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Spectroscopic studies of cutaneous photo sensitizing agents 1. spin trapping of photolysis products from sulfanilamide 4 amino benzoic acid and related compounds



Spectroscopic studies of cutaneous photo sensitizing agents 1. spin trapping of photolysis products from sulfanilamide 4 amino benzoic acid and related compounds



Photochemistry and Photobiology 32(5): 563-572



The photodecomposition of sulfanilamide, 4-aminobenzoic acid and other related analogs was studied with the aid of the spin trap 2-methyl-2-nitrosopropane. UV photolysis of an aqueous solution of sulfanilamide yielded the following radicals .ovrhdot.C6H4SO2NH2, C6H5SO.ovrhdot.2, .ovrhdot.SO2NH2 and .**GRAPHIC**. (or .**GRAPHIC**. Under the same conditions 4-aminobenzoic acid gave .ovrhdot.C6H4COOH. Sulfanilamide and 4-aminobenzoic acid, but not 4-dimethylaminobenzoic acid, generated .**GRAPHIC**. or H during UV irradiation. The .ovrhdot.C6H4SO2NH2 radical was produced by photolysis of 4-iodobenzenesulfonamide and 4-nitrobenzenesulfonamide. The .ovrhdot.C6H4COOH radical was generated by photolysis of 4-nitrobenzoic acid and 4-iodobenzoic acid. The .ovrhdot.C6H4NO2 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 humans.

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