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Bioanalytical

Determination of Cotinine, 3′-Hydroxycotinine, and Their Glucuronides in Urine by Ultra-high Performance Liquid Chromatography

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Pages 1217-1233 | Received 03 Aug 2014, Accepted 16 Oct 2014, Published online: 16 Mar 2015

REFERENCES

  • Benowitz, N. L. 1996. Pharmacology of nicotine: addiction and therapeutics. Annual Review of Pharmacology and Toxicology 36: 597–613. doi:10.1146/annurev.pharmtox.36.1.597
  • Benowitz, N. L., K. M. Dains, D. Dempsey, B. Herrera, L. Yu, and P. Jacob. 2009. Urine nicotine metabolite concentrations in relation to plasma cotinine during low-level nicotine exposure. Nicotine & Tobacco Research 11: 954–60. doi:10.1093/ntr/ntp092
  • Benowitz, N. L., P. Jacob, I. Fong, and S. Gupta. 1994. Nicotine metabolic profile in man: comparison of cigarette smoking and transdermal nicotine. Journal of Pharmacology and Experimental Therapeutics 268: 296–303.
  • Benowitz, N. L., E. J. Perez-Stable, I. Fong, G. Modin, B. Herrera, and P. Jacob. 1999. Ethnic differences in N-glucuronidation of nicotine and cotinine. Journal of Pharmacology and Experimental Therapeutics 291: 1196–203.
  • Benowitz, N. L., O. F. Pomerleau, C. S. Pomerleau, and P. Jacob. 2003. Nicotine metabolite ratio as a predictor of cigarette consumption. Nicotine & Tobacco Research 5: 621–24. doi:10.1080/1462220031000158717
  • Berg, J. Z., L. B. von Weymarn, E. A. Thompson, K. M. Wickham, N. A. Weisensel, D. K. Hatsukami, and S. E. Murphy. 2010. UGT2B10 genotype influences nicotine glucuronidation, oxidation, and consumption. Cancer Epidemiology Biomarkers & Prevention 19: 1423–31. doi:10.1158/1055-9965.epi-09-0959
  • Bernert, J. T., W. E. Turner, J. L. Pirkle, C. S. Sosnoff, J. R. Akins, M. K. Waldrep, Q. Ann, T. R. Covey, W. E. Whitfield, E. W. Gunter, B. B. Miller, D. G. Patterson, L. L. Needham, W. H. Hannon, and E. J. Sampson. 1997. Development and validation of sensitive method for determination of serum cotinine in smokers and nonsmokers by liquid chromatography/atmospheric pressure ionization tandem mass spectrometry. Clinical Chemistry 43: 2281–91.
  • Byrd, G. D., R. A. Davis, and M. W. Ogden. 2005. A rapid LC-MS-MS method for the determination of nicotine and cotinine in serum and saliva samples from smokers: validation and comparison with a radioimmunoassay method. Journal of Chromatographic Science 43: 133–40. doi:10.1093/chromsci/43.3.133
  • Chen, G., N. E. Giambrone, D. F. Dluzen, J. E. Muscat, A. Berg, C. J. Gallagher, and P. Lazarus. 2010. Glucuronidation genotypes and nicotine metabolic phenotypes: importance of functional UGT2B10 and UGT2B17 polymorphisms. Cancer Research 70: 7543–52. doi:10.1158/0008-5472.can-09-4582
  • de Beyer, J., C. Lovelace, and A. Yürekli. 2001. Poverty and tobacco. Tobacco Control 10: 210–11. doi:10.1136/tc.10.3.210
  • De Cremer, K., I. Van Overmeire, and J. Van Loco. 2013. On-line solid-phase extraction with ultra performance liquid chromatography and tandem mass spectrometry for the detection of nicotine, cotinine and trans-3′-hydroxycotinine in urine to strengthen human biomonitoring and smoking cessation studies. Journal of Pharmaceutical and Biomedical Analysis 76: 126–33. doi:10.1016/j.jpba.2012.12.018
  • Dempsey, D., P. Tutka, P. Jacob, F. Allen, K. Schoedel, R. F. Tyndale, and N. L. Benowitz. 2004. Nicotine metabolite ratio as an index of cytochrome P450 2A6 metabolic activity. Clinical Pharmacology & Therapeutics 76: 64–72. doi:10.1016/j.clpt.2004.02.011
  • Derby, K. S., K. Cuthrell, C. Caberto, S. G. Carmella, A. A. Franke, S. S. Hecht, S. E. Murphy, and L. Le Marchand. 2008. Nicotine metabolism in three ethnic/racial groups with different risks of lung cancer. Cancer Epidemiology Biomarkers & Prevention 17: 3526–35. doi:10.1158/1055-9965.epi-08-0424
  • Dhar, P. 2004. Measuring tobacco smoke exposure: quantifying nicotine/cotinine concentration in biological samples by colorimetry, chromatography and immunoassay methods. Journal of Pharmaceutical and Biomedical Analysis 35: 155–68. doi:10.1016/j.jpba.2004.01.009
  • Dobrinas, M., E. Choong, M. Noetzli, J. Cornuz, N. Ansermot, and C. B. Eap. 2011. Quantification of nicotine, cotinine, trans-3′-hydroxycotinine and varenicline in human plasma by a sensitive and specific UPLC–tandem mass-spectrometry procedure for a clinical study on smoking cessation. Journal of Chromatography B 879: 3574–82. doi:10.1016/j.jchromb.2011.09.046
  • Hecht, S. S., S. G. Carmella, and S. E. Murphy. 1999. Effects of watercress consumption on urinary metabolites of nicotine in smokers. Cancer Epidemiology Biomarkers & Prevention 8: 907–13.
  • Ho, M. K., J. C. Mwenifumbo, N. Al Koudsi, K. S. Okuyemi, J. S. Ahluwalia, N. L. Benowitz, and R. F. Tyndale. 2009. Association of nicotine metabolite ratio and CYP2A6 genotype with smoking cessation treatment in African-American light smokers. Clinical Pharmacology & Therapeutics 85: 635–43. doi:10.1038/clpt.2009.19
  • Hukkanen, J., P. Jacob, and N. L. Benowitz. 2005. Metabolism and disposition kinetics of nicotine. Pharmacological Reviews 57: 79–115. doi:10.1124/pr.57.1.3
  • ICH Harmonised Tripartite Guideline. 1994. Validation of analytical procedures: text and methodology Q2(R1): 11–12.
  • Jacob, P., A. T. Shulgin, and N. L. Benowitz. 1990. Synthesis of (3′R,5′S)-trans-3′-hydroxycotinine, a major metabolite of nicotine. Metabolic formation of 3′-hydroxycotinine in humans is highly stereoselective. Journal of Medicinal Chemistry 33: 1888–91. doi:10.1021/jm00169a009
  • Jacob, P., L. Yu, M. Duan, L. Ramos, O. Yturralde, and N. L. Benowitz. 2011. Determination of the nicotine metabolites cotinine and trans-3′-hydroxycotinine in biologic fluids of smokers and non-smokers using liquid chromatography-tandem mass spectrometry: biomarkers for tobacco smoke exposure and for phenotyping cytochrome P450 2A6 activity. Journal of Chromatography B 879: 267–76. doi:10.1016/j.jchromb.2010.12.012
  • Ji, A. J., G. M. Lawson, R. Anderson, L. C. Dale, I. T. Croghan, and R. D. Hurt. 1999. A new gas chromatography-mass spectrometry method for simultaneous determination of total and free trans-3′-hydroxycotinine and cotinine in the urine of subjects receiving transdermal nicotine. Clinical Chemistry 45: 85–91.
  • Kim, I., and M. A. Huestis. 2006. A validated method for the determination of nicotine, cotinine, trans-3′-hydroxycotinine, and norcotinine in human plasma using solid-phase extraction and liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry. Journal of Mass Spectrometry 41: 815–21. doi:10.1002/jms.1039
  • Kuo, H. W., J. S. Yang, and M. C. Chiu. 2002. Determination of urinary and salivary cotinine using gas and liquid chromatography and enzyme-linked immunosorbent assay. Journal of Chromatography B 768(2): 297–303. doi:10.1016/s1570-0232(01)00613-4
  • Lerman, C., C. Jepson, E. P. Wileyto, F. Patterson, R. Schnoll, M. Mroziewicz, N. Benowitz, and R. F. Tyndale. 2010. Genetic variation in nicotine metabolism predicts the efficacy of extended-duration transdermal nicotine therapy. Clinical Pharmacology & Therapeutics 87: 553–57. doi:10.1038/clpt.2010.3
  • Messina, E. S., R. F. Tyndale, and E. M. Sellers. 1997. A major role for CYP2A6 in nicotine C-oxidation by human liver microsomes. Journal of Pharmacology and Experimental Therapeutics 282: 1608–14.
  • Moolchan, E. T., C. S. Parzynski, M. Jaszyna-Gasior, C. C. Collins, M. K. Leff, and D. L. Zimmerman. 2009. A link between adolescent nicotine metabolism and smoking topography. Cancer Epidemiology Biomarkers & Prevention 18: 1578–83. doi:10.1158/1055-9965.epi-08-0592
  • Moyer, T. P., J. R. Charlson, R. J. Enger, L. C. Dale, J. O. Ebbert, D. R. Schroeder, and R. D. Hurt. 2002. Simultaneous analysis of nicotine, nicotine metabolites, and tobacco alkaloids in serum or urine by tandem mass spectrometry, with clinically relevant metabolic profiles. Clinical Chemistry 48: 1460–71.
  • Mwenifumbo, J. C., and R. F. Tyndale. 2007. Genetic variability in CYP2A6 and the pharmacokinetics of nicotine. Pharmacogenomics 8: 1385–402. doi:10.2217/14622416.8.10.1385
  • Nakajima, M., T. Yamamoto, K. Nunoya, T. Yokoi, K. Nagashima, K. Inoue, Y. Funae, N. Shimada, T. Kamataki, and Y. Kuroiwa. 1996. Characterization of CYP2A6 involved in 3′-hydroxylation of cotinine in human liver microsomes. Journal of Pharmacology and Experimental Therapeutics 277: 1010–15.
  • Pellegrini, M., E. Marchei, S. Rossi, F. Vagnarelli, A. Durgbanshi, O. Garcia-Algar, O. Vall, and S. Pichini. 2007. Liquid chromatography/electrospray ionization tandem mass spectrometry assay for determination of nicotine and metabolites, caffeine and arecoline in breast milk. Rapid Communications in Mass Spectrometry 21: 2693–703. doi:10.1002/rcm.3137
  • Rangiah, K., W.-T. Hwang, C. Mesaros, A. Vachani, and I. A. Blair. 2011. Nicotine exposure and metabolizer phenotypes from analysis of urinary nicotine and its 15 metabolites by LC–MS. Bioanalysis 3: 745–61. doi:10.4155/bio.11.42
  • Schnoll, R. A., F. Patterson, E. P. Wileyto, R. F. Tyndale, N. Benowitz, and C. Lerman. 2009. Nicotine metabolic rate predicts successful smoking cessation with transdermal nicotine: a validation study. Pharmacological Biochemistry and Behavior 92: 6–11. doi:10.1016/j.pbb.2008.10.016
  • Shakleya, D. M., and M. A. Huestis. 2009a. Simultaneous and sensitive measurement of nicotine, cotinine, trans-3′-hydroxycotinine and norcotinine in human plasma by liquid chromatography-tandem mass spectrometry. Journal of Chromatography B 877: 3537–42. doi:10.1016/j.jchromb.2009.08.033
  • Shakleya, D. M., and M. A. Huestis. 2009b. Optimization and validation of a liquid chromatography-tandem mass spectrometry method for the simultaneous quantification of nicotine, cotinine, trans-3′-hydroxycotinine and norcotinine in human oral fluid. Analytical and Bioanalytical Chemistry 395: 2349–57. doi:10.1007/s00216-009-3157-2
  • Tuomi, T., T. Johnsson, and K. Reijula. 1999. Analysis of nicotine, 3-hydroxycotinine, cotinine, and caffeine in urine of passive smokers by HPLC-tandem mass spectrometry. Clinical Chemistry 45: 2164–72.
  • Whitmire, M., J. Ammerman, P. de Lisio, J. Killmer, D. Kyle, E. Mainstone, L. Porter, and T. Zhang. 2011. LC-MS/MS bioanalysis method development, validation, and sample analysis: points to consider when conducting nonclinical and clinical studies in accordance with current regulatory guidances. Journal of Analytical & Bioanalytical Techniques. S4: 001. doi:10.4172/2155-9872.S4-001
  • Xu, X., M. M. Iba, and C. P. Weisel. 2004. Simultaneous and sensitive measurement of anabasine, nicotine, and nicotine metabolites in human urine by liquid chromatography–tandem mass spectrometry. Clinical Chemistry 50: 2323–30. doi:10.1373/clinchem.2004.038489
  • Zhu, A. Z. X., Q. Zhou, L. S. Cox, J. S. Ahluwalia, N. L. Benowitz, and R. F. Tyndale. 2013. Variation in trans-3′-hydroxycotinine glucuronidation does not alter the nicotine metabolite ratio or nicotine intake. PloS One. 8: e70938. doi:10.1371/journal.pone.0070938

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