Covalent binding of the 13C-labeled skin sensitizers 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) to a model peptide and glutathione

Bioorg Med Chem Lett. 2004 Jan 19;14(2):365-8. doi: 10.1016/j.bmcl.2003.11.002.

Abstract

The reactivity of 4-[13C]- and 5-[13C]-5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI) towards a model peptide and glutathione was followed by 13C and 1H[13C] NMR spectroscopy. Both molecules were found to react with GSH but in addition MCI was found to react with histidine and lysine to form adducts of a different nature. Reaction with histidine led to stable substitution adducts through an addition-elimination reaction at position 5 while reaction with lysine led to the formation of open adducts of the thioamide or amide type.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Binding Sites / physiology
  • Carbon Isotopes
  • Dermatitis, Allergic Contact / metabolism*
  • Glutathione / chemistry
  • Glutathione / metabolism*
  • Peptides / chemistry
  • Peptides / metabolism
  • Thiazoles / chemistry
  • Thiazoles / metabolism*

Substances

  • Carbon Isotopes
  • Peptides
  • Thiazoles
  • 2-methyl-4-isothiazolin-3-one
  • 5-chloro-2-methyl-4-isothiazolin-3-one
  • Glutathione