Non-enzymatic glutathione conjugation of 2-nitroso-6-methyldipyrido [1,2-a: 3',2'-d] imidazole (NO-Glu-P-1) in vitro: N-hydroxy-sulfonamide, a new binding form of arylnitroso compounds and thiols.

doi:10.1016/0009-2797(88)90006-3

Paper

DOI: 10.1016/0009-2797(88)90006-3

Non-enzymatic glutathione conjugation of 2-nitroso-6-methyldipyrido [1,2-a: 3',2'-d] imidazole (NO-Glu-P-1) in vitro: N-hydroxy-sulfonamide, a new binding form of arylnitroso compounds and thiols.

Published 1988 · A. Umemoto, S. Grivas, Z. Yamaizumi

Chemico-biological interactions

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Abstract

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In Vitro Study

Study Snapshot

The N-hydroxy-sulfonamide structure is a new binding form between arylnitroso compounds and thiols, potentially aiding in detoxification of toxic arylamines in organs like the liver and kidney.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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References

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Oxidation of the 2-hydroxyamino derivative of 2-amino-6-methyl-dipyrido[1,2-a: 3',2'-d] imidazole (Glu-P-1) to its 2-nitroso form, an ultimate form reacting with hemoglobin thiol groups.

Oxidation of toxic arylhydroxylamines to DNA-nonreactive nitroso compounds and binding to abundant hemoglobin thiol groups could potentially serve as a detoxification process.

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GSH conjugates can be activated and detoxicated, but CH-3 is a more potent mutagen than N-OH-Trp-P-2, due to its direct action.

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Citations

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Metabolism and biomarkers of heterocyclic aromatic amines in humans

Heterocyclic aromatic amines (HAAs) form during high-temperature cooking of meats, poultry, and fish, and their metabolism in humans can lead to DNA damage and carcinogenesis.

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Genes and Environment

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Ncm, a Photolabile Group for Preparation of Caged Molecules: Synthesis and Biological Application

Ncm is a photolabile group that can be used to create caged molecules for neuronal photostimulation, with photorelease occurring in microseconds and quantum efficiencies ranging from 0.05-0.08.

2016·19citations·S. Muralidharan et al.·PLoS ONE

PLoS ONE

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Long-term biomarkers of heterocyclic aromatic amines (HAAs) are needed to establish their association with cancer risk and improve molecular epidemiology studies.

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DOI: 10.1002/9780470682531.PAT0093

Reactions of Nitrosoarenes with SH Groups

Nitrosoarene reactions with SH groups produce biologically significant compounds, such as nitrosobenzene, polycyclic nitrosoaromatics, and heterocyclic N-oxygenated compounds from food mutagens.

2009·3citations·P. Eyer et al.·Patai's Chemistry of Functional Groups

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Potential chemotherapeutic activity of 4-iodo-3-nitrobenzamide. Metabolic reduction to the 3-nitroso derivative and induction of cell death in tumor cells in culture.

4-iodo-3-nitrobenzamide effectively kills tumor cells by reducing nitro group to nitroso and inducing tumor apoptosis, with no toxicity observed in hamsters.

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