Epothilone B

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Cat.No. 3502 - Epothilone B | C27H41NO6S | CAS No. 152044-54-7
Description: Microtubule stabilization agent; promotes tubulin polymerization
Alternative Names: Patupilone
Chemical Name: (1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
Purity: ≥98% (HPLC)
Datasheet
Citations
Literature

Biological Activity

Microtubule stabilization agent that promotes tubulin polymerization and induces G2-M cell cycle arrest (EC50 = 32 nM in HeLa cells). Inhibits proliferation of human carcinoma cell lines in vitro, including MDR cells overexpressing the P-glycoprotein efflux pump. Exhibits potent cytotoxicity in MCF-7 and A549 cells (EC50 values are 0.3 and 2.7 nM respectively). Inhibits growth of HCT-15 tumors in mice in vivo.

Technical Data

M. Wt 507.68
Formula C27H41NO6S
Storage Store at -20°C
Purity ≥98% (HPLC)
CAS Number 152044-54-7
PubChem ID 448013
InChI Key QXRSDHAAWVKZLJ-PVYNADRNSA-N
Smiles CC1=NC(/C=[C@](C)/[C@@H](OC2=O)C[C@H]3[C@@](O3)(C)CCC[C@H](C)[C@H](O)[C@H](C([C@@](C)(C)[C@@H](O)C2)=O)C)=CS1

The technical data provided above is for guidance only. For batch specific data refer to the Certificate of Analysis.

All Tocris products are intended for laboratory research use only.

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 5.08 10

Preparing Stock Solutions

The following data is based on the product molecular weight 507.68. Batch specific molecular weights may vary from batch to batch due to solvent of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.97 mL 9.85 mL 19.7 mL
5 mM 0.39 mL 1.97 mL 3.94 mL
10 mM 0.2 mL 0.98 mL 1.97 mL
50 mM 0.04 mL 0.2 mL 0.39 mL

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Product Datasheets

Safety Datasheet

References

References are publications that support the products' biological activity.

Altmann et al (2000) Epothilones and related structures - a new class of microtubule inhibitors with potent in vivo antitumor activity. Biochim.Biophys.Acta 1470 M79 PMID: 10799747

O'Reilly et al (2008) Pharmacokinetic profile of the microtubule stabilizer patupilone in tumor-bearing rodents and comparison of anti-cancer activity with other MTS in vitro and in vivo. Cancer Chemother.Pharmacol. 62 1045 PMID: 18301895

Narvi et al (2013) Altered TUBB3 expression contributes to the epothilone response of mitotic cells. Br.J.Cancer 108 82 PMID: 23321512


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Keywords: Microtubule stabilization agent promotes tubulin polymerization G2-M cell cycle arrest Tau Tubulin Mitosis EpothiloneB Patupilone Microtubules

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Literature in this Area

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