ACS Publications. Most Trusted. Most Cited. Most Read
My Activity

Figure 1Loading Img

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

View Author Information
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
Copyright © 2011 American Chemical Society

    Article Views





    Other access options


    Abstract Image

    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.

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.


    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. You can change your affiliated institution below.

    Cited By

    This article is cited by 247 publications.

    1. Özge Edebali, Simona Krupčíková, Anna Goellner, Branislav Vrana, Melis Muz, Lisa Melymuk. Tracking Aromatic Amines from Sources to Surface Waters. Environmental Science & Technology Letters 2024, 11 (5) , 397-409.
    2. Siddharam Shivappa Bagale, Priyanka U. Deshmukh, Shailesh B. Lad, Akhil Sudarsan, Sruthi Sudhakar, Soumyadeep Mandal, Kiran Kondabagil, P. I. Pradeepkumar. Synthesis of N2-trans-isosafrole-dG-adduct Bearing DNAs and the Bypass Studies with Human TLS Polymerases κ and η. The Journal of Organic Chemistry 2024, Article ASAP.
    3. Yunfan Qiu, Lili Du, Sarah D. Cady, David Lee Phillips, Arthur H. Winter. Optical and EPR Detection of a Triplet Ground State Phenyl Nitrenium Ion. Journal of the American Chemical Society 2024, 146 (15) , 10679-10686.
    4. Angela L. Caipa Garcia, Jill E. Kucab, Halh Al-Serori, Rebekah S. S. Beck, Madjda Bellamri, Robert J. Turesky, John D. Groopman, Hayley E. Francies, Mathew J. Garnett, Meritxell Huch, Jarno Drost, Matthias Zilbauer, Volker M. Arlt, David H. Phillips. Tissue Organoid Cultures Metabolize Dietary Carcinogens Proficiently and Are Effective Models for DNA Adduct Formation. Chemical Research in Toxicology 2024, 37 (2) , 234-247.
    5. Nagarjunachary Ragi, Scott J. Walmsley, Foster C. Jacobs, Thomas A. Rosenquist, Viktoriya S. Sidorenko, Lihua Yao, Laura A. Maertens, Christopher J. Weight, Silvia Balbo, Peter W. Villalta, Robert J. Turesky. Screening DNA Damage in the Rat Kidney and Liver by Untargeted DNA Adductomics. Chemical Research in Toxicology 2024, 37 (2) , 340-360.
    6. Saba A. Gheni, Mudheher M. Ali, Goh C. Ta, Hannah J. Harbin, Saad A. Awad. Toxicity, Hazards, and Safe Handling of Primary Aromatic Amines. ACS Chemical Health & Safety 2024, 31 (1) , 8-21.
    7. Huihua Ji, Zhenyu Jin, Laura Fenton, Stacey Slone. Evaluation of Six Aromatic Amines in the Mainstream Smoke of Commercial Cigars. Chemical Research in Toxicology 2023, 36 (12) , 2001-2009.
    8. Medjda Bellamri, Kyle Brandt, Kari Cammerrer, Tauqeerunnisa Syeda, Robert J. Turesky, Jason R. Cannon. Nuclear DNA and Mitochondrial Damage of the Cooked Meat Carcinogen 2-Amino-1-methyl-6-phenylimidazo[4,5-b]pyridine in Human Neuroblastoma Cells. Chemical Research in Toxicology 2023, 36 (8) , 1361-1373.
    9. Chi Zhang, Man Fang, Yuanbo Gao, Yunchao Li, Louzhen Fan, Xiaohong Li. Valence-Engineered Oxidase-Mimicking Nanozyme with Specificity for Aromatic Amine Oxidation and Identification. Analytical Chemistry 2023, 95 (28) , 10713-10720.
    10. Gerhard Scherer, Kirsten Riedel, Nikola Pluym, Max Scherer. Assessment of the Exposure to Aromatic Amines in Users of Various Tobacco/Nicotine Products. ACS Omega 2022, 7 (45) , 41775-41782.
    11. 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.
    12. 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.
    13. 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.
    14. Tauqeerunnisa Syeda, Jason R. Cannon. Potential Role of Heterocyclic Aromatic Amines in Neurodegeneration. Chemical Research in Toxicology 2022, 35 (1) , 59-72.
    15. 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.
    16. 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.
    17. 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.
    18. 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.
    19. Yang Yu, Pengcheng Wang, Yuxiang Cui, and Yinsheng Wang . Chemical Analysis of DNA Damage. Analytical Chemistry 2018, 90 (1) , 556-576.
    20. 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.
    21. 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.
    22. Gabriele Sabbioni . Hemoglobin Adducts and Urinary Metabolites of Arylamines and Nitroarenes. Chemical Research in Toxicology 2017, 30 (10) , 1733-1766.
    23. Nicholas E. Geacintov and Suse Broyde . Repair-Resistant DNA Lesions. Chemical Research in Toxicology 2017, 30 (8) , 1517-1548.
    24. 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.
    25. 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.
    26. 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.
    27. 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.
    28. 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.
    29. 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.
    30. 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.
    31. 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.
    32. 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.
    33. 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.
    34. 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.
    35. 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.
    36. 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.
    37. 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.
    38. 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.
    39. 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.
    40. 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.
    41. 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.
    42. 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.
    43. 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.
    44. 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.
    45. 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.
    46. 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.
    47. 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.
    48. 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.
    49. 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.
    50. 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.
    51. Justine Ferey, Loïc Mervant, Nathalie Naud, Emilien L. Jamin, Fabrice Pierre, Laurent Debrauwer, Françoise Guéraud. Spatial metabolomics using mass-spectrometry imaging to decipher the impact of high red meat diet on the colon metabolome in rat. Talanta 2024, 276 , 126230.
    52. Xiao Tang, Yukang Jiang, Liangliang Song, Erik V. Van der Eycken. Recent Advances in the Synthesis of Rosettacin. Molecules 2024, 29 (10) , 2176.
    53. Jabril R. Johnson, Nicole Mavingire, Leanne Woods-Burnham, Mya Walker, Deyana Lewis, Stanley E. Hooker, Dorothy Galloway, Brian Rivers, Rick A. Kittles. The complex interplay of modifiable risk factors affecting prostate cancer disparities in African American men. Nature Reviews Urology 2024, 73
    54. M. Meurillon, E. Engel. Potential chemical hazards linked to meat processing. 2024, 708-715.
    55. Eyad Aoudeh, Emel Oz, Fatih Oz. Understanding the heterocyclic aromatic amines: An overview and recent findings. 2024
    56. B.L. Alman, G.A. Casillas, B.N. Szafran. High temperature cooked meats. 2024, 291-295.
    57. Medjda Bellamri. Heterocyclic aromatic amines (HAA), exposure, metabolism, macromolecular adducts, and cancer risk. 2024, 187-206.
    58. Michael Dolan, Nick St. John, Faizan Zaidi, Francis Doyle, Michael Fasullo, . High-throughput screening of the Saccharomyces cerevisiae genome for 2-amino-3-methylimidazo [4,5- f ] quinoline resistance identifies colon cancer-associated genes. G3: Genes, Genomes, Genetics 2023, 13 (12)
    59. 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)
    60. Hui-Jun Feng, Peng-Hua Zhi, Jun-Wen Wang. A novel thiazole-based covalent organic framework as turn-off fluorescent sensor for detection of aniline and triethylamine in liquid and vapor phase. Dyes and Pigments 2023, 220 , 111699.
    61. Samara B. Rifkin, Anna K. Miller, Eleazar E. Montalvan-Sanchez, Dalton A. Norwood, Enrique Martinez, Tim Waterboer, T. Mark Beasley, Ricardo L. Dominguez, Scott M. Williams, Douglas R. Morgan. Wood cookstove use is associated with gastric cancer in Central America and mediated by host genetics. Scientific Reports 2023, 13 (1)
    62. Tiffany Seyler, Shrila Mazumder, Rayaj Ahamed, Wanzhe Zhu, Benjamin C. Blount, Benjamin J. Apelberg, Lanqing Wang. Tobacco Smoke Is a Major Source of Aromatic Amine Exposure in U.S. Adults: 2013–2014 National Health and Nutrition Examination Survey (NHANES). Cancer Epidemiology, Biomarkers & Prevention 2023, 32 (7) , 986-994.
    63. 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.
    64. Kennedy M. Walls, Kyung U. Hong, David W. Hein. Induction of glucose production by heterocyclic amines is dependent on N-acetyltransferase 2 genetic polymorphism in cryopreserved human hepatocytes. Toxicology Letters 2023, 383 , 192-195.
    65. 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.
    66. 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.
    67. 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.
    68. 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.
    69. 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, 488 , 153483.
    70. 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, 377 , 71-82.
    71. 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.
    72. Carlos Hernandez-Castillo, Sarah C. Shuck, John Termini. DNA Adducts as Biomarkers in Toxicology. 2023, 351-382.
    73. 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
    74. Wendy A. Bedale, Andrew L. Milkowski, Charles J. Czuprynski, Mark P. Richards. Mechanistic Development of Cancers Associated with Processed Meat Products: A Review. Meat and Muscle Biology 2023, 7 (1)
    75. 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)
    76. Michael Fasullo, Michael Dolan. The continuing evolution of barcode applications: Functional toxicology to cell lineage. Experimental Biology and Medicine 2022, 247 (23) , 2119-2127.
    77. 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.
    78. 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.
    79. 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.
    80. Giorgia La Barbera, Katrine Dalmo Nommesen, Catalina Cuparencu, Jan Stanstrup, Lars Ove Dragsted. A Comprehensive Database for DNA Adductomics. Frontiers in Chemistry 2022, 10
    81. 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.
    82. 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.
    83. 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.
    84. 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.
    85. 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.
    86. 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.
    87. Carlos Hernandez-Castillo, Sarah C. Shuck, John Termini. DNA Adducts as Biomarkers in Toxicology. 2022, 1-32.
    88. 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.
    89. Sümeyra Çetinkaya, Kevser Taban Akça, Ipek Süntar. Flavonoids and anticancer activity: Structure–activity relationship. 2022, 81-115.
    90. 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)
    91. Loïc Le Marchand. The role of heterocyclic aromatic amines in colorectal cancer: the evidence from epidemiologic studies. Genes and Environment 2021, 43 (1)
    92. Medjda Bellamri, Scott J. Walmsley, Robert J. Turesky. Metabolism and biomarkers of heterocyclic aromatic amines in humans. Genes and Environment 2021, 43 (1)
    93. 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.
    94. Stephan Kirchner, Patrick Schnider. Genotoxicity. 2021, 331-363.
    95. 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.
    96. Olga Savinova, Mira Yerzhanova. Heterocyclic aromatic amines in food as mutagenesis factors. Journal of Food Processing and Preservation 2021, 45 (7)
    97. 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.
    98. 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.
    99. 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.
    100. 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.
    Load more citations

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    Pair your accounts.

    Export articles to Mendeley

    Get article recommendations from ACS based on references in your Mendeley library.

    You’ve supercharged your research process with ACS and Mendeley!

    STEP 1:
    Click to create an ACS ID

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Please note: If you switch to a different device, you may be asked to login again with only your ACS ID.

    Your Mendeley pairing has expired. Please reconnect