LKT Labs

Biochemicals for Life Science Research

Epothilone B

Epothilone B

Product ID E6257
Cas No. 152044-54-7
Purity ≥98%
Product Unit SizeCostQuantityStock
1 mg $112.20 In stock
5 mg $245.30 In stock
10 mg $428.70 In stock
25 mg $918.80 In stock
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Description

Epothilone is an anticancer chemotherapeutic and neuroprotective compound that acts as an antimitotic compound; it binds the taxane pocket of β-tubulin, using side chains to induce formation of a short helix and preventing microtubule depolymerization. Epothilone displays activity against lung cancer and prostate cancer in clinical trials and may show benefit in treatment of neurodegenerative diseases such as Alzheimer’s disease. Additionally, epothilone B inhibits glioblastoma cell migration. In animal models of spinal cord injury, epothilone B decreases scarring, stimulates axonal regeneration, and improves motor deficits. Typically, the degree of chemotherapeutic activity of the three epothilone subtypes follows the alphabet, where Epo A> Epo B> Epo D.

Product Info

Cas No.

152044-54-7
Purity

≥98%
Formula

C27H41NO6S
Formula Wt.

507.68
Chemical Name

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

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

Patupilone
Solubility

Soluble in DMSO (≥102mg/mL) and Ethanol (≥102mg/mL). Practically insoluble in Water (<1mg/mL).

Appearance

White Crystal Powder

Shipping and Storage

Store Temp

-20°C
Ship Temp

Ambient

Downloads

MSDS

E6257 MSDS PDF
Info Sheet

E6257 Info Sheet PDF

References

Ruschel J, Hellal F, Flynn KC, et al. Systemic administration of epothilone B promotes axon regeneration after spinal cord injury. Science. 2015 Mar 12. [Epub ahead of print]. PMID: 25765066.

Prota AE, Bargsten K, Zurwerra D, et al. Molecular mechanism of action of microtubule-stabilizing anticancer agents. Science. 2013 Feb 1;339(6119):587-90. PMID: 23287720.

Entwistle RA, Rizk RS, Cheng DM, et al. Differentiating between models of epothilone binding to microtubules using tubulin mutagenesis, cytotoxicity, and molecular modeling. ChemMedChem. 2012 Sep;7(9):1580-6. PMID: 22807375.

Pagano A, Honoré S, Mohan R, et al. Epothilone B inhibits migration of glioblastoma cells by inducing microtubule catastrophes and affecting EB1 accumulation at microtubule plus ends. Biochem Pharmacol. 2012 Aug 15;84(4):432-43. PMID: 22634050.

Edelman MJ, Shvartsbeyn M. Epothilones in development for non--small-cell lung cancer: novel anti-tubulin agents with the potential to overcome taxane resistance. Clin Lung Cancer. 2012 May;13(3):171-80. PMID: 22133291

Kelly WK. Epothilones in prostate cancer. Urol Oncol. 2011 Jul-Aug;29(4):358-65. PMID: 19914096.

Khrapunovich-Baine M, Menon V, Yang CP, et al. Hallmarks of molecular action of microtubule stabilizing agents: effects of epothilone B, ixabepilone, peloruside A, and laulimalide on microtubule conformation. J Biol Chem. 2011 Apr 1;286(13):11765-78. PMID: 21245138.

Lee JJ, Kelly WK. Epothilones: tubulin polymerization as a novel target for prostate cancer therapy. Nat Clin Pract Oncol. 2009 Feb;6(2):85-92. PMID: 19048010.

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