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SPECTROSCOPIC STUDIES OF CUTANEOUS PHOTOSENSITIZING AGENTS—I. SPIN TRAPPING OF PHOTOLYSIS PRODUCTS FROM SULFANILAMIDE, 4‐AMINOBENZOIC ACID AND RELATED COMPOUNDS
Author(s) -
Chignell Colin F.,
Kalyanaraman B.,
Mason Ronald P.,
Sik Robert H.
Publication year - 1980
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.1980.tb04023.x
Subject(s) - sulfanilamide , chemistry , photodissociation , photochemistry , radical , spin trapping , aminobenzoic acid , medicinal chemistry , aqueous solution , p aminobenzoic acid , sulfanilic acid , organic chemistry , biochemistry
— The photodecomposition of sulfanilamide, 4‐aminobenzoic acid and other related analogs has been studied with the aid of the spin trap 2‐methyl‐2‐nitrosopropane. UV photolysis of an aqueous solution of sulfanilamide yielded the following radicals C˙ 6 H 4 SO 2 NH 2 , C 6 H 5 SO 2˙ , S˙O 2 NH 2 and SO ‐ #˙ (or SO ‐ 2dot; ). Under the same conditions 4‐aminobenzoic acid gave C˙ 6 H 4 COOH. In addition both sulfanilamide and 4‐aminobenzoic acid, but not 4‐dimethylaminobenzoic acid, generated e ‐ aq or hydrogen atoms during UV irradiation. The C 6 H 4 SO 2 NH 2 radical was also produced by photolysis of 4‐iodobenzenesul‐fonamide and 4‐nitrobenzenesulfonamide. The C 6 H 4 COOH radical was generated by photolysis of 4‐nitrobenzoic acid and 4‐iodobenzoic acid. Finally the C 6 H 4 NO 2 radical was formed during the irradiation of 4‐nitroaniline, 1,4‐dinitrobenzene and 4‐iodonitrobenzene. The free radicals generated by sulfanilamide and 4‐aminobenzoic acid may play an important role in the phototoxic and photoallergic responses elicited by these drugs in certain individuals.