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E3656

(−)-Epothilone A

Name: (−)-Epothilone A
Brand: SIGMA

from Sorangium cellulosum, >95% (HPLC), solid

Synonym(s):

EpoA

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About This Item

Empirical Formula (Hill Notation):

C₂₆H₃₉NO₆S

CAS Number:

152044-53-6

Molecular Weight:

493.66

NACRES:

NA.77

PubChem Substance ID:

24724476

UNSPSC Code:

12352200

MDL number:

MFCD26960884

Assay:

>95% (HPLC)

Form:

solid

Storage condition:

desiccated, protect from light

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Properties

biological source

Sorangium cellulosum

assay

>95% (HPLC)

form

solid

storage condition

desiccated, protect from light

storage temp.

−20°C

SMILES string

O=C(O[C@@](/C(C)=C/C1=CSC(C)=N1)([H])C[C@@](O2)([H])[C@@]2([H])CCC[C@H](C)[C@H](O)[C@H]3C)C[C@H](O)C(C)(C)C3=O

InChI

1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3/b15-10+/t14-,16+,19+,20-,21-,22-,24-/m0/s1

InChI key

HESCAJZNRMSMJG-KKQRBIROSA-N

Description

Biochem/physiol Actions

(-)-Epothilone A is a microtubule (MT) stabilizing drug and natural macrolide antitumor from myxobacteria Sorangium cellulosum. EpoA exhibits kinetics similar to paclitaxel by inducing tubulin polymerization in vitro and producing enhanced microtubule stability and bundling in cultured cells. In contrast to paclitaxel, Epothilone A exhibits a greater cytotoxicity against P-glycoprotein-expressing multidrug resistant (MDR) cells (IC₅₀ = 20 nM for MDR CCRF-CEM/VBL₁₀₀ cells). Epothilone A is a competitve inhibitor of ³H-paclitaxel binding with comparable IC₅₀ to paclitaxel in displacement competition assays. EpoA causes cell cycle arrest at the G₂/M transition leading to cytotoxicity.

EpoA is a microtubule stabilizing drug and natural macrolide antitumor.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number

086K4708

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Global Trade Item Number

SKU	GTIN
E3656-10UG	04061833065938