An antimicrotubule agent
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Epothilone A

Item No. 16482

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1S,16R)-7S,11S-dihydroxy-8,8,10R,12S-tetramethyl-3S-[(1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione
CAS Number
152044-53-6
Synonyms
  • Epo A
Molecular Formula
C26H39NO6S
Formula Weight
493.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 15 mg/mlEthanol: 20 mg/mlEthanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
λmax
211, 250 nm
SMILES
C/C([C@H](C[C@H]1[C@H](O1)CCC[C@@]2(C)[H])OC(C[C@H](O)C(C([C@@H]([C@H]2O)C)=O)(C)C)=O)=C\C3=CSC(C)=N3
InChi Code
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
InChi Key
HESCAJZNRMSMJG-KKQRBIROSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    10 mg

    $236

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    Product Description

    Epothilone A (Epo A) is a biologically active macrolide produced from the fermentation of the soil bacteria S. cellulosum that was discovered as a potent antimicrotubule agent.1,2,3 In competition assays, epo A binds to β-tubulin with a similar order of magnitude as the binding of paclitaxel (Item No. 10461) to β-tubulin (IC50s = 2.3 and 3.6 µM, respectively).1,2,3,4 Epo A is cytotoxic to human T-24 bladder carcinoma cells (IC50 = 0.05 µM in vitro) but has poor pharmacological properties and is 2-fold less potent in stabilizing microtubules compared to epothilone B (Item No. 10924).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Cheng, K.L., Bradley, T., and Budman, D.R. Novel microtubule-targeting agents - the epothilones. Biologics 2(4), 789-811 (2008).

    2. Bollag, D.M., McQueney, P.A., Zhu, J., et al. Epothilones, a new class of microtubule-stabilizing agents with a taxol-like mechanism of action. Cancer Res. 55(11), 2325-2333 (1995).

    3. Goodin, S., Kane, M.P., and Rubin, E.H. Epothilones: Mechanism of action and biologic activity. J. Clin. Oncol. 22(10), 2015-2025 (2011).

    4. Kowalski, R.J., Giannakakou, P., and Hamel, E. Activities of the microtubule-stabilizing agents epothilones A and B with purified tubulin and in cells resistant to paclitaxel (Taxol(R)). The Journal of Biological Chemisty 272(4), 2534-2541 (1997).