3371-85-5
Chemical Structure
Voacamine
- CAS No.: 3371-85-5
- Formula:C43H52N4O5
- Molecular Weight:704.90
IUPAC Name: methyl (6R,6aR,7R,11S)-7-ethyl-3-((2R,6R,8R,14S,E)-5-ethylidene-14-(methoxycarbonyl)-3-methyl-2,3,4,5,6,7,8,9-octahydro-1H-2,6-methanoazecino[5,4-b]indol-8-yl)-2-methoxy-7,8,9,10,12,13-hexahydro-5H-6,9-methanopyrido[1',2':1,2]azepino[4,5-b]indole-6(6aH)-carboxylate
InChIKey: VCMIRXRRQJNZJT-HSZGNUMYSA-N
SMILES: O=C(OC)[C@]1([C@@H]2[N@](CC(C[C@H]2CC)C1)CC3)C4=C3C(C=C5OC)=C(N4)C=C5[C@](C[C@@H]6[C@H](C(OC)=O)[C@H](N(C)C/C6=C/C)C7)([H])C8=C7C9=C(N8)C=CC=C9
Biological Activity: Voacamine is an indole alkaloid with cannabinoid 1 (CB1) antagonistic activity. Voacamine can inhibit nuclear translocation. Voacamine is effective in enhancing the effect of Doxorubicin (HY-15142A) as it interferes with the P-glycoprotein (P-gp) function. Voacamine promotes apoptosis-independent autophagic cell death in human osteosarcoma cells. Voacamine activates mitochondrial-associated apoptosis signaling pathway and inhibition of PI3K/Akt/mTOR signaling pathway to suppress breast cancer progression. Voacamine inhibits EGFR to exert oncogenic activity against colorectal cancer[1][2][3][4][5].
| Cat. No. | Product Name | Purity | Description | Pricing | |||||||||||||||||||
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Voacamine | 99.64% | Voacamine is an indole alkaloid with cannabinoid 1 (CB1) antagonistic activity. Voacamine can inhibit nuclear translocation. Voacamine is effective in enhancing the effect of Doxorubicin (HY-15142A) as it interferes with the P-glycoprotein (P-gp) function. Voacamine promotes apoptosis-independent autophagic cell death in human osteosarcoma cells. Voacamine activates mitochondrial-associated apoptosis signaling pathway and inhibition of PI3K/Akt/mTOR signaling pathway to suppress breast cancer progression. Voacamine inhibits EGFR to exert oncogenic activity against colorectal cancer. | ||||||||||||||||||||
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References
- [1]. Kitajima M, et al. Discovery of indole alkaloids with cannabinoid CB1 receptor antagonistic activity. Bioorg Med Chem Lett. 2011 Apr 1;21(7):1962-4. [Content Brief]
- [2]. Pellegrini, E., et al., (2022). A natural product, voacamine, sensitizes paclitaxel-resistant human ovarian cancer cells. Toxicology and applied pharmacology, 434, 115816. [Content Brief]
- [3]. Zuo, Y., et al., (2022). Activation of mitochondrial-associated apoptosis signaling pathway and inhibition of PI3K/Akt/mTOR signaling pathway by voacamine suppress breast cancer progression. Phytomedicine : international journal of phytotherapy and phytopharmacology, 99, 154015. [Content Brief]
- [4]. Meschini, S., et al., (2008). The plant alkaloid voacamine induces apoptosis-independent autophagic cell death on both sensitive and multidrug resistant human osteosarcoma cells. Autophagy, 4(8), 1020–1033. [Content Brief]
- [5]. Chen, Y., et al., (2022). Voacamine is a novel inhibitor of EGFR exerting oncogenic activity against colorectal cancer through the mitochondrial pathway. Pharmacological research, 184, 106415. [Content Brief]
