Photolysis of a Mutagenic Biphenyldiquinone Derivative that Induces a Desmutagen to Trp-P-1 and Trp-P-2

Abstract

The yellow mutagen, 3,3′-di-tert-butyl-biphenyldiquinone-(2,5,2′,5′), which was formed from butylated hydroxyanisole when reacted with sodium nitrite under acidic conditions, was transformed into a red crystal by irradiation with sunlight in an ether solution. The photolytic product was identified as 2,6-di-tert-butyl-8-hydroxy-dibenzofuran-l,4-quinone from instrumental analyses. During the irradiation, two kinds of free radicals were detected by electron spin resonance spectroscopy. A photolytic reaction mechanism, in which radical intermediates participate, is proposed on the basis of the data obtained. The photolytic product showed potent desmutagenic activity to frameshift-type reverse mutations induced by Trp-P-1 and Trp-P-2 for a strain of Salmonella typhimurium TA 98.