E2656

(−)-Epothilone B

from Sorangium cellulosum, ≥98% (HPLC)

• Synonym(s): EPO906, EpoB, Patupilone
• Empirical Formula (Hill Notation): C₂₇H₄₁NO₆S
• CAS Number: 152044-54-7
• Molecular Weight: 507.68
• MDL number: MFCD02101921
• UNSPSC Code: 12352200
• PubChem Substance ID: 24724475
• NACRES: NA.77

Properties

• biological source: Sorangium cellulosum
• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: lyophilized powder
• storage condition: desiccated; protect from light
• color: white to off-white
• storage temp.: −20°C
• SMILES string: [H][C@]1(C[C@]2([H])O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)\C(C)=C\c3csc(C)n3
• InChI: 1S/C27H41NO6S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)33-23(30)13-21(29)26(5,6)25(32)17(3)24(15)31/h11,14-15,17,20-22,24,29,31H,8-10,12-13H2,1-7H3/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
• InChI key: QXRSDHAAWVKZLJ-PVYNADRNSA-N

Description

General description

Epothilones has antimitotic properties. It prevents microtubule depolymerization and competitively blocks paclitaxel binding to microtubules. Epothilone B is used to treat metastatic breast cancer (MBC).

Biochem/physiol Actions

(-)-Epothilone B is a microtubule (MT) stabilizing drug and natural macrolide antitumor from myxobacteria Sorangium cellulosum. EpoB has similar biological properties to EpoA. However, EpoB is 10-fold more potent than EpoA against P-glycoprotein-expressing multidrug resistant (MDR) cells (IC₅₀ = 2 nM for MDR CCRF-CEM/VBL₁₀₀ cells). (-)-Epothilone B is similar to paclitaxel in binding displacement, and a substitution for paclitaxel in dependent cell growth. EpoB causes cell cycle arrest (IC₅₀ = 3.5 nM).

Safety Information

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