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- W2765984673 abstract "Abstract MS-based proteomic analysis was combined with in silico quantum mechanical calculations to improve understanding of protein adduction by N-phenylhydroxylamine (PhNHOH) and nitrosobenzene (NOB), metabolic products of aniline. In vitro adduction of model peptides containing nucleophilic sidechains (Cys, His, and Lys) and selected proteins (bovine and human hemoglobin and β-lactoglobulin-A) were characterized. Peptide studies identified the Cys thiolate as the most reactive nucleophile for these metabolites, a result consistent with in silico calculations of reactivity parameters. For PhNHOH, sulfinamides were identified as the primary adduction products, which were stable following tryptic digestion. Conversely, reactions with NOB yielded an additional oxidized adduct, the sulfonamide. In vitro exposure of human whole blood to PhNHOH and NOB demonstrated that only sulfinamides were formed. In addition to previously reported adduction of β 93 Cys of human Hb, two novel sites of adduction were found; α 104 Cys and β 112 Cys. We also report CD and UV-Vis spectroscopy studies of adducted human Hb that revealed loss of α-helical content and deoxygenation. The results provide additional understanding of the covalent interaction of aromatic amine metabolites with protein nucleophiles." @default.
- W2765984673 created "2017-11-10" @default.
- W2765984673 creator A5008500895 @default.
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- W2765984673 date "2017-11-01" @default.
- W2765984673 modified "2023-10-18" @default.
- W2765984673 title "Proteomic Analysis of Thiol Modifications and Assessment of Structural Changes in Hemoglobin Induced by the Aniline Metabolites N-Phenylhydroxylamine and Nitrosobenzene" @default.
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- W2765984673 doi "https://doi.org/10.1038/s41598-017-14653-w" @default.
- W2765984673 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/5665987" @default.
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- W2765984673 hasPublicationYear "2017" @default.
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