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Photochemical transformations in salicylanilide photoallergy

Photochemical transformations in salicylanilide photoallergy

Photochemistry & Photobiology 47(2): 167-172

The photochemical transformations of 3,3',4',5-tetrachlorosalicylanilide, have been characterized by isolation and spectroscopic determination of the primary and secondary photoproducts. The photoreactivity cleanly involves photochemical dechlorination; three chlorines are ultimately lost in an efficient stepwise fashion. A radical mechanism was implicated by formation of a dimer and hydrogen atom abstraction from cysteine when present during photolysis. In the presence of HSA or BSA, the initial dehalogenation leads to a photoadduct with the protein, but dehalogenation of the primary photoproduct, a trichloro compound, does not lead to an efficient photobinding to protein.

Accession: 006110245

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PMID: 3344285

DOI: 10.1111/j.1751-1097.1988.tb02709.x

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