ArticleChemical research in toxicology2013
Reduction of aromatic and heterocyclic aromatic N-hydroxylamines by human cytochrome P450 2S1.
Article in Chemical research in toxicology, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed, 36 citations in OpenAlex.
- Distinct Oxidoreductases Orchestrate Indolethiophene Skeleton Formation and N-Hydroxylation-Mediated Bioactivation in Thienoxidolin Biosynthesis.Angewandte Chemie (International ed. in English) · 2026Article
- Role of P450 enzymes of the Cyp2abfgs gene subfamilies in tobacco smoke-induced lung tumorigenesis in mice.Carcinogenesis · 2026Article
- Roles of Individual Human Cytochrome P450 Enzymes in Drug Metabolism.Pharmacological reviews · 2024Review
- Nitroreduction: A Critical Metabolic Pathway for Drugs, Environmental Pollutants, and Explosives.Chemical research in toxicology · 2022Review
- CytochromeDrug metabolism and disposition: the biological fate of chemicals · 2021Article
- A Role for the Orphan Human Cytochrome P450 2S1 in Polyunsaturated Fatty AcidDrug metabolism and disposition: the biological fate of chemicals · 2019Article
- Xenobiotica-metabolizing enzymes in the skin of rat, mouse, pig, guinea pig, man, and in human skin models.Archives of toxicology · 2018Review
- Evaluating Metabolite-Related DNA Oxidation and Adduct Damage from Aryl Amines Using a Microfluidic ECL Array.Analytical chemistry · 2017Article
- Erectile Dysfunction Drugs Changed the Protein Expressions and Activities of Drug-Metabolising Enzymes in the Liver of Male Rats.Oxidative medicine and cellular longevity · 2016Article
- Xenobiotic-metabolizing enzymes in the skin of rat, mouse, pig, guinea pig, man, and in human skin models.Archives of toxicology · 2014Review
- Human cytochrome P450 oxidation of 5-hydroxythalidomide and pomalidomide, an amino analogue of thalidomide.Chemical research in toxicology · 2014Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Many aromatic amines and heterocyclic aromatic amines (HAAs) are known carcinogens for animals, and there is also strong evidence of some in human cancer. The activation of these compounds, including some arylamine drugs, involves N-hydroxylation, usually by cytochrome P450 enzymes (P450) in Family 1 (1A2, 1A1, and 1B1). We previously demonstrated that the bioactivation product of the anticancer agent 2-(4-amino-3-methylphenyl)-5-fluorobenzothiazole (5F 203), an N-hydroxylamine, can be reduced by P450 2S1 to its amine precursor under anaerobic conditions and, to a lesser extent, under aerobic conditions [Wang, K., and Guengerich, F. P. (2012) Chem. Res. Toxicol. 25, 1740-1751]. In the study presented here, we tested the hypothesis that P450 2S1 is involved in the reductive biotransformation of known carcinogenic aromatic amines and HAAs. The N-hydroxylamines of 4-aminobiphenyl (4-ABP), 2-naphthylamine (2-NA), and 2-aminofluorene (2-AF) were synthesized and found to be reduced by P450 2S1 under both anaerobic and aerobic conditions. The formation of amines due to P450 2S1 reduction also occurred under aerobic conditions but was less apparent because the competitive disproportionation reactions (of the N-hydroxylamines) also yielded amines. Further, some nitroso and nitro derivatives of the arylamines could also be reduced by P450 2S1. None of the amines tested were oxidized by P450 2S1. These results suggest that P450 2S1 may be involved in the reductive detoxication of several of the activated products of carcinogenic aromatic amines and HAAs.
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