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.
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.
Alvarez-Sánchez
Rubén
R
Laboratoire de Dermatochimie (UMR 7123), Université Louis Pasteur, Clinique Dermatologique, CHU, Strasbourg, France
Basketter
David
D
Pease
Camilla
C
Lepoittevin
Jean Pierre
JP
D001665:Binding Sites / Q000502:physiology; D002247:Carbon Isotopes; D017449:Dermatitis, Allergic Contact / Q000378:metabolism*; D005978:Glutathione / Q000737:chemistry / Q000378:metabolism*; D010455:Peptides / Q000737:chemistry / Q000378:metabolism; D013844:Thiazoles / Q000737:chemistry / Q000378:metabolism*
D002247:Carbon Isotopes; D010455:Peptides; D013844:Thiazoles; C011506:2-methyl-4-isothiazolin-3-one; C011421:5-chloro-2-methyl-4-isothiazolin-3-one; D005978:Glutathione