Skip to Content
Merck
CN

Key Documents

View All Documentation

E3656

(−)-Epothilone A

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

Synonym(s):

EpoA

Sign In to View Organizational & Contract Pricing.

Select a Size

Change View

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
Quality level:
100
Storage condition:
desiccated, protect from light
Technical Service
Need help? Our team of experienced scientists is here for you.
Let Us Assist

biological source

Sorangium cellulosum

Quality Level

100

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

Related Categories

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

新产品

This item has

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
086K4708

Don't see the Right Version?

If you require a particular version, you can look up a specific certificate by the Lot or Batch number.

Search for a COA

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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
Bernhard Pfeiffer et al.
Bioorganic & medicinal chemistry letters, 19(14), 3760-3763 (2009-05-13)
The SAR of a series of new epothilone A derivatives with a 2-substituted-1,3-oxazoline moiety trans-fused to the C12-C13 bond of the deoxy macrocycle have been investigated with regard to tubulin polymerization induction and cancer cell growth inhibition. Significant differences in
Máté Erdélyi et al.
Journal of medicinal chemistry, 51(5), 1469-1473 (2008-02-15)
The conformational properties of the microtubule-stabilizing agent epothilone A ( 1a) and its 3-deoxy and 3-deoxy-2,3-didehydro derivatives 2 and 3 have been investigated in aqueous solution by a combination of NMR spectroscopic methods, Monte Carlo conformational searches, and NAMFIS calculations.
View All Related Papers

Global Trade Item Number

SKUGTIN
E3656-10UG04061833065938

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service