G. Bellec et al., EFFECT OF THE LENGTH OF ALKYL CHAIN ON THE CYTOCHROME-P450 DEPENDENT METABOLISM OF N-DIALKYLNITROSAMINES, Cancer letters, 100(1-2), 1996, pp. 115-123
Liver microsomes from control and treated rats (P4501A, 2B, 2E1-induce
d) metabolize at variable metabolic rates eight N-nitroso-di-n-alkylam
ines, including five symmetrical (N-nitroso-dimethyl, -diethyl, -dipro
pyl, -dibutyl and -diamyl amines) and four asymmetrical (N-nitroso-met
hylethyl, methylpropyl, methylbutyl, and methylamyl-amines), into alde
hydes. Thus, the longer the alkyl chain of symmetrical N-nitrosamines,
the smaller was the metabolic rate of the corresponding aldehyde form
ation. The chain length of the alkyl group of N-nitroso-methylalkylami
nes modified the oxidation of the alkyl moiety; the oxidation by CYP2E
1 decreased as the n-alkyl chain length increased and conversely for t
he oxidation by CYP1A and CYP2B. Finally, the longer the n-alkyl chain
of asymmetrical N-nitrosamines, the greater was the oxidation of meth
yl groups.