E3656

(−)-Epothilone A

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

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

Propriétés

• Source biologique: Sorangium cellulosum
• Niveau de qualité: 100
• Essai: >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

Description

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.

EpoA is a microtubule stabilizing drug and natural macrolide antitumor.

Informations sur la sécurité

• 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