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Metabolism and Biomarkers of Heterocyclic Aromatic Amines in Molecular Epidemiology Studies: Lessons Learned from Aromatic Amines

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† Division of Environmental Health Sciences, Wadsworth Center, Albany, New York 12201, United States
‡ University of Hawaii Cancer Center, University of Hawaii, Honolulu, Hawaii 96813, United States
(R.J.T.) Tel: 518-474-4151. Fax: 518-473-2095. E-mail: [email protected]. (L.L.M.) Tel: 808-586-2988. Fax: 808-586-2982. E-mail: [email protected]
Cite this: Chem. Res. Toxicol. 2011, 24, 8, 1169–1214
Publication Date (Web):June 20, 2011
https://doi.org/10.1021/tx200135s
Copyright © 2011 American Chemical Society
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Abstract

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Aromatic amines and heterocyclic aromatic amines (HAAs) are structurally related classes of carcinogens that are formed during the combustion of tobacco or during the high-temperature cooking of meats. Both classes of procarcinogens undergo metabolic activation by N-hydroxylation of the exocyclic amine group to produce a common proposed intermediate, the arylnitrenium ion, which is the critical metabolite implicated in toxicity and DNA damage. However, the biochemistry and chemical properties of these compounds are distinct, and different biomarkers of aromatic amines and HAAs have been developed for human biomonitoring studies. Hemoglobin adducts have been extensively used as biomarkers to monitor occupational and environmental exposures to a number of aromatic amines; however, HAAs do not form hemoglobin adducts at appreciable levels, and other biomarkers have been sought. A number of epidemiologic studies that have investigated dietary consumption of well-done meat in relation to various tumor sites reported a positive association between cancer risk and well-done meat consumption, although some studies have shown no associations between well-done meat and cancer risk. A major limiting factor in most epidemiological studies is the uncertainty in quantitative estimates of chronic exposure to HAAs, and thus, the association of HAAs formed in cooked meat and cancer risk has been difficult to establish. There is a critical need to establish long-term biomarkers of HAAs that can be implemented in molecular epidemioIogy studies. In this review, we highlight and contrast the biochemistry of several prototypical carcinogenic aromatic amines and HAAs to which humans are chronically exposed. The biochemical properties and the impact of polymorphisms of the major xenobiotic-metabolizing enzymes on the biological effects of these chemicals are examined. Lastly, the analytical approaches that have been successfully employed to biomonitor aromatic amines and HAAs, and emerging biomarkers of HAAs that may be implemented in molecular epidemiology studies are discussed.

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  2. Medjda Bellamri, Scott J. Walmsley, Christina Brown, Kyle Brandt, Dmitri Konorev, Abderrahman Day, Chia-Fang Wu, Ming Tsang Wu, Robert J. Turesky. DNA Damage and Oxidative Stress of Tobacco Smoke Condensate in Human Bladder Epithelial Cells. Chemical Research in Toxicology 2022, 35 (10) , 1863-1880. https://doi.org/10.1021/acs.chemrestox.2c00153
  3. Dmitri Konorev, Lihua Yao, Robert. J. Turesky. Multi-DNA Adduct and Abasic Site Quantitation In Vivo by Nano-Liquid Chromatography/High-Resolution Orbitrap Tandem Mass Spectrometry: Methodology for Biomonitoring Colorectal DNA Damage. Chemical Research in Toxicology 2022, 35 (9) , 1519-1532. https://doi.org/10.1021/acs.chemrestox.2c00177
  4. Jingshu Guo, Joseph S. Koopmeiners, Scott J. Walmsley, Peter W. Villalta, Lihua Yao, Paari Murugan, Resha Tejpaul, Christopher J. Weight, Robert J. Turesky. The Cooked Meat Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine Hair Dosimeter, DNA Adductomics Discovery, and Associations with Prostate Cancer Pathology Biomarkers. Chemical Research in Toxicology 2022, 35 (5) , 703-730. https://doi.org/10.1021/acs.chemrestox.2c00012
  5. Tauqeerunnisa Syeda, Jason R. Cannon. Potential Role of Heterocyclic Aromatic Amines in Neurodegeneration. Chemical Research in Toxicology 2022, 35 (1) , 59-72. https://doi.org/10.1021/acs.chemrestox.1c00274
  6. Zhizhao Wang, Guoren Yue, Xiangdong Ji, Hai Song, Penji Yan, Jixing Zhao, Xin Jia. Tandem Michael Addition–Cyclization of Nitroalkenes with 1,3-Dicarbonyl Compounds Accompanied by Removal of Nitro Group. The Journal of Organic Chemistry 2021, 86 (20) , 14131-14143. https://doi.org/10.1021/acs.joc.1c01586
  7. Igor Shamovsky, Lena Ripa, Frank Narjes, Britta Bonn, Stefan Schiesser, Ina Terstiege, Christian Tyrchan. Mechanism-Based Insights into Removing the Mutagenicity of Aromatic Amines by Small Structural Alterations. Journal of Medicinal Chemistry 2021, 64 (12) , 8545-8563. https://doi.org/10.1021/acs.jmedchem.1c00514
  8. Jingshu Guo, Peter W. Villalta, Christopher J. Weight, Radha Bonala, Francis Johnson, Thomas A. Rosenquist, Robert J. Turesky. Targeted and Untargeted Detection of DNA Adducts of Aromatic Amine Carcinogens in Human Bladder by Ultra-Performance Liquid Chromatography-High-Resolution Mass Spectrometry. Chemical Research in Toxicology 2018, 31 (12) , 1382-1397. https://doi.org/10.1021/acs.chemrestox.8b00268
  9. Byeong Hwa Yun, Medjda Bellamri, Thomas A. Rosenquist, Robert J. Turesky. Method for Biomonitoring DNA Adducts in Exfoliated Urinary Cells by Mass Spectrometry. Analytical Chemistry 2018, 90 (16) , 9943-9950. https://doi.org/10.1021/acs.analchem.8b02170
  10. Yang Yu, Pengcheng Wang, Yuxiang Cui, and Yinsheng Wang . Chemical Analysis of DNA Damage. Analytical Chemistry 2018, 90 (1) , 556-576. https://doi.org/10.1021/acs.analchem.7b04247
  11. Itti Bist, Snehasis Bhakta, Di Jiang, Tia E. Keyes, Aaron Martin, Robert J. Forster, and James F. Rusling . Evaluating Metabolite-Related DNA Oxidation and Adduct Damage from Aryl Amines Using a Microfluidic ECL Array. Analytical Chemistry 2017, 89 (22) , 12441-12449. https://doi.org/10.1021/acs.analchem.7b03528
  12. Jingshu Guo, Peter W. Villalta, and Robert J. Turesky . Data-Independent Mass Spectrometry Approach for Screening and Identification of DNA Adducts. Analytical Chemistry 2017, 89 (21) , 11728-11736. https://doi.org/10.1021/acs.analchem.7b03208
  13. Gabriele Sabbioni . Hemoglobin Adducts and Urinary Metabolites of Arylamines and Nitroarenes. Chemical Research in Toxicology 2017, 30 (10) , 1733-1766. https://doi.org/10.1021/acs.chemrestox.7b00111
  14. Nicholas E. Geacintov and Suse Broyde . Repair-Resistant DNA Lesions. Chemical Research in Toxicology 2017, 30 (8) , 1517-1548. https://doi.org/10.1021/acs.chemrestox.7b00128
  15. Falco Beer, Felix Urbat, Jan Steck, Melanie Huch, Diana Bunzel, Mirko Bunzel, and Sabine E. Kulling . Metabolism of Foodborne Heterocyclic Aromatic Amines by Lactobacillus reuteri DSM 20016. Journal of Agricultural and Food Chemistry 2017, 65 (32) , 6797-6811. https://doi.org/10.1021/acs.jafc.7b01663
  16. Medjda Bellamri, Ludovic Le Hegarat, Robert J. Turesky, and Sophie Langouët . Metabolism of the Tobacco Carcinogen 2-Amino-9H-pyrido[2,3-b]indole (AαC) in Primary Human Hepatocytes. Chemical Research in Toxicology 2017, 30 (2) , 657-668. https://doi.org/10.1021/acs.chemrestox.6b00394
  17. Yi Wang, Peter W. Villalta, Lijuan Peng, Karen Dingley, Michael A. Malfatti, K. W. Turteltaub, and Robert J. Turesky . Mass Spectrometric Characterization of an Acid-Labile Adduct Formed with 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine and Albumin in Humans. Chemical Research in Toxicology 2017, 30 (2) , 705-714. https://doi.org/10.1021/acs.chemrestox.6b00426
  18. Gabriele Sabbioni and Robert J. Turesky . Biomonitoring Human Albumin Adducts: The Past, the Present, and the Future. Chemical Research in Toxicology 2017, 30 (1) , 332-366. https://doi.org/10.1021/acs.chemrestox.6b00366
  19. Shun Xiao, Jingshu Guo, Byeong Hwa Yun, Peter W. Villalta, Suprita Krishna, Resha Tejpaul, Paari Murugan, Christopher J. Weight, and Robert J. Turesky . Biomonitoring DNA Adducts of Cooked Meat Carcinogens in Human Prostate by Nano Liquid Chromatography–High Resolution Tandem Mass Spectrometry: Identification of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine DNA Adduct. Analytical Chemistry 2016, 88 (24) , 12508-12515. https://doi.org/10.1021/acs.analchem.6b04157
  20. Bernardo Brito Palma, Charles W. Fisher, José Rueff, and Michel Kranendonk . Prototype Systems Containing Human Cytochrome P450 for High-Throughput Real-Time Detection of DNA Damage by Compounds That Form DNA-Reactive Metabolites. Chemical Research in Toxicology 2016, 29 (5) , 747-756. https://doi.org/10.1021/acs.chemrestox.5b00455
  21. Jonathan Sheng, Yi Wang, Robert J. Turesky, Kerri Kluetzman, Qing-Yu Zhang, and Xinxin Ding . Novel Transgenic Mouse Model for Studying Human Serum Albumin as a Biomarker of Carcinogenic Exposure. Chemical Research in Toxicology 2016, 29 (5) , 797-809. https://doi.org/10.1021/acs.chemrestox.5b00529
  22. Tingting Cai, Lihua Yao, and Robert J. Turesky . Bioactivation of Heterocyclic Aromatic Amines by UDP Glucuronosyltransferases. Chemical Research in Toxicology 2016, 29 (5) , 879-891. https://doi.org/10.1021/acs.chemrestox.6b00046
  23. Khyatiben V. Pathak, Ting-Lan Chiu, Elizabeth Ambrose Amin, and Robert J. Turesky . Methemoglobin Formation and Characterization of Hemoglobin Adducts of Carcinogenic Aromatic Amines and Heterocyclic Aromatic Amines. Chemical Research in Toxicology 2016, 29 (3) , 255-269. https://doi.org/10.1021/acs.chemrestox.5b00418
  24. Megha Anand, Raghavan B. Sunoj, and Henry F. Schaefer, III . Palladium–Silver Cooperativity in an Aryl Amination Reaction through C–H Functionalization. ACS Catalysis 2016, 6 (2) , 696-708. https://doi.org/10.1021/acscatal.5b02639
  25. Robert J. Turesky, Kami K. White, Lynne R. Wilkens, and Loïc Le Marchand . Caffeine Cytochrome P450 1A2 Metabolic Phenotype Does Not Predict the Metabolism of Heterocyclic Aromatic Amines in Humans. Chemical Research in Toxicology 2015, 28 (8) , 1603-1615. https://doi.org/10.1021/acs.chemrestox.5b00177
  26. Kallie M. Stavros, Edward K. Hawkins, Carmelo J. Rizzo, and Michael P. Stone . Base-Displaced Intercalated Conformation of the 2-Amino-3-methylimidazo[4,5-f]quinoline N2-dG DNA Adduct Positioned at the Nonreiterated G1 in the NarI Restriction Site. Chemical Research in Toxicology 2015, 28 (7) , 1455-1468. https://doi.org/10.1021/acs.chemrestox.5b00140
  27. Jingshu Guo, Kim Yonemori, Loïc Le Marchand, and Robert J. Turesky . Method to Biomonitor the Cooked Meat Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Dyed Hair by Ultra-Performance Liquid Chromatography–Orbitrap High Resolution Multistage Mass Spectrometry. Analytical Chemistry 2015, 87 (12) , 5872-5877. https://doi.org/10.1021/acs.analchem.5b01129
  28. Antonín Králík, Igor Linhart, Lubomír Váňa, and Alena Moulisová . Identification of New DNA Adducts of Phenylnitrenium. Chemical Research in Toxicology 2015, 28 (6) , 1317-1325. https://doi.org/10.1021/acs.chemrestox.5b00120
  29. Yi Wang, Lijuan Peng, Medjda Bellamri, Sophie Langouët, and Robert J. Turesky . Mass Spectrometric Characterization of Human Serum Albumin Adducts Formed with N-Oxidized Metabolites of 2-Amino-1-methylphenylimidazo[4,5-b]pyridine in Human Plasma and Hepatocytes. Chemical Research in Toxicology 2015, 28 (5) , 1045-1059. https://doi.org/10.1021/acs.chemrestox.5b00075
  30. Sivaprasad Attaluri, Charles R. Iden, Radha R. Bonala, and Francis Johnson . Total Synthesis of the Aristolochic Acids, Their Major Metabolites, and Related Compounds. Chemical Research in Toxicology 2014, 27 (7) , 1236-1242. https://doi.org/10.1021/tx500122x
  31. Jiadan Xue, Lili Du, Ruixue Zhu, Jinqing Huang, and David Lee Phillips . Direct Time-Resolved Spectroscopic Observation of Arylnitrenium Ion Reactions with Guanine-Containing DNA Oligomers. The Journal of Organic Chemistry 2014, 79 (8) , 3610-3614. https://doi.org/10.1021/jo500484s
  32. Gwendoline Nauwelaërs, Medjda Bellamri, Valérie Fessard, Robert J. Turesky, and Sophie Langouët . DNA Adducts of the Tobacco Carcinogens 2-Amino-9H-pyrido[2,3-b]indole and 4-Aminobiphenyl Are Formed at Environmental Exposure Levels and Persist in Human Hepatocytes. Chemical Research in Toxicology 2013, 26 (9) , 1367-1377. https://doi.org/10.1021/tx4002226
  33. Kai Wang and F. Peter Guengerich . Reduction of Aromatic and Heterocyclic Aromatic N-Hydroxylamines by Human Cytochrome P450 2S1. Chemical Research in Toxicology 2013, 26 (6) , 993-1004. https://doi.org/10.1021/tx400139p
  34. Yasuhiro Kosaki, Hironori Izawa, Shinsuke Ishihara, Kohsaku Kawakami, Masato Sumita, Yoshitaka Tateyama, Qingmin Ji, Venkata Krishnan, Shunichi Hishita, Yusuke Yamauchi, Jonathan P. Hill, Ajayan Vinu, Seimei Shiratori, and Katsuhiko Ariga . Nanoporous Carbon Sensor with Cage-in-Fiber Structure: Highly Selective Aniline Adsorbent toward Cancer Risk Management. ACS Applied Materials & Interfaces 2013, 5 (8) , 2930-2934. https://doi.org/10.1021/am400940q
  35. Tsutomu Shimada, Donghak Kim, Norie Murayama, Katsuhiro Tanaka, Shigeo Takenaka, Leslie D. Nagy, Lindsay M. Folkman, Maryam K. Foroozesh, Masayuki Komori, Hiroshi Yamazaki, and F. Peter Guengerich . Binding of Diverse Environmental Chemicals with Human Cytochromes P450 2A13, 2A6, and 1B1 and Enzyme Inhibition. Chemical Research in Toxicology 2013, 26 (4) , 517-528. https://doi.org/10.1021/tx300492j
  36. Lijuan Peng and Robert J. Turesky . Capturing Labile Sulfenamide and Sulfinamide Serum Albumin Adducts of Carcinogenic Arylamines by Chemical Oxidation. Analytical Chemistry 2013, 85 (2) , 1065-1072. https://doi.org/10.1021/ac3028273
  37. Pek Chong, Paul Sebahar, Michael Youngman, Dulce Garrido, Huichang Zhang, Eugene L. Stewart, Robert T. Nolte, Liping Wang, Robert G. Ferris, Mark Edelstein, Kurt Weaver, Amanda Mathis, and Andrew Peat . Rational Design of Potent Non-Nucleoside Inhibitors of HIV-1 Reverse Transcriptase. Journal of Medicinal Chemistry 2012, 55 (23) , 10601-10609. https://doi.org/10.1021/jm301294g
  38. Lijuan Peng, Surendra Dasari, David L. Tabb, and Robert J. Turesky . Mapping Serum Albumin Adducts of the Food-Borne Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine by Data-Dependent Tandem Mass Spectrometry. Chemical Research in Toxicology 2012, 25 (10) , 2179-2193. https://doi.org/10.1021/tx300253j
  39. Dan Gu, Zachary L. Neuman, Jaime F. Modiano, and Robert J. Turesky . Biomonitoring the Cooked Meat Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Canine Fur. Journal of Agricultural and Food Chemistry 2012, 60 (36) , 9371-9375. https://doi.org/10.1021/jf302969h
  40. V. G. Vaidyanathan and Bongsup P. Cho . Sequence Effects on Translesion Synthesis of an Aminofluorene–DNA Adduct: Conformational, Thermodynamic, and Primer Extension Kinetic Studies. Biochemistry 2012, 51 (9) , 1983-1995. https://doi.org/10.1021/bi2017443
  41. Lijuan Peng and Robert J. Turesky . Mass Spectrometric Characterization of 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine N-Oxidized Metabolites Bound at Cys34 of Human Serum Albumin. Chemical Research in Toxicology 2011, 24 (11) , 2004-2017. https://doi.org/10.1021/tx2003504
  42. Razzagh Rahimpoor, Khaled Murtada, Ali Firoozichahak, Babak Pashaei, Danial Soleymani-ghoozhdi, Houman Serkan, Faeze Mehregan, Saber Alizadeh. Urinary bio-monitoring of aromatic amine derivatives by new needle trap device packed with the multi-component adsorbent. Scientific Reports 2023, 13 (1) https://doi.org/10.1038/s41598-023-31108-7
  43. Hui Teng, Hongting Deng, Chang Zhang, Hui Cao, Qun Huang, Lei Chen. The role of flavonoids in mitigating food originated heterocyclic aromatic amines that concerns human wellness. Food Science and Human Wellness 2023, 12 (4) , 975-985. https://doi.org/10.1016/j.fshw.2022.10.019
  44. Lili Shi, Ziyu Cui, Wei Liu. Effect of Chemical Refining on the Reduction of β-Carboline Content in Sesame Seed Oil. Molecules 2023, 28 (11) , 4503. https://doi.org/10.3390/molecules28114503
  45. Payungsak Tantipaiboonwong, Komsak Pintha, Wittaya Chaiwangyen, Maitree Suttajit, Chakkrit Khanaree, Orawan Khantamat. Bioefficacy of Nga-Mon (Perilla frutescens) Fresh and Dry Leaf: Assessment of Antioxidant, Antimutagenicity, and Anti-Inflammatory Potential. Plants 2023, 12 (11) , 2210. https://doi.org/10.3390/plants12112210
  46. Yilun Wang, Yuxuan Liu, Xiaohong Huang, Zihan Xiao, Yifang Yang, Qinxin Yu, Shujuan Chen, Li He, Aiping Liu, Shuliang Liu, Likou Zou, Yong Yang. A Review on Mechanistic Overview on the Formation of Toxic Substances during the Traditional Fermented Food Processing. Food Reviews International 2023, 39 (3) , 1275-1292. https://doi.org/10.1080/87559129.2021.1933021
  47. Ji-Eun Seo, Xilin Li, Yuan Le, Nan Mei, Tong Zhou, Xiaoqing Guo. High-throughput micronucleus assay using three-dimensional HepaRG spheroids for in vitro genotoxicity testing. Archives of Toxicology 2023, 97 (4) , 1163-1175. https://doi.org/10.1007/s00204-023-03461-z
  48. Yuka Yokota, Shugo Suzuki, Min Gi, Yukie Yanagiba, Nao Yoneda, Masaki Fujioka, Anna Kakehashi, Shigeki Koda, Hiroshi Suemizu, Hideki Wanibuchi. o-Toluidine metabolism and effects in the urinary bladder of humanized-liver mice. Toxicology 2023, 30 , 153483. https://doi.org/10.1016/j.tox.2023.153483
  49. Li Zhu, Wei Jia, Xuzhi Wan, Pan Zhuang, Guicen Ma, Jingjing Jiao, Yu Zhang. Advancing metabolic networks and mapping updated urinary metabolic fingerprints after exposure to typical carcinogenic heterocyclic aromatic amines. Environmental Pollution 2023, 319 , 120936. https://doi.org/10.1016/j.envpol.2022.120936
  50. Carlos A. Pérez Montilla, Samanta Moroni, Guillermo Moscatelli, Daniela M. Rocco, Nicolas González, Jaime M. Altcheh, Facundo García Bournissen. Major benznidazole metabolites in patients treated for Chagas disease: mass spectrometry-based identification, structural analysis and detoxification pathways. Toxicology Letters 2023, 12 https://doi.org/10.1016/j.toxlet.2023.02.001
  51. Mariya Gover Antoniraj, Kasi Pandima Devi, Ioana Berindan-Neagoe, Seyed Fazel Nabavi, Hamid Reza Khayat Kashani, Safieh Aghaabdollahian, Farzaneh Afkhami, Philippe Jeandet, Zahra Lorigooini, Maryam Khayatkashani, Seyed Mohammad Nabavi. Oral microbiota in cancer: could the bad guy turn good with application of polyphenols?. Expert Reviews in Molecular Medicine 2023, 25 https://doi.org/10.1017/erm.2022.39
  52. Carlos Hernandez-Castillo, Sarah C. Shuck, John Termini. DNA Adducts as Biomarkers in Toxicology. 2023, 351-382. https://doi.org/10.1007/978-3-031-07392-2_21
  53. Medjda Bellamri. Heterocyclic aromatic amines (HAA), exposure, metabolism, macromolecular adducts, and cancer risk. 2023https://doi.org/10.1016/B978-0-12-824315-2.00717-X
  54. B.L. Alman, G.A. Casillas, B.N. Szafran. High temperature cooked meats. 2023https://doi.org/10.1016/B978-0-12-824315-2.00723-5
  55. Lili Du, Juanjuan Wang, Yunfan Qiu, Runhui Liang, Penglin Lu, Xuebo Chen, David Lee Phillips, Arthur H. Winter. Generation and direct observation of a triplet arylnitrenium ion. Nature Communications 2022, 13 (1) https://doi.org/10.1038/s41467-022-31091-z
  56. Michael Fasullo, Michael Dolan. The continuing evolution of barcode applications: Functional toxicology to cell lineage. Experimental Biology and Medicine 2022, 247 (23) , 2119-2127. https://doi.org/10.1177/15353702221121600
  57. Wylly Ramsés García-Niño, Luz Ibarra-Lara, Mayra Yael Cuevas-Magaña, Alicia Sánchez-Mendoza, Elisabeth Armada. Protective activities of ellagic acid and urolithins against kidney toxicity of environmental pollutants: A review. Environmental Toxicology and Pharmacology 2022, 95 , 103960. https://doi.org/10.1016/j.etap.2022.103960
  58. Jianghui Liu, Hiu Lam So, Wei Chu. Degradation of 1-naphthylamine by a UV enhanced Fe2+/peroxymonosulfate system: A novel pH-dependent activation pathway. Chemical Engineering Journal 2022, 443 , 136299. https://doi.org/10.1016/j.cej.2022.136299
  59. Huihua Ji, Zhenyu Jin. Analysis of six aromatic amines in the mainstream smoke of tobacco products. Analytical and Bioanalytical Chemistry 2022, 414 (14) , 4227-4234. https://doi.org/10.1007/s00216-022-04075-7
  60. Yang Wang, Kunna Li, Ying Zou, Mengyue Zhou, Jing Li, Chutian Wu, Rong Tan, Yufen Liao, Weiwei Li, Jiang Zheng. Metabolic activation of 3-aminodibenzofuran mediated by P450 enzymes and sulfotransferases. Toxicology Letters 2022, 360 , 44-52. https://doi.org/10.1016/j.toxlet.2022.03.005
  61. Yi-Fan Wei, Ming-Li Sun, Zhao-Yan Wen, Fang-Hua Liu, Ya-Shu Liu, Shi Yan, Xue Qin, Song Gao, Xiu-Qin Li, Yu-Hong Zhao, Ting-Ting Gong, Qi-Jun Wu. Pre-diagnosis meat intake and cooking method and ovarian cancer survival: results from the Ovarian Cancer Follow-Up Study (OOPS). Food & Function 2022, 13 (8) , 4653-4663. https://doi.org/10.1039/D1FO03825G
  62. Wen-Long Yu, Shi-Lei Zhao, Guang-Wen Xu, Xin Li, Xiao-Lei Zhang, Yu-Ling Shan, Jun-Wei Ding, Guo-Hui Qin, Jun-Mei Zhang, Xiang Feng, De Chen. Facile fabrication of phenylenediamine residue derived N, O co-doped hierarchical hyperporous carbon for high-efficient chloroxylenol removal. Chemical Engineering Journal 2022, 433 , 133635. https://doi.org/10.1016/j.cej.2021.133635
  63. Wei Jia, Pan Zhuang, Qiao Wang, Xuzhi Wan, Lei Mao, Xinyu Chen, Hong Miao, Dawei Chen, Yiping Ren, Yu Zhang. Urinary non-targeted toxicokinetics and metabolic fingerprinting of exposure to 3-monochloropropane-1,2-diol and glycidol from refined edible oils. Food Research International 2022, 152 , 110898. https://doi.org/10.1016/j.foodres.2021.110898
  64. Akaash Kannan, Nicholas Perpetua, Michael Dolan, Michael Fasullo. CYP1B1 converts procarcinogens into genotoxins in Saccharomyces cerevisiae. Mutation Research/Genetic Toxicology and Environmental Mutagenesis 2022, 874-875 , 503440. https://doi.org/10.1016/j.mrgentox.2022.503440
  65. Moamen M. Elmassry, Ahmed Zayed, Mohamed A. Farag. Gut homeostasis and microbiota under attack: impact of the different types of food contaminants on gut health. Critical Reviews in Food Science and Nutrition 2022, 62 (3) , 738-763. https://doi.org/10.1080/10408398.2020.1828263
  66. İbrahim Özçeşmeci, Ramazan Katırcı, B. Sebnem Sesalan. The analysis of interactions between DNA and small molecules: proposals for binding mechanisms based on computational data. Monatshefte für Chemie - Chemical Monthly 2022, 153 (1) , 113-124. https://doi.org/10.1007/s00706-021-02872-x
  67. Carlos Hernandez-Castillo, Sarah C. Shuck, John Termini. DNA Adducts as Biomarkers in Toxicology. 2022, 1-32. https://doi.org/10.1007/978-3-030-87225-0_21-1
  68. Sümeyra Çetinkaya, Kevser Taban Akça, Ipek Süntar. Flavonoids and anticancer activity: Structure–activity relationship. 2022, 81-115. https://doi.org/10.1016/B978-0-323-91099-6.00017-7
  69. Loïc Le Marchand. The role of heterocyclic aromatic amines in colorectal cancer: the evidence from epidemiologic studies. Genes and Environment 2021, 43 (1) https://doi.org/10.1186/s41021-021-00197-z
  70. Medjda Bellamri, Scott J. Walmsley, Robert J. Turesky. Metabolism and biomarkers of heterocyclic aromatic amines in humans. Genes and Environment 2021, 43 (1) https://doi.org/10.1186/s41021-021-00200-7
  71. Mael Conan, Nathalie Théret, Sophie Langouet, Anne Siegel. Constructing xenobiotic maps of metabolism to predict enzymes catalyzing metabolites capable of binding to DNA. BMC Bioinformatics 2021, 22 (1) https://doi.org/10.1186/s12859-021-04363-6
  72. Matthew Devall, Christopher H. Dampier, Stephen Eaton, Mourad W. Ali, Virginia Díez-Obrero, Ferran Moratalla-Navarro, Jennifer Bryant, Lucas T. Jennelle, Victor Moreno, Steven M. Powell, Ulrike Peters, Graham Casey. Novel insights into the molecular mechanisms underlying risk of colorectal cancer from smoking and red/processed meat carcinogens by modeling exposure in normal colon organoids. Oncotarget 2021, 12 (19) , 1863-1877. https://doi.org/10.18632/oncotarget.28058
  73. Stephan Kirchner, Patrick Schnider. Genotoxicity. 2021, 331-363. https://doi.org/10.1039/9781788016414-00331
  74. Masaki Kumondai, Evelyn Gutiérrez Rico, Eiji Hishinuma, Yuya Nakanishi, Shuki Yamazaki, Akiko Ueda, Sakae Saito, Shu Tadaka, Kengo Kinoshita, Daisuke Saigusa, Tomoki Nakayoshi, Akifumi Oda, Noriyasu Hirasawa, Masahiro Hiratsuka. Functional Characterization of 21 Rare Allelic CYP1A2 Variants Identified in a Population of 4773 Japanese Individuals by Assessing Phenacetin O-Deethylation. Journal of Personalized Medicine 2021, 11 (8) , 690. https://doi.org/10.3390/jpm11080690
  75. Hafiz Rehan Nadeem, Saeed Akhtar, Tariq Ismail, Piero Sestili, Jose Manuel Lorenzo, Muhammad Modassar Ali Nawaz Ranjha, Leonie Jooste, Christophe Hano, Rana Muhammad Aadil. Heterocyclic Aromatic Amines in Meat: Formation, Isolation, Risk Assessment, and Inhibitory Effect of Plant Extracts. Foods 2021, 10 (7) , 1466. https://doi.org/10.3390/foods10071466
  76. Olga Savinova, Mira Yerzhanova. Heterocyclic aromatic amines in food as mutagenesis factors. Journal of Food Processing and Preservation 2021, 45 (7) https://doi.org/10.1111/jfpp.15589
  77. Ruba Ibrahim, Amy Brix, David E. Malarkey, Abraham Nyska, Michal Asif, Yuval Ramot. Chemical-Induced Oral Squamous Cell Neoplasms in Rodents: An Overview of NTP 2-Year Cancer Studies. Toxicologic Pathology 2021, 49 (5) , 1062-1076. https://doi.org/10.1177/0192623321989956
  78. Medjda Bellamri, Kyle Brandt, Christina V. Brown, Ming-Tsang Wu, Robert J. Turesky. Cytotoxicity and genotoxicity of the carcinogen aristolochic acid I (AA-I) in human bladder RT4 cells. Archives of Toxicology 2021, 95 (6) , 2189-2199. https://doi.org/10.1007/s00204-021-03059-3
  79. Zhi Li, Peipei Cao, Huiling Meng, Dan Li, Yan Zhang, Yuhao Li, Shuo Wang. Long-term exposure to 2-amino-3-methylimidazo[4,5-f]quinoline can trigger a potential risk of Parkinson's disease. Journal of Hazardous Materials 2021, 412 , 125230. https://doi.org/10.1016/j.jhazmat.2021.125230
  80. Lisa Hölzl‐Armstrong, Jill E. Kucab, Edwin P. Zwart, Mirjam Luijten, David H. Phillips, Volker M. Arlt. Mutagenicity of N ‐hydroxy‐4‐aminobiphenyl in human TP53 knock‐in (Hupki) mouse embryo fibroblasts. Environmental and Molecular Mutagenesis 2021, 62 (4) , 252-264. https://doi.org/10.1002/em.22429
  81. Hernâni Marques, Pedro Cruz-Vicente, Tiago Rosado, Mário Barroso, Luís A. Passarinha, Eugenia Gallardo. Recent Developments in the Determination of Biomarkers of Tobacco Smoke Exposure in Biological Specimens: A Review. International Journal of Environmental Research and Public Health 2021, 18 (4) , 1768. https://doi.org/10.3390/ijerph18041768
  82. Martina Štampar, Helle Sedighi Frandsen, Adelina Rogowska-Wrzesinska, Krzysztof Wrzesinski, Metka Filipič, Bojana Žegura. Hepatocellular carcinoma (HepG2/C3A) cell-based 3D model for genotoxicity testing of chemicals. Science of The Total Environment 2021, 755 , 143255. https://doi.org/10.1016/j.scitotenv.2020.143255
  83. Michael Fasullo. Genotoxic Assays for Measuring P450 Activation of Chemical Mutagens. 2021https://doi.org/10.5772/intechopen.90356
  84. Takashi Ueno, Tomomi Ishida, Jagadeesh Aluri, Michiyuki Suzuki, Carsten T. Beuckmann, Takaaki Kameyama, Shoji Asakura, Kazutomi Kusano. Disposition and Metabolism of [ 14 C]Lemborexant in Healthy Human Subjects and Characterization of Its Circulating Metabolites. Drug Metabolism and Disposition 2021, 49 (1) , 31-38. https://doi.org/10.1124/dmd.120.000229
  85. Lisa Hölzl-Armstrong, Sarah Moody, Jill E. Kucab, Edwin P. Zwart, Medjda Bellamri, Mirjam Luijten, Robert J. Turesky, Michael R. Stratton, Volker M. Arlt, David H. Phillips. Mutagenicity of 2-hydroxyamino-1-methyl-6-phenylimidazo[4,5-b]pyridine (N–OH-PhIP) in human TP53 knock-in (Hupki) mouse embryo fibroblasts. Food and Chemical Toxicology 2021, 147 , 111855. https://doi.org/10.1016/j.fct.2020.111855
  86. Jianghui Liu, Hiu Lam So, Wei Chu. Degradation of 1-Naphthylamine by A Uv Enhanced Fe2+/Oxone System: A Novel Ph-Dependent Activation Pathway. SSRN Electronic Journal 2021, 31 https://doi.org/10.2139/ssrn.3983685
  87. Lisa Hölzl-Armstrong, Andrea Nævisdal, Julie A Cox, Alexandra S Long, Nikolai L Chepelev, David H Phillips, Paul A White, Volker M Arlt. In vitro mutagenicity of selected environmental carcinogens and their metabolites in MutaMouse FE1 lung epithelial cells. Mutagenesis 2020, 35 (6) , 453-463. https://doi.org/10.1093/mutage/geaa032
  88. Lisa A. Peterson, Silvia Balbo, Naomi Fujioka, Dorothy K. Hatsukami, Stephen S. Hecht, Sharon E. Murphy, Irina Stepanov, Natalia Y. Tretyakova, Robert J. Turesky, Peter W. Villalta. Applying Tobacco, Environmental, and Dietary-Related Biomarkers to Understand Cancer Etiology and Evaluate Prevention Strategies. Cancer Epidemiology, Biomarkers & Prevention 2020, 29 (10) , 1904-1919. https://doi.org/10.1158/1055-9965.EPI-19-1356
  89. Samaria L. Gutiérrez-Pacheco, Martin Valenzuela-Melendres, Adrián Hernández-Mendoza, Armando Burgos-Hernández, Ramón E. Robles-Zepeda, E. Aída Peña-Ramos. Antimutagenic effect of an Asclepias subulata extract against heterocyclic aromatic amines commonly found in cooked meat and its heat stability. Food Chemistry 2020, 322 , 126725. https://doi.org/10.1016/j.foodchem.2020.126725
  90. Shabana Akhtar, Mojgan Najafzadeh, Mohammad Isreb, Lisa Newton, Rajendran C. Gopalan, Diana Anderson. Ex vivo/in vitro protective effect of myricetin bulk and nano-forms on PhIP-induced DNA damage in lymphocytes from healthy individuals and pre-cancerous MGUS patients. Archives of Toxicology 2020, 94 (7) , 2349-2357. https://doi.org/10.1007/s00204-020-02754-x
  91. Т.О. Shchutska, T.V. Adamchuk, A.E. Podrushnyak, H.А. Demich. Heterocyclic aromatic amines as a safety criteriа for meat and fish products. One Health and Nutrition Problems of Ukraine 2020, 52 (1) , 64-69. https://doi.org/10.33273/2663-9726-2020-52-1-64-69
  92. Andrea Hartwig, Michael Arand, Bernd Epe, Sabine Guth, Gunnar Jahnke, Alfonso Lampen, Hans-Jörg Martus, Bernhard Monien, Ivonne M. C. M. Rietjens, Simone Schmitz-Spanke, Gerlinde Schriever-Schwemmer, Pablo Steinberg, Gerhard Eisenbrand. Mode of action-based risk assessment of genotoxic carcinogens. Archives of Toxicology 2020, 94 (6) , 1787-1877. https://doi.org/10.1007/s00204-020-02733-2
  93. Tauqeerunnisa Syeda, Rachel M. Foguth, Emily Llewellyn, Jason R. Cannon. PhIP exposure in rodents produces neuropathology potentially relevant to Alzheimer’s disease. Toxicology 2020, 437 , 152436. https://doi.org/10.1016/j.tox.2020.152436
  94. Marzieh Kamankesh, Afsaneh Mollahosseini, Abdorreza Mohammadi, Shahram Seidi. Haas in grilled meat: Determination using an advanced lab-on-a-chip flat electromembrane extraction coupled with on-line HPLC. Food Chemistry 2020, 311 , 125876. https://doi.org/10.1016/j.foodchem.2019.125876
  95. Byeong Hwa Yun, Jingshu Guo, Medjda Bellamri, Robert J. Turesky. DNA adducts: Formation, biological effects, and new biospecimens for mass spectrometric measurements in humans. Mass Spectrometry Reviews 2020, 39 (1-2) , 55-82. https://doi.org/10.1002/mas.21570
  96. Cristina Montes, Ana M. Contento, María J. Villaseñor, Ángel Ríos. A screen-printed electrode modified with silver nanoparticles and carbon nanofibers in a nafion matrix for ionic liquid-based dispersive liquid-liquid microextraction and voltammetric assay of heterocyclic amine 8-MeIQx in food. Microchimica Acta 2020, 187 (3) https://doi.org/10.1007/s00604-020-4138-6
  97. Abdullah M. Alzahrani, Peramaiyan Rajendran. The Multifarious Link between Cytochrome P450s and Cancer. Oxidative Medicine and Cellular Longevity 2020, 2020 , 1-18. https://doi.org/10.1155/2020/3028387
  98. Stephen C. Mitchell. N-acetyltransferase: the practical consequences of polymorphic activity in man. Xenobiotica 2020, 50 (1) , 77-91. https://doi.org/10.1080/00498254.2019.1618511
  99. Lang Zhang, Hongzhen Du, Pin Zhang, Baohua Kong, Qian Liu. Heterocyclic aromatic amine concentrations and quality characteristics of traditional smoked and roasted poultry products on the northern Chinese market. Food and Chemical Toxicology 2020, 135 , 110931. https://doi.org/10.1016/j.fct.2019.110931
  100. Vivek Lawana, Se Young Um, Jean-Christophe Rochet, Robert J Turesky, Jonathan H Shannahan, Jason R Cannon. Neuromelanin Modulates Heterocyclic Aromatic Amine-Induced Dopaminergic Neurotoxicity. Toxicological Sciences 2020, 173 (1) , 171-188. https://doi.org/10.1093/toxsci/kfz210
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