An alkaloid with diverse biological activities
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Cyclovirobuxine D

Item No. 22260

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(3β,5α,16α,20S)-4,4,14-trimethyl-3,20-bis(methylamino)-9,19-cyclopregnan-16-ol
CAS Number
860-79-7
Synonyms
  • CVB-D
  • NSC 91722
Molecular Formula
C26H46N2O
Formula Weight
402.7
Purity
≥90%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 25 mg/mlDMF:PBS (pH 7.2) (1:4): 0.2 mg/mlDMSO: 0.25 mg/mlEthanol: 1 mg/ml
SMILES
C[C@H](NC)[C@@]1([H])[C@H](O)C[C@@]2(C)[C@]3([H])CC[C@@]4([H])C(C)(C)[C@@H](NC)CC[C@]4(C5)[C@]35CC[C@@]21C
InChi Code
InChI=1S/C26H46N2O/c1-16(27-6)21-17(29)14-24(5)19-9-8-18-22(2,3)20(28-7)10-11-25(18)15-26(19,25)13-12-23(21,24)4/h16-21,27-29H,8-15H2,1-7H3/t16-,17+,18-,19-,20-,21-,23+,24-,25+,26-/m0/s1
InChi Key
GMNAPBAUIVITMI-ABNIRSKTSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    Product Description

    Cyclovirobuxine D (CVB-D) is an alkaloid, and the main active component of the traditional Chinese medicine B. microphylla, that has diverse biological activities.1,2,3,4,5,6 It is an ether-a-go-go related gene (ERG) potassium channel blocker with an IC50 value of 19.7 μM using whole-cell patch-clamp electrophysiology in HEK293 cells expressing the human receptor.1 IERG blockade is activation-dependent, indicating CVB-D binds to open ERG channels. CVB-D increases the amount and rate of calcium release from intracellular stores in healthy neonatal rat cardiac myocytes and those isolated from adult rats with heart failure in a concentration-dependent manner.2 It also increases expression of ryanodine receptor 2 (Ryr2) and sarcoplasmic reticulum calcium ATPase 2a (Serca2a) and decreases expression of the sodium-calcium exchanger (Ncx). In vivo, CVB-D (0.5-2.0 mg/kg) reduces mortality and improves cardiac function in a rat model of congestive heart failure.3 CVB-D pretreatment (1 mg/kg per day for 4 days) inhibits myocardial apoptosis and mitochondrial cytochrome C release induced by doxorubicin (Item No. 15007) in mice.4 CVB-D also induces cellular autophagy and inhibits growth of MCF-7 breast cancer cells and induces mitochondrial apoptosis in MGC803 and MKN26 gastric cancer cells.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Zhao, J., Wang, Q., Xu, J., et al. Cyclovirobuxine D inhibits the currents of HERG potassium channels stably expressed in HEK293 cells. Eur. J. Pharmacol. 660(2-3), 259-267 (2011).

    2. Yu, B., Ruan, M., Zhou, L., et al. Influence of cyclovirobuxine D on intracellular [Ca2+] regulation and the expression of the calcium cycling proteins in rat myocytes. Fitoterapia 83(8), 1653-1665 (2012).

    3. Yu, B., Fang, T.-H., Lü, G.-H., et al. Beneficial effect of cyclovirobuxine D on heart failure rats following myocardial infarction. Fitoterapia 82(6), 868-877 (2011).

    4. Guo, Q., Guo, J., Yang, R., et al. Cyclovirobuxine D attenuates doxorubicin-induced cardiomyopathy by suppression of oxidative damage and mitochondrial biogenesis impairment. Oxid. Med. Cell. Longev. 2015(151972), (2015).

    5. Lu, J., Sun, D., Gao, S., et al. Cyclovirobuxine D induces autophagy-associated cell death via the Akt/mTOR pathway in MCF-7 human breast cancer cells. J. Pharmacol. Sci. 125(1), 74-82 (2014).

    6. Wu, J., Tan, Z., Chen, J., et al. Cyclovirobuxine D inhibits cell proliferation and induces mitochondria-mediated apoptosis in human gastric cancer cells. Molecules 20(11), 20659-20668 (2015).