Membrane actions of male contraceptive gossypol tautomers

Juan Reyes, Steven D. Wyrick, Laura Borriero, Dale J. Benos

Research output: Contribution to journalArticlepeer-review

23 Scopus citations


The role of different gossypol tautomers in the interaction of this molecule with membranes has been investigated using the isolated hemiacetal moiety of gossypol and the pH dependency of the keto-enol tautomeric equilibrium. Our results indicate that: (a) the actions of the hemiacetal tautomer cannot explain the effects of gossypol on mitochondrial oxidative phosphorylation, lipid membrane interfacial potentials, and proton conductance of lipid bilayers; (b) the enolate forms of gossypol are the species that bind to the membrane interface and decrease the electrostatic interfacial potential; and (c) the uncharged (keto and/or enol) species in equilibrium with the enolate forms of gossypol give the molecule the ability to carry protons across biological membranes.

Original languageEnglish
Pages (from-to)101-109
Number of pages9
JournalBiochimica et Biophysica Acta - Biomembranes
Issue number1
StatePublished - 1 Dec 1986
Externally publishedYes


  • Gossypol tautomer
  • Membrane interaction
  • Membrane potential
  • Oxidative phosphorylation
  • Phosphorylation


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