Intraindividual and interindividual differences in metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers' urine

Infection and Cancer: Biology, Therapeutics, and Prevention

Cancer Health Disparities Conference 2009

Intraindividual and interindividual differences in metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers' urine

SG Carmella, SA Akerkar, JP Richie Jr and SS Hecht
American Health Foundation, Valhalla, New York 10595, USA.

This study describes quantitation in smokers' urine of two metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). The metabolites are 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL), which is also a lung carcinogen, and its O-glucuronide (NNAL-Gluc), a presumed detoxification product of NNK. Using updated methodology, levels of NNAL, NNAL-Gluc, and cotinine were determined in the urine of 61 smokers. The NNAL-Gluc: NNAL ratio, a potential marker for NNK detoxification potential, varied 16-fold in this group. Two phenotypes of this ratio were apparent; one ranging from 0 to 6 and found in 85% of the smokers and a second ranging from 6 to 11. The short-term and long-term consistency of the ratio was investigated. Studies carried out over a 4-5 day period indicated that the NNAL-Gluc: NNAL ratio was reasonably stable. Subjects who donated urine samples on two occasions separated by 4-16 months were classified in the same group (ratio range, 0-6 or 6-11) each time. Different urine collection protocols appeared to have little influence on the NNAL-Gluc: ratio. Thus, intraindividual differences in the NNAL-Gluc:NNAL ratio were generally small, whereas interindividual differences were large. Amounts of NNAL, NNAL-Gluc, and cotinine excreted by smokers were constant in 24-h samples obtained over a 3-day period of constant cigarette intake and controlled diet. Levels of NNAL, NNAL-Gluc, and NNAL plus NNAL-Gluc correlated with cotinine in a study of 61 smokers without controlled diet or smoking (r = 0.58; P < 0.0001).(ABSTRACT TRUNCATED AT 250 WORDS)

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Annual Meeting Education Book	Meeting Abstracts Online

				G. Chen, R. W. Dellinger, D. Sun, T. E. Spratt, and P. Lazarus Glucuronidation of Tobacco-Specific Nitrosamines by UGT2B10 Drug Metab. Dispos., May 1, 2008; 36(5): 824 - 830. [Abstract] [Full Text] [PDF]

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				S. S. Hecht, S. G. Carmella, I. Stepanov, J. Jensen, A. Anderson, and D. K. Hatsukami Metabolism of the Tobacco-Specific Carcinogen 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone to Its Biomarker Total NNAL in Smokeless Tobacco Users Cancer Epidemiol. Biomarkers Prev., March 1, 2008; 17(3): 732 - 735. [Abstract] [Full Text] [PDF]

				S. S. Hecht, S. G. Carmella, S. E. Murphy, W. T. Riley, C. Le, X. Luo, M. Mooney, and D. K. Hatsukami Similar Exposure to a Tobacco-Specific Carcinogen in Smokeless Tobacco Users and Cigarette Smokers Cancer Epidemiol. Biomarkers Prev., August 1, 2007; 16(8): 1567 - 1572. [Abstract] [Full Text] [PDF]

				I. Stepanov, S. S. Hecht, B. Lindgren, P. Jacob III, M. Wilson, and N. L. Benowitz Relationship of Human Toenail Nicotine, Cotinine, and 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanol to Levels of These Biomarkers in Plasma and Urine Cancer Epidemiol. Biomarkers Prev., July 1, 2007; 16(7): 1382 - 1386. [Abstract] [Full Text] [PDF]

				C. J. Gallagher, J. E. Muscat, A. N. Hicks, Y. Zheng, A.-M. Dyer, G. A. Chase, J. Richie, and P. Lazarus The UDP-Glucuronosyltransferase 2B17 Gene Deletion Polymorphism: Sex-Specific Association with Urinary 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanol Glucuronidation Phenotype and Risk for Lung Cancer Cancer Epidemiol. Biomarkers Prev., April 1, 2007; 16(4): 823 - 828. [Abstract] [Full Text] [PDF]

				I. Stepanov, R. Feuer, J. Jensen, D. Hatsukami, and S. S. Hecht Mass Spectrometric Quantitation of Nicotine, Cotinine, and 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanol in Human Toenails Cancer Epidemiol. Biomarkers Prev., December 1, 2006; 15(12): 2378 - 2383. [Abstract] [Full Text] [PDF]

				S. G. Carmella, A. Yoder, and S. S. Hecht Combined Analysis of r-1,t-2,3,c-4-Tetrahydroxy-1,2,3,4-Tetrahydrophenanthrene and 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanol in Smokers' Plasma. Cancer Epidemiol. Biomarkers Prev., August 1, 2006; 15(8): 1490 - 1494. [Abstract] [Full Text] [PDF]

				J. H. Lubin and N. E. Caporaso Cigarette smoking and lung cancer: modeling total exposure and intensity. Cancer Epidemiol. Biomarkers Prev., March 1, 2006; 15(3): 517 - 523. [Abstract] [Full Text] [PDF]

				I. Stepanov, S. S. Hecht, G. Duca, and I. Mardari Uptake of the Tobacco-Specific Lung Carcinogen 4-(Methylnitrosamino)-1-(3-pyridyl)-1-Butanone by Moldovan Children Cancer Epidemiol. Biomarkers Prev., January 1, 2006; 15(1): 7 - 11. [Abstract] [Full Text] [PDF]

				A. M. Joseph, S. S. Hecht, S. E. Murphy, S. G. Carmella, C. T. Le, Y. Zhang, S. Han, and D. K. Hatsukami Relationships between Cigarette Consumption and Biomarkers of Tobacco Toxin Exposure Cancer Epidemiol. Biomarkers Prev., December 1, 2005; 14(12): 2963 - 2968. [Abstract] [Full Text] [PDF]

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				D. Wiener, J.-L. Fang, N. Dossett, and P. Lazarus Correlation between UDP-Glucuronosyltransferase Genotypes and 4-(Methylnitrosamino)-1-(3-Pyridyl)-1-Butanone Glucuronidation Phenotype in Human Liver Microsomes Cancer Res., February 1, 2004; 64(3): 1190 - 1196. [Abstract] [Full Text] [PDF]

				D. Wiener, D. R. Doerge, J.-L. Fang, P. Upadhyaya, and P. Lazarus CHARACTERIZATION OF N-GLUCURONIDATION OF THE LUNG CARCINOGEN 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANOL (NNAL) IN HUMAN LIVER: IMPORTANCE OF UDP-GLUCURONOSYLTRANSFERASE 1A4 Drug Metab. Dispos., January 1, 2004; 32(1): 72 - 79. [Abstract] [Full Text] [PDF]

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Intraindividual and interindividual differences in metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers' urine

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				P. G. Shields Tobacco Smoking, Harm Reduction, and Biomarkers J Natl Cancer Inst, October 2, 2002; 94(19): 1435 - 1444. [Abstract] [Full Text] [PDF]

				S. S. Hecht Human urinary carcinogen metabolites: biomarkers for investigating tobacco and cancer Carcinogenesis, June 1, 2002; 23(6): 907 - 922. [Abstract] [Full Text] [PDF]

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				Q. Ren, S. E. Murphy, Z. Zheng, and P. Lazarus O-Glucuronidation of the Lung Carcinogen 4-(methylnitrosamino)-1- (3-Pyridyl)-1-Butanol (nnal) by Human Udp-Glucuronosyltransferases 2b7 and 1a9 Drug Metab. Dispos., November 1, 2000; 28(11): 1352 - 1360. [Abstract] [Full Text]

				P. Upadhyaya, S. G. Carmella, F.P. Guengerich, and S. S. Hecht Formation and metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol enantiomers in vitro in mouse, rat and human tissues Carcinogenesis, June 1, 2000; 21(6): 1233 - 1238. [Abstract] [Full Text] [PDF]

				S. S. Hecht, N. Trushin, S. K. Chhabra, L. M. Anderson, and P. V. Nerurkar Short Communication: Metabolism of 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone by Cultured Monkey Lung Explants Drug Metab. Dispos., January 1, 2000; 28(1): 5 - 9. [Abstract] [Full Text]

				Q. Ren, S. E. Murphy, A. J. Dannenberg, J. Y. Park, T. R. Tephly, and P. Lazarus Glucuronidation of the Lung Carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) by Rat UDP-Glucuronosyltransferase 2B1 Drug Metab. Dispos., September 1, 1999; 27(9): 1010 - 1016. [Abstract] [Full Text]

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