E3656
(−)-Epothilone A
from Sorangium cellulosum, >95% (HPLC), solid
Synonym(s):
EpoA
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About This Item
Empirical Formula (Hill Notation):
C26H39NO6S
CAS Number:
Molecular Weight:
493.66
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
biological source
Sorangium cellulosum
Quality Level
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
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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Rubén M Buey et al.
Nature chemical biology, 3(2), 117-125 (2007-01-09)
Cyclostreptin (1), a natural product from Streptomyces sp. 9885, irreversibly stabilizes cellular microtubules, causes cell cycle arrest, evades drug resistance mediated by P-glycoprotein in a tumor cell line and potently inhibits paclitaxel binding to microtubules, yet it only weakly induces
Isao Kobayashi et al.
Scientific reports, 9(1), 14205-14205 (2019-10-04)
Hematopoietic stem cells (HSCs) maintain the entire blood system throughout life and are utilized in therapeutic approaches for blood diseases. Prospective isolation of highly purified HSCs is crucial to understand the molecular mechanisms underlying regulation of HSCs. The zebrafish is
Daniele Passarella et al.
Bioorganic & medicinal chemistry, 17(21), 7435-7440 (2009-10-07)
The preparation and biological evaluation of a novel series of dimeric epothilone A derivatives (1-6) are described. Two types of diacyl spacers were introduced to establish the various dimeric epothilone A constructs. The effect of these compounds on tubulin polymerization
Global Trade Item Number
| SKU | GTIN |
|---|---|
| E3656-10UG | 04061833065938 |