A steroid glycoside with diverse biological activities
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Cinobufotalin

Item No. 19845

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
16β-(acetyloxy)-14,15β-epoxy-3β,5β-dihydroxy-bufa-20,22-dienolide
CAS Number
1108-68-5
Synonyms
  • NSC 90326
Molecular Formula
C26H34O7
Formula Weight
458.6
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMF:PBS (pH 7.2) (1:1): 0.5 mg/mlDMSO: 5 mg/mlEthanol: 5 mg/ml
λmax
296 nm
SMILES
O[C@H]1CC[C@@]2(C)[C@@](CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@]3(O5)[C@H]5[C@H](OC(C)=O)[C@@H]4C6=COC(C=C6)=O)(O)C1
InChi Code
InChI=1S/C26H34O7/c1-14(27)32-21-20(15-4-5-19(29)31-13-15)24(3)10-7-17-18(26(24)22(21)33-26)8-11-25(30)12-16(28)6-9-23(17,25)2/h4-5,13,16-18,20-22,28,30H,6-12H2,1-3H3/t16-,17-,18+,20-,21+,22+,23+,24+,25-,26+/m0/s1
InChi Key
KBKUJJFDSHBPPA-ZNCGZLKOSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Cinobufotalin is a steroid glycoside originally isolated from the Asiatic toad (B. gargarizans) and has diverse biological activities.1,2 It reduces SRC-3 protein levels in MCF-7 breast cancer cells when used at concentrations ranging from 10 to 100 nM.1 Cinobufotalin (1 μM) reduces Na+/K+ pump activity, viability, and cell attachment of C7-MDCK cells.2 It reduces expression of the epithelial-mesenchymal (EMT) markers E-cadherin, vimentin, ZEB1, and Slug in and migration and invasion of PC3 cells.3 Cinobufotalin (0.1-10 μM) is cytotoxic to A549, H460, and HTB-58 lung cancer cells.4 In vivo, cinobufotalin (1 and 5 mg/kg) reduces tumor volume and increases survival in an A549 mouse xenograft model.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Wang, Y., Lonard, D.M., Yu, Y., et al. Bufalin is a potent small-molecule inhibitor of the steroid receptor coactivators SRC-3 and SRC-1. Cancer Res. 74(5), 1506-1517 (2014).

    2. Akimova, O.A., Bagrov, A.Y., Lopina, O.D., et al. Cardiotonic steroids differentially affect intracellular Na+ and [Na+]i/[K+]i-independent signaling in C7-MDCK cells. The Journal of Biological Chemisty 280(1), 832-839 (2005).

    3. Chen, L., Mai, W., Chen, M., et al. Arenobufagin inhibits prostate cancer epithelial-mesenchymal transition and metastasis by down-regulating β-catenin. Pharmacol. Res. 123, 130-142 (2017).

    4. Kai, S., Lu, J.-H., Hui, P.-P., et al. Pre-clinical evaluation of cinobufotalin as a potential anti-lung cancer agent. Biochem. Biophys. Res. Commun. 452(3), 768-774 (2014).