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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Vinleurosine | Vinleurosine is an indole alkaloid with antineoplastic activity. | |||||||||||||||||||||
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Vinorelbine | Vinorelbine is an anti-mitotic agent which inhibits the proliferation of Hela cells with IC50 of 1.25 nM. | |||||||||||||||||||||
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Desacetylvinblastine hydrazide | Desacetylvinblastine hydrazide (Deacetylvinblastine hydrazide; DAVLBH) is an active component of EC145, a folate-targeted drug conjugate. Desacetylvinblastine hydrazide interferes with the formation of the mitotic spindle, and thus inhibits cell division and leads to cell death. Desacetylvinblastine hydrazide exhibits antitumor activity against folate receptor (FR)-positive tumor. | |||||||||||||||||||||
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Desacetylvinblastine | Desacetylvinblastine (4-Desacetylvinblastine) is the major metabolite of Vinblastine (HY-13780) and a cytotoxic agent. When used alone, desacetylvinblastine has poor anti-tumor effects, but it can exert significant anti-tumor activity when in the presence of specific conjugates. | |||||||||||||||||||||
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Vindesine | 98.73% | Vindesine is a derivative of Vinblastine (HY-13780). Vindesine binds to and stabilizes tubulin. Vindesine inhibits mitosis in cancer cells and prevents the invasion of normal tissues by malignant cells. Vindesine can be used in cancer research. | ||||||||||||||||||||
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Vincristine | 99.14% | Vincristine (Leurocristine; NSC-67574; 22-Oxovincaleukoblastine) is a microtubule inhibitor that disrupts microtubule polymerization by binding to β-tubulin (with a Ki of 85 nM in bovine), arrests the cell cycle and induces apoptosis. Vincristine inhibits cell replication, tumor blood flow and the proliferation of various cancer cells, while triggering effects such as oxidative stress, inflammation, calcium overload, epithelial-mesenchymal transition and peripheral neuropathic pain. Vincristine upregulates the expression of various transporters and nuclear receptors, and enriches gastric cancer stem-like cells. Vincristine is used in research related to various tumors including acute lymphoblastic leukemia, lymphoma, melanoma, gastric cancer, solid tumors and sarcomas. | ||||||||||||||||||||
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Anhydrovinblastine | Anhydrovinblastine is a monoterpenoid indole alkaloid that can be isolated from Catharanthus roseus leaves. | |||||||||||||||||||||
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Tabernaecorymbosine A | Tabernaecorymbosine A is a natural alkaloid. | |||||||||||||||||||||
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Conopharyngine | Conopharyngine (12,13-Dimethoxycoronaridine) is the indole-alkaloid that can be isolated from Tabernaemontana pachysiphon. Conopharyngine affects the functions of cardiovascular and smooth muscle, and exhibits analgesic and nervous system stimulating activity. | |||||||||||||||||||||
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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]
