Voacamine

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].

Product Specifications

CAS Number

[3371-85-5]

UNSPSC

12352005

Target

Akt; Apoptosis; Autophagy; Cannabinoid Receptor; EGFR; mTOR; P-glycoprotein; PI3K

Type

Natural Products

Related Pathways

Apoptosis; Autophagy; GPCR/G Protein; JAK/STAT Signaling; Membrane Transporter/Ion Channel; Neuronal Signaling; PI3K/Akt/mTOR; Protein Tyrosine Kinase/RTK

Applications

Metabolism-protein/nucleotide metabolism

Field of Research

Cancer; Metabolic Disease

Assay Protocol

https://www.medchemexpress.com/voacamine.html

Purity

99.64

Solubility

DMSO : ≥ 100 mg/mL

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

Molecular Formula

C43H52N4O5

Molecular Weight

704.90

References & Citations

[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.|[2]Pellegrini, E., et al., (2022) . A natural product, voacamine, sensitizes paclitaxel-resistant human ovarian cancer cells. Toxicology and applied pharmacology, 434, 115816.|[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. |[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. |[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.