alpha-Hydroxylation pathway in the in vitro metabolism of …
Evolution of 15N2-labeled molecular nitrogen was used to gauge the extent of alpha-hydroxylation during rat liver homogenate metabolism of doubly 15N-labeled N-nitrosodimethylamine (DMN) and N-nitrosomethylaniline (NMA).
Computational Prediction of Metabolic α-Carbon Hydroxylation …
2023年6月23日 · In this paper, we present a novel method for predicting the likelihood of α-carbon hydroxylation, one of the crucial steps in the metabolic activation of nitrosamines leading to carcinogenicity. α-Hydroxylation is the rate-limiting step in cytochrome P450 (CYP) mediated metabolic activation of nitrosamines, forming a nitrosocarbinolamine ...
Literature reported that cytochrome (CYP) P450 subfamilies are involved in nitrosamines metabolism that catalyze specifically alpha but sometimes beta hydroxylation of nitrosamine to form hydroxylated product. Reports suggest the specific relationship between cytochrome and nitrosamine metabolism.
A deep dive into historical Ames study data for N-nitrosamine …
2023年9月1日 · Mochizuki et al. (1987) investigated the decomposition of a series of alpha-acetoxy-N-nitrosamines in phosphate buffer; these compounds were shown to yield both the alpha-hydroxynitrosamine via O-alkyl fission, and the alpha-N-nitrosocarbonium ion via O-alkyl fission, which was trapped with phosphate to afford the alpha-phosphonooxynitrosamine.
alpha-Hydroxylation of nitrogen-15 labelled N-nitrosamines by …
The principal pathway of nitrosamine metabolism has long been considered to be alpha-hydroxylation. For N-nitrosodialkylamines, this hypothesis requires that a molecule of molecular nitrogen be released for every molecule of nitrosamine that is alpha-hydroxylated.
Formation and chemistry of alpha- and beta-oxidized nitrosamines
The enzymatic hydroxylation of the alpha-carbon of nitrosamines has long been held to be an important process in the formation of carcinogenic metabolites. The present work suggests, however, that there may be other processes which also result in …
An update on the current status and prospects of nitrosation …
2023年2月1日 · CYP P450 enzymes associated with hydroxylation at the α-position of the carbon atom to the N-nitroso moiety results in the formation of an N-nitrosocarbinolamine species (α-hydroxylation of nitrosamines), which subsequently decomposes to the corresponding aldehyde and diazohydroxide intermediates (enol form of nitroso primary amine).
(PDF) α-Hydroxylation pathway in the in vitro metabolism of ...
1981年11月1日 · Evolution of 15N2-labeled molecular nitrogen was used to gauge the extent of alpha-hydroxylation during rat liver homogenate metabolism of doubly 15N-labeled N-nitrosodimethylamine (DMN) and...
Developing structure-activity relationships for N-nitrosamine …
2021年11月1日 · This investigation into the structure–activity relationships responsible for differences in the relative carcinogenic potency (as defined using rodent TD 50 values) of dialkyl N-nitrosamines examined in detail the structural effects on the main driver of high-potency nitrosamines, namely α-carbon hydroxylation via metabolic activation. While ...
An Organic Chemist’s Guide to N-Nitrosamines: Their Structure ...
2021年1月21日 · Nitrosamine 2 first undergoes enzymatic α-hydroxylation with cytochrome P450 and subsequently forms the dealkylated primary nitrosamine.