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Maitansine

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Maitansine (INN), or maytansine (USAN), is a cytotoxic agent. It inhibits the assembly of microtubules by binding to tubulin at the rhizoxin binding site.[1] The maytansine binding site and binding mode has been characterized.[2]

Maitansine
Names
Other names
Maytansin
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.047.944 Edit this at Wikidata
UNII
  • 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
    Key: WKPWGQKGSOKKOO-RSFHAFMBSA-N
  • C/C(CC1=CC(OC)=C(Cl)C(N3C)=C1)=C\C=C\[C@@H](OC)[C@@]2(O)C[C@]([C@@H](C)[C@H]4[C@](O4)(C)[C@@H](OC([C@H](C)N(C)C(C)=O)=O)CC3=O)([H])OC(N2)=O
Properties
C34H46ClN3O10
Molar mass 692.20 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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It is a macrolide of the ansamycin type and can be isolated from plants of the genus Maytenus.[1]

Maytansinoids

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Derivatives of maitansine are known as maytansinoids.[3][4] Some are being investigated as the cytotoxic component of antibody-drug conjugates for cancer treatment,[5] and the antibody-drug conjugate trastuzumab emtansine is an approved drug for the treatment of certain kinds of breast cancer in the EU and in the US.[6][7]

Examples of maytansinoids are:

See also

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  • ImmunoGen, developer of maytansinoid based drugs

References

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  1. ^ a b National Cancer Institute: Definition of Maytansine
  2. ^ Menchon, Grégory; Prota, Andrea E.; Lucena-Agell, Daniel; Bucher, Pascal; Jansen, Rolf; Irschik, Herbert; Müller, Rolf; Paterson, Ian; Díaz, J. Fernando; Altmann, Karl-Heinz; Steinmetz, Michel O. (2018-05-29). "A fluorescence anisotropy assay to discover and characterize ligands targeting the maytansine site of tubulin". Nature Communications. 9 (1). Springer Science and Business Media LLC. doi:10.1038/s41467-018-04535-8. ISSN 2041-1723. PMC 5974090.
  3. ^ a b Yu, T.-W.; Bai, L; Clade, D; Hoffmann, D; Toelzer, S; Trinh, KQ; Xu, J; Moss, SJ; Leistner, E (2002). "The biosynthetic gene cluster of the maytansinoid antitumor agent ansamitocin from Actinosynnemapretiosum". Proceedings of the National Academy of Sciences. 99 (12): 7968–7973. Bibcode:2002PNAS...99.7968Y. doi:10.1073/pnas.092697199. PMC 123004. PMID 12060743.
  4. ^ Lopus, M; Oroudjev, E; Wilson, L; Wilhelm, S; Widdison, W; Chari, R; Jordan, MA (2010). "Maytansine and cellular metabolites of antibody-maytansinoid conjugates strongly suppress microtubule dynamics by binding to microtubules". Mol Cancer Ther. 9 (10): 2689–99. doi:10.1158/1535-7163.MCT-10-0644. PMC 2954514. PMID 20937594.
  5. ^ Chari, RV; Martell, BA; Gross, JL; et al. (January 1992). "Immunoconjugates containing novel maytansinoids: promising anticancer drugs" (PDF). Cancer Res. 52 (1): 127–31. PMID 1727373.
  6. ^ "Kadcyla EPAR". European Medicines Agency (EMA). 17 September 2018.
  7. ^ "Drug Approval Package: ado-trastuzumab emtansine". U.S. Food and Drug Administration (FDA). 22 February 2013. Archived from the original on 4 December 2019. Retrieved 3 December 2019.
 

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