Identification of carbon-centred radicals derived from linalyl hydroperoxide, a strong skin sensitizer: a possible route for protein modifications.
Few studies are reported on the formation of reactive carbon-centred radical species from toxic xenobiotics. In this paper the formation of carbon radicals derived from the skin sensitizer linalyl hydroperoxide is described using radical trapping and EPR studies. Radical trapping used TMIO as scavenger agent and light, heat or TPP-Fe(3+) as radical inducers. EPR spin trapping was based on the use of the parent alcohol, generating the same allyloxyl radical than the hydroperoxide by photolysis of the corresponding nitrite formed with t-BuONO, also playing the role of the spin trap. It is suggested that the generation of these carbon radical species could play an important role for the binding of the hydroperoxide with skin proteins to form antigenic structures, the first step of the skin sensitization mechanism.
Bezard
Michael
M
Laboratoire de Dermatochimie, Université Louis Pasteur, CNRS-UMR 7123, Clinique Dermatologique CHU, 1 Place de l'Hôpital, 67091 Strasbourg, France.
Giménez-Arnau
Elena
E
Meurer
Bernard
B
Grossi
Loris
L
Lepoittevin
Jean-Pierre
JP
D002244:Carbon / Q000737:chemistry; D003497:Cyclic N-Oxides; D004578:Electron Spin Resonance Spectroscopy; D016166:Free Radical Scavengers / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry*; D006801:Humans; D007211:Indoles; D039821:Monoterpenes / Q000737:chemistry*; D010545:Peroxides / Q000737:chemistry*; D011506:Proteins / Q000187:drug effects; D011838:Radiation-Sensitizing Agents / Q000737:chemistry* / Q000494:pharmacology; D012867:Skin / Q000737:chemistry / Q000187:drug effects*; D019097:Spin Trapping
C502049:1,1,3,3-tetramethylisoindolin-2-yloxy; D003497:Cyclic N-Oxides; D016166:Free Radical Scavengers; D005609:Free Radicals; D007211:Indoles; D039821:Monoterpenes; D010545:Peroxides; D011506:Proteins; D011838:Radiation-Sensitizing Agents; C109614:linalyl hydroperoxide; D002244:Carbon