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Spectroscopic studies of cutaneous photo sensitizing agents 2. spin trapping of photolysis products from sulfanilamide and 4 amino benzoic acid using 5 5 di methyl 1 pyrroline 1 oxide


, : Spectroscopic studies of cutaneous photo sensitizing agents 2. spin trapping of photolysis products from sulfanilamide and 4 amino benzoic acid using 5 5 di methyl 1 pyrroline 1 oxide. Photochemistry and Photobiology 34(2): 147-156

Photodecomposition of sulfanilamide [an antibacterial drug], 4-aminobenzoic acid [a component of sunscreen preparations] and related analogs in aqueous solution was studied with spin traps 5,5-dimethyl-1-pyrroline-1-oxide (DMPO) and CH3NO2 and, by direct ESR techniques. The .ovrhdot.NH2 radical was trapped by DMPO during the photolysis of aqueous solutions of sulfanilamide with a Xe arc lamp. Studies with [15N1]-sulfanilamide indicated that the .ovrhdot.NH2 radical was generated by homolytic fission of the S-N bond. Under the same conditions DMPO trapped the H. and SO3.- radicals during photolysis of sulfanic acid. Direct photolysis of sulfanilamide, sulfanilic acid and Na2SO3 in the absence of any spin trap yielded the SO3.- radical. Photolysis of 4-aminobenzoic acid at pH 7 gave the H. radical which was trapped by DMPO. At low pH values OH. and .ovrhdot.C6H4 COOH radicals were generated during the photolysis of 4-aminobenzoic acid. No eaq- [aqueous electrons] were trapped by CH3NO2 when acid (pH 4) and neutral aqueous solutions of sulfanilamide or 4-aminobenzoic acid were photoirradiated. Mechanism of formation of known photoproducts from the free radicals generated by sulfanilamide and 4-aminobenzoic acid during irradiation are discussed. The free radicals generated by these agents may play an important role in their phototoxic and photoallergic effects in animals.

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