E3656

(−)-Epothilone A

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

• Synonym(s): EpoA
• Empirical Formula (Hill Notation): C₂₆H₃₉NO₆S
• CAS Number: 152044-53-6
• Molecular Weight: 493.66
• MDL number: MFCD26960884
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724476
• NACRES: NA.77

Properties

• 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

Description

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable