Biochemistry, Biology, and Carcinogenicity of Tobacco-Specific N-Nitrosamines†Click to copy article linkArticle link copied!
†
This paper is dedicated to the memory of my niece, Grace Anne Ossing, Nov 5, 1993−Dec 22, 1997. Grace's brain tumor (pineal parenchymal tumor) was diagnosed at age 1. While unrelated to the compounds discussed here, her cancer dramatically illustrates the need to understand the causes of cancer and develop preventive measures.
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(9)
, 1515-1523. https://doi.org/10.1021/acs.chemrestox.4c00109
- Shu Yu, J. Christopher McWilliams, Olivier Dirat, Krista L. Dobo, Amit S. Kalgutkar, Michelle O. Kenyon, Matthew T. Martin, Eric D. Watt, Maik Schuler. A Kinetic Model for Assessing Potential Nitrosamine Carcinogenicity. Chemical Research in Toxicology 2024, 37
(8)
, 1382-1393. https://doi.org/10.1021/acs.chemrestox.4c00133
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(6)
, 957-967. https://doi.org/10.1021/acs.chemrestox.4c00025
- David J. Snodin, Alejandra Trejo-Martin, David J. Ponting, Graham F. Smith, Andreas Czich, Kevin Cross, Laura Custer, Joanne Elloway, Nigel Greene, Amit S. Kalgutkar, Susanne A. Stalford, Rachael E. Tennant, Esther Vock, Adam Zalewski, Verena Ziegler, Krista L. Dobo. Mechanisms of Nitrosamine Mutagenicity and Their Relationship to Rodent Carcinogenic Potency. Chemical Research in Toxicology 2024, 37
(2)
, 181-198. https://doi.org/10.1021/acs.chemrestox.3c00327
- Francisco Gomez, Olalekan Ayo-Yusuf, Katrina Yershova, Vipin Jain, Aleksandra Alcheva, Dorothy K. Hatsukami, Mark Parascandola, Irina Stepanov. Heterogeneity of Harmful Constituent Profiles in Smokeless Tobacco Products from Five African Countries. Chemical Research in Toxicology 2023, 36
(12)
, 1901-1911. https://doi.org/10.1021/acs.chemrestox.3c00181
- Jiahui Tian, Wenli Zhao, Yanran Wu, Ying Shi, Jianqiang Yu, Wannian Zhang, Chengguo Xing, Chunlin Zhuang, Zhuo Qu. Diallyl Disulfide Blocks Cigarette Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone-Induced Lung Tumorigenesis via Activation of the Nrf2 Antioxidant System and Suppression of NF-κB Inflammatory Response. Journal of Agricultural and Food Chemistry 2023, 71
(46)
, 17763-17774. https://doi.org/10.1021/acs.jafc.3c02007
- Yupeng Li, Romel P. Dator, Laura A. Maertens, Silvia Balbo, Stephen S. Hecht. Mass Spectrometry-Based Metabolic Profiling of Urinary Metabolites of N′-Nitrosonornicotine (NNN) in the Rat. Chemical Research in Toxicology 2023, 36
(5)
, 769-781. https://doi.org/10.1021/acs.chemrestox.3c00025
- Xinqi Zhang, Qianyu Han, Ruilin Hou, Lijuan Xu, Wannian Zhang, Chengguo Xing, Lei Xue, Chunlin Zhuang. Targeting Receptor-Interacting Protein Kinase 1 by Novel Benzothiazole Derivatives: Treatment of Acute Lung Injury through the Necroptosis Pathway. Journal of Medicinal Chemistry 2023, 66
(7)
, 5261-5278. https://doi.org/10.1021/acs.jmedchem.3c00197
- Ru-Qiang Lu, Weize Yuan, Haosheng Feng, Shao-Xiong Lennon Luo, You-Chi Mason Wu, Samuel I. Etkind, Mohanraja Kumar, Timothy M. Swager. Porous Polymers Containing Metallocalix[4]arene for the Extraction of Tobacco-Specific Nitrosamines. Chemistry of Materials 2022, 34
(23)
, 10623-10630. https://doi.org/10.1021/acs.chemmater.2c02713
- David J. Ponting, Krista L. Dobo, Michelle O. Kenyon, Amit S. Kalgutkar. Strategies for Assessing Acceptable Intakes for Novel N-Nitrosamines Derived from Active Pharmaceutical Ingredients. Journal of Medicinal Chemistry 2022, 65
(23)
, 15584-15607. https://doi.org/10.1021/acs.jmedchem.2c01498
- Romel P. Dator, Kevin J. Murray, Matthew W. Luedtke, Foster C. Jacobs, Fekadu Kassie, Hai Dang Nguyen, Peter W. Villalta, Silvia Balbo. Identification of Formaldehyde-Induced DNA–RNA Cross-Links in the A/J Mouse Lung Tumorigenesis Model. Chemical Research in Toxicology 2022, 35
(11)
, 2025-2036. https://doi.org/10.1021/acs.chemrestox.2c00206
- Robert Thomas, Rachael E. Tennant, Antonio Anax F. Oliveira, David J. Ponting. What Makes a Potent Nitrosamine? Statistical Validation of Expert-Derived Structure–Activity Relationships. Chemical Research in Toxicology 2022, 35
(11)
, 1997-2013. https://doi.org/10.1021/acs.chemrestox.2c00199
- Lisa A. Peterson, Donna Seabloom, William E. Smith, Karin R. Vevang, Davis M. Seelig, Lin Zhang, Timothy S. Wiedmann. Acrolein Increases the Pulmonary Tumorigenic Activity of the Tobacco-Specific Nitrosamine 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Chemical Research in Toxicology 2022, 35
(10)
, 1831-1839. https://doi.org/10.1021/acs.chemrestox.2c00135
- Yupeng Li, Stephen S. Hecht. Mass Spectrometric Quantitation of N′-Nitrosonornicotine-1N-oxide in the Urine of Cigarette Smokers and Smokeless Tobacco Users. Chemical Research in Toxicology 2022, 35
(9)
, 1579-1588. https://doi.org/10.1021/acs.chemrestox.2c00195
- Xiaochen Tang, Neal Benowitz, Lara Gundel, Bo Hang, Christopher M. Havel, Eunha Hoh, Peyton Jacob III, Jian-Hua Mao, Manuela Martins-Green, Georg E. Matt, Penelope J. E. Quintana, Marion L. Russell, Altaf Sarker, Suzaynn F. Schick, Antoine M. Snijders, Hugo Destaillats. Thirdhand Exposures to Tobacco-Specific Nitrosamines through Inhalation, Dust Ingestion, Dermal Uptake, and Epidermal Chemistry. Environmental Science & Technology 2022, 56
(17)
, 12506-12516. https://doi.org/10.1021/acs.est.2c02559
- Dilip V. Patil, Yulim Lee, Hun Young Kim, Kyungsoo Oh. Visible-Light-Promoted Photoaddition of N-Nitrosopiperidines to Alkynes: Continuous Flow Chemistry Approach to Tetrahydroimidazo[1,2-a]pyridine 1-Oxides. Organic Letters 2022, 24
(31)
, 5840-5844. https://doi.org/10.1021/acs.orglett.2c02402
- Xiaohong C. Jin, Karl A. Wagner, Matt S. Melvin, Donna C. Smith, Yezdi B. Pithawalla, William P. Gardner, Karen C. Avery, Georgios D. Karles. Influence of Nitrite on Formation of Tobacco-Specific Nitrosamines in Electronic Cigarette Liquids and Aerosols. Chemical Research in Toxicology 2022, 35
(5)
, 782-791. https://doi.org/10.1021/acs.chemrestox.1c00417
- Krista L. Dobo, Michelle O. Kenyon, Olivier Dirat, Maria Engel, Andrew Fleetwood, Matthew Martin, Susan Mattano, Alyssa Musso, James Christopher McWilliams, Alexandros Papanikolaou, Patricia Parris, Jessica Whritenour, Shu Yu, Amit S. Kalgutkar. Practical and Science-Based Strategy for Establishing Acceptable Intakes for Drug Product N-Nitrosamine Impurities. Chemical Research in Toxicology 2022, 35
(3)
, 475-489. https://doi.org/10.1021/acs.chemrestox.1c00369
- Priya Bhutani, Makay T. Murray, Craig W. Sommer, Katie A. Wilson, Stacey D. Wetmore. Structural Rationalization for the Nonmutagenic and Mutagenic Bypass of the Tobacco-Derived O4-4-(3-Pyridyl)-4-oxobut-1-yl-thymine Lesion by Human Polymerase η: A Multiscale Computational Study. Chemical Research in Toxicology 2021, 34
(6)
, 1619-1629. https://doi.org/10.1021/acs.chemrestox.1c00063
- Yupeng Li, Erik S. Carlson, Adam T. Zarth, Pramod Upadhyaya, Stephen S. Hecht. Investigation of 2′-Deoxyadenosine-Derived Adducts Specifically Formed in Rat Liver and Lung DNA by N′-Nitrosonornicotine Metabolism. Chemical Research in Toxicology 2021, 34
(4)
, 1004-1015. https://doi.org/10.1021/acs.chemrestox.1c00012
- Yupeng Li, Stephen S. Hecht. Identification of an N′-Nitrosonornicotine-Specific Deoxyadenosine Adduct in Rat Liver and Lung DNA. Chemical Research in Toxicology 2021, 34
(4)
, 992-1003. https://doi.org/10.1021/acs.chemrestox.1c00013
- Dilip V. Patil, Tengda Si, Hun Young Kim, Kyungsoo Oh. Visible-Light-Induced Photoaddition of N-Nitrosoalkylamines to Alkenes: One-Pot Tandem Approach to 1,2-Diamination of Alkenes from Secondary Amines. Organic Letters 2021, 23
(8)
, 3105-3109. https://doi.org/10.1021/acs.orglett.1c00786
- Lisa A. Peterson, Marissa K. Oram, Monica Flavin, Donna Seabloom, William E. Smith, M. Gerard O’Sullivan, Karin R. Vevang, Pramod Upadhyaya, Alessia Stornetta, Andrew C. Floeder, Yen-Yi Ho, Lin Zhang, Stephen S. Hecht, Silvia Balbo, Timothy S. Wiedmann. Coexposure to Inhaled Aldehydes or Carbon Dioxide Enhances the Carcinogenic Properties of the Tobacco-Specific Nitrosamine 4-Methylnitrosamino-1-(3-pyridyl)-1-butanone in the A/J Mouse Lung. Chemical Research in Toxicology 2021, 34
(3)
, 723-732. https://doi.org/10.1021/acs.chemrestox.0c00350
- Xiaomei He, Pengcheng Wang, Yinsheng Wang. Mitochondrial Transcription Factor A Binds to and Promotes Mutagenic Transcriptional Bypass of O4-Alkylthymidine Lesions. Analytical Chemistry 2021, 93
(2)
, 1161-1169. https://doi.org/10.1021/acs.analchem.0c04224
- Claudia M. N. Aloisi, Emma S. Sandell, Shana J. Sturla. A Chemical Link between Meat Consumption and Colorectal Cancer Development?. Chemical Research in Toxicology 2021, 34
(1)
, 12-23. https://doi.org/10.1021/acs.chemrestox.0c00395
- Tengda Si, Hun Young Kim, Kyungsoo Oh. One-Pot Tandem ortho-Naphthoquinone-Catalyzed Aerobic Nitrosation of N-Alkylanilines and Rh(III)-Catalyzed C–H Functionalization Sequence to Indole and Aniline Derivatives. The Journal of Organic Chemistry 2021, 86
(1)
, 1152-1163. https://doi.org/10.1021/acs.joc.0c02776
- Jiehong Guo, Haoqing Chen, Pramod Upadhyaya, Yingchun Zhao, Robert J. Turesky, Stephen S. Hecht. Mass Spectrometric Quantitation of Apurinic/Apyrimidinic Sites in Tissue DNA of Rats Exposed to Tobacco-Specific Nitrosamines and in Lung and Leukocyte DNA of Cigarette Smokers and Nonsmokers. Chemical Research in Toxicology 2020, 33
(9)
, 2475-2486. https://doi.org/10.1021/acs.chemrestox.0c00265
- Rumasha N. T. Kankanamage, Abhisek Brata Ghosh, Di Jiang, Karmel Gkika, Tia Keyes, Laura A. Achola, Steven Suib, James F. Rusling. Metabolites of Tobacco- and E-Cigarette-Related Nitrosamines Can Drive Cu2+-Mediated DNA Oxidation. Chemical Research in Toxicology 2020, 33
(8)
, 2072-2086. https://doi.org/10.1021/acs.chemrestox.0c00027
- Qi Hu, Pedro Corral, Sreekanth C. Narayanapillai, Pablo Leitzman, Pramod Upadhyaya, M. Gerard O'Sullivan, Stephen S. Hecht, Junxuan Lu, Chengguo Xing. Oral Dosing of Dihydromethysticin Ahead of Tobacco Carcinogen NNK Effectively Prevents Lung Tumorigenesis in A/J Mice. Chemical Research in Toxicology 2020, 33
(7)
, 1980-1988. https://doi.org/10.1021/acs.chemrestox.0c00161
- Jorddy Neves Cruz, Mozaniel Santana de Oliveira, Sebastião Gomes Silva, Antonio Pedro da Silva Souza Filho, Daniel Santiago Pereira, Anderson Henrique Lima e Lima, Eloisa Helena de Aguiar Andrade. Insight into the Interaction Mechanism of Nicotine, NNK, and NNN with Cytochrome P450 2A13 Based on Molecular Dynamics Simulation. Journal of Chemical Information and Modeling 2020, 60
(2)
, 766-776. https://doi.org/10.1021/acs.jcim.9b00741
- Carlos Hernandez-Castillo, John Termini, Sarah Shuck. DNA Adducts as Biomarkers To Predict, Prevent, and Diagnose Disease—Application of Analytical Chemistry to Clinical Investigations. Chemical Research in Toxicology 2020, 33
(2)
, 286-307. https://doi.org/10.1021/acs.chemrestox.9b00295
- Guangcai Ma, Haiying Yu, Xiaoqin Xu, Liming Geng, Xiaoxuan Wei, Jiale Wen, Zhiguo Wang. Molecular Basis for Metabolic Regioselectivity and Mechanism of Cytochrome P450s toward Carcinogenic 4-(Methylnitrosamino)-(3-pyridyl)-1-butanone. Chemical Research in Toxicology 2020, 33
(2)
, 436-447. https://doi.org/10.1021/acs.chemrestox.9b00353
- Zhuochen Zhuang, Jintao Li, Guohui Sun, Xin Cui, Na Zhang, Lijiao Zhao, Paul K. S. Chan, Rugang Zhong. Synergistic Effect between Human Papillomavirus 18 and 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone on Malignant Transformation of Immortalized SHEE Cells. Chemical Research in Toxicology 2020, 33
(2)
, 470-481. https://doi.org/10.1021/acs.chemrestox.9b00371
- Jiabin Wu, Yinsheng Wang. Replication of Pyridyloxobutyl Phosphotriester Lesions in Cells. Chemical Research in Toxicology 2020, 33
(2)
, 308-311. https://doi.org/10.1021/acs.chemrestox.9b00485
- Shannon Kozlovich, Gang Chen, Christy J. W. Watson, Philip Lazarus. Prominent Stereoselectivity of NNAL Glucuronidation in Upper Aerodigestive Tract Tissues. Chemical Research in Toxicology 2019, 32
(8)
, 1689-1698. https://doi.org/10.1021/acs.chemrestox.9b00217
- Katie
A. Wilson, Josh L. Garden, Natasha T. Wetmore, Lindey R. Felske, Stacey D. Wetmore. DFT and MD Studies of Formaldehyde-Derived DNA Adducts: Molecular-Level Insights into the Differential Mispairing Potentials of the Adenine, Cytosine, and Guanine Lesions. The Journal of Physical Chemistry A 2019, 123
(29)
, 6229-6240. https://doi.org/10.1021/acs.jpca.9b03899
- Su Guo, Jiapeng Leng, Ying Tan, Nathan E. Price, Yinsheng Wang. Quantification of DNA Lesions Induced by 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol in Mammalian Cells. Chemical Research in Toxicology 2019, 32
(4)
, 708-717. https://doi.org/10.1021/acs.chemrestox.8b00374
- Yupeng Li, Bin Ma, Qing Cao, Silvia Balbo, Lijiao Zhao, Pramod Upadhyaya, Stephen S. Hecht. Mass Spectrometric Quantitation of Pyridyloxobutyl DNA Phosphate Adducts in Rats Chronically Treated with N′-Nitrosonornicotine. Chemical Research in Toxicology 2019, 32
(4)
, 773-783. https://doi.org/10.1021/acs.chemrestox.9b00007
- Hauh-Jyun Candy Chen, Sun Wai Ip. Age-Associated Methylation in Human Hemoglobin and Its Stability on Dried Blood Spots As Analyzed by Nanoflow Liquid Chromatography Tandem Mass Spectrometry. Chemical Research in Toxicology 2018, 31
(11)
, 1240-1247. https://doi.org/10.1021/acs.chemrestox.8b00224
- Guangcai Ma, Haiying Yu, Ting Xu, Xiaoxuan Wei, Jianrong Chen, Hongjun Lin, Gerrit Schüürmann. Computational Insight into the Activation Mechanism of Carcinogenic N’-Nitrosonornicotine (NNN) Catalyzed by Cytochrome P450. Environmental Science & Technology 2018, 52
(20)
, 11838-11847. https://doi.org/10.1021/acs.est.8b02795
- Samuel Kaiser, Frederico L. F. Soares, Jorge A. Ardila, Marcelo C. A. Marcelo, Jailson C. Dias, Liliane M. F. Porte, Carlos Gonçalves, Oscar F. S. Pontes, Guilherme P. Sabin. Innovative Approaches for Estimating the Levels of Tobacco-Specific Nitrosamines in Cured Tobacco Samples. Chemical Research in Toxicology 2018, 31
(9)
, 964-973. https://doi.org/10.1021/acs.chemrestox.8b00154
- Yi Wang, Sreekanth Narayanapillai, Qi Hu, Naomi Fujioka, Chengguo Xing. Contribution of Tobacco Use and 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone to Three Methyl DNA Adducts in Urine. Chemical Research in Toxicology 2018, 31
(9)
, 836-838. https://doi.org/10.1021/acs.chemrestox.8b00155
- Gabriela Bustamante, Bin Ma, Galina Yakovlev, Katrina Yershova, Chap Le, Joni Jensen, Dorothy K. Hatsukami, Irina Stepanov. Presence of the Carcinogen N′-Nitrosonornicotine in Saliva of E-cigarette Users. Chemical Research in Toxicology 2018, 31
(8)
, 731-738. https://doi.org/10.1021/acs.chemrestox.8b00089
- Erik S. Carlson, Pramod Upadhyaya, Peter W. Villalta, Bin Ma, Stephen S. Hecht. Analysis and Identification of 2′-Deoxyadenosine-Derived Adducts in Lung and Liver DNA of F-344 Rats Treated with the Tobacco-Specific Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone and Enantiomers of its Metabolite 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol. Chemical Research in Toxicology 2018, 31
(5)
, 358-370. https://doi.org/10.1021/acs.chemrestox.8b00056
- Bin Ma, Adam T. Zarth, Erik S. Carlson, Peter W. Villalta, Pramod Upadhyaya, Irina Stepanov, and Stephen S. Hecht . Methyl DNA Phosphate Adduct Formation in Rats Treated Chronically with 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone and Enantiomers of Its Metabolite 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol. Chemical Research in Toxicology 2018, 31
(1)
, 48-57. https://doi.org/10.1021/acs.chemrestox.7b00281
- Manohar Puppala, Sreekanth C. Narayanapillai, Pablo Leitzman, Haifeng Sun, Pramod Upadhyaya, M. Gerard O’Sullivan, Stephen S. Hecht, and Chengguo Xing . Pilot in Vivo Structure–Activity Relationship of Dihydromethysticin in Blocking 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone-Induced O6-Methylguanine and Lung Tumor in A/J Mice. Journal of Medicinal Chemistry 2017, 60
(18)
, 7935-7940. https://doi.org/10.1021/acs.jmedchem.7b00921
- Jiapeng Leng and Yinsheng Wang . Liquid Chromatography-Tandem Mass Spectrometry for the Quantification of Tobacco-Specific Nitrosamine-Induced DNA Adducts in Mammalian Cells. Analytical Chemistry 2017, 89
(17)
, 9124-9130. https://doi.org/10.1021/acs.analchem.7b01857
- Katie A. Wilson and Stacey D. Wetmore . Molecular Insights into the Translesion Synthesis of Benzyl-Guanine from Molecular Dynamics Simulations: Structural Evidence of Mutagenic and Nonmutagenic Replication. Biochemistry 2017, 56
(13)
, 1841-1853. https://doi.org/10.1021/acs.biochem.6b01247
- Anna K. Michel, Adam T. Zarth, Pramod Upadhyaya, and Stephen S. Hecht . Identification of 4-(3-Pyridyl)-4-oxobutyl-2′-deoxycytidine Adducts Formed in the Reaction of DNA with 4-(Acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone: A Chemically Activated Form of Tobacco-Specific Carcinogens. ACS Omega 2017, 2
(3)
, 1180-1190. https://doi.org/10.1021/acsomega.7b00072
- Vipin Jain, Apurva Garg, Mark Parascandola, Pankaj Chaturvedi, Samir S. Khariwala, and Irina Stepanov . Analysis of Alkaloids in Areca Nut-Containing Products by Liquid Chromatography–Tandem Mass Spectrometry. Journal of Agricultural and Food Chemistry 2017, 65
(9)
, 1977-1983. https://doi.org/10.1021/acs.jafc.6b05140
- Selvin H. Edwards, Lana M. Rossiter, Kenneth M. Taylor, Matthew R. Holman, Liqin Zhang, Yan S. Ding, and Clifford H. Watson . Tobacco-Specific Nitrosamines in the Tobacco and Mainstream Smoke of U.S. Commercial Cigarettes. Chemical Research in Toxicology 2017, 30
(2)
, 540-551. https://doi.org/10.1021/acs.chemrestox.6b00268
- Lisa A. Peterson . Context Matters: Contribution of Specific DNA Adducts to the Genotoxic Properties of the Tobacco-Specific Nitrosamine NNK. Chemical Research in Toxicology 2017, 30
(1)
, 420-433. https://doi.org/10.1021/acs.chemrestox.6b00386
- Erik S. Carlson, Pramod Upadhyaya, and Stephen S. Hecht . Evaluation of Nitrosamide Formation in the Cytochrome P450-Mediated Metabolism of Tobacco-Specific Nitrosamines. Chemical Research in Toxicology 2016, 29
(12)
, 2194-2205. https://doi.org/10.1021/acs.chemrestox.6b00384
- Dinesh K. Barupal, Kent E. Pinkerton, Carol Hood, Tobias Kind, and Oliver Fiehn . Environmental Tobacco Smoke Alters Metabolic Systems in Adult Rats. Chemical Research in Toxicology 2016, 29
(11)
, 1818-1827. https://doi.org/10.1021/acs.chemrestox.6b00187
- Sreekanth C. Narayanapillai, Shang-Hsuan Lin, Pablo Leitzman, Pramod Upadhyaya, Carolyn J. Baglole, and Chengguo Xing . Dihydromethysticin (DHM) Blocks Tobacco Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK)-Induced O6-Methylguanine in a Manner Independent of the Aryl Hydrocarbon Receptor (AhR) Pathway in C57BL/6 Female Mice. Chemical Research in Toxicology 2016, 29
(11)
, 1828-1834. https://doi.org/10.1021/acs.chemrestox.6b00203
- Bin Ma, Chris Ruszczak, Vipin Jain, Samir S. Khariwala, Bruce Lindgren, Dorothy K. Hatsukami, and Irina Stepanov . Optimized Liquid Chromatography Nanoelectrospray–High-Resolution Tandem Mass Spectrometry Method for the Analysis of 4-Hydroxy-1-(3-pyridyl)-1-butanone-Releasing DNA Adducts in Human Oral Cells. Chemical Research in Toxicology 2016, 29
(11)
, 1849-1856. https://doi.org/10.1021/acs.chemrestox.6b00254
- Jingshu Guo, Byeong Hwa Yun, Pramod Upadhyaya, Lihua Yao, Sesha Krishnamachari, Thomas A. Rosenquist, Arthur P. Grollman, and Robert J. Turesky . Multiclass Carcinogenic DNA Adduct Quantification in Formalin-Fixed Paraffin-Embedded Tissues by Ultraperformance Liquid Chromatography–Tandem Mass Spectrometry. Analytical Chemistry 2016, 88
(9)
, 4780-4787. https://doi.org/10.1021/acs.analchem.6b00124
- Bin Cai, Huihua Ji, Franklin F. Fannin, and Lowell P. Bush . Contribution of Nicotine and Nornicotine toward the Production of N′-Nitrosonornicotine in Air-Cured Tobacco (Nicotiana tabacum). Journal of Natural Products 2016, 79
(4)
, 754-759. https://doi.org/10.1021/acs.jnatprod.5b00678
- A. S. Prakasha Gowda and Thomas E. Spratt . DNA Polymerases η and ζ Combine to Bypass O2-[4-(3-Pyridyl)-4-oxobutyl]thymine, a DNA Adduct Formed from Tobacco Carcinogens. Chemical Research in Toxicology 2016, 29
(3)
, 303-316. https://doi.org/10.1021/acs.chemrestox.5b00468
- Adam T. Zarth, Pramod Upadhyaya, Jing Yang, and Stephen S. Hecht . DNA Adduct Formation from Metabolic 5′-Hydroxylation of the Tobacco-Specific Carcinogen N′-Nitrosonornicotine in Human Enzyme Systems and in Rats. Chemical Research in Toxicology 2016, 29
(3)
, 380-389. https://doi.org/10.1021/acs.chemrestox.5b00520
- Stephen S. Hecht, Irina Stepanov, and Steven G. Carmella . Exposure and Metabolic Activation Biomarkers of Carcinogenic Tobacco-Specific Nitrosamines. Accounts of Chemical Research 2016, 49
(1)
, 106-114. https://doi.org/10.1021/acs.accounts.5b00472
- Jing Yang, Peter W. Villalta, Pramod Upadhyaya, and Stephen S. Hecht . Analysis of O6-[4-(3-Pyridyl)-4-oxobut-1-yl]-2′-deoxyguanosine and Other DNA Adducts in Rats Treated with Enantiomeric or Racemic N′-Nitrosonornicotine. Chemical Research in Toxicology 2016, 29
(1)
, 87-95. https://doi.org/10.1021/acs.chemrestox.5b00425
- Wolfgang Zwickenpflug, Christof Högg, Johannes Feierfeil, Manuel Dachs, and Thomas Gudermann . Isolation of Nicotinic Acid (Vitamin B3) and N-Propylamine after Myosmine Peroxidation. Journal of Agricultural and Food Chemistry 2016, 64
(1)
, 178-184. https://doi.org/10.1021/acs.jafc.5b04913
- Shannon Kozlovich, Gang Chen, and Philip Lazarus . Stereospecific Metabolism of the Tobacco-Specific Nitrosamine, NNAL. Chemical Research in Toxicology 2015, 28
(11)
, 2112-2119. https://doi.org/10.1021/acs.chemrestox.5b00278
- Bin Ma, Peter W. Villalta, Adam T. Zarth, Delshanee Kotandeniya, Pramod Upadhyaya, Irina Stepanov, and Stephen S. Hecht . Comprehensive High-Resolution Mass Spectrometric Analysis of DNA Phosphate Adducts Formed by the Tobacco-Specific Lung Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone. Chemical Research in Toxicology 2015, 28
(11)
, 2151-2159. https://doi.org/10.1021/acs.chemrestox.5b00318
- Delshanee Kotandeniya, Steven G. Carmella, Xun Ming, Sharon E. Murphy, and Stephen S. Hecht . Combined Analysis of the Tobacco Metabolites Cotinine and 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol in Human Urine. Analytical Chemistry 2015, 87
(3)
, 1514-1517. https://doi.org/10.1021/ac504047j
- Gerhard Lang and Aline Vuarnoz . Matrix-Bound 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone in Tobacco: Quantification and Evidence for an Origin from Lignin-Incorporated Alkaloids. Journal of Natural Products 2015, 78
(1)
, 85-92. https://doi.org/10.1021/np500725a
- Beibei Chen, Yichao Qian, Minghuo Wu, Lifang Zhu, Bin Hu, and Xing-Fang Li . Identification of Precursors and Mechanisms of Tobacco-Specific Nitrosamine Formation in Water during Chloramination. Environmental Science & Technology 2015, 49
(1)
, 459-466. https://doi.org/10.1021/es505057h
- Xuetuan Wei, Xiaowu Deng, Dongbo Cai, Zhixia Ji, Changjun Wang, Jun Yu, Jinping Li, and Shouwen Chen . Decreased Tobacco-Specific Nitrosamines by Microbial Treatment with Bacillus amyloliquefaciens DA9 during the Air-Curing Process of Burley Tobacco. Journal of Agricultural and Food Chemistry 2014, 62
(52)
, 12701-12706. https://doi.org/10.1021/jf504084z
- Meng Jing, Yaohua Wang, Pramod Upadhyaya, Vipin Jain, Jian-Min Yuan, Dorothy K. Hatsukami, Stephen S. Hecht, and Irina Stepanov . Liquid Chromatography–Electrospray Ionization–Tandem Mass Spectrometry Quantitation of Urinary [Pyridine-D4]4-hydroxy-4-(3-pyridyl)butanoic Acid, a Biomarker of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone Metabolic Activation in Smokers. Chemical Research in Toxicology 2014, 27
(9)
, 1547-1555. https://doi.org/10.1021/tx5001915
- Minghuo Wu, Yichao Qian, Jessica M. Boyd, Shannon Leavey, Steve E. Hrudey, Stuart W. Krasner, and Xing-Fang Li . Identification of Tobacco-Specific Nitrosamines as Disinfection Byproducts in Chloraminated Water. Environmental Science & Technology 2014, 48
(3)
, 1828-1834. https://doi.org/10.1021/es405075g
- Hongzhi Shi, Ruiyun Wang, Lowell P. Bush, Jun Zhou, Huijuan Yang, Neil Fannin, and Ruoshi Bai . Changes in TSNA Contents during Tobacco Storage and the Effect of Temperature and Nitrate Level on TSNA Formation. Journal of Agricultural and Food Chemistry 2013, 61
(47)
, 11588-11594. https://doi.org/10.1021/jf404813m
- Lisa A. Peterson, Anna M. Urban, Choua C. Vu, Meredith E. Cummings, Lee C. Brown, Janel K. Warmka, Li Li, Elizabeth V. Wattenberg, Yesha Patel, Daniel O. Stram, and Anthony E. Pegg . Role of Aldehydes in the Toxic and Mutagenic Effects of Nitrosamines. Chemical Research in Toxicology 2013, 26
(10)
, 1464-1473. https://doi.org/10.1021/tx400196j
- Lijiao Zhao, Silvia Balbo, Mingyao Wang, Pramod Upadhyaya, Samir S. Khariwala, Peter W. Villalta, and Stephen S. Hecht . Quantitation of Pyridyloxobutyl-DNA Adducts in Tissues of Rats Treated Chronically with (R)- or (S)-N′-Nitrosonornicotine (NNN) in a Carcinogenicity Study. Chemical Research in Toxicology 2013, 26
(10)
, 1526-1535. https://doi.org/10.1021/tx400235x
- Delshanee Kotandeniya, Daniel Murphy, Shuo Yan, Soobong Park, Uthpala Seneviratne, Joseph S. Koopmeiners, Anthony Pegg, Sreenivas Kanugula, Fekadu Kassie, and Natalia Tretyakova . Kinetics of O6-Pyridyloxobutyl-2′-deoxyguanosine Repair by Human O6-alkylguanine DNA Alkyltransferase. Biochemistry 2013, 52
(23)
, 4075-4088. https://doi.org/10.1021/bi4004952
- Silvia Balbo, Pramod Upadhyaya, Peter W. Villalta, Xuemin Qian, and Fekadu Kassie . DNA Adducts in Aldehyde Dehydrogenase-Positive Lung Stem Cells of A/J Mice Treated with the Tobacco Specific Lung Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Chemical Research in Toxicology 2013, 26
(4)
, 511-513. https://doi.org/10.1021/tx400054s
- John M. Prins and Yinsheng Wang . Quantitative Proteomic Analysis Revealed N′-Nitrosonornicotine-induced Down-regulation of Nonmuscle Myosin II and Reduced Cell Migration in Cultured Human Skin Fibroblast Cells. Journal of Proteome Research 2013, 12
(3)
, 1282-1288. https://doi.org/10.1021/pr3009397
- Irina Stepanov, John Muzic, Chap T. Le, Erin Sebero, Peter Villalta, Bin Ma, Joni Jensen, Dorothy Hatsukami, and Stephen S. Hecht . Analysis of 4-Hydroxy-1-(3-pyridyl)-1-butanone (HPB)-Releasing DNA Adducts in Human Exfoliated Oral Mucosa Cells by Liquid Chromatography–Electrospray Ionization–Tandem Mass Spectrometry. Chemical Research in Toxicology 2013, 26
(1)
, 37-45. https://doi.org/10.1021/tx300282k
- Bin Cai and Lowell P. Bush . Variable Nornicotine Enantiomeric Composition Caused by Nicotine Demethylase CYP82E4 in Tobacco Leaf. Journal of Agricultural and Food Chemistry 2012, 60
(46)
, 11586-11591. https://doi.org/10.1021/jf303681u
- Anna M. Urban, Pramod Upadhyaya, Qing Cao, and Lisa A. Peterson . Formation and Repair of Pyridyloxobutyl DNA Adducts and Their Relationship to Tumor Yield in A/J Mice. Chemical Research in Toxicology 2012, 25
(10)
, 2167-2178. https://doi.org/10.1021/tx300245w
- Ramsey S. Lewis, Robert G. Parker, David A. Danehower, Karen Andres, Anne M. Jack, D. Scott Whitley, and Lowell P. Bush . Impact of Alleles at the Yellow Burley (Yb) Loci and Nitrogen Fertilization Rate on Nitrogen Utilization Efficiency and Tobacco-Specific Nitrosamine (TSNA) Formation in Air-Cured Tobacco. Journal of Agricultural and Food Chemistry 2012, 60
(25)
, 6454-6461. https://doi.org/10.1021/jf2053614
- A. S. Prakasha Gowda, Gowdahalli Krishnegowda, Zucai Suo, Shantu Amin, and Thomas E. Spratt . Low Fidelity Bypass of O2-(3-Pyridyl)-4-oxobutylthymine, the Most Persistent Bulky Adduct Produced by the Tobacco Specific Nitrosamine 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone by Model DNA Polymerases. Chemical Research in Toxicology 2012, 25
(6)
, 1195-1202. https://doi.org/10.1021/tx200483g
- John M. Prins and Yinsheng Wang . Quantitative Proteomic Analysis Revealed 4-(Methylnitrosamino)-1-(3-pyridinyl)-1-butanone-Induced Up-Regulation of 20S Proteasome in Cultured Human Fibroblast Cells. Journal of Proteome Research 2012, 11
(4)
, 2347-2354. https://doi.org/10.1021/pr201088z
- Dhanuka P. Wasalathanthri, Vigneshwaran Mani, Chi K. Tang, and James F. Rusling . Microfluidic Electrochemical Array for Detection of Reactive Metabolites Formed by Cytochrome P450 Enzymes. Analytical Chemistry 2011, 83
(24)
, 9499-9506. https://doi.org/10.1021/ac202269t
- Delshanee Kotandeniya, Dan Murphy, Uthpala Seneviratne, Rebecca Guza, Anthony Pegg, Sreenivas Kanugula, and Natalia Tretyakova . Mass Spectrometry Based Approach to Study the Kinetics of O6-Alkylguanine DNA Alkyltransferase-Mediated Repair of O6-Pyridyloxobutyl-2′-deoxyguanosine Adducts in DNA. Chemical Research in Toxicology 2011, 24
(11)
, 1966-1975. https://doi.org/10.1021/tx2002993
- Vijay P. Jasti, Thomas E. Spratt, and Ashis K. Basu . Tobacco-Specific Nitrosamine-Derived O2-Alkylthymidines Are Potent Mutagenic Lesions in SOS-Induced Escherichia coli. Chemical Research in Toxicology 2011, 24
(11)
, 1833-1835. https://doi.org/10.1021/tx200435d
- Changguo Wang, Ya Dai, Guanglin Feng, Rong He, Wenmin Yang, Dongliang Li, Xuezheng Zhou, Lijun Zhu, and Lanlan Tan . Addition of Porphyrins to Cigarette Filters To Reduce the Levels of Benzo[a]pyrene (B[a]P) and Tobacco-Specific N-Nitrosamines (TSNAs) in Mainstream Cigarette Smoke. Journal of Agricultural and Food Chemistry 2011, 59
(13)
, 7172-7177. https://doi.org/10.1021/jf200966p
- Sadagopan Krishnan, John B. Schenkman, and James F. Rusling . Bioelectronic Delivery of Electrons to Cytochrome P450 Enzymes. The Journal of Physical Chemistry B 2011, 115
(26)
, 8371-8380. https://doi.org/10.1021/jp201235m
- Zhi Sun, Yong Dong Liu, and Ru Gang Zhong . Carbon Dioxide in the Nitrosation of Amine: Catalyst or Inhibitor?. The Journal of Physical Chemistry A 2011, 115
(26)
, 7753-7764. https://doi.org/10.1021/jp202002m
- Stephen S. Hecht, Pramod Upadhyaya, and Mingyao Wang . Evolution of Research on the DNA Adduct Chemistry of N-Nitrosopyrrolidine and Related Aldehydes. Chemical Research in Toxicology 2011, 24
(6)
, 781-790. https://doi.org/10.1021/tx200064a
- Gowdahalli Krishnegowda, Arun K. Sharma, Jacek Krzeminski, A. S. Prakasha Gowda, Jyh-Ming Lin, Dhimant Desai, Thomas E. Spratt, and Shantu Amin . Facile Syntheses of O2-[4-(3-Pyridyl-4-oxobut-1-yl]thymidine, the Major Adduct Formed by Tobacco Specific Nitrosamine 4-methylnitrosamino-1-(3-pyridyl)-1-butanone (NNK) in vivo, and Its Site-Specifically Adducted Oligodeoxynucleotides. Chemical Research in Toxicology 2011, 24
(6)
, 960-967. https://doi.org/10.1021/tx200127j
- Shenmin Pan, Linlin Zhao, John B. Schenkman, and James F. Rusling . Evaluation of Electrochemiluminescent Metabolic Toxicity Screening Arrays Using a Multiple Compound Set. Analytical Chemistry 2011, 83
(7)
, 2754-2760. https://doi.org/10.1021/ac200050n
- Sadagopan Krishnan, Dhanuka Wasalathanthri, Linlin Zhao, John B. Schenkman, and James F. Rusling . Efficient Bioelectronic Actuation of the Natural Catalytic Pathway of Human Metabolic Cytochrome P450s. Journal of the American Chemical Society 2011, 133
(5)
, 1459-1465. https://doi.org/10.1021/ja108637s
- Stephen S. Hecht, Jian-Min Yuan and Dorothy Hatsukami. Applying Tobacco Carcinogen and Toxicant Biomarkers in Product Regulation and Cancer Prevention. Chemical Research in Toxicology 2010, 23
(6)
, 1001-1008. https://doi.org/10.1021/tx100056m
- Jessica M. Fautch and Jonathan J. Wilker. Solution Speciation, Kinetics, and Observing Reaction Intermediates in the Alkylation of Oxidovanadium Compounds. Inorganic Chemistry 2010, 49
(11)
, 4791-4801. https://doi.org/10.1021/ic901922m
- Nan Xu, Lauren E. Goodrich, Nicolai Lehnert, Douglas R. Powell and George B. Richter-Addo . Five- and Six-Coordinate Adducts of Nitrosamines with Ferric Porphyrins: Structural Models for the Type II Interactions of Nitrosamines with Ferric Cytochrome P450. Inorganic Chemistry 2010, 49
(10)
, 4405-4419. https://doi.org/10.1021/ic901751z
- Irina Stepanov, Peter W. Villalta, Aleksandar Knezevich, Joni Jensen, Dorothy Hatsukami and Stephen S. Hecht. Analysis of 23 Polycyclic Aromatic Hydrocarbons in Smokeless Tobacco by Gas Chromatography−Mass Spectrometry. Chemical Research in Toxicology 2010, 23
(1)
, 66-73. https://doi.org/10.1021/tx900281u
- Zhi Sun, Yong Dong Liu and Ru Gang Zhong. Theoretical Investigation of N-Nitrosodimethylamine Formation from Nitrosation of Trimethylamine. The Journal of Physical Chemistry A 2010, 114
(1)
, 455-465. https://doi.org/10.1021/jp9056219
- Sadagopan Krishnan, Amila Abeykoon, John B Schenkman and James F Rusling. Control of Electrochemical and Ferryloxy Formation Kinetics of Cyt P450s in Polyion Films by Heme Iron Spin State and Secondary Structure. Journal of the American Chemical Society 2009, 131
(44)
, 16215-16224. https://doi.org/10.1021/ja9065317
- James D. Bortner, Jr., Arunangshu Das, Todd M. Umstead, Williard M. Freeman, Richard Somiari, Cesar Aliaga, David S. Phelps and Karam El-Bayoumy . Down-Regulation of 14-3-3 Isoforms and Annexin A5 Proteins in Lung Adenocarcinoma Induced by the Tobacco-Specific Nitrosamine NNK in the A/J Mouse Revealed by Proteomic Analysis. Journal of Proteome Research 2009, 8
(8)
, 4050-4061. https://doi.org/10.1021/pr900406g
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