399
Views
26
CrossRef citations to date
0
Altmetric
Review Article

A review of the analysis of tobacco-specific nitrosamines in biological matrices

&
Pages 305-327 | Received 24 Aug 2009, Accepted 07 Oct 2009, Published online: 09 Mar 2010

References

  • Adams JD, Brunnemann KD, Hoffmann D (1983). Chemical studies on tobacco smoke: LXXV. Rapid method for the analysis of tobacco-specific N-nitrosamines by gas–liquid chromatography with a thermal energy analyser. J Chromatogr A 256:347–351.
  • American Cancer Society (2009). Cancer Facts and Figures. June 2009.
  • Anderson KE, Carmella SG, Ye M, Bliss RL, Le C, Murphy L, Hecht SS (2001). Metabolites of a tobacco-specific lung carcinogen in nonsmoking women exposed to environmental tobacco smoke. J Natl Cancer Inst. 93:378–381.
  • Anderson KE, Kliris J, Murphy L, Carmella SG, Han S, Link C, Bliss RL, Puumala S, Murphy SE, Hecht SS (2003). Metabolites of a tobacco-specific lung carcinogen in nonsmoking casino patrons. Cancer Epidemiol Biomarkers Prev. 12:1544–1546.
  • Annesley TM (2003). Ion suppression in mass spectrometry. Clin Chem. 49:1041–1044.
  • Avery MJ (2003). Quantitative characterization of differential ion suppression on liquid chromatography/atmospheric pressure ionization mass spectrometric bioanalytical methods. Rapid Commun Mass Spectrom. 17:197–201.
  • Bartsch H (1996). DNA adducts in human carcinogenesis: Etiological relevance and structure-activity relationship. Mutat Res. 340:67–79.
  • Beveridge A (1998). Forensic Investigation of Explosions. London: Taylor & Francis.
  • Blau K, Halket JM, eds. (1993). Handbook of Derivatives for Chromatography. 2nd ed. New York: Wiley.
  • Bonfiglio R, King RC, Olah TV, Merkle K (1999). The effects of sample preparation methods on the variability of the electrospray ionization response for model drug compounds. Rapid Commun Mass Spectrom. 13:1175–1185.
  • Brittebo E, Tjalve H (1980). Autoradiographic observations on the distribution and metabolism of N’-/14C/nitrosonornicotine in mice. J Cancer Res Clin Oncol. 98:233–242.
  • Brittebo EB, Tjalve H (1981). Formation of tissue-bound N’-nitrosonornicotine metabolites by the target tissues of Sprague-Dawley and Fisher rats. Carcinogenesis. 2:959–963.
  • Brunnemann KD, Hoffmann D (1981). Assessment of the carcinogenic N-nitrosodiethanolamine in tobacco products and tobacco smoke. Carcinogenesis. 2:1123–1127.
  • Brunnemann KD, Genoble L, Hoffmann D (1987). Identification and analysis of a new tobacco-specific N-nitrosamine, 4-(methylnitrosamino)-4-(3-pyridyl)-1-butanol. Carcinogenesis. 8:465–469.
  • Brunnemann KD, Hoffmann D (1991). Analytical studies on tobacco-specific N-nitrosamines in tobacco and tobacco smoke. Crit Rev Toxicol. 21:235–240.
  • Brunnemann KD, Cox JE, Hoffmann D (1992). Analysis of tobacco-specific N-nitrosamines in indoor air. Carcinogenesis. 13:2415–2418.
  • Byrd GD, Ogden M. W (2003). Liquid chromatographic/tandem mass spectrometric method for the determination of the tobacco-specific nitrosamine metabolite NNAL in smokers’ urine. J Mass Spectrom. 38:98–107.
  • Campo VL, Bernardes LS, Carvalho I (2009). Stereoselectivity in drug metabolism: molecular mechanisms and analytical methods. Curr Drug Metab. 10:188–205.
  • Carmella SG, Akerkar S, Hecht SS (1993a). Metabolites of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers’ urine. Cancer Res. 53:721–724.
  • Carmella SG, Akerkar SA, Richie JP Jr, Hecht SS (1995). Intraindividual and interindividual differences in metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK) in smokers’ urine. Cancer Epidemiol Biomarkers Prev. 4:635–642.
  • Carmella SG, Borukhova A, Akerkar SA, Hecht SS (1997). Analysis of human urine for pyridine-N-oxide metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, a tobacco-specific lung carcinogen. Cancer Epidemiol Biomarkers Prev. 6:113–120.
  • Carmella SG, Ye M, Upadhyaya P, Hecht SS (1999). Stereochemistry of metabolites of a tobacco-specific lung carcinogen in smokers’ urine. Cancer Res. 59:3602–3605.
  • Carmella SG, Le Ka KA, Upadhyaya P, Hecht SS (2002). Analysis of N- and O-glucuronides of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine. Chem Res Toxicol. 15:545–550.
  • Carmella SG, Han S, Fristad A, Yang Y, Hecht SS (2003). Analysis of total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) in human urine. Cancer Epidemiol Biomarkers Prev. 12(11 Pt 1):1257–1261.
  • Carmella SG, Han S, Villalta PW, Hecht SS (2005). Analysis of total 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in smokers’ blood. Cancer Epidemiol Biomarkers Prev. 14(11 Pt 1):2669–2672.
  • Carmella SG, Yoder A, Hecht SS (2006). 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. 15:1490–1494.
  • Carmella SG, Chen M, Han S, Briggs A, Jensen J, Hatsukami DK, Hecht SS (2009). Effects of smoking cessation on eight urinary tobacco carcinogen and toxicant biomarkers. Chem Res Toxicol. 22:734–741.
  • Castonguay A, Lin D, Stoner GD, Radok P, Furuya K, Hecht SS, Schut HA, Klaunig JE (1983a). Comparative carcinogenicity in A/J mice and metabolism by cultured mouse peripheral lung of N’-nitrosonornicotine, 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone, their analogues. Cancer Res. 43:1223–1229.
  • Castonguay A, Tjalve H, Hecht SS (1983b). Tissue distribution of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone and its metabolites in F344 rats. Cancer Res. 43:630–638.
  • Castonguay A, Tjalve H, Trushin N, Hecht SS (1984). Perinatal metabolism of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in C57BL mice. J Natl Cancer Inst. 72:1117–1126.
  • Castonguay A, Tjalve H, Trushin N, d’Argy R, Sperber G (1985). Metabolism and tissue distribution of tobacco-specific N-nitrosamines in the marmoset monkey (Callithrix jacchus). Carcinogenesis. 6:1543–1550.
  • Chen Y, Guo Z, Wang X, Qiu C (2008). Sample preparation. J Chromatogr A. 1184:191–219.
  • Church TR, Anderson KE, Caporaso NE, Geisser MS, Le CT, Zhang Y, Benoit AR, Carmella SG, Hecht SS (2009). A prospectively measured serum biomarker for a tobacco-specific carcinogen and lung cancer in smokers. Cancer Epidemiol Biomarkers Prev. 18:260–266.
  • Curfman GD, Morrissey S, Drazen JM (2009). Tobacco, public health, and the FDA. N Engl J Med. 361:402–403.
  • De Bont R, van Larebeke N (2004). Endogenous DNA damage in humans: A review of quantitative data. Mutagenesis. 19:169–185.
  • Dejaegher B, Mangelings D, Vander Heyden Y, (2008). Method development for HILIC assays. J Sep Sci. 31:1438–1448.
  • Djordjevic MV, Brunnemann KD, Hoffmann D (1989). Identification and analysis of a nicotine-derived N-nitrosamino acid and other nitrosamino acids in tobacco. Carcinogenesis. 10:1725–1731.
  • Djordjevic MV, Sigountos CW, Brunnemann KD, Hoffmann D (1991). Formation of 4-(methylnitrosamino)-1-(3-pyridyl) butyric acid in vitro and in mainstream cigarette smoke. J Agric Food Chem. 39:209–213.
  • Evans G (2004). A Handbook of Bioanalysis and Drug Metabolism. Boca Raton, FL, London: CRC Press.
  • Falter B, Kutzer C, Richter E (1994). Biomonitoring of hemoglobin adducts: Aromatic amines and tobacco-specific nitrosamines. Clin Invest 72:364–371.
  • Fine DH, Rufeh F, Gunther B (1973). A group specific procedure for the analysis of both volatile and nonvolatile N-nitroso compounds in picogram amounts. Anal Lett 6:731 - 733.
  • Fine DH, Rufeh F, Lieb D (1974). Group analysis of volatile and non-volatile N-nitroso compounds. Nature. 247:309–310.
  • Fine DH, Lieb D, Rufeh F (1975a). Principle of operation of the thermal energy analyzer for the trace analysis of volatile and non-volatile N-nitroso compounds. J Chromatogr. 107:351–357.
  • Fine DH, Rufeh F, Lieb D, Rounbehler DP (1975b). Description of the thermal energy analyzer (TEA) for trace determination of volatile and nonvolatile N-nitroso compounds. Anal Chem. 47:1188–1191.
  • Fischer S, Spiegelhalder B, Preussmann R (1989). Preformed tobacco-specific nitrosamines in tobacco—role of nitrate and influence of tobacco type. Carcinogenesis. 10:1511–1517.
  • Foiles PG, Akerkar SA, Carmella SG, Kagan M, Stoner GD, Resau JH, Hecht SS (1991). Mass spectrometric analysis of tobacco-specific nitrosamine-DNA adducts in smokers and nonsmokers. Chem Res Toxicol. 4:364–368.
  • Fu I, Woolf EJ, Matuszewski BK (1998). Effect of the sample matrix on the determination of indinavir in human urine by HPLC with turbo ion spray tandem mass spectrometric detection. J Pharm Biomed Anal. 18:347–357.
  • Hatsukami DK, Lemmonds C, Zhang Y, Murphy SE, Le C, Carmella SG, Hecht SS (2004). Evaluation of carcinogen exposure in people who used “reduced exposure” tobacco products. J Natl Cancer Inst. 96:844–852.
  • Hecht SS (1998a). Biochemistry, biology, and carcinogenicity of tobacco-specific N-nitrosamines. Chem Res Toxicol. 11:559–603.
  • Hecht SS (1998b). In:Rom WN, ed. Environmental and Occupational Medicine. N-Nitrosamines New York: Lippincott-Raven, 1479–1499.
  • Hecht S. S (1999). Tobacco smoke carcinogens and lung cancer. J Natl Cancer Inst. 91:1194–1210.
  • Hecht SS (2002). Human urinary carcinogen metabolites: Biomarkers for investigating tobacco and cancer. Carcinogenesis. 23:907–922.
  • Hecht SS (2003). Tobacco carcinogens, their biomarkers and tobacco-induced cancer. Nat Rev Cancer. 3:733–744.
  • Hecht SS (2008). Progress and challenges in selected areas of tobacco carcinogenesis. Chem Res Toxicol. 21:160–171.
  • Hecht SS, Hoffmann D (1988). Tobacco-specific nitrosamines, an important group of carcinogens in tobacco and tobacco smoke. Carcinogenesis. 9:875–884.
  • Hecht SS, Rivenson A, Braley J, DiBello J, Adams JD, Hoffmann D (1986). Induction of oral cavity tumors in F344 rats by tobacco-specific nitrosamines and snuff. Cancer Res. 46:4162–4166.
  • Hecht SS, Carmella SG, Murphy SE, Akerkar S, Brunnemann KD, Hoffmann D (1993a). A tobacco-specific lung carcinogen in the urine of men exposed to cigarette smoke. N Engl J Med. 329:1543–1546.
  • Hecht SS, Trushin N, Reid-Quinn CA, Burak ES, Jones AB, Southers JL, Gombar CT, Carmella SG, Anderson LM, Rice JM (1993b). Metabolism of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in the patas monkey: Pharmacokinetics and characterization of glucuronide metabolites. Carcinogenesis. 14:229–236.
  • Hecht SS, Chung FL, Richie JP Jr, Akerkar SA, Borukhova A, Skowronski L, Carmella SG (1995). Effects of watercress consumption on metabolism of a tobacco-specific lung carcinogen in smokers. Cancer Epidemiol Biomarkers Prev. 4:877–884.
  • Hecht SS, Carmella SG, Chen M, Dor Koch JF, Miller AT, Murphy SE, Jensen JA, Zimmerman CL, Hatsukami DK (1999). Quantitation of urinary metabolites of a tobacco-specific lung carcinogen after smoking cessation. Cancer Res. 59:590–596.
  • Hecht SS, Ye M, Carmella SG, Fredrickson A, Adgate JL, Greaves IA, Church TR, Ryan AD, Mongin SJ, Sexton K (2001). Metabolites of a tobacco-specific lung carcinogen in the urine of elementary school-aged children. Cancer Epidemiol Biomarkers Prev. 10:1109–1116.
  • Hecht SS, Carmella SG, Ye M, Le KA, Jensen JA, Zimmerman CL, Hatsukami DK (2002). Quantitation of metabolites of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone after cessation of smokeless tobacco use. Cancer Res. 62:129–134.
  • Hecht SS, Carmella SG, Kenney PM, Low SH, Arakawa K, Yu MC (2004a). Effects of cruciferous vegetable consumption on urinary metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in singapore chinese. Cancer Epidemiol Biomarkers Prev. 13:997–1004.
  • Hecht SS, Murphy SE, Carmella SG, Zimmerman CL, Losey L, Kramarczuk I, Roe MR, Puumala SS, Li YS, Le C, Jensen J, Hatsukami DK (2004b). Effects of reduced cigarette smoking on the uptake of a tobacco-specific lung carcinogen. J Natl Cancer Inst. 96:107–115.
  • Hecht SS, Carmella SG, Le KA, Murphy SE, Boettcher AJ, Le C, Koopmeiners J, An L, Hennrikus DJ (2006). 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol and its glucuronides in the urine of infants exposed to environmental tobacco smoke. Cancer Epidemiol Biomarkers Prev. 15:988–992.
  • Hecht SS, Carmella SG, Murphy SE, Riley WT, Le C, Luo X, Mooney M, Hatsukami DK (2007). Similar exposure to a tobacco-specific carcinogen in smokeless tobacco users and cigarette smokers. Cancer Epidemiol Biomarkers Prev. 16:1567–1572.
  • Hecht SS, Carmella SG, Edmonds A, Murphy SE, Stepanov I, Luo X, Hatsukami DK (2008). Exposure to nicotine and a tobacco-specific carcinogen increase with duration of use of smokeless tobacco. Tob Control. 17:128–131.
  • Henry MC, Yonker C. R (2006). Supercritical fluid chromatography, pressurized liquid extraction, and supercritical fluid extraction. Anal Chem. 78:3909–3916.
  • Hoffmann D, Adams JD (1981). Carcinogenic tobacco-specific N-nitrosamines in snuff and in the saliva of snuff dippers. Cancer Res. 41(11 Pt 1):4305–4308.
  • Hoffmann D, Adams JD, Brunnemann KD, Hecht SS (1979). Assessment of tobacco-specific N-nitrosamines in tobacco products. Cancer Res. 39(7 Pt 1):2505–2509.
  • Hoffmann D, Adams JD, Brunnemann KD, Rivenson A, Hecht SS (1982). Tobacco specific N-nitrosamines: occurrence and bioassays. IARC Sci Publ. 41:309–318.
  • Hoffmann D, Adams JD, Lisk D, Fisenne I, Brunnemann KD (1987). Toxic and carcinogenic agents in dry and moist snuff. J Natl Cancer Inst. 79:1281–1286.
  • Hoffmann D, Brunnemann KD, Prokopczyk B, Djordjevic MV (1994). Tobacco-specific N-nitrosamines and Areca-derived N-nitrosamines: Chemistry, biochemistry, carcinogenicity, and relevance to humans. J Toxicol Environ Health. 41:1–52.
  • Hoffmann D, Djordjevic MV, Fan J, Zang E, Glynn T, Connolly GN (1995). Five leading U.S. commercial brands of moist snuff in 1994: Assessment of carcinogenic N-nitrosamines. J Natl Cancer Inst. 87:1862–1869.
  • Hoffmann D, Hoffmann I, El-Bayoumy K (2001). The less harmful cigarette: A controversial issue. A tribute to Ernst L. Wynder. Chem Res Toxicol. 14:767–790.
  • Hsieh Y (2008). Potential of HILIC-MS in quantitative bioanalysis of drugs and drug metabolites. J Sep Sci. 31:1481–1491.
  • Hurt RD, Croghan GA, Wolter TD, Croghan IT, Offord KP, Williams GM, Djordjevic MV, Richie JP Jr, Jeffrey AM (2000). Does smoking reduction result in reduction of biomarkers associated with harm? A pilot study using a nicotine inhaler. Nicotine Tob Res 2:327–336.
  • International Agency for Research on Cancer (1985). Tobacco habits other than smoking: betel quid and areca nut chewing and some related nitrosamines. In: IARC Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Lyon, France: IARC, 37:37–140.
  • International Agency for Research on Cancer (1995). Occurence of and exposure to N-nitroso compounds in tobacco. In: Relevance to Human Cancer of N-nitroso Compounds, Tobacco Smoke and Mycotoxins. Lyon, France: IARC, 493–495.
  • International Agency for Research on Cancer (2002). Tobacco smoke and involuntary smoking. In: IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Lyon, France: IARC, 83:1012–1065.
  • International Agency for Research on Cancer (2007). Smokeless tobacco and some tobacco-specific nitrosamines. In: IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. Lyon, France: IARC, 89:166–370.
  • Jacob P 3rd, Havel C, Lee DH, Yu L, Eisner MD, Benowitz NL (2008). Subpicogram per milliliter determination of the tobacco-specific carcinogen metabolite 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human urine using liquid chromatography-tandem mass spectrometry. Anal Chem. 80:8115–8121.
  • Jemal M (2000). High-throughput quantitative bioanalysis by LC/MS/MS. Biomed Chromatogr. 14:422–429.
  • Jemal M, Xia YQ (2006). LC-MS Development strategies for quantitative bioanalysis. Curr Drug Metab. 7:491–502.
  • Joseph AM, Hecht SS, Murphy SE, Carmella SG, Le CT, Zhang Y, Han S, Hatsukami DK (2005). Relationships between cigarette consumption and biomarkers of tobacco toxin exposure. Cancer Epidemiol Biomarkers Prev. 14:2963–2968.
  • Kavvadias D, Scherer G, Urban M, Cheung F, Errington G, Shepperd J, McEwan M (2009). Simultaneous determination of four tobacco-specific N-nitrosamines (TSNA) in human urine. J Chromatogr B Analyt Technol Biomed Life Sci. 877:1185–1192.
  • King R, Bonfiglio R, Fernandez-Metzler C, Miller-Stein C, Olah T (2000). Mechanistic investigation of ionization suppression in electrospray ionization. J Am Soc Mass Spectrom. 11:942–950.
  • Kresty LA, Carmella SG, Borukhova A, Akerkar SA, Gopalakrishnan R, Harris RE, Stoner GD, Hecht SS (1996). Metabolites of a tobacco-specific nitrosamine, 4-(methylnitrosamino)- 1-(3-pyridyl)-1-butanone (NNK), in the urine of smokeless tobacco users: Relationship between urinary biomarkers and oral leukoplakia. Cancer Epidemiol Biomarkers Prev. 5:521–525.
  • Lackmann GM, Salzberger U, Tollner U, Chen M, Carmella SG, Hecht SS (1999). Metabolites of a tobacco-specific carcinogen in urine from newborns. J Natl Cancer Inst. 91:459–465.
  • Lagerwerf FM, van Dongen WD, Steenvoorden RJJM, Honing M, Jonkman JHG (2000). Exploring the boundaries of bioanalytical quantitative LC-MS-MS. Trends Anal Chem 19:418–427.
  • Lasakova M, Jandera P (2009). Molecularly imprinted polymers and their application in solid phase extraction. J Sep Sci. 32:799–812.
  • Matuszewski BK, Constanzer ML, Chavez-Eng CM (2003). Strategies for the assessment of matrix effect in quantitative bioanalytical methods based on HPLC-MS/MS. Anal Chem. 75:3019–3030.
  • Mazzeo JR, D.,?Neue U, Kele M, Plumb RS (2005). Advancing LC performance with smaller particles and higher pressure. Anal Chem 77:460A–467A.
  • Meger M, Richter E, Zwickenpflug W, Oehlmann C, Hargaden MB, YI AR, Vesell ES (1999). Metabolism and disposition of 4-(methylnitrosamino)-1-(3-pyridyl)-1- butanone (NNK) in rhesus monkeys. Drug Metab Dispos. 27:471–478.
  • Meulemans A, Delsenne F (1994). Measurement of nitrite and nitrate levels in biological samples by capillary electrophoresis. J Chromatogr B Biomed Appl. 660:401–404.
  • Milunsky A, Carmella SG, Ye M, Hecht SS (2000). A tobacco-specific carcinogen in the fetus. Prenat Diagn. 20:307–310.
  • Morcos E, Wiklund N. P (2001). Nitrite and nitrate measurement in human urine by capillary electrophoresis. Electrophoresis. 22:2763–2768.
  • Morse MA, Eklind KI, Toussaint M, Amin SG, Chung FL (1990). Characterization of a glucuronide metabolite of 4-(methyl-nitrosamino)-1-(3-pyridyl)-1-butanone (NNK) and its dose-dependent excretion in the urine of mice and rats. Carcinogenesis. 11:1819–1823.
  • Murphy SE, Carmella SG, Idris AM, Hoffmann D (1994). Uptake and metabolism of carcinogenic levels of tobacco-specific nitrosamines by Sudanese snuff dippers. Cancer Epidemiol Biomarkers Prev. 3:423–428.
  • Murphy SE, Link CA, Jensen J, Le C, Puumala SS, Hecht SS, Carmella SG, Losey L, Hatsukami DK (2004). A comparison of urinary biomarkers of tobacco and carcinogen exposure in smokers. Cancer Epidemiol Biomarkers Prev. 13:1617–1623.
  • Muscat JE, Djordjevic MV, Colosimo S, Stellman SD, Richie JP Jr (2005). Racial differences in exposure and glucuronidation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK). Cancer. 103:1420–1426.
  • Nair J, Ohshima H, Friesen M, Croisy A, Bhide SV, Bartsch H (1985). Tobacco-specific and betel nut-specific N-nitroso compounds: Occurrence in saliva and urine of betel quid chewers and formation in vitro by nitrosation of betel quid. Carcinogenesis. 6:295–303.
  • Pan J, Song Q, Shi H, King M, Junga H, Zhou S, Naidong W (2004). Development, validation and transfer of a hydrophilic interaction liquid chromatography/tandem mass spectrometric method for the analysis of the tobacco-specific nitrosamine metabolite NNAL in human plasma at low picogram per milliliter concentrations. Rapid Commun Mass Spectrom. 18:2549–2557.
  • Parsons WD, Carmella SG, Akerkar S, Bonilla LE, Hecht SS (1998). A metabolite of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in the urine of hospital workers exposed to environmental tobacco smoke. Cancer Epidemiol Biomarkers Prev. 7:257–260.
  • Phillips DH (1996). DNA adducts in human tissues: Biomarkers of exposure to carcinogens in tobacco smoke. Environ Health Perspect. 104(Suppl 3):453–458.
  • Pichon V (2007). Selective sample treatment using molecularly imprinted polymers. J Chromatogr A. 1152:41–53.
  • Poirier MC, Weston A (1996). Human DNA adduct measurements: state of the art. Environ Health Perspect. 104(Suppl 5):883–893.
  • Poirier MC, Santella RM, Weston A (2000). Carcinogen macromolecular adducts and their measurement. Carcinogenesis. 21:353–359.
  • Prokopczyk B, Wu M, Cox JE, Amin S, Desai D (1995). Improved methodology for the quantitative assessment of tobacco specific N-nitrosamines in tobacco by supercritical fluid extraction. J Agric Food Chem. 43:916–922.
  • Prokopczyk B, Cox JE, Hoffmann D, Waggoner SE (1997). Identification of tobacco-specific carcinogen in the cervical mucus of smokers and nonsmokers. J Natl Cancer Inst. 89:868–873.
  • 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 HG, El-Bayoumy K (2002). Identification of tobacco-derived compounds in human pancreatic juice. Chem Res Toxicol. 15:677–685.
  • Richie JP Jr, Carmella SG, Muscat JE, Scott DG, Akerkar SA, Hecht SS (1997). Differences in the urinary metabolites of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in black and white smokers. Cancer Epidemiol Biomarkers Prev. 6:783–790.
  • Richter E, Engl J, Friesenegger S, Tricker AR (2009). Biotransformation of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in lung tissue from mouse, rat, hamster, and man. Chem Res Toxicol. 22:1008–1017.
  • Rodgman A, Perfetti TA (2009) The Chemical Components of Tobacco and Tobacco Smoke. Boca Raton, FL, London: CRC Press.
  • Schaffler G, Betz C, Richter E (1993). Mass spectrometric analysis of tobacco-specific hemoglobin adducts. Environ Health Perspect. 99:187–189.
  • Scherer G, Engl J, Urban M, Gilch G, Janket D, Riedel K (2007). Relationship between machine-derived smoke yields and biomarkers in cigarette smokers in Germany. Regul Toxicol Pharmacol. 47:171–183.
  • Shah K, Peoples MC, Halquist MS, James JR, Karnes HT (2009a). Online coupling of molecularly imprinted polymeric micro-column with tandem MS for analysis of a urinary tobacco specific nitrosamine by direct injection. Presented at the 2009 Joint Conference of SRNT and SRNT-Europe, April 27–30, Dublin, Ireland.
  • Shah K, Peoples M. C, Halquist MS, Karnes HT (2009b). On-line microfluidic extraction using molecularly imprinted polymers for analysis of urinary tobacco specific nitrosamines. Presented at the 2009 AAPS Annual Meeting and Exposition, November 8–12, Los Angeles, CA, USA.
  • Shah KA, Halquist MS, Karnes HT (2009c). A modified method for the determination of tobacco specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human urine by solid phase extraction using a molecularly imprinted polymer and liquid chromatography tandem mass spectrometry. J Chromatogr B Anal Technol Biomed Life Sci. 877:1575–1582.
  • Shargel L, Yu ABC (1999). Applied Biopharmaceutics and Pharmacokinetics. 4th ed. Stamford, CT: Appleton & Lange.
  • Smith RM (1999). Supercritical fluids in separation science—The dreams, the reality and the future. J Chromatogr A. 856:83–115.
  • Spiegelhalder B, Bartsch H (1996). Tobacco-specific nitrosamines. Eur J Cancer Prev. 5(Suppl 1):33–38.
  • Srinivas NR (2009). Dodging matrix effects in liquid chromatography tandem mass spectrometric assays—Compilation of key learnings and perspectives. Biomed Chromatogr. 23:451–454.
  • Stepanov I, Hecht SS (2005). Tobacco-specific nitrosamines and their pyridine-N-glucuronides in the urine of smokers and smokeless tobacco users. Cancer Epidemiol Biomarkers Prev. 14:885–891.
  • Stepanov I, Hecht SS (2008). Detection and quantitation of N’-nitrosonornicotine in human toenails by liquid chromatography-electrospray ionization-tandem mass spectrometry. Cancer Epidemiol Biomarkers Prev. 17:945–948.
  • Stepanov I, Feuer R, Jensen J, Hatsukami D, Hecht SS (2006a). Mass spectrometric quantitation of nicotine, cotinine, and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in human toenails. Cancer Epidemiol Biomarkers Prev. 15:2378–2383.
  • Stepanov I, Hecht SS, Duca G, Mardari I (2006b). Uptake of the tobacco-specific lung carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone by Moldovan children. Cancer Epidemiol Biomarkers Prev. 15:7–11.
  • Stepanov I, Upadhyaya P, Carmella SG, Feuer R, Jensen J, Hatsukami DK, Hecht SS (2008). Extensive metabolic activation of the tobacco-specific carcinogen 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers. Cancer Epidemiol Biomarkers Prev. 17:1764–1773.
  • Sterner JL, Johnston MV, Nicol GR, Ridge DP (2000). Signal suppression in electrospray ionization Fourier transform mass spectrometry of multi-component samples. J Mass Spectrom. 35(3):385–391.
  • Stokvis E, Rosing H, Beijnen JH (2005). Stable isotopically labeled internal standards in quantitative bioanalysis using liquid chromatography/mass spectrometry: Necessity or not? Rapid Commun Mass Spectrom. 19:401–407.
  • Swauger JE, Steichen TJ, Murphy PA, Kinsler S (2002). An analysis of the mainstream smoke chemistry of samples of the U.S. cigarette market acquired between 1995 and 2000. Regul Toxicol Pharmacol. 35(2 Pt 1):142–156.
  • Taioli E, Garbers S, Bradlow HL, Carmella SG, Akerkar S, Hecht SS (1997). Effects of indole-3-carbinol on the metabolism of 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone in smokers. Cancer Epidemiol Biomarkers Prev. 6:517–522.
  • Taylor PJ (2005). Matrix effects: The Achilles heel of quantitative high-performance liquid chromatography-electrospray-tandem mass spectrometry. Clin Biochem. 38:328–334.
  • Tricker AR, Ditrich C, Preussmann R (1991). N-nitroso compounds in cigarette tobacco and their occurrence in mainstream tobacco smoke. Carcinogenesis. 12:257–261.
  • Tricker AR, Scherer G, Conze C, Adlkofer F, Pachinger A, Klus H (1993). Evaluation of 4-(N-methylnitrosamino)-4-(3-pyridyl)butyric acid as a potential monitor of endogenous nitrosation of nicotine and its metabolites. Carcinogenesis. 14:1409–1414.
  • Tulunay OE, Hecht SS, Carmella SG, Zhang Y, Lemmonds C, Murphy S, Hatsukami DK (2005). Urinary metabolites of a tobacco-specific lung carcinogen in nonsmoking hospitality workers. Cancer Epidemiol Biomarkers Prev. 14:1283–1286.
  • Tyroller S, Zwickenpflug W, Richter E (2002). New sources of dietary myosmine uptake from cereals, fruits, vegetables, and milk. J Agric Food Chem 50:4909–4915.
  • Urban M, Scherer G, Kavvadias D, Hagedorn H-W, Feng S, Serafin R, Kapur S, Muhammad R, Jin Y, Mendes P, Roethig H (2009). Quantitation of N’-nitrosonornicotine (NNN) in smokers urine by liquid chromatography–tandem mass spectrometry. J Anal Toxicol 33:260–265.
  • US Department of Health and Human Services (2004). The Health Consequences of Smoking—A Report of the Surgeon General.
  • US Food and Drug Administration (2001). Guidance for Industry—Bioanalytical Method Validation. http://www.fda.gov/downloads/Drugs/GuidanceComplianceRegulatoryInformation/Guidances/UCM070107.pdf.
  • van Hout MW, Niederlander HA, de Zeeuw RA, de Jong GJ (2003). Ion suppression in the determination of clenbuterol in urine by solid-phase extraction atmospheric pressure chemical ionisation ion-trap mass spectrometry. Rapid Commun Mass Spectrom. 17:245–250.
  • Venn RF (2000) Principles and Practice of Bioanalysis. London: Taylor & Francis.
  • Wang S, Cyronak M, Yang E (2007). Does a stable isotopically labeled internal standard always correct analyte response?: A matrix effect study on a LC/MS/MS method for the determination of carvedilol enantiomers in human plasma. J of Pharmaceut Biomed Anal 43:701–707.
  • Wild CP, Pisani P (1998). Carcinogen DNA and protein adducts as biomarkers of human exposure in environmental cancer epidemiology. Cancer Detect Prev. 22:273–283.
  • Wu J, Joza P, Sharifi M, Rickert WS, Lauterbach JH (2008). Quantitative method for the analysis of tobacco-specific nitrosamines in cigarette tobacco and mainstream cigarette smoke by use of isotope dilution liquid chromatography tandem mass spectrometry. Anal Chem. 80:1341–1345.
  • Xia Y, McGuffey JE, Bhattacharyya S, Sellergren B, Yilmaz E, Wang L, Bernert JT (2005). Analysis of the tobacco-specific nitrosamine 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol in urine by extraction on a molecularly imprinted polymer column and liquid chromatography/atmospheric pressure ionization tandem mass spectrometry. Anal Chem. 77:7639–7645.
  • Xu RN, Fan L, Rieser MJ, El-Shourbagy TA (2007). Recent advances in high-throughput quantitative bioanalysis by LC-MS/MS. J Pharmceut Biomed Anal. 44:342–355.
  • Young DS (1987). Implementation of SI units for clinical laboratory data. Style specifications and conversion tables. Ann Intern Med. 106:114–129.
  • Yuan JM, Koh WP, Murphy SE, Fan Y, Wang R, Carmella SG, Han S, Wickham K, Gao YT, Yu MC, Hecht SS (2009). Urinary levels of tobacco-specific nitrosamine metabolites in relation to lung cancer development in two prospective cohorts of cigarette smokers. Cancer Res. 69:2990–2995.
  • Zougagh M, Valcárcel M, Ríos A (2004). Supercritical fluid extraction: A critical review of its analytical usefulness. Trends Anal Chem 23:399–405.
  • Zwickenpflug W (2000). N-nitrosation of myosmine yields HPB (4-hydroxy-1-(3-pyridyl)-1-butanone) and NNN (N-nitrosonornicotine). J Agric Food Chem 48:392–394.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.