Therapeutic potential of gossypol: An overview

References

• Adams R, Geissman TA, Edwards JD. (1960). Gossypol, a pigment of cottonseed. Chem Rev 60:555–74
   PubMed Web of Science ®Google Scholar
• Balakrishnan K, Wierda WG, Keating MJ, Gandhi V. (2008). Gossypol, a BH3 mimetic, induces apoptosis in chronic lymphocytic leukemia cells. Blood 112:1971–80
   PubMed Web of Science ®Google Scholar
• Bi XF, Ye YX, Yang HF, Zhang ZR. (1981). Preliminary study on gossypol induced hypokalemia. Zhongguo Yi Xue Ke Xue Yuan Xue Bao 3:175–78
   PubMedGoogle Scholar
• Coutinho EM. (2002). Gossypol: A contraceptive for men. Contraception 65:259–63
   PubMed Web of Science ®Google Scholar
• Dodou K. (2005). Investigations on gossypol: Past and present developments. Expert Opin Investig Drugs 14:1419–34
   PubMed Web of Science ®Google Scholar
• Dodou K, Anderson RJ, Lough WJ, et al. (2005). Synthesis of gossypol atropisomers and derivatives and evaluation of their antiproliferative and antioxidant activity. Expert Opin Investig Drugs 13:4228–37
   Google Scholar
• Flack MR, Pyle RG, Mullen NM, et al. (1993). Oral gossypol in the treatment of metastatic adrenal cancer. J Clin Endocrinol Metab 76:1019–24
   PubMed Web of Science ®Google Scholar
• Freedman TB, Cao X, Oliviera RV, et al. (2003). Determination of the absolute configuration and solution conformation of gossypol by vibrational circular dichroism. Chirality 15:196–200
   PubMed Web of Science ®Google Scholar
• Gonzalez-Garza MT, Matlin SA, Mata-Cardenas B, Said-Fernandez S. (1993). Differential effects of the (+) and (−)-gossypol enantiomers upon Entamoeba histolytica axenic cultures. J Pharm Pharmacol 45:144–5
   PubMed Web of Science ®Google Scholar
• Hove EL. (1944). Gossypol as a carotene-protecting antioxidant, in vivo and in vitro. J Biol Chem 156:633–42
   Google Scholar
• Hove EL, Hove Z. (1944). A method for estimating total fat-soluble antioxidants based on the relation between fat peroxides and carotene destruction. J Biol Chem 156:611–22
   Google Scholar
• Ikeda M. (1990). Inhibition kinetics of NAD-linked enzymes by gossypol acetic acid. Andrologia 22:409–16
   PubMed Web of Science ®Google Scholar
• James AK. (2006). Reaction chemistry of gossypol and its derivatives. JAOCS 83:269–302
   Web of Science ®Google Scholar
• Jaroszewski JW, Strom-Hansen T, Hansen SH, et al. (1992a). On the botanical distribution of chiral forms of gossypol. Planta Med 58:454–8
   PubMed Web of Science ®Google Scholar
• Jaroszewski JW, Strom-Hansen T, Hansen LL. (1992b). Optical stability of gossypol. Chirality 4:216–21
   Web of Science ®Google Scholar
• Keniry MA, Hollander C, Benz CC. (1989). The effect of gossypol and 6-aminonicotinamide on tumor cell metabolism: A 31P-magnetic resonance spectroscopic study. Biochem Biophys Res Commun 164:947–53
   PubMed Web of Science ®Google Scholar
• King TJ, de Silva LB. (1968). Optically active gossypol from Thespesia populnea. Tet Lett 3:261–3
   Google Scholar
• Kitada S, Leone M, Sareth S, et al. (2003). Discovery, characterization, and structure–activity relationships studies of proapoptotic polyphenols targeting B-cell lymphocyte/leukemia-2 proteins. J Med Chem 46:4259–64
   PubMed Web of Science ®Google Scholar
• Laughton MJ, Halliwell B, Evans PJ, Hoult JR. (1989). Antioxidant and prooxidant actions of the phenolics quercetin, gossypol, and myricetin. Biochem Pharmacol 38:2859–65
   PubMed Web of Science ®Google Scholar
• Li A, Bandy B, Tsang SS, Davison AJ. (2000). DNA-breaking versus DNA-protecting activity of four phenolic compounds in vitro. Free Rad Res 33:551–66
   PubMed Web of Science ®Google Scholar
• Ligueros M, Jeoun D, Tang B, et al. (1997). Gossypol inhibition of mitosis, cyclin D1 and Rb protein in human mammary cancer cells and cyclin D1 transfected human fibrosarcoma cells. Br J Cancer 76:21–8
   PubMed Web of Science ®Google Scholar
• Lin TS, Schinazi RF, Zhu J, et al. (1993). Anti-HIV-1 activity and cellular pharmacology of various analogs of gossypol. Biochem Pharmacol 46:251–5
   PubMed Web of Science ®Google Scholar
• Lin TS, Schinazi R, Griffith BP, et al. (1989). Selective inhibition of human immunodeficiency virus type 1 replication by the (−) but not the (+) enantiomer of gossypol. Antimicrob Agents Chemother 33:2149–51
   PubMed Web of Science ®Google Scholar
• Liu S, Kulp SK, Sugimoto Y, et al. (2002). The (−)-enantiomer of gossypol possesses higher anticancer potency than racemic gossypol in human breast cancer. Anticancer Res 22:33–8
   PubMed Web of Science ®Google Scholar
• Longmore J. (1886). Cotton seed oil: Its colouring matter and mucilage, and description of a new method of recovering the loss occurring in the refining process. J Chem Ind 5:200–6
   Google Scholar
• Marchlewski L. (1899). Gossypol, ein Bestandtheil der Baumwollsamen. J Prakt Chem 60:84–94
   Google Scholar
• Margalith P. (1967). Inhibitory effect of gossypol on microorganisms. Appl Microbiol 15:952–3
   PubMedGoogle Scholar
• McClarty GA, Chan AK, Creasy DC, Wright JA. (1985). Ribonucleotide reductase: An intracellular target for the male antifertility agent, gossypol. Biochem Biophys Res Commun 133:300–5
   PubMed Web of Science ®Google Scholar
• Mendis K, Sina BJ, Marchesini P, Carter R. (2001). The neglected burden of Plasmodium vivax malaria. Am J Trop Med Hyg 64:97–106
   PubMed Web of Science ®Google Scholar
• Meng Y, Tang W, Dai Y, et al. (2008). Natural BH3 mimetic (−)-gossypol chemosensitizes human prostate cancer via Bcl-xL inhibition accompanied by increase of Puma and Noxa. Mol Cancer Ther 7:2192–202
   PubMed Web of Science ®Google Scholar
• Moon DO, Kim MO, Choi YH, et al. (2008a). Gossypol suppresses telomerase activity in human leukemia cells via regulating hTERT. FEBS Lett 582:3367–73
   PubMed Web of Science ®Google Scholar
• Moon DO, Kim MO, Lee JD, Kim GY. (2008b). Gossypol suppresses NF-kappaB activity and NF-kappaB-related gene expression in human leukemia U937 cells. Cancer Lett 264:192–200
   PubMed Web of Science ®Google Scholar
• Montamat EE, Burgos C, Gerez de Burgos NM, et al. (1982). Inhibitory action of gossypol on enzymes and growth of Trypanosoma cruzi. Science 218:288–9
   PubMed Web of Science ®Google Scholar
• Oliver CL, Bauer JA, Wolter KG, et al. (2004). In vitro effects of the BH3 mimetic, (−)-gossypol, on head and neck squamous cell carcinoma cells. Clin Cancer Res 10:7757–63
   PubMed Web of Science ®Google Scholar
• Prasad MRN, Diczfalusy E. (1982). Gossypol. Int J Androl 5:53–70
   Google Scholar
• Qian S-Z, Wang, Z-G. (1984). Gossypol: A potential antifertility agent for males. Ann Rev Pharm Toxicol 24:329–60
   PubMed Web of Science ®Google Scholar
• Razakantoanina V, Nguyen Kim PP, Jaureguiberry G. (2000). Antimalarial activity of new gossypol derivatives. Parasitol Res 86:665–8
   PubMed Web of Science ®Google Scholar
• Rosenberg LJ, Adlakha RC, Desai DM, Rao PN. (1986). Inhibition of DNA polymerase alpha by gossypol. Biochim Biophys Acta 866:258–67
   PubMed Web of Science ®Google Scholar
• Royer RE, Deck LM, Campos NM, et al. (1986). Biologically active derivatives of gossypol: Synthesis and antimalarial activities of peri-acylated gossylic nitriles. J Med Chem 29:1799–801
   PubMed Web of Science ®Google Scholar
• Shandilya LN, Clarkson TB, Adams MR, Lewis JC. (1982). Effects of gossypol on reproductive and endocrine functions of male cynomolgus monkeys (Macaca fascicularis). Biol Reprod 27:241–52
   PubMed Web of Science ®Google Scholar
• Shidaifat F, Canatan H, Kulp S, et al. (1997). Gossypol arrests human benign prostatic hyperplastic cell growth at G0/G1 phase of the cell cycle. Anticancer Res 17:1003–9
   PubMed Web of Science ®Google Scholar
• Stipanovic R, Stoessl A, Stothers JB, et al. (1986). The stereochemistry of the biosynthetic precursor of gossypol. J Chem Soc Chem Commun 2:100–2
   Google Scholar
• Taylor GT, Griffin MG, Bardgett M. (1991). Search for a male contraceptive: The effect of gossypol on sexual motivation and epididymal sperm. J Med 22:29–44
   PubMedGoogle Scholar
• Teng CS. (1995). Gossypol-induced apoptotic DNA fragmentation correlates with inhibited protein kinase C activity in spermatocytes. Contraception 52:389–95
   PubMed Web of Science ®Google Scholar
• Tso W-W. (1984). Gossypol inhibits Erhlich ascites tumour cells. Cancer Lett 24:257–61
   PubMed Web of Science ®Google Scholar
• Tuszynski GP, Cossu G. (1984). Differential cytotoxic effect of gossypol on human melanoma, colon carcinoma, and other tissue culture cell lines. Cancer Res 44:768–71
   PubMed Web of Science ®Google Scholar
• Ueno H, Sahni MK, Segal SJ, Koide SS. (1988). Interaction of gossypol with sperm macromolecules and enzymes. Contraception 37:333–41
   PubMed Web of Science ®Google Scholar
• Vadehra DV, Kalla NR, Saxena M, et al. (1985). Antimicrobial activity of gossypol acetic acid. IRCS Med Sci 13:10–11
   Google Scholar
• Vainio P, Thuren T, Wichman K, et al. (1985). Hydrolysis of phospholipids monolayers by human spermatozoa: Inhibition by male contraceptive gossypol. Biochim Biophys Acta 814:405–8
   PubMedGoogle Scholar
• Vander Jagt DL, Deck LM, Royer RE. (2000). Gossypol: Prototype of inhibitors targeted to dinucleotide folds. Curr Med Chem 7:479–98
   PubMed Web of Science ®Google Scholar
• Wang X, Beckham T, Morris J, et al. (2008). Bioactivities of gossypol, 6-methoxy gossypol and 6,6′-dimethoxy gossypol. J Agric Food Chem 56:4393–8
   PubMed Web of Science ®Google Scholar
• Wang X, Howell CP, Chen F, et al. (2009). Gossypol a polyphenolic compound from cotton plants. Adv Food Nutr Res 58:215–63
   PubMedGoogle Scholar
• Wang YC, Rao PN. (1984). Effect of gossypol on DNA synthesis and cell cycle progression of mammalian cells in vitro. Cancer Res 44:35–8
   PubMed Web of Science ®Google Scholar
• Xu LY, Wang S, Tang W, et al. (2005). (−)-Gossypol enhances response to radiation therapy and results in tumor regression of human prostate cancer. Mol Cancer Ther 4:197–205
   PubMed Web of Science ®Google Scholar
• Yu Y, Deck A, Hunsaker LA, et al. (2001). Selective active site inhibitors of human lactate dehydrogenases A4, B4 and C4. Biochem Pharmacol 62:81–9
   PubMed Web of Science ®Google Scholar
• Zhai D, Jin C, Satterthwait AC, Reed JC. (2006). Comparison of chemical inhibitors of antiapoptotic Bcl2 family proteins. Cell Death Differ 13:1419–21
   PubMed Web of Science ®Google Scholar