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Chemical Compound Review

gossypol     2,3,8-trihydroxy-6-methyl-4- propan-2-yl-7...

Synonyms: Pogosin, UPCMLD-DP103, No Fertil, Tash 1, Prestwick_1031, ...
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Disease relevance of gossypol


High impact information on gossypol

  • Cytogenetic analysis of gossypol acetate-induced murine myxosarcoma demonstrated a stemline of 78 chromosomes and the presence of three marker (M) chromosomes produced by robertsonian translocation [2].
  • Induction of DNA fragmentation by chelerythrine, calphostin C, and gossypol was biphasic, resulting in a sharp decline in effect at concentrations above 5 microM, 0.1 microM, and 100 microM, respectively, whereas maximal and more stable effects were observed in response to H7 (100 microM) [5].
  • The action of gossypol, a polyphenolic bisnaphthalene aldehyde, on a number of drug-sensitive and multidrug-resistant cell lines, in particular MCF-7 WT and MCF-7 ADR cells, was studied and compared to the effects of rhodamine 123 [6].
  • The resistance to rhodamine 123 and sensitivity to gossypol was also observed with cells transfected with the MDR1 gene, showing that the difference in toxicity is mainly due to the different response to the P-170 drug efflux pump [6].
  • The membranes of viable SW-13 cells exposed to gossypol became more rigid after a 1-day exposure to gossypol, the polarization constant, P, increasing from 0.229 to 0.352 [3].

Chemical compound and disease context of gossypol


Biological context of gossypol


Anatomical context of gossypol


Associations of gossypol with other chemical compounds

  • In HeLa cells pretreated with gossypol (3.4-17.5 microM) for 8-16 h we observed a dose- and time-dependent decrease (50-75%) in DNA cleavage compared to that quantified in cells treated with m-AMSA alone [18].
  • In recent years, two antispermatogenic drugs - gossypol and lonidamine (Fig. I) - have been reported to inhibit the growth of Trypanosoma cruzi in culture [19].
  • The remaining anti-aggregatory effect of endothelial cells could be prevented with the EDRF inhibitors, gossypol, haemoglobin and methylene blue [20].
  • In cotton (Gossypium hirsutum) the enzyme (+)-delta-cadinene synthase (CDNS) catalyzes the first committed step in the biosynthesis of cadinane-type sesquiterpenes, such as gossypol, that provide constitutive and inducible protection against pests and diseases [21].
  • The adenosine triphosphate (ATP) content in spermatids was reduced markedly, although lactate oxidation to CO2 and mitochondrial respiration were stimulated by gossypol [22].
  • In vitro, Bcl-2-expressing B cells from transgenic mice were more sensitive to cytotoxicity induced by apogossypol than gossypol, with LD50 values of 3 to 5 microM and 7.5 to 10 microM, respectively [23].

Gene context of gossypol


Analytical, diagnostic and therapeutic context of gossypol


  1. Lactic dehydrogenase isozymes, 31P magnetic resonance spectroscopy, and in vitro antimitochondrial tumor toxicity with gossypol and rhodamine-123. Benz, C., Hollander, C., Keniry, M., James, T.L., Mitchell, M. J. Clin. Invest. (1987) [Pubmed]
  2. Cytogenetic analysis of a gossypol-induced murine myxosarcoma. Dhaliwal, M.K., Norman, J.O., Pathak, S., Busbee, D.L. J. Natl. Cancer Inst. (1987) [Pubmed]
  3. An in vitro and in vivo study of antitumor effects of gossypol on human SW-13 adrenocortical carcinoma. Wu, Y.W., Chik, C.L., Knazek, R.A. Cancer Res. (1989) [Pubmed]
  4. Differential cytotoxic effect of gossypol on human melanoma, colon carcinoma, and other tissue culture cell lines. Tuszynski, G.P., Cossu, G. Cancer Res. (1984) [Pubmed]
  5. Induction of apoptotic DNA fragmentation and cell death in HL-60 human promyelocytic leukemia cells by pharmacological inhibitors of protein kinase C. Jarvis, W.D., Turner, A.J., Povirk, L.F., Traylor, R.S., Grant, S. Cancer Res. (1994) [Pubmed]
  6. Action of gossypol and rhodamine 123 on wild type and multidrug-resistant MCF-7 human breast cancer cells: 31P nuclear magnetic resonance and toxicity studies. Jaroszewski, J.W., Kaplan, O., Cohen, J.S. Cancer Res. (1990) [Pubmed]
  7. Prolactin-dependent mitogenesis in Nb 2 node lymphoma cells: effects of immunosuppressive cyclopeptides. Russell, D.H., Buckley, A.R., Montgomery, D.W., Larson, N.A., Gout, P.W., Beer, C.T., Putnam, C.W., Zukoski, C.F., Kibler, R. J. Immunol. (1987) [Pubmed]
  8. Gossypol: prototype of inhibitors targeted to dinucleotide folds. Vander Jagt, D.L., Deck, L.M., Royer, R.E. Current medicinal chemistry. (2000) [Pubmed]
  9. Effect of gossypol on the thyroid in young rats. Rikihisa, Y., Lin, Y.C. J. Comp. Pathol. (1989) [Pubmed]
  10. Antiproliferative activity of gossypol and gossypolone on human breast cancer cells. Gilbert, N.E., O'Reilly, J.E., Chang, C.J., Lin, Y.C., Brueggemeier, R.W. Life Sci. (1995) [Pubmed]
  11. The effect of the association of Gossypol and Lonidamine on the energy metabolism of Ehrlich ascites tumor cells. Floridi, A., D'Atri, S., Menichini, R., Marcante, M.L., Nista, A., Silvestrini, B., Caputo, A., De Martino, C. Exp. Mol. Pathol. (1983) [Pubmed]
  12. Effect of gossypol on DNA synthesis and cell cycle progression of mammalian cells in vitro. Wang, Y., Rao, P.N. Cancer Res. (1984) [Pubmed]
  13. Reversible inhibition of calcineurin by the polyphenolic aldehyde gossypol. Baumgrass, R., Weiwad, M., Erdmann, F., Liu, J.O., Wunderlich, D., Grabley, S., Fischer, G. J. Biol. Chem. (2001) [Pubmed]
  14. Gossypol induces DNA strand breaks in human fibroblasts and sister chromatid exchanges in human lymphocytes in vitro. Nordenskjöld, M., Lambert, B. J. Med. Genet. (1984) [Pubmed]
  15. Gossypol modification of Ala-1 of secreted phospholipase A2: a probe for the kinetic effects of sulfate glycoconjugates. Yu, B.Z., Rogers, J., Ranadive, G., Baker, S., Wilton, D.C., Apitz-Castro, R., Jain, M.K. Biochemistry (1997) [Pubmed]
  16. S-100 modulates Ca2+-independent phosphorylation of an endogenous protein (Mr = 19K) in brain. Qi, D.F., Kuo, J.F. J. Neurochem. (1984) [Pubmed]
  17. Gossypol, a hyperthermic sensitizer of HeLa cells. Kim, S.H., Kim, J.H., Alfieri, A.A., He, S.Q., Young, C.W. Cancer Res. (1985) [Pubmed]
  18. Modulation of 4'-(9-acridinylamino)methanesulfon-m-anisidide-induced, topoisomerase II-mediated DNA cleavage by gossypol. Adlakha, R.C., Ashorn, C.L., Chan, D., Zwelling, L.A. Cancer Res. (1989) [Pubmed]
  19. The potential of antispermatogenic drugs against trypanosomatids. Turrens, J.F. Parasitol. Today (Regul. Ed.) (1986) [Pubmed]
  20. Endothelium-derived relaxing factor (EDRF): a defence mechanism against platelet aggregation and vasospasm in human coronary arteries. Förstermann, U., Mügge, A., Alheid, U., Bode, S.M., Frölich, J.C. Eur. Heart J. (1989) [Pubmed]
  21. Antisense suppression of a (+)-delta-cadinene synthase gene in cotton prevents the induction of this defense response gene during bacterial blight infection but not its constitutive expression. Townsend, B.J., Poole, A., Blake, C.J., Llewellyn, D.J. Plant Physiol. (2005) [Pubmed]
  22. Metabolism of round spermatids: gossypol induces uncoupling of respiratory chain and oxidative phosphorylation. Nakamura, M., Ikeda, M., Suzuki, A., Okinaga, S., Arai, K. Biol. Reprod. (1988) [Pubmed]
  23. Bcl-2 antagonist apogossypol (NSC736630) displays single-agent activity in Bcl-2-transgenic mice and has superior efficacy with less toxicity compared with gossypol (NSC19048). Kitada, S., Kress, C.L., Krajewska, M., Jia, L., Pellecchia, M., Reed, J.C. Blood (2008) [Pubmed]
  24. Upregulation of Fas/Fas ligand-mediated apoptosis by gossypol in an immortalized human alveolar lung cancer cell line. Chang, J.S., Hsu, Y.L., Kuo, P.L., Chiang, L.C., Lin, C.C. Clin. Exp. Pharmacol. Physiol. (2004) [Pubmed]
  25. Gossypol induces Bax/Bak-independent activation of apoptosis and cytochrome c release via a conformational change in Bcl-2. Lei, X., Chen, Y., Du, G., Yu, W., Wang, X., Qu, H., Xia, B., He, H., Mao, J., Zong, W., Liao, X., Mehrpour, M., Hao, X., Chen, Q. FASEB J. (2006) [Pubmed]
  26. Effects of gossypol on the antioxidant defense system of the rat testis. Bender, H.S., Derolf, S.Z., Misra, H.P. Arch. Androl. (1988) [Pubmed]
  27. Gossypol inhibition of mitosis, cyclin D1 and Rb protein in human mammary cancer cells and cyclin-D1 transfected human fibrosarcoma cells. Ligueros, M., Jeoung, D., Tang, B., Hochhauser, D., Reidenberg, M.M., Sonenberg, M. Br. J. Cancer (1997) [Pubmed]
  28. Blockade of swelling-induced chloride channels by phenol derivatives. Gschwentner, M., Jungwirth, A., Hofer, S., Wöll, E., Ritter, M., Susanna, A., Schmarda, A., Reibnegger, G., Pinggera, G.M., Leitinger, M., Frick, J., Deetjen, P., Paulmichl, M. Br. J. Pharmacol. (1996) [Pubmed]
  29. Molecular cloning and functional identification of (+)-delta-cadinene-8-hydroxylase, a cytochrome P450 mono-oxygenase (CYP706B1) of cotton sesquiterpene biosynthesis. Luo, P., Wang, Y.H., Wang, G.D., Essenberg, M., Chen, X.Y. Plant J. (2001) [Pubmed]
  30. Synthesis and anti-HIV activity of 1,1'-dideoxygossypol and related compounds. Royer, R.E., Deck, L.M., Vander Jagt, T.J., Martinez, F.J., Mills, R.G., Young, S.A., Vander Jagt, D.L. J. Med. Chem. (1995) [Pubmed]
  31. Segmental aplasia of the mitochondrial sheath and sequelae induced by gossypol in rat spermatozoa. Oko, R., Hrudka, F. Biol. Reprod. (1982) [Pubmed]
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