From Wikipedia, the free encyclopedia
Maitansine
Names
Other names
Maytansin
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.047.944
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
C34 H46 ClN3 O10
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).
Chemical compound
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]
It is a
macrolide of the
ansamycin type and can be isolated from plants of the genus
Maytenus .
[1]
Maytansinoids
Derivatives of maitansine are known as maytansinoids.
[2]
[3]
Some are being investigated as the cytotoxic component of
antibody-drug conjugates for cancer treatment,
[4] 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.
[5]
[6]
Examples of maytansinoids are:
See also
ImmunoGen , developer of maytansinoid based drugs
References
^
a
b
National Cancer Institute: Definition of Maytansine
^
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 .
^ 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 .
^ 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 .
^
"Kadcyla EPAR" .
European Medicines Agency (EMA) . 17 September 2018.
^
"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 .