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Key Documents

Altri documenti

E3656

Sigma-Aldrich

(−)-Epothilone A

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

Sinonimo/i:

EpoA

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About This Item

Formula empirica (notazione di Hill):
C26H39NO6S
Numero CAS:
152044-53-6
Peso molecolare:
493.66
Numero MDL:
MFCD26960884
Codice UNSPSC:
12352200
ID PubChem:
24724476
NACRES:
NA.77

Origine biologica

Sorangium cellulosum

Livello qualitativo

100

Saggio

>95% (HPLC)

Forma fisica

solid

Condizioni di stoccaggio

desiccated
protect from light

Temperatura di conservazione

−20°C

Stringa SMILE

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
HESCAJZNRMSMJG-KKQRBIROSA-N

Azioni biochim/fisiol

(-)-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.

Prodotti correlati

N° Catalogo
Descrizione
Determinazione del prezzo

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Certificati d'analisi (COA)

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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
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
Joys of molecules. 2. Endeavors in chemical biology and medicinal chemistry.
K C Nicolaou
Journal of medicinal chemistry, 48(18), 5613-5638 (2005-09-02)
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.
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