Gossypol
Gossypol is a polyphenol found in Gossypium that exhibits anti-fertility, antimalarial, immunosuppressive, antiviral, and anticancer chemotherapeutic activities. Gossypol inhibits calcineurin, PKC, and other kinases. Gossypol is under consideration for use as a male contraceptive as it induces spermatogenesis arrest. Gossypol also inactivates HIV-1 in vitro and inhibits viral entry of H5N1 influenza virus. In vitro, gossypol inhibits ConA-induced increases in NF-κB, NFAT, and AP-1 signaling, suppressing T cell activation in vitro. Gossypol also acts as a BH3 mimetic, inhibiting Bcl-2 and Bcl-xl, inducing G2/M phase cell cycle arrest in wild type and B-RAF mutant melanoma and myeloma cells.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18928899
| Cas No. |
303-45-7 |
|---|---|
| Purity |
≥98% |
| Formula |
C30H30O8 |
| Formula Wt. |
518.55 |
| Chemical Name |
1,1,6,6,7,7-Hexahydroxy-3,3-dimethyl-5,5-bis(1- methylethyl)[2,2-binaphthalene]-8,8-dicarboxaldehyde |
| IUPAC Name |
7-(8-formyl-1,6,7-trihydroxy-3-methyl-5-propan-2-ylnaphthalen-2-yl)-2,3,8-trihydroxy-6-methyl-4-propan-2-ylnaphthalene-1-carbaldehyde |
| Synonym |
2,2-bis(8-Formyl-1,6,7-trihydroxy-5-isopropyl-3-methylnaphthalene) |
| Melting Point |
198 |
| Solubility |
Soluble in DMSO, methanol or ethanol. Insoluble in water. |
| Appearance |
Bright Yellow Powder |
Jang GH, Lee M. BH3-mimetic gossypol-induced autophagic cell death in mutant BRAF melanoma cells with high expression of p21Cip¹.). Life Sci. 2014 Apr 25;102(1):41-8. PMID: 24625733.
Song B, Huang G, Tong C, et al. Gossypol suppresses mouse T lymphocytes via inhibition of NFκB, NFAT and AP-1 pathways. Immunopharmacol Immunotoxicol. 2013 Oct;35(5):615-21. PMID: 23981004.
Lin J, Wu Y, Yang D, et al. Induction of apoptosis and antitumor effects of a small molecule inhibitor of Bcl-2 and Bcl-xl, gossypol acetate, in multiple myeloma in vitro and in vivo. Oncol Rep. 2013 Aug;30(2):731-8. PMID: 23708869.
Yang J, Chen G, Li LL, et al. Synthesis and anti-H5N1 activity of chiral gossypol derivatives and its analogs implicated by a viral entry blocking mechanism. Bioorg Med Chem Lett. 2013 May 1;23(9):2619-23. PMID: 23538114.
Coutinho EM. Gossypol: a contraceptive for men. Contraception. 2002 Apr;65(4):259-63. PMID: 12020773.
Polsky B, Segal SJ, Baron PA, et al. Inactivation of human immunodeficiency virus in vitro by gossypol. Contraception. 1989 Jun;39(6):579-87. PMID: 2473865.
Volate SR, Kawasaki BT, Hurt EM, et al. Gossypol induces apoptosis by activating p53 in prostate cancer cells and prostate tumor-initiating cells. Mol Cancer Ther. 2010 Feb;9(2):461-470. PMID: 20124455.
