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Biochemistry, Biology, and Carcinogenicity of Tobacco-Specific N-Nitrosamines
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    Biochemistry, Biology, and Carcinogenicity of Tobacco-Specific N-Nitrosamines
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    University of Minnesota Cancer Center, Box 806 Mayo, 420 Delaware Street S.E., Minneapolis, Minnesota 55455
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    Chemical Research in Toxicology

    Cite this: Chem. Res. Toxicol. 1998, 11, 6, 559–603
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    https://doi.org/10.1021/tx980005y
    Published June 2, 1998
    Copyright © 1998 American Chemical Society
    Copyright © 1998 American Chemical Society

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     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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    61. 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
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    63. 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
    64. 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
    65. 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
    66. 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
    67. 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
    68. 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
    69. 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
    70. 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
    71. 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
    72. 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
    73. 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
    74. 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
    75. 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
    76. 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
    77. 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
    78. 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
    79. 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
    80. 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
    81. 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
    82. 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
    83. 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
    84. 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
    85. 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
    86. 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
    87. 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
    88. 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
    89. 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
    90. 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
    91. 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
    92. 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
    93. 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
    94. 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
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    96. 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
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    98. 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
    99. 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
    100. 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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    Cite this: Chem. Res. Toxicol. 1998, 11, 6, 559–603
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    Published June 2, 1998
    Copyright © 1998 American Chemical Society

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