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Occurrence of primary aromatic amines and nicotine in sediments collected from the United States.

ABSTRACT: Despite extensive use of primary aromatic amines (AAs) in consumer products, little is known about their occurrence in the environment. In this study, we investigated the occurrence of 14 AAs and nicotine in 75 sediment samples collected from seven estuarine and freshwater ecosystems in the Unites States. Additionally, risk quotients (RQs) were calculated to assess potential risks of these chemicals to aquatic organisms. Of the 14 AAs analyzed, seven of them were found in sediments. The sum concentrations of seven AAs in sediments were in the range of 10.2 to 1810 ng/g, dry wt (mean: 388 ng/g). Aniline was the most abundant compound, accounting for, on average, 53 % of the total concentrations. Nicotine was found in sediments at a concentration range of

SUBMITTER: Urbaniak M

PROVIDER: S-EPMC10116586 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature

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Occurrence of primary aromatic amines and nicotine in sediments collected from the United States.

Urbaniak Magdalena M Chinthakindi Sridhar S Martinez Andres A Hornbuckle Keri C KC Kannan Kurunthachalam K

The Science of the total environment 20220817 Pt 1

Despite extensive use of primary aromatic amines (AAs) in consumer products, little is known about their occurrence in the environment. In this study, we investigated the occurrence of 14 AAs and nicotine in 75 sediment samples collected from seven estuarine and freshwater ecosystems in the Unites States. Additionally, risk quotients (RQs) were calculated to assess potential risks of these chemicals to aquatic organisms. Of the 14 AAs analyzed, seven of them were found in sediments. The sum conc ...[more]

PMID: 35987249

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Project description:Arylamines (AAs) and heterocyclic aromatic amines (HAAs) are structurally related carcinogens formed during the combustion of tobacco or cooking of meat. They undergo cytochrome P450 mediated N-hydroxylation to form metabolites which bind to DNA and lead to mutations. The N-hydroxylated metabolites of many AAs also can undergo a co-oxidation reaction with oxy-hemolgobin (HbO2) to form methemoglobin (met-Hb) and the arylnitroso intermediates, which react with the β-Cys(93) chain of Hb to form Hb-arylsulfinamide adducts. The biochemistry of arylamine metabolism has been exploited to biomonitor certain AAs through their Hb arylsulfinamide adducts in humans. We examined the reactivity of HbO2 with the N-hydroxylated metabolites of 4-aminobiphenyl (ABP, HONH-ABP), aniline (ANL, HONH-ANL), and the HAAs 2-amino-9H-pyrido[2,3-b]indole (AαC, HONH-AαC), 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP, HONH-PhIP), and 2-amino-3,8-dimethylimidazo[4,5-f]quinoxaline (MeIQx, HONH-MeIQx). HONH-ABP, HO-ANL, and HONH-AαC induced methemoglobinemia and formed Hb sulfinamide adducts. However, HONH-MeIQx and HONH-PhIP did not react with the oxy-heme complex, and met-Hb formation and chemical modification of the β-Cys(93) residue were negligible. Molecular modeling studies showed that the distances between the H-ON-AA or H-ON-HAA substrates and the oxy-heme complex of HbO2 were too far away to induce methemoglobinemia. Different conformational changes in flexible helical and loop regions around the heme pocket induced by the H-ON-AA or H-ON-HAAs may explain the different proclivities of these chemicals to induce methemoglobinemia. Hb-Cys(93β) sulfinamide and sulfonamide adducts of ABP, ANL, and AαC were identified, by Orbitrap MS, following the proteolysis of Hb with trypsin, Glu-C, or Lys-C. Hb sulfinamide and sulfonamide adducts of ABP were identified in the blood of mice exposed to ABP, by Orbitrap MS. This is the first report of the identification of intact Hb sulfinamide adducts of carcinogenic AAs in vivo. The high reactivity of HONH-AαC with HbO2 suggests that the Hb sulfinamide adduct of AαC may be a promising biomarker of exposure to this HAA in humans.

Dataset Information

Occurrence of primary aromatic amines and nicotine in sediments collected from the United States.

Publications

Occurrence of primary aromatic amines and nicotine in sediments collected from the United States.

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