Deoxyribonucleic acid modification by mutagenic 3-amino-1-methyl-5H-pyrido(4,3-b)indole: The chemical events.

Abstract
3-Amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) is a mutagen/carcinogen isolated from a pyrolysate of L-Trp. The active metabolite of Trp-P-2, 3-hydroxyamino-1-methyl-5H-pyrido[4,3-b]indole (N-OH-Trp-P-2), was synthesized and the chemical reactions of N-OH-Trp-P-2 with DNA were investigated. The structure of the nucleic acid base covalently bound with Trp-P-2 was elucidated as 3-(C8-guanyl)amino-1-methyl-5H-pyridol[4,3-b]indole (Gua-Trp-P-2) by comparison with a synthetic sample. The initial chemical events in carcinogenesis caused by Trp-P-2 were established.

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