Importance of thiols in the reductive binding of 2-nitroimidazoles to macromolecules

Biochem Pharmacol. 1990 Dec 1;40(11):2457-64. doi: 10.1016/0006-2952(90)90086-z.

Abstract

Reductive activation of 2-nitroimidazoles in the presence of bovine serum albumin (BSA) led to binding of the nitroheterocycles to the protein. The binding was most efficient to BSA in which protein disulfides had been reduced to thiol groups. Protein thiols were at least twenty times more efficient than other protein, RNA or DNA nucleophiles in binding the reductively-activated nitroheterocycles. This result is of practical importance in the development of immunoassays for 2-nitroimidazoles as hypoxia markers in normal and tumor tissue.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Glyoxal / metabolism
  • Hydroxides
  • Hydroxyl Radical
  • Nitroimidazoles / metabolism*
  • Oxidation-Reduction
  • Oxygen / pharmacology
  • Protein Binding
  • Serum Albumin, Bovine / metabolism
  • Sulfhydryl Compounds / metabolism*

Substances

  • Hydroxides
  • Nitroimidazoles
  • Sulfhydryl Compounds
  • Serum Albumin, Bovine
  • Hydroxyl Radical
  • Glyoxal
  • Oxygen