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Maytansine

Maytansine structure

CAS No:
35846-53-8
Formula:
C34H46ClN3O10
Chemical Name:
Maytansine
Synonyms:
maitansine;Maytansine;NSC 153858;(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;Maitansina;Microtubule/Tubulin,tumor,mitotic,microtubule-targeted,arrest,Inhibitor,potent,subnanomolar,Maytansine,inhibit;(1S,2R,3S,5S,6R,16E,18E,20R,21S)-11-chloro-21-hydroxy-12,20-dimethoxy-2,5,9,16-tetramethyl-8,23-dioxo-4,24-dioxa-9,22-diazatetracyclo[19.3.1.11?,1?.03,?]hexacosa-10,12,14(26),16,18-pentaen-6-yl (2S)-2-(N-methylacetamido)propanoate;Maytansine, 10 mM in DMSO
Categories:
Organic Chemistry > Lactones

Description

An ansa macrolide isolated from the MAYTENUS genus of East African shrubs.

This novel ansa macrolide alkaloid occurs in a number of May tan us species. The structure given has been elucidated from chemical and spectroscopic data. In low doses (25-50 mcg/kg), maytansine prolonged the survival of mice bearing vincristine-sensitive P388 leukemia but not those bearing vincristine-resistant tumour lines. In vitro, it suppressed the growth of U21 0, LSl78Y and P388 leukemia cells with ED50of 2 X 10-9, 1.5 X 10-9and 6 X 10-10M respectively and elevated the mitotic index in L 121 0 cells. From labelling studies it was shown that the alkaloid inhibited DNA formation by P388 cells to a greater extent than RNA and protein synthesis. Maytensine did not inhibit RNA polymerase from Escherichia coli at levels as high as 1 X 10-4M.

ChEBI: An organic heterotetracyclic compound and 19-membered macrocyclic lactam antibiotic originally isolated from the Ethiopian shrub Maytenus serrata but also found in other Maytenus species. It exhibits cytotoxicity against many tumo r cell lines.

Maytansine Basic Attributes

Molecular Weight：

692.2

Exact Mass：

692.20

EC Number：

252-754-7

Color/Form：

white to beige

Characteristics

PSA：

157 Å²

Density：

1.1049 (rough estimate)

Melting Point：

183.5-184℃

Boiling Point：

895.1±65.0 °C(Predicted)

Refractive Index：

1.6000 (estimate)

Toxicity：

LD50 in rats (mg/kg): 0.48 s.c. (Mugera, Ward)

PKA：

9.82±0.70(Predicted)

Critical Temperature & Pressure：

Store at -20°C

Safety Information

wgk germany：

WGK 3

Drug Information

MeSH：

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)|Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

MeSH Entry Terms：

DM1, Maytansinoid

Maytansine Use and Manufacturing

Antineoplastic.

Computed Properties

Molecular Weight:692.2
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:6
Exact Mass:691.2871724
Monoisotopic Mass:691.2871724
Topological Polar Surface Area:157
Heavy Atom Count:48
Complexity:1300
Undefined Atom Stereocenter Count:8
Undefined Bond Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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