Epothilone B (EPO906, Patupilone)
Epothilone B (EPO906, Patupilone; CAS 152044-54-7) is a naturally occurring macrocyclic lactone initially isolated from the myxobacterium Sorangium cellulosum. Sharing a mechanism of action similar to paclitaxel, Epothilone B stabilizes microtubules, thereby inhibiting cellular mitosis. In vitro, Epothilone B displays potent cytotoxic activity with an EC0.01 of approximately 1.8 nM. Importantly, Epothilone B effectively counters resistance mediated via P-glycoprotein, which confers paclitaxel resistance, and exhibits superior aqueous solubility compared to paclitaxel. Research indicates Epothilone B treatment elevates intracellular free calcium and cytosolic cytochrome C in ovarian cancer SKOV-3 cells, highlighting its utility as a research tool in cancer biology and chemotherapy resistance studies.
| Physical Appearance | A solid |
| Storage | Store at -20°C |
| M.Wt | 507.68 |
| Cas No. | 152044-54-7 |
| Formula | C27H41NO6S |
| Solubility | ≥25.4 mg/mL in DMSO; insoluble in H2O; ≥12.44 mg/mL in EtOH |
| 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 |
| SDF | Download SDF |
| Canonical SMILES | CC1CCCC2(C(O2)CC(OC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C)C |
| Shipping Condition | Small Molecules with Blue Ice, Modified Nucleotides with Dry Ice. |
| General tips | We do not recommend long-term storage for the solution, please use it up soon. |
| Kinase experiment [1]: | |
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Tubulin polymerization assay |
Calf brain microtubule proteins (MTP) were purified, which included approximately 15% ~ 20% microtubule associated proteins. The buffer (MES buffer) used for the Epothilone B-microtubule studies contained 0.1 M 2-morpholinoethanesulfonic acid (MES), 1 mM EGTA, 0.5 mM MgCl2 and 3 M glycerol at pH 6.6. Samples for electron microscopy were placed on carbon-over-Parlodion-coated grids (300 mesh) and negatively stained with 2% uranyl acetate. Microtubule assembly in the presence or absence of Epothilone B was monitored spectrophotometrically by using a spectrophotometer equipped with a thermostatically regulated liquid circulator. The temperature was held at 35 °C and changes in turbidity (representative of polymer mass) were monitored at 350 nm. |
| Cell experiment [2]: | |
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Cell lines |
Hs578T and Hela cells |
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Preparation method |
The solubility of this compound in DMSO is > 25.4 mg/mL. General tips for obtaining a higher concentration: Please warm the tube at 37 °C for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below - 20 °C for several months. |
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Reacting condition |
100 nM; 24 hrs |
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Applications |
In Hs578T and Hela cells, Epothilone B arrested cells at the G2-M phase, causing cytotoxicity. In Hs578T cells treated with Epothilone B, there was a larger percentage (up to 38%) of cells showing multimininucleation. |
| Animal experiment [3]: | |
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Animal models |
Mouse xenograft models of RPMI 8226 cells |
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Dosage form |
1-time dose at 4 mg/kg or weekly dose at 2.5 mg/kg (given on days 6, 13, 20 and 27); i.v. |
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Applications |
In mouse xenograft models of RPMI 8226 cells, Epothilone B (2.5 ~ 4 mg/kg) prolonged survival and inhibited tumor growth. |
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Other notes |
Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
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References: [1]. Regueiro-Ren A1, Borzilleri RM, Zheng X, Kim SH, Johnson JA, Fairchild CR, Lee FY, Long BH, Vite GD. Synthesis and biological activity of novel epothilone aziridines. Org Lett. 2001 Aug 23;3(17):2693-6 [2]. Bollag DM, McQueney PA, Zhu J, Hensens O, Koupal L, Liesch J, Goetz M, Lazarides E, Woods CM. Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action. Cancer Res. 1995 Jun 1;55(11):2325-33. [3]. Lin B, Catley L, LeBlanc R, Mitsiades C, Burger R, Tai YT, Podar K, Wartmann M, Chauhan D, Griffin JD, Anderson KC. Patupilone (epothilone B) inhibits growth and survival of multiple myeloma cells in vitro and in vivo. Blood. 2005 Jan 1;105(1):350-7. |
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| Description | Epothilone B is a macrolide antitumor agent with microtubule-stabilizing activity. | |||||
| Targets | Hs578T cells | HeLa cells | KB3-1 cells | KBV-1 cells | ||
| IC50 | 3 nM | 32 nM | 16 nM | 92 nM | ||
Quality Control & MSDS
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Chemical structure
