Reactions of Nitrosoarenes with SH Groups

Eyer, Peter; Gallemann, Dieter

doi:10.1002/9780470682531.pat0093

Cited by 5 publications

(9 citation statements)

References 146 publications

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“…C-Oxidation yielding phenolic metabolites is generally involved in the detoxification process. However, aminophenols can be metabolized to reactive iminoquinones . Acetylases and deacetylases (DAC) have an important role in the metabolism of arylamines.…”

Section: Metabolism Of Arylamines and Nitroarenesmentioning

confidence: 99%

“…Lotlikar et al found that nitrosofluorene forms hydrolyzable adducts with cysteine of peptides . Eyer , and Neumann , studied the adduct formation of nitrosoarenes with GSH and Hb in erythrocytes (Figure ). N -Hydroxyarylamines are oxidized in the erythrocytes to nitrosoarenes, which form semimercaptals with the thiol group of cysteine.…”

Section: Introductionmentioning

confidence: 99%

“…For arylamine adducts with plasma proteins, the amounts hydrolyzed varied from 0 to 58% of the bound adduct . According to current knowledge of Hb-adduct formation, the hydrolyzable fraction originates from the reaction of nitrosoarenes with cysteines yielding arylsulfinamide adducts. , The nonhydrolyzable fraction probably derives from the reaction of activated N -hydroxyarylamines or their nitrenium/carbenium ion species with other amino acids. Protein adducts formed with nitrosoarenes are generally higher with Hb than with plasma proteins.…”

Section: Introductionmentioning

confidence: 99%

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Hemoglobin Adducts and Urinary Metabolites of Arylamines and Nitroarenes

Sabbioni

2017

Chem. Res. Toxicol.

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Arylamines and nitroarenes are intermediates in the production of pharmaceuticals, dyes, pesticides, and plastics and are important environmental and occupational pollutants. N-Hydroxyarylamines are the toxic common intermediates of arylamines and nitroarenes. N-Hydroxyarylamines and their derivatives can form adducts with hemoglobin (Hb-adducts), albumin, DNA, and tissue proteins in a dose-dependent manner. Most of the arylamine Hb-adducts are labile and undergo hydrolysis in vitro, by mild acid or base, to form the arylamines. According to current knowledge of arylamine adduct-formation, the hydrolyzable fraction is derived from the reaction products of the arylnitroso derivatives that yield arylsulfinamide adducts with cysteine. Hb-adducts are markers for the bioavailability of N-hydroxyarylamines. Hb-adducts of arylamines and nitroarenes have been used for many biomonitoring studies for over 30 years. Hb-adducts reflect the exposure history of the last four months. Biomonitoring of urinary metabolites is a less invasive process than biomonitoring blood protein adducts, and urinary metabolites have served as short-lived biomarkers of exposure to these hazardous chemicals. However, in case of intermittent exposure, urinary metabolites may not be detected, and subjects may be misclassified as nonexposed. Arylamines and nitroarenes and/or their metabolites have been measured in urine, especially to monitor the exposure of workers. This review summarizes the results of human biomonitoring studies involving urinary metabolites and Hb-adducts of arylamines and nitroarenes. In addition, studies about the relationship between Hb-adducts and diseases are summarized.

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Section: Metabolism Of Arylamines and Nitroarenesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Hemoglobin Adducts and Urinary Metabolites of Arylamines and Nitroarenes

Sabbioni

2017

Chem. Res. Toxicol.

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“…186 According to our current knowledge of arylamine adduct formation, the hydrolyzable fraction is derived from the reaction products of the arylnitrosoderivatives yielding aryl sulfinamide adducts with cysteine. 53,187 The nonhydrolyzable fraction probably results from the reaction products of activated N-hydroxyarylamines or their nitrenium/ carbenium ion species with other amino acids. Protein adducts formed with nitrosoarenes are generally higher with Hb than with PP.…”

Section: Albumin Adducts Formed With Toxicantsmentioning

confidence: 99%

“…52 The reactivity of Hb with aromatic amines and production of methemoglobin by genotoxic arylhydroxylamines has also been well studied and reviewed. 53,54 Pereira et al showed a linear relationship between Hb-adducts and DNA-adducts for 2-acetylaminofluorene in mice and rats. 55 Hb adduct formation for many aromatic amines occurs as a sulfinamide linkage formed by reaction of the arylnitroso intermediates with the β-Cys 93 chain of Hb.…”

Section: Introduction To Human Biomonitoring and History Of Protein A...mentioning

confidence: 99%

Biomonitoring Human Albumin Adducts: The Past, the Present, and the Future

Sabbioni¹,

Turesky

2016

Chem. Res. Toxicol.

105

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Serum albumin (Alb) is the most abundant protein in blood plasma. Alb reacts with many carcinogens and/or their electrophilic metabolites. Studies conducted over 20 years ago showed that Alb forms adducts with the human carcinogens aflatoxin B1 and benzene, which were successfully used as biomarkers in molecular epidemiology studies designed to address the role of these chemicals in cancer risk. Alb forms adducts with many therapeutic drugs or their reactive metabolites such as β-lactam antibiotics, acetylsalicylic acid, acetaminophen, nonsteroidal anti-inflammatory drugs, chemotherapeutic agents, and antiretroviral therapy drugs. The identification and characterization of the adduct structures formed with Alb have served to understand the generation of reactive metabolites and to predict idiosyncratic drug reactions and toxicities. The reaction of candidate drugs with Alb is now exploited as part of the battery of screening tools to assess the potential toxicities of drugs. The use of gas chromatography-mass spectrometry, liquid chromatography, or liquid chromatography-mass spectrometry (LC-MS) enabled the identification and quantification of multiple types of Alb xenobiotic adducts in animals and humans during the past three decades. In this perspective, we highlight the history of Alb as a target protein for adduction to environmental and dietary genotoxicants, pesticides, and herbicides, common classes of medicinal drugs, and endogenous electrophiles, and the emerging analytical mass spectrometry technologies to identify Alb-toxicant adducts in humans.

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