Nornicotine nitrosation in saliva and its relation to endogenous synthesis of n'-nitrosonornicotine in humans

Nicotine and Tobacco Research

Volumn 15, Issue 2, 2013, Pages 591-595

  Knezevich, Aleksandar ^a   Muzic, John ^a   Hatsukami, Dorothy K ^a,b   Hecht, Stephen S ^a,b   Stepanov, Irina ^a,b  

^a UNIVERSITY OF MINNESOTA   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

[PYRIDINE D4]NICOTINE; [PYRIDINE D4]NORNICOTINE; NITROSONORNICOTINE; NORNICOTINE; PYRIDINE; SODIUM NITRITE; UNCLASSIFIED DRUG;

ADULT; ARTICLE; CONTROLLED STUDY; FEMALE; HUMAN; LIQUID CHROMATOGRAPHY; MALE; MOUTH CAVITY; NITROSATION; PRIORITY JOURNAL; SALIVA ANALYSIS; SYNTHESIS; TANDEM MASS SPECTROMETRY;

HUMANS; NICOTINE; NITROSAMINES; NITROSATION; SALIVA; SMOKING; SMOKING CESSATION;

EID: 84869383033     PISSN: 14622203     EISSN: 1469994X     Source Type: Journal    
DOI: 10.1093/ntr/nts172     Document Type: Article

References (29)

1. Bartsch, H., Ohshima, H., & Pignatelli, B. (1988). Inhibitors of endogenous nitrosation. Mechanisms and implications in human cancer prevention. Mutation Research, 202, 307 - 324. doi: 10.1016/0027-5107(88)90194-7.
2. Bartsch, H., Ohshima, H., Pignatelli, B., & Calmels, S. (1989). Human exposure to endogenous N-nitroso compounds: Quantitative estimates in subjects at high risk for cancer of the oral cavity, oesophagus, stomach and urinary bladder. Cancer Surveys, 8, 335 - 362.
3. Benowitz, N. L., Jacob, P., III, Fong, I., & Gupta, S. (1994). Nicotine metabolic profile in man: Comparison of cigarette smoking and transdermal nicotine. Journal of Pharmacology and Experimental Th erapeutics, 268, 296 - 303.
4. Benowitz, N. L., Jacob, P., III, & Savanapridi, C. (1987). Determinants of nicotine intake while chewing nicotine polacrilex gum. Clinical Pharmacology and Th erapeutics, 41, 467 - 473. doi: 10.1038/clpt.1987.58.
5. Carmella, S. G., Borukhova, A., Desai, D., & Hecht, S. S. (1997). Evidence for endogenous formation of tobacco-specific nitrosamines in rats treated with tobacco alkaloids and sodium nitrite. Carcinogenesis, 18, 587 - 592. doi: 10.1093/carcin/18.3.587.
6. Granli, T., Dahl, R., Brodin, P., & Bøckman, O. C. (1989). Nitrate and nitrite concentrations in human saliva: Variations with salivary flow-rate. Food and Chemical Toxicology, 27, 675-680. doi:10.1016/0278-6915(89)90122-1.
7. Hecht, S. S. (1998). Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chemical Research in Toxicology, 11, 559-603. doi:10.1021/tx980005y.
8. Hoffmann, D., & Adams, J. D. (1981). Carcinogenic tobaccospecific N-nitrosamines in snuff and in the saliva of snuff dippers. Cancer Research, 41, 4305-4308.
9. Hukkanen, J., Jacob, P., III, & Benowitz, N. L. (2005). Metabolism and disposition kinetics of nicotine. Pharmacological Reviews, 57, 79-115. doi:10.1124/pr.57.1.3.
10. International Agency for Research on Cancer. (2007). Smokeless tobacco and tobacco-specific nitrosamines. In IARC monographs on the evaluation of carcinogenic risks to humans. (Vol. 89). Lyon, France: IARC.
11. Jiebarth, D., Spiegelhalder, B., & Bartsch, H. (1997). N-nitrosation of medicinal drugs catalysed by bacteria from human saliva and gastro-intestinal tract, including Helicobacter pylori. Carcinogenesis, 18, 383-389. doi:10.1093/carcin/18.2.383.
12. Marletta, M. A. (1988). Mammalian synthesis of nitrite, nitrate, nitric oxide, and N-nitrosating agents. Chemical Research in Toxicology, 1, 249-257. doi:10.1021/tx00005a001.
13. McColl, K. E. L. (2005). When saliva meets acid: Chemical warfare at the oesophagogastric junction. Gut, 54, 1-3. doi:10.1136/gut.2004.047126.
14. Mirvish, S. S. (1975). Formation of N-nitroso compounds: Chemistry, kinetics, and in vivo occurrence. Toxicology and Applied Pharmacology, 31, 325-351. doi:10.1016/0041-008X(75)90255-0.
15. Mirvish, S. S. (1995). Role of N-nitroso compounds (NOC) and N-nitrosation in etiology of gastric, esophageal, nasopharyngeal and bladder cancer and contribution to cancer of known exposures to NOC. Cancer Letters, 93, 17-48. doi:10.1016/0304-3835(95)03786-V.
16. Mirvish, S. S., Sams, J., & Hecht, S. S. (1977). Kinetics of nornicotine and anabasine nitrosation in relation to N'-nitrosonornicotine occurrence in tobacco and to tobacco-induced cancer. Journal of the National Cancer Institute, 59, 1211-1213.
17. Mirvish, S. S., Wallcave, L., Eagen, M., & Shubik, P. (1972). Ascorbate-nitrite reaction: Possible means of blocking the formation of carcinogenic N-nitroso compounds. Science (New York, N.Y.), 177, 65-67. doi:10.1126/science.177.4043.65.
18. Porubin, D., Hecht, S. S., Li, Z. Z., Gonta, M., & Stepanov, I. (2007). Endogenous formation of N'-nitrosonornicotine in F344 rats in the presence of some antioxidants and grape seed extract. Journal of Agricultural and Food Chemistry, 55, 7199-7204. doi:10.1021/jf0712191.
19. Rao, G. S., & McLennon, D. A. (1977). High-pressure liquid chromatographic analysis of carcinogenic N-nitroso derivatives of piperazine resulting from drug-nitrite interactions. Journal of Analytical Toxicology, 1, 43-45.
20. Rose, J. E., Levin, E. D., & Benowitz, N. (1993). Saliva nicotine as an index of plasma levels in nicotine skin patch users. Therapeutic Drug Monitoring, 15, 431-435. doi:10.1097/00007691-199310000-00012.
21. Shapiro, K. B., Hotchkill, J. H., & Roe, D. A. (1991). Quantitative relationship between oral nitrate-reducing activity and the endogenous formation of N-nitrosoamino acids in humans. Food and Chemical Toxicology, 29, 751-755. doi:10.1016/0278-6915(91)90183-8.
22. Shepard, S. E., Schlatter, C., & Lutz, W. K. (1987). Assessment of the risk of formation of carcinogenic N-nitroso compounds from dietary precursors in the stomach. Food and Chemical Toxicology, 25, 91-108. doi:10.1016/0278-6915(87)90311-5.
23. Stepanov, I., Carmella, S. G., Briggs, A., Hertsgaard, L., Lindgren, B., Hatsukami, D., & Hecht, S. S. (2009a). Presence of the carcinogen N'-nitrosonornicotine in the urine of some users of oral nicotine replacement therapy products. Cancer Research, 69, 8236-8240. doi:10.1158/0008-5472.CAN-09-1084.
24. Stepanov, I., Carmella, S. G., Han, S., Pinto, A., Strasser, A. A., Lerman, C., & Hecht, S. S. (2009b). Evidence for endogenous formation of N'-nitrosonornicotine in some long term nicotine patch users. Nicotine & Tobacco Research, 11, 95-105. doi:10.1093/ntr/ntn004.
25. Stepanov, I., & Hecht, S. S. (2005). Tobacco-specific nitrosamines and their N-glucuronides in the urine of smokers and smokeless tobacco users. Cancer Epidemiology, Biomarkers & Prevention, 14, 885-891. doi:10.1158/1055-9965.EPI-04-0753.
26. Stepanov, I., & Hecht, S. S. (2008). Detection and quantitation of N'-nitrosonornicotine in human toenails by liquid chromatography-electrospray ionization-tandem mass spectrometry. Cancer Epidemiology, Biomarkers & Prevention, 17, 945-948. doi:10.1158/1055-9965.EPI-07-2711.
27. Stepanov, I., Jensen, J., Hatsukami, D., & Hecht, S. S. (2008). New and traditional smokeless tobacco: Comparison of toxicant and carcinogen levels. Nicotine & Tobacco Research, 10, 1773-1782. doi:10.1080/14622200802443544.
28. U.S. Department of Health and Human Services. (2004). The health consequences of involuntary exposure to tobacco smoke: A report of the surgeon general. Washington, DC: U.S. Government Printing Office.
29. Yuan, J. M., Knezevich, A. D., Wang, R., Gao, Y. T., Hecht, S. S., & Stepanov, I. (2011). Urinary levels of the tobacco-specific carcinogen N'-nitrosonornicotine and its glucuronide are strongly associated with esophageal cancer risk in smokers. Carcinogenesis, 32, 1366-1371. doi:10.1093/carcin/bgr125.