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E3656

Sigma-Aldrich

(−)-Epothilone A

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

Synonyme(s) :

EpoA

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About This Item

Formule empirique (notation de Hill):
C26H39NO6S
Numéro CAS:
152044-53-6
Poids moléculaire :
493.66
Numéro MDL:
MFCD26960884
Code UNSPSC :
12352200
ID de substance PubChem :
24724476
Nomenclature NACRES :
NA.77

Source biologique

Sorangium cellulosum

Niveau de qualité

100

Pureté

>95% (HPLC)

Forme

solid

Conditions de stockage

desiccated
protect from light

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

HESCAJZNRMSMJG-KKQRBIROSA-N

Actions biochimiques/physiologiques

(-)-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.

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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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
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.
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
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