Epothilone A

Epothilone A is a taxol-like microtubule (MT) stabilizing agent.

Product information

CAS Number: 152044-53-6

Molecular Weight: 493.66

Formula: C26H39NO6S

Synonym:

EpoA

Chemical Name: (1R, 5S, 6S, 7R, 10S, 14S, 16S)-6, 10-Dihydroxy-5, 7, 9, 9-tetramethyl-14-[(E)-1-(2-methyl-1, 3-thiazol-4-yl)prop-1-en-2-yl]-13, 17-dioxabicyclo[14.1.0]heptadecane-8, 12-dione

Smiles: CC1=NC(=CS1)/C=C(\C)/[C@@H]1C[C@@H]2O[C@@H]2CCC[C@H](C)[C@H](O)[C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1

InChiKey: HESCAJZNRMSMJG-KKQRBIROSA-N

InChi: 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

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: DMSO : 125 mg/mL (253.21 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥12 months if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

In Vitro:

Epothilone A, discovered from the myxobacterium Sorangium cellulosum, is a Taxol-like microtubule-stabilizing agent that induces tubulin polymerization, leading to cell cycle arrest at the G2-M transition, cytotoxicity, and apoptosis.Epothilone A potently inhibits cell proliferation in HCT116 cells, with IC50 of 4.4 nM. Epothilone A also displays cytotoxicity in KB3-1, KBV-1, Hela, and Hs578T cells, with IC50 values ranging from 13 nM to 160 nM. Epothilone A is more water soluble than Taxol and competes with Taxol in binding with microtubules, with IC50 of 2.3 μM. However, both Epothilone A and Taxol don't share a common pharmacophore and exploits the tubulin-binding pocket uniquely and independently. Recently, it is found that microbiological transformation of Epothilone A by Aspergillus niger AS 3.739 yields several metabolites that is also toxic to MCF-7 cells, but with much higher IC50 values.

References:

1. Nettles JH, et al. Science, 2004, 305(5685), 866-869.
2. Bollag DM, et al. Cancer Res, 1995, 55(11), 2325-2333.
3. Regueiro-Ren A , et al. Org Lett, 2001, 3(17), 2693-2696.
4. Regueiro-Ren A , et al. Org Lett, 2001, 3(17), 2693-2696.

Products are for research use only. Not for human use.