S. Hecht, C. H. B. Chen, D. Hoffmann
1978
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Influential Citations
58
Citations
Journal
Cancer Research
Abstract
Abstract Metabolic α hydroxylation of cyclic nitrosamines is important in the activation of these compounds to their ultimate carcinogenic forms. Direct evidence for this process is presented. Both α-hydroxynitrosopyrrolidine and 3-formyl-1-propanediazohydroxide, which are unstable intermediates resulting from α hydroxylation of nitrosopyrrolidine, were generated in aqueous solution from the stable precursors α-acetoxynitrosopyrrolidine and 4-( N -carbethoxy- N -nitrosamino)butanal. The major product resulting from the decomposition of α-hydroxynitrosopyrrolidine and 3-formyl-1-propanediazohydroxide was 2-hydroxytetrahydrofuran, the cyclic hemiacetal of 4-hydroxybutyraidehyde. The same product was isolated as its dinitrophenylhydrazone derivative after incubation of rat liver microsomes with nitrosopyrrolidine and after treatment of rats with nitrosopyrrolidine.