. eCollection 2014. PMID: 25360217 Free PMC Article5:A study of the bacterial community in the root system of the maytansine containing plant Putterlickia verrucosa. Wings S, Müller H, Berg G, Lamshöft M, Leistner E.Phytochemistry. 2013 Jul;91:158-64. doi: 10.1016/j.phytochem.2012.06.016. Epub 2012 Jul 14. PMID: 22795602 6:Maytansine and cellular metabolites of antibody-maytansinoid conjugates strongly suppress microtubule dynamics by binding to microtubules. Lopus M, Oroudjev E, Wilson L, Wilhelm S, Widdison W, Chari R, Jordan MA.Mol Cancer Ther. 2010 Oct;9(10):2689-99. doi: 10.1158/1535-7163.MCT-10-0644. PMID: 20937594 Free PMC Article7:Semisynthetic maytansine analogues for the targeted treatment of cancer. 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.J Med Chem. 2006 Jul 13;49(14):4392-408. PMID: 16821799 8:Metabolism studies of the anti-tumor agent maytansine and its analog ansamitocin P-3 using liquid chromatography/tandem mass spectrometry. Liu Z, Floss HG, Cassady JM, Chan KK.J Mass Spectrom. 2005 Mar;40(3):389-99. PMID: 15674857 9:In vitro and in vivo activity of the maytansinoid immunoconjugate huN901-N2/’-deacetyl-N2/’-(3-mercapto-1-oxopropyl)-maytansine against CD56+ multiple myeloma cells. Tassone P, Gozzini A, Goldmacher V, Shammas MA, Whiteman KR, Carrasco DR, Li C, Allam CK, Venuta S, Anderson KC, Munshi NC.Cancer Res. 2004 Jul 1;64(13):4629-36. PMID: 15231675 Free Article10:[Inhibitors of tubulin assembly: specially on rhizoxin-maytansine site ligands]. Iwasaki S.Tanpakushitsu Kakusan Koso. 1993 Aug;38(11):1742-52. Review. Japanese. No abstract available. PMID: 8210422