E3656

(−)-Epothilone A

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

• Sinónimos: EpoA
• Fórmula empírica (notación de Hill): C₂₆H₃₉NO₆S
• Número de CAS: 152044-53-6
• Peso molecular: 493.66
• Número MDL: MFCD26960884
• Código UNSPSC: 12352200
• ID de la sustancia en PubChem: 24724476
• NACRES: NA.77

Propiedades

• origen biológico: Sorangium cellulosum
• Nivel de calidad: 100
• Análisis: >95% (HPLC)
• formulario: solid
• condiciones de almacenamiento: desiccated; protect from light
• temp. de almacenamiento: −20°C
• cadena 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
• Clave InChI: HESCAJZNRMSMJG-KKQRBIROSA-N

Descripción

Acciones bioquímicas o fisiológicas

(-)-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.

Información de seguridad

• Código de clase de almacenamiento: 11 - Combustible Solids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): Not applicable
• Punto de inflamabilidad (°C): Not applicable