An inhibitor of microtubule assembly
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Combretastatin A1

Item No. 19750

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
3-methoxy-6-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]-1,2-benzenediol
CAS Number
109971-63-3
Synonyms
  • CA1
Molecular Formula
C18H20O6
Formula Weight
332.4
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 5 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/mlEthanol: 3 mg/ml
SMILES
COC(C(O)=C1O)=CC=C1/C=C\C2=CC(OC)=C(OC)C(OC)=C2
InChi Code
InChI=1S/C18H20O6/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h5-10,19-20H,1-4H3/b6-5-
InChi Key
YUSYSJSHVJULID-WAYWQWQTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

    $94

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    10 mg

    $157

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    25 mg

    $343

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    50 mg

    $592

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    Cayman Chemical
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    Product Description

    Combretastatin A1 is a cis-stilbene originally isolated from C. caffrum that inhibits microtubule assembly (ID50 = 2 µM) by binding to the colchicine (Item No. 9000760) binding site on β-tubulin.1,2 It inhibits proliferation of hepatocellular carcinoma (IC50s = 9.2-728.2 nM) and other carcinoma cell lines (IC50s = 12.2-2,247 nM).2 Combretastatin A1 increases apoptosis of HepG2 cells in a GSK3β-dependent manner by decreasing the levels of MCL-1 and β-catenin. It inhibits tumor growth in a hepatocellular carcinoma mouse xenograft model when administered at doses of 2 or 4 mg/kg for 4 weeks. It also enhances the effects of carboplatin (Item No. 13112), paclitaxel (Item No. 10461), and cisplatin (Item No. 13119) in murine models of cancer.3,4 Combretastatin A1 decreases functional vascular volume within hours in a well-vascularized murine colon adenocarcinoma model.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Pettit, G.R., Singh, S.B., Niven, M.L., et al. Isolation, structure, and synthesis of combretastatins A-1 and B-1, potent new inhibitors of microtubule assembly, derived from Combretum caffrum. J. Nat. Prod. 50(1), 119-131 (1987).

    2. Mao, J., Wang, D., Wang, Z., et al. Combretastatin A-1 phosphate, a microtubule inhibitor, acts on both hepatocellular carcinoma cells and tumor-associated macrophages by inhibiting the Wnt/β-catenin pathway. Cancer Lett. 380(1), 134-143 (2016).

    3. Staflin, K., Järnum, S., Hua, J., et al. Combretastatin A-1 phosphate potentiates the antitumor activity of carboplatin and paclitaxel in a severe combined immunodeficiency disease (SCID) mouse model of human ovarian carcinoma. Int. J. Gynecol. Cancer 16(4), 1557-1564 (2006).

    4. Shnyder, S.D., Cooper, P.A., Pettit, G.R., et al. Combretastatin A-1 phosphate potentiates the antitumour activity of cisplatin in a murine adenocarcinoma model. Anticancer Res. 23(2B), 1619-1623 (2003).

    5. Holwell, S.E., Cooper, P.A., Thompson, M.J., et al. Anti-tumor and anti-vascular effects of the novel tubulin-binding agent combretastatin A-1 phosphate. Anticancer Res. 22(6C), 3933-3940 (2002).