The molecular basis for induction of human cancers by tobacco specific nitrosamines

Regulatory Toxicology and Pharmacology

Volumn 60, Issue 2, 2011, Pages 268-280

  Nilsson, Robert ^a,b  

^a STOCKHOLM UNIVERSITY   (Sweden)

^b UNIVERSITY OF TUSCIA   (Italy)

Author keywords

Cancer; DNA adducts; Nitrosamines; Risk assessment; Snuff; Tobacco; TSNA

Indexed keywords

HEMOGLOBIN; NITROSAMINE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PYRIDYLOXOBUTYL; UNCLASSIFIED DRUG;

ARTICLE; BASE MISPAIRING; CARCINOGENESIS; CONCENTRATION (PARAMETERS); DNA ADDUCT; DNA DAMAGE; EPIDEMIOLOGICAL DATA; EXPERIMENTAL ANIMAL; HUMAN; NONHUMAN; PRIORITY JOURNAL; SMOKELESS TOBACCO; SPECIES DIFFERENCE; SWEDEN; TOBACCO;

ANIMALS; CARCINOGENS; DNA ADDUCTS; DNA DAMAGE; HUMANS; NEOPLASMS; NITROSAMINES; SPECIES SPECIFICITY; SWEDEN; TOBACCO, SMOKELESS;

ANIMALIA; NICOTIANA TABACUM; RODENTIA;

EID: 79958257522     PISSN: 02732300     EISSN: 10960295     Source Type: Journal    
DOI: 10.1016/j.yrtph.2011.02.014     Document Type: Article

References (142)

1. Adams J.D., Owens-Tucciarone P., Hoffmann D. Tobacco specific N-nitrosamines in dry snuff. Food Chem. Toxicol. 1987, 25:245-246.
2. Ahlbom, A., Olsson, U.A., Pershagen, G., 1997. Health hazards of moist snuff. Report to the Swedish National Board of Health and Welfare, SoS-report 1997:11, Stockholm.
3. Ahmed H.G., Mahgoob R.M. Impact of Toombak dipping in the etiology of oral cancer: gender-exclusive hazard in the Sudan. J. Cancer Res. Ther. 2007, 3:127-130.
4. Andersson G., Björnberg G., Curvall M. Oral mucosal change and nicotine disposition in users of Swedish smokeless tobacco products: a comparative study. J. Oral Pathol. Med. 1994, 23:161-167.
5. Belinsky S.A., White C.M., Boucheron J.A., Richardson F.C., Swenberg J.A., Anderson M.W. Accumulation and persistence of DNA adducts in respiratory tissue of rats following multiple administrations of the tobacco specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 1986, 46:1280-1284.
6. Belinsky S.A., Walker V.E., Maronpot R.R., Swenberg J.A., Anderson M.W. Molecular dosimetry of DNA adduct formation and cell toxicity in rat nasal mucosa following exposure to 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and their relationship to induction of neoplasia. Cancer Res. 1987, 47:6058-6065.
7. Belinsky S.A., White C.M., Devereux T.R., Swenberg J.A., Anderson M.W. Cell selective alkylation of DNA in rat lung following low dose exposure to the tobacco specific carcinogen 4-(N-methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 1987, 47:1143-1148.
8. Belinsky S.A., Dolan M.E., White C.M., Maronpot R.R., Pegg A.E., Anderson M.W. Cell specific differences in O6-methylguanine-DNA methyltransferase activity and removal of O6-methylguanine in rat pulmonary cells. Carcinogenesis 1988, 9:2053-2058.
9. Belinsky S.A., Devereux T.R., Maronpot R.R., Stoner G.D., Anderson M.W. Relationship between the formation of promutagenic adducts and the activation of the K-ras protooncogene in lung tumours from A/J mouse lung treated with nitrosamines. Cancer Res. 1989, 49:5305-5311.
10. Belinsky S., Foley J.F., White C.M., Anderson M.W., Maronpot R.R. Dose-response relationship between the formation of O6-methylguanine in Clara cells and induction of pulmonary neoplasia in the rat by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 1990, 50:3772-3780.
11. Belinsky S., Devereux T.R., White C.M., Foley J.F., Maronpot R.R., Anderson M.W. Role of Clara cells and Type II cells in the development of pulmonary tumours in rats and mice following exposure to a tobacco-specific nitrosamine. Exp. Lung Res. 1991, 17:263-278.
12. Bertuccio P., La Vecchia C., Silverman D.T., Petersen G.M., Bracci P.M., Negri E., Li D., Risch H.A., Olson S.H., Gallinger S., Miller A.B., Bueno-de-Mesquita H.B., Talamini R., Polesel J., Ghadirian P., Baghurst P.A., Zatonski W., Fontham E.T., Bamlet W.R., Holly E.A., Lucenteforte E., Hassan M., Yu H., Kurtz R.C., Cotterchio M., Su J., Maisonneuve P., Duell E.J., Bosetti C., Boffetta P. Cigar and pipe smoking, smokeless tobacco use and pancreatic cancer: an analysis from the International Pancreatic Cancer Case-Control Consortium (PanC4). Ann. Oncol. Jan 2011, 18. [Epub ahead of print].
13. Bianchini F., Wild C.P. Effect of route of administration of environmental methylating agents on 7-methylguanine formation in white blood cells and internal organs: implications for molecular epidemiology. Cancer Lett. 1994, 87:131-137.
14. Blömeke B., Greenblatt M.J., Doan V.D., Bowman E.D., Murphy S.E., Chen C.C., Kato S., Shields P.G. Distribution of 7-alkyl-2'-deoxuguanosine adduct levels in human lung. Carcinogenesis 1996, 17:741-748.
15. Bofetta P., Aagnes B., Weiderpass E., Andersen A. Smokeless tobacco use and risk of cancer of the pancreas and other organs. Int. J. Cancer. 2005, 114:992-995. (Comments by: Nilsson, R., 2006. Possible carcinogenicity of smokeless tobacco. Int. J. Cancer. 118, 1582-1583; Rutqvist, L.E., Lewin, F., Flawed methods. Ibid.118, 1581; Ramström, L., Re: " Smokeless tobacco use and risk of cancer of the pancreas and other organs" by Boffetta et al. Ibid. 118, 1584; Rodu, B., Cole, P., A deficient study of smokeless tobacco use and cancer. Ibid. 118, 1585).
16. Bolt H.M. Quantification of endogenous carcinogens. The ethylene oxide paradox. Biochem. Pharmacol. 1996, 52:1-5.
17. Brunnemann K.D., Hoffmann D. Analytical studies on N-nitrosamines in tobacco and tobacco smoke. Recent Adv. Tobacco Sci. 1991, 17:71-112.
18. Bundgaard T., Wildt J., Frydenberg M., Elbrønd O., Nielsen J.E. Case-control study of squamous cell cancer of the oral cavity in Denmark. Cancer Causes Control 1995, 6:57-67.
19. Carmella S.G., Hecht S.S. Formation of hemoglobin adducts upon treatment of F344 rats with the tobacco-specific nitrosamines 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and N'-nitrosonornicotine. Cancer Res. 1987, 47:2626-2630.
20. Carmella S.G., Kagan S.S., Kagan M., Foiles P.G., Palladino G., Quart A.M., Quart E., Hecht S.S. Mass spectrometric analysis of tobacco-specific nitrosamine hemoglobin adducts in snuff dippers, smokers, and nonsmokers. Cancer Res. 1990, 50:5438-5445.
21. Carmella S.G., Akerkar S., Hecht S.S. Metabolites of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers' urine. Cancer Res. 1993, 53:721-724.
22. Carmella S.G., McIntee E.J., Chen M., Hecht S.S. Enantiomeric composition of N'-nitrosonornicotine and N'-nitrosoanatabine in tobacco. Carcinogenesis 2000, 21:839-843.
23. Cleaver J.E. Defective repair replication of DNA in xeroderma pigmentosum. Nature 1968, 218:652-656.
24. Davidson I.W., Parker J.C., Beliles R.P. Biological basis for extrapolation across mammalian species. Regul. Toxicol. Pharmacol. 1986, 6:211-237.
25. D́Andres S., Boudoux R., Renaud J.-M., Zuber J. TSNA levels in the main stream smoke of simplified blend prototypes. Beiträge zur Tabaksforsch. Int. 2003, 20:331-340.
26. Deilhaug T., Myrnes B., Aune T., Krokan H., Haugen A. Differential capacities for DNA repair in Clara cells, alveolar type II cells and macrophages of rabbit lung. Carcinogenesis 1985, 6:661-663.
27. Den Engelse L., Menkveld G.J., De Bry R.-J., Tates Ad.D. Formation and stability of alkylated pyrimidines and purines (including imidazole ring-opened 7-alkylguanine) and alkylphosphotriesters in liver DNA of adult rats treated with ethylnitrosourea or dimethylnitrosamine. Carcinogenesis 1986, 7:393-403.
28. Derby K.S., Cuthrell K., Caberto C., Carmella S., Murphy S.E., Hecht S.S., Le Marchand L. Exposure to the carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers from 3 populations with different risks of lung cancer. Int. J. Cancer 2009, 125:2418-2424.
29. Derelanko M.J. Determination of erythrocyte life span in F-344, Wistar, and Sprague-Dawley rats using a modification of the [3H]diisopropylfluorophosphate ([3H]DFP) method. Fundam. Appl. Toxicol. 1987, 9:271-276.
30. Eadie J.S., Conrad M., Toorchen D., Topal M.D. Mechanism of mutagenesis by O6-methylguanine. Nature 1984, 308(5955):201-203.
31. EU DG Research, 2007. Dietary exposures to polycyclic aromatic hydrocarbons and DNA damage. Final Activity Report to the Directorate General for Research of the European Commission. Project No.: FOOD-CT-2003-505609.
32. EUROGAST The EUROGAST Study Group O6-Methylguanine in blood leucocyte DNA: an association with the geographic prevalence of gastric cancer and with low levels of serum pepsinogen A, a marker of severe chronic atrophic gastritis. Carcinogenesis (Lond.) 1994, 15:1815-1820.
33. Falter B., Kutzer C., Richter E. Biomonitoring of hemoglobin adducts: aromatic amines and tobacco specific nitrosamines. Clin. Invest. 1994, 72:364-371.
34. Fukami T., Nakajima M., Sakai H., Katoh M., Yokoi T. CYP2A13 metabolizes the substrates of human CYP1A2, phenacetin, and theophylline. Drug Metab. Dispos. 2007, 35:335-339.
35. Georgiadis P., Samoli E., Kaila S., Katsouyanni K., Kyrtopoulos S.A. Ubiquitous presence of O6-methylguanine in human peripheral and cord blood DNA. Cancer Epidemiol. Biomarkers Prev. 2000, 9:299-305.
36. Grasso P., Mann A.H. Smokeless tobacco and oral cancer: an assessment of evidence derived from laboratory animals. Food Chem. Toxicol. 1998, 36:1015-1029.
37. Griciute L., Castegnaro M., Bereziat J.C., Cabral J.R.P. Influence of ethyl alcohol on the carcinogenic activity of N-nitrosonornicotine. Cancer Lett. 1986, 31:267-275.
38. Haglund J., Henderson A.P., Golding B.T., Törnqvist M. Evidence for phosphate adducts in DNA from mice treated with 4-(N-Methyl-N-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Chem. Res. Toxicol. 2002, 15:773-779.
39. Hansson L.E., Baron J., Nyrén O., Bergström R., Wolk A., Adami H.O. Tobacco, alcohol and the risk of gastric cancer. A population-based case-control study in Sweden. Int. J. Cancer 1994, 57:26-31.
40. Harris J.E. Incomplete compensation does not imply reduced harm: yields of 40 smoke toxicants per mg nicotine in regular filter versus low-tar cigarettes in the 1999 Massachusetts benchmark study. Nicotine Tob. Res. 2004, 6:797-807.
41. Hecht S.S. Recent studies on the mechanism of bioactivation and detoxification of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) a tobacco-specific lung carcinogen. Crit. Rev. Toxicol. 1996, 26:163-181.
42. Hecht S.S. Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem. Res. Toxicol. 1998, 11:559-603.
43. Hecht S.S. Human urinary carcinogen metabolites: biomarkers for investigating tobacco and cancer. Carcinogenesis 2002, 23:907-922.
44. Hecht S.S. Progress and challenges in selected areas of tobacco carcinogenesis. Chem Res. Toxicol. 2008, 21:160-171.
45. Hecht S.S. Smoking and lung cancer - a new role for an old toxicant?. Proc. Natl. Acad. Sci. USA 2006, 103:15725-15726.
46. Hecht S.S., Lin D., Chen C.B. Comprehensive analysis of urinary metabolites of N'-nitrosonornicotine. Carcinogenesis 1981, 2:833-838.
47. Hecht, S.S., Carmella, S.G., Trushin, N., Foiles, P.G., Lin, D., Rubin J.M. Chung F.L., 1987. Investigations on the molecular dosimetry of tobacco specific nitrosamines. In: Bartsch, H., ÓNeill, I.K., Schulte Hermann, R. (Eds.). The Relevance of N Nitroso Compounds to Human Cancer: Exposures & Mechanisms. IARC Sci. Publ. No. 84, Lyon, pp. 423-429.
48. Hecht S.S., Carmella S.G., Murphy S.E. Hemoglobin adducts as biomarkers of exposure to and metabolic activation of carcinogenic tobacco-specific nitrosamines. Biomed. Environ. Sci. 1991, 4:93-103.
49. Hecht S.S., Carmella S.G., Murphy S.E., Riley W.T., Le C., Luo X., Mooney M., Hatsukami D.K. Similar exposure to a tobacco-specific carcinogen in smokeless tobacco users and cigarette smokers. Cancer Epidemiol. Biomarkers Prev. 2007, 16:1567-1572.
50. Hecht S.S., Han S., Kenney P.M., Wang M., Lindgren B., Wang Y., Lao Y., Hochalter J.B., Upadhyaya P. Investigation of the reaction of myosmine with sodium nitrite in vitro and in rats. Chem. Res. Toxicol. 2007, 20:543-549.
51. Hewett, C.F., 1987. Nitrosamine levels in German brands. Rep. No. RD. 2094. 5.10.1987. British American Tobacco Co. Tobacco documents online. Tobaccodocuments.org. http://tobaccodocuments.org/product_design/954791.html.
52. Hoffmann D., Adams J.D. Carcinogenic tobacco-specific N-nitrosamines in snuff and in the saliva of snuff dippers. Cancer Res. 1981, 41:4305-4308.
53. Hoffmann D., Hoffmann I. Tobacco smoke components. Beitr. Tabaksforsch. Int. 1998, 18:49-52.
54. Hoffmann D., Rivenson A., Amin S., Hecht S.S. Dose-response study of the carcinogenicity of tobacco-specific N-nitrosamines in F344 rats. J Cancer Res. Clin. Oncol. 1984, 108:81-86.
55. Hoffmann D., Harley N.H., Fisenne I., Adams J.D., Brunnemann K.D. Carcinogenic agents in snuff. J. Natl. Cancer Inst. 1986, 76:435-437.
56. Hoffmann D., Djordjevic M.V., Fan J., Zang E., Glynn T., Connolly G.N. Five leading U.S. commercial brands of moist snuff in 1994: assessment of carcinogenic N-nitrosamines. J. Natl. Cancer Inst. 1995, 87:1862-1869.
57. Hölzle D., Schlöbe D., Tricker A.R., Richter E. Mass spectrometric analysis of 4-hydroxy-1-(3-pyridyl)-1-butanone-releasing DNA adducts in human lung. Toxicology 2007, 232:277-285.
58. IARC, 1985. International Agency for Research on Cancer. IARC Monographs on the Evaluation of the Carcinogenic Risks to Humans - Tobacco Habits Other than Smoking: Betel-Quid, and Areca Nut Chewing and Some Related Nitrosamines. IARC Sci. Publ. No. 37. WHO, Lyon.
59. IARC, 2007a. International Agency for Research on Cancer. IARC Monographs on the Evaluation of the Carcinogenic Risks to Humans - Smokeless Tobacco and Some Tobacco-specific N-Nitrosamines, Vol. 89. WHO, Lyon.
60. IARC, 2007b. International Agency for Research on Cancer. Cancer Incidence in Five Continents. Vol. IX. http://www-dep.iarc.fr/.
61. Ibrahim S.O., Vasstrand E.N., Johannessen A.C., Idris A.M., Magnusson B., Nilsen R., Lillehaug J.R. Mutations of the p53 gene in oral squamous-cell carcinomas from Sudanese dippers of nitrosamine-rich toombak and non-snuff-dippers from the Sudan and Scandinavia. Int. J. Cancer 1999, 81:527-534.
62. Idris A.M., Nair J., Oshima H., Friesen M., Brouet I., Faustman E.M., Bartsch H. Unusually high levels of carcinogenic nitrosamines in Sudan snuff (toombak). Carcinogenesis 1991, 12:1115-1118.
63. Idris A.M., Prokopczyk B., Hoffmann D. Toombak: a major risk factor for cancer of the oral cavity in Sudan. Prev. Med. 1994, 23:832-839.
64. Jalas J.R., Hecht S.S., Murphy S.E. Cytochrome P450 enzymes as catalysts of metabolism of 4-(methylnitros-amino)-1-(3-pyridyl)-1-butanone, a tobacco specific carcinogen. Chem. Res. Toxicol. 2005, 18:95-110.
65. Jansen J.G., de Groot A.J.L., van Teijlingen C.M.M., Tates A.D., Vrieling H., van Zeeland A.A. Induction of hprt gene mutations in splenic T-lymphocytes from the rat exposed in vivo to DNA methylating agents is correlated with formation of O6-methylguanine in bone marrow and not in the spleen. Carcinogenesis 1996, 17:2183-2191.
66. Jarabek A.M., Pottenger L.H., Andrews L.S., Casciano D., Embry M.R., Kim J.H., Preston R.J., Reddy M.V., Schoeny R., Shuker D., Skare J., Swenberg J., Williams G.M., Zeiger E. Creating context for the use of DNA adduct data in cancer risk assessment: I. Data organization. Crit. Rev. Toxicol. 2009, 39:659-678.
67. Kang H., Konishi C., Kuroki T., Huh N. Detection of O6-methylguanine, O4-methylthymine and O4-ethylthymine in human liver and peripheral blood leukocyte DNA. Carcinogenesis 1995, 16:1277-1280.
68. Kumar R., Hemminki K. Separation of 7-methyl- and 7-(2-hydroxyethyl)-guanine adducts in human DNA samples using a combination of TLC and HPLC. Carcinogenesis 1996, 17:485-492.
69. Lagergren J., Bergstrom R., Lindgren A., Nyrén O. The role of tobacco, snuff and alcohol use in the aetiology of cancer of the oesophagus and gastric cardia. Int. J. Cancer 2000, 85:340-346.
70. Larsson B.K., Sahlberg G.P., Eriksson A.T., Busk L.A. Polycyclic aromatic hydrocarbons in grilled food. J. Agric. Food Chem. 1983, 31:867-873.
71. Lao Y., Yu N., Kassie F., Villalta P.W., Hecht S.S. Analysis of pyridyloxobutyl DNA adducts in F344 rats chronically treated with (R)- and (S)-N'-nitrosonornicotine. Chem. Res. Toxicol. 2007, 20:246-256.
72. Lee P.N., Hamling J. The relation between smokeless tobacco and cancer in Northern Europe and North America. A commentary on differences between the conclusions reached by two recent reviews. BMC Cancer 2009, 9:256.
73. Lee P.N. Summary of the epidemiological evidence relating snus to health. Regul. Toxicol. Pharmacol. 2011, 59:197-214.
74. Lewin F., Norell S.E., Johansson H., Gustavsson P., Wennerberg J., Björklund A., Rutqvist L.E. Smoking tobacco, oral snuff, and alcohol in the etiology of squamous cell carcinoma of the head and neck. A population based case-referent study in Sweden. Cancer 1998, 82:1367-1375.
75. Lewis S.J., Cherry N.M., Niven R.M., Barber P.V., Povey A.C. Associations between smoking, GST genotypes and N7-methylguanine levels in DNA extracted from bronchial lavage cells. Mutat. Res. 2004, 559:11-18.
76. Li L., Perdigao J., Pegg A.E., Lao Y., Hecht S.S., Lindgren B.R., Reardon J.T., Sancar A., Wattenberg E.V., Peterson L.A. The Influence of repair pathways on the cytotoxicity and mutagenicity Induced by the pyridyloxobutylation pathway of tobacco-specific nitrosamines. Chem. Res. Toxicol. 2009, 22:1464-1472.
77. Liu L., Castonguay A., Gerson S.L. Lack of correlation between DNA methylation and hepatocarcinogenesis in rats and hamsters treated with 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Carcinogenesis 1992, 13:2137-2140.
78. Lunell E., Lunell M. Steady-state nicotine plasma levels following use of four different types of Swedish snus compared with 2-mg Nicorette chewing gum: a crossover study. Nicotine Tob. Res. 2005, 7:397-403.
79. Luo J., Ye W., Zendehdel K., Adam i J., Adami H.O., Boffetta P., Nyrén O. Oral use of Swedish moist oral snuff (snus) and risk for cancer of the mouth, lung, and pancreas in male construction workers: a retrospective cohort study. Lancet 2007, 369(9578):2015-2020.
80. Margison G.P., Santibáñez Koref M.F., Povey A.C. Mechanisms of carcinogenicity/chemotherapy by O6-methylguanine. Mutagenesis 2002, 17:483-487.
81. Meger M., Meger-Kossien I., Dietrich M., Tricker A.R., Scherer G., Adlkofer F. Metabolites of 4-(N-methylnitrosamino)-1-(3-pyridyl)-1-butanone in urine of smokers. Eur. J. Cancer Prev. 1996, 5(Suppl. 1):121-124.
82. Murphy S.E., Palomino A., Hecht S.S., Hoffmann D. Dose-response study of DNA and hemoglobin adduct formation by 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in F334 rats. Cancer Res. 1990, 50:5446-5452.
83. Mustonen R., Hemminki K. 7-Methylguanine levels in DNA of smokers' and non-smokers' total white blood cells, granulocytes and lymphocytes. Carcinogenesis 1992, 13:1951-1955.
84. Mustonen R., Schoket B., Hemminki K. Smoking-related DNA adducts: 32P-postlabelling analysis of 7-methylguanine in human bronchial and lymphocyte DNA. Carcinogenesis 1993, 14:151-154.
85. Nishikawa A., Yukio Mori Y., Lee I.-S., Tanaka T., Hirose M. Cigarette smoking, metabolic activation and carcinogenesis. Curr. Drug Metab. 2004, 5:363-373.
86. Nilsson R. A qualitative quantitative risk assessment of oral snuff dipping. Regul. Toxicol. Pharmacol. 1998, 28:1-16.
87. Österdahl B.-G., Slorach S.A. Volatile N-nitrosamines in oral snuff and chewing tobacco on the Swedish market. Food Chem. Toxicol. 1983, 21:759-762.
88. Österdahl B.-G., Slorach S.A. N-Nitrosamines in oral snuff and chewing tobacco on the Swedish market in 1983. Food Addit. Contam. 1984, 1:299-305.
89. Österdahl B.G., Jansson C., Paccou A. Decreased levels of tobacco-specific N-nitrosamines in moist oral snuff on the Swedish market. J. Agric. Food Chem. 2004, 52:5085-5088.
90. Pegg A.E., Hui G. Formation and subsequent removal of O6-methylguanine from deoxyribonucleic acid in rat liver and kidney after small doses of dimethylnitrosamine. Biochem. J. 1978, 173:739-748.
91. Peterson L.A., Hecht S.S. O6-methylguanine is a critical determinant of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone tumourigenesis in A/J mouse lung. Cancer Res. 1991, 51:5557-5564.
92. Pfeifer G.P., Denissenko M.F., Olivier M., Tretyakova N., Hecht S.S., Hainaut P. Tobacco smoke carcinogens, DNA damage and p53 mutations in smoking-associated cancers. Oncogene 2002, 21:7435-7451.
93. Pfeifer G.P., Hainaut P. On the origin of G→T transversions in lung cancer. Mutat. Res. 2003, 526:39-43.
94. Pleasance E.D., Stephens P.J., O'Meara S., McBride D.J., Meynert A., Jones D., Lin M.L., et al. A small-cell lung cancer genome with complex signatures of tobacco exposure. Nature 2010, 463(7278):184-190.
95. Plosky B., Samson L., Engelward B.P., Gold B., Schlaen B., Millas T., Magnotti M., Schor J., Scicchitano D.A. Base excision repair and nucleotide excision repair contribute to the removal of N-methylpurines from active genes. DNA Repair 2002, 1:683-696.
96. Povey A.C. DNA adducts: endogenous and induced. Toxicol. Pathol. 2000, 28:405-414.
97. Povey A.C., Hall C.N., Badawi A.F., Cooper D.P., O'Connor P.J. Elevated levels of the pro-carcinogenic adduct, O(6)-methylguanine, in normal DNA from the cancer prone regions of the large bowel. Gut 2000, 47:362-365.
98. Prokopczyk B., Hoffmann D., Bologna M., Cunningham A.J., Trushin N., Akerkar S., Boyiri T., Amin S., Desai D., Colosimo S., Pittman B., Leder G., Ramadani M., Henne-Bruns D., Beger H.G., El-Bayoumy K. Identification of tobacco-derived compounds in human pancreatic juice. Chem. Res. Toxicol. 2002, 15:677-685.
99. Prokopczyk B., Leder G., Trushin N., Cunningham A.J., Akerkar S., Pittman B., Ramadani M., Straeter J., Beger H.G., Henne-Bruns D., El-Bayoumy K. 4-Hydroxy-1-(3-pyridyl)-1-butanone, an indicator for 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone-induced DNA damage, is not detected in human pancreatic tissue. Cancer Epidemiol. Biomarkers Prev. 2005, 14:540-541.
100. Richter E., Schlöbe D., Hölzle D., Wilp J. Comparative DNA and hemoglobin adduct formation by dietary myosmine and N'-nitrosonornicotine in rats. Naunyn Schmiedebergs Arch. Pharmacol 2002, 365(Suppl. 1):R140.
101. Richter E., Engl J., Friesenegger S., Tricker A.R. Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in lung tissue from mouse, rat, hamster, and man. Chem. Res. Toxicol. 2009, 22:1008-1117.
102. Richter E., Hölzle D., Schlöbe D., Heling A.-K., Heppel C., Eggert H. TSNA adducts in smokers, nonsmokers and snuffers. 46th Congress of the European Society of Toxicology. Toxicol. Lett. 2009, 1895:S08-03.
103. Rivenson A., Hoffmann D., Prokopczyk B., Amin S., Hecht S.S. Induction of lung and exocrine pancreas tumours in F344 rats by tobacco specific and areca-derived N-nitrosamines. Cancer Res. 1988, 48:6912-6917.
104. Rodu B., Jansson C. Smokeless tobacco and oral cancer: a review of the risks and determinants. Crit. Rev. Oral Biol. Med. 2004, 15:252-263.
105. Ronai Z.A., Gradia S., Peterson L.A., Hecht S.S. G to A transitions and G to T transversions in codon 12 of the Ki-ras oncogene isolated from mouse lung tumours induced by 4-(methylnitrosoamino)-(3-pyridyl)-1-butanone (NNK) and related DNA methylating and pyridyloxobutylating agents. Carcinogenesis 1993, 14:2419-2422.
106. Roosaar A., Johansson A.L., Sandborgh-Englund G., Axéll T., Nyrén O. Cancer and mortality among users and nonusers of snus. Int. J. Cancer 2008, 123:168-173.
107. Rosenquist K., Wennerberg J., Schildt E.B., Bladström A., Hansson B.G., Andersson G. Use of Swedish moist oral snuff, smoking and alcohol consumption in the aetiology of oral and oropharyngeal squamous cell carcinoma. A population-based case-control study in southern Sweden. Acta Otolaryngol. 2005, 125:991-998.
108. Rutqvist,L.-E., 2010. GothiaTek® Limits for Undesired Components.
109. Schildt EB., Erikssson M., Hardell L., Magnusson.A. Oral snuff, smoking habits, and alcohol consumption in relation to oral cancer in a Swedish case-control study. Int. J. Cancer 1998, 77:341-346.
110. Schlöbe D., Hölzle D., Hatz D., von Meyer L., Tricker A.R., Richter E. 4-Hydroxy-1- (3-pyridyl)-1-butanone (HPB) releasing DNA adducts in lung, esophagus and cardia of sudden death victims. Toxicology 2008, 245:154-161.
111. Souliotis V.L., Sfikakis P.P., Anderson L.M., Kyrtopoulos S.A. Intra- and intercellular variations in the repair efficiency of O6-methylguanine, and their contribution to kinetic complexity. Mutat. Res. 2004, 568:155-170.
112. Stegmayr B., Eliasson M., Rodu B. The decline of smoking in northern Sweden. Scand. J. Public Health 2005, 33:321-324.
113. Stepanov I., Steven G., Carmella S.G., Stephen S., Hecht S.S., Duca G. Analysis of tobacco-specific nitrosamines in Moldovan cigarette tobacco. J. Agric. Food Chem. 2002, 50:2793-2797.
114. Stepanov I., Hecht S.S. Tobacco-specific nitrosamines and their pyridine-N-glucuronides in the urine of smokers and smokeless tobacco users. Cancer Epidemiol. Biomarkers Prev. 2005, 14:885-891.
115. Stepanov I., Hecht S.S., Ramakrishnan S., Gupta P.C. Tobacco-specific nitrosamines in smokeless tobacco products marketed in India. Int. J. Cancer 2005, 116:16-19.
116. Stepanov I., Jensen J., Hatsukami D., Hecht S.S. New and traditional smokeless tobacco: comparison of toxicant and carcinogen levels. Nicotine Tob. Res. 2008, 10:1773-1782.
117. Stepanov I., Upadhyaya P., Carmella S.G., Feuer R., Jensen J., Hatsukami D.K., Hecht S.S. Extensive metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers. Cancer Epidemiol. Biomarkers Prev. 2008, 17:1764-1773.
118. Stepanov I., Carmella S.G., Briggs A., Hertsgaard L., Lindgren B., Hatsukami D., Hecht S.S. Presence of the carcinogen N'-nitrosonornicotine in the urine of some users of oral nicotine replacement therapy products. Cancer Res. 2009, 69:8236-8240.
119. Stepanov I., Villalta P.W., Knezevich A., Jensen J., Hatsukami D., Hecht S.S. Analysis of 23 polycyclic aromatic hydrocarbons in smokeless tobacco by gas chromatography-mass spectrometry. Chem. Res. Toxicol. 2010, 23:66-73.
120. Su T., Bao Z., Zhang Q.Y., Smith T.J., Hong J.Y., Ding X. Human cytochrome P450 CYP2A13: predominant expression in the respiratory tract and its high efficiency metabolic activation of a tobacco-specific carcinogen, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Cancer Res. 2000, 60:5074-5079.
121. Subar A.F., Harlan L.C. Nutrient and food group intake by tobacco use status: the 1987 National Health Interview Survey. Ann. NY Acad. Sci. 1993, 686:310-321.
122. Szyfter K., Hemminki K., Szyfter W., Szmeja Z., Banaszewski J., Pabiszczak M. Tobacco smoke-associated 7-alkylguanine in DNA of larynx tissue and leucocytes. Carcinogenesis 1996, 17:501-506.
123. Törnqvist M., Osterman-Golkar S., Kautiainen A., Jensen S., Farmer P.B., Ehrenberg L. Tissue doses of ethylene oxide in cigarette smokers determined from adduct levels in hemoglobin. Carcinogenesis 1986, 7:1519-1521.
124. Tricker A.R., Ditrich C., Preussman R. N-Nitroso compounds in cigarette tobacco and their occurrence in mainstream tobacco smoke. Carcinogenesis 1991, 12:157-161.
125. Trushin N., Rivenson A., Hecht S.S. Evidence supporting the role of DNA pyridyloxobutylation in rat nasal carcinogenesis by tobacco-specific nitrosamines. Cancer Res. 1994, 54:1205-1211.
126. Tyroller S., Zwickenpflug W., Richter E. New sources of dietary myosmine uptake from cereals, fruits, vegetables, and milk. J. Agric. Food Chem. 2002, 50:4909-4915.
127. Upadhyaya P., Zimmerman C.L., Hecht S.S. Metabolism and pharmacokinetics of N'-nitrosonornicotine in the patas monkey. Drug Metab. Dispos. 2002, 30:1115-1122.
128. Upadhyaya P., Lindgren B.R., Hecht S.S. Comparative levels of O6-methylguanine, pyridyloxobutyl-, and pyridylhydroxybutyl-DNA adducts in lung and liver of rats treated chronically with the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone. Drug Metab. Dispos. 2009, 37:1147-1151.
129. Villard P.H., Herber R., Sérée E.M., Attolini L., Magdalou J., Lacarelle B. Effect of cigarette smoke on UDP-glucuronosyltransferase activity and cytochrome P450 content in liver, lung and kidney microsomes in mice. Pharmacol. Toxicol. 1998, 82:74-79.
130. Wang M., Cheng G., Sturla S.J., Shi Y., McIntee E.J., Villalta P.W., Upadhyaya P., Hecht S.S. Identification of adducts formed by pyridyloxobutylation of deoxyguanosine and DNA by 4-(acetoxymethylnitrosamino)-1-(3-pyridyl)-1-butanone, a chemically activated form of tobacco specific carcinogens. Chem. Res. Toxicol. 2003, 16:616-626.
131. Wilp J., Zwickenpflug W., Richter E. Nitrosation of dietary myosmine as risk factor of human cancer. Food Chem. Toxicol. 2002, 40:1223-1228.
132. Wilson V.L., Weston A., Manchester D.K., Trivers G.E., Roberts D.W., Kadlubar F.F., Wild C.P., Montesano R., Willey J.C., Mann D.L., et al. Alkyl and aryl carcinogen adducts detected in human peripheral lung. Carcinogenesis 1989, 11:2149-2153.
133. Winn D.M., Blot W.J., Shy C.M., Pickle L.W., Toledo A., Fraumeni J.F. Oral snuff dipping and oral cancer among women in the southern United States. New Engl. J. Med. 1981, 304:745-749.
134. Yuan J.M., Koh W.P., Murphy S.E., Fan Y., Wang R., Carmella S.G., Han S., Wickham K., Gao Y.T., Yu M.C., Hecht S.S. Urinary levels of tobacco-specific nitrosamine metabolites in relation to lung cancer development in two prospective cohorts of cigarette smokers. Cancer Res. 2009, 69:2990-2995.
135. Zendehdel K., Nyrén O., Luo J., Dickman W., Boffetta P., Englund A., Ye W. Risk of gastroesophageal cancer among smokers and users of Scandinavian moist oral snuff. Int. J. Cancer 2008, 122:1095-1099.
136. Zhang S., Wang M., Villalta P.W., Lindgren B.R., Lao Y., Hecht S.S. Quantitation of pyridyloxobutyl DNA adducts in nasal and oral mucosa of rats treated chronically with enantiomers of N'-nitrosonornicotine. Chem. Res. Toxicol. 2009, 22(5):949-956.
137. Zhao C., Tyndyk M., Eide I., Hemminki K. Endogenous and background DNA adducts by methylating and 2-hydroxyethylating agents. Mutat. Res. 1999, 424:117-125.
138. Zhou Z.Q., Manguino D., Kewitt K., Intano G.W., McMahan C.A., Herbert D.C., Hanes M., Reddick R., Ikeno Y., Walter C.A. Spontaneous hepatocellular carcinoma is reduced in transgenic mice overexpressing human O6- methylguanine-DNA methyltransferase. Proc. Natl. Acad. Sci. USA 2001, 98:12566-12571.
139. Zhu L.R., Thomas P.E., Lu G., Reuhl K.R., Yang G.Y., Wang L.D., Wang S.L., Yang C.S., He X.Y., Hong J.Y. CYP2A13 in human respiratory tissues and lung cancers: an immunohistochemical study with a new peptide-specific antibody. Drug Metab. Dispos. 2006, 34:1672-1676.
140. Zwickenpflug W. N-nitrosation of myosmine yields HPB (4-hydroxy-1-(3-pyridyl)-1-butanone) and NNN (N-nitrosonornicotine). J. Agric. Food Chem. 2000, 48:392-394.
141. Zwickenpflug W., Tyroller S., Richter E. Metabolism of myosmine in Wistar rats. Drug Metab. Dispos. 2005, 33:1648-1656.
142. Zwickenpflug W., Tyroller S. Reaction of the tobacco alkaloid myosmine with hydrogen peroxide. Chem. Res. Toxicol. 2006, 19:150-155.