Epothilone B

Epothilone B is a microtubule stabilizer with a Ki of 0.71μM. It acts by binding to the αβ-tubulin heterodimer subunit which causes decreasing of αβ-tubulin dissociation.

Product information

CAS Number: 152044-54-7

Molecular Weight: 507.68

Formula: C27H41NO6S

Synonym:

EPO906

EPO-906

EPO 906

EPO 906A

EPO B

(-)-Epothilone B

patupilone

Chemical Name: (1S, 3S, 7S, 10R, 11S, 12S, 16R)-7, 11-dihydroxy-8, 8, 10, 12, 16-pentamethyl-3-((E)-1-(2-methylthiazol-4-yl)prop-1-en-2-yl)-4, 17-dioxabicyclo[14.1.0]heptadecane-5, 9-dione

Smiles: CC1(C)[C@@H](O)CC(=O)O[C@@H](C[C@@H]2O[C@]2(C)CCC[C@H](C)[C@H](O)[C@@H](C)C1=O)/C(/C)=C/C1=CSC(C)=N1

InChiKey: QXRSDHAAWVKZLJ-PVYNADRNSA-N

InChi: 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

Technical Data

Appearance: Solid Power

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

Solubility: DMSO: 102 mg/mL(200.91 mM). Water: Insoluble.

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 B shows better activity than Epothilone A. The EC0.01 of Epothilone B is 1.8 μM. Epothilone B potently inhibits cell proliferation in HCT116 cells, with IC50 of 0.8 nM. Epothilone B induces mitotic arrest and displays cytotoxicity in KB3-1, KBV-1, Hela, and Hs578T cells, with IC50 of 3 nM to 92 nM. Epothilone B competes with Taxol in binding to microtubules, with IC50 of 3.3 μM. In MCF-7 cells overexpressing GFP-α-tubulin, Epothilone B (3.5 nM) efficiently blocks microtubule dynamics. Meanwhile, Epothilone B induces mitotic arrest with IC50 of 3.5 nM. In multiple myeloma (MM) cells, including RPMI 8226, U266, MM.1S, LR5, and MR20, Epothilone B directly suppresses proliferation with IC50 of 1 nM to 10 nM. Similarly, Epothilone B (10 nM) also induces cell cycle arrest and apoptosis. A recent study reveals that, in ovarian cancer Hey cells, Epothilone B (5 nM–100 nM) enhances surface epithelial cell adhesion antigen (EpCAM), without affecting the transcription or the total cellular level of EpCAM.

In Vivo:

In a mouse xenograft model of RPMI 8226 cells, Epothilone B (2.5 mg/kg–4 mg/kg) prolongs survival and suppresses tumor growth. Similarly, in mouse xenograft models of prostate cancer cells, including DU145 and PC3, Epothilone B at the same dose also inhibits tumor growth.

References:

1. Regueiro-Ren A , et al. Org Lett, 2001, 3(17), 2693-2696.
2. Bollag DM, et al. Cancer Res, 1995, 55(11), 2325-2333.
3. Kamath K, et al. Cancer Res, 2003, 63(18), 6026-6031.
4. Lin B, et al. Blood, 2005, 105(1), 350-357.
5. Shahabi S, et al. Gynecol Oncol, 2010, 119(2), 345-350.
6. O'Reilly T, et al. Prostate, 2005, 65(3), 231-240.
7. Swindell CS, et al. J Med Chem, 1991, 34(3), 1176-1184.

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