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LC-MS Method Development for Simultaneous Determination of Trans-3′-hydroxycotinine and Three Mercapturic Acids in Urine

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Abstract

The negative impact of tobacco smoke on the human body is due to a wide range of harmful substances including volatile organic compounds (VOCs). Some VOCs of tobacco smoke metabolize in human organism into mercapturic acids (MAs). The determination of the amount of MAs in readily available biological fluids, for example in urine, allows to assess the level of exposure of these VOCs in a particular person. It is useful to assess the impact of individual VOCs on the body together with the assessment of the intake of nicotine. The intake of nicotine can be determined by the content of its metabolites in the urine, in particular by the content of trans-3′-hydroxycotinine (tH-Cot). A joint assessment of the concentrations of trans-3′-hydroxycotinine and MAs in urine allows obtaining selective information about effects of different VOCs and nicotine on the smoker’s body. We have developed a liquid chromatography–mass spectrometry (LC-MS) method for simultaneous quantifying of tH-Cot and three MAs: N-Acetyl-S-(3-hydroxypropyl)cysteine (HPMA), N-Acetyl-S-(3-hydroxypropyl-1-methyl)-L-cysteine (HMPMA), N-Acetyl-S-(2-cyanoethyl)-L-cysteine (CEMA). We used this method to quantify the levels of MAs and tH-Cot in the urine of a group of 15 smokers just before and 5 days after smoking cessation. For all studied compounds, we have found statistically significant changes in concentration on the fifth day of smoking cessation. The method developed can be used to jointly assess the levels of exposure to nicotine and VOCs in the study of various tobacco products.

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References

  1. Ding, Y. S., Blount, B. C., Valentin-Blasini, L., Applewhite, H. S., Xia, Y., Watson, C. H., & Ashley, D. L. (2009). Simultaneous determination of six mercapturic acid metabolites of volatile organic compounds in human urine. Chemical Research in Toxicology, 22, 1018–1025. https://doi.org/10.1021/tx800468w.

    Article  Google Scholar 

  2. Zhang, X., Xiong, W., Shi, L., Hou, H., & Hu, Q. (2014). Simultaneous determination of five mercapturic acid derived from volatile organic compounds in human urine by LC–MS/MS and its application to relationship study. Journal of Chromatography B, 967, 102–109. https://doi.org/10.1016/j.jchromb.2014.07.013.

    Article  Google Scholar 

  3. International Agency for Research on Cancer. (1995). Dry cleaning, some chlorinated solvents and other industrial chemicals. In IARC monographs on the evaluation of carcinogenic risks to humans (Vol. 63, pp. 337–372). IARC: Lyon.

    Google Scholar 

  4. International Agency for Research on Cancer. (1995). Dry cleaning, some chlorinated solvents and other industrial chemicals. In IARC monographs on the evaluation of carcinogenic risks to humans (Vol. 63, pp. 373–391). IARC: Lyon.

    Google Scholar 

  5. Park, S. L., Carmella, S. G., Chen, M., Patel, Y., Stram, D. O., Haiman, C. A., Le Marchand, L., & Hecht, S. S. (2015). Mercapturic acids derived from the toxicants acrolein and crotonaldehyde in the urine of cigarette smokers from five ethnic groups with differing risks for lung cancer. PLoS One, 10(6), e0124841. https://doi.org/10.1371/journal.pone.0124841.

    Article  Google Scholar 

  6. Neurath, G. B., Dünger, M., Orth, D., & Pein, F. G. (1987). Trans-3′-hydroxycotinine as a main metabolite in urine of smokers. International Archives of Occupational and Environmental Health, 59(2), 199–201.

    Article  Google Scholar 

  7. Rangiah, K., Hwang, W., Mesaros, C., Vachani, A., & Blair, I. A. (2011). Nicotine exposure and metabolizer phenotypes from analysis of urinary nicotine and its 15 metabolites by LC–MS. Bioanalysis, 3(7), 745–761. https://doi.org/10.4155/bio.11.42.

    Article  Google Scholar 

  8. Moyer, T. P., Charlson, J. R., Enger, R. J., Dale, L. C., Ebbert, J. O., Schroeder, D. R., & Hurt, R. D. (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(9), 1460–1471.

    Google Scholar 

  9. Miller, E. I., Norris, H. R., Rollins, D. E., Tiffany, S. T., & Wilkins, D. G. (2010). A novel validated procedure for the determination of nicotine, eight nicotine metabolites and two minor tobacco alkaloids in human plasma or urine by solid-phase extraction coupled with liquid chromatography-electrospray ionization-tandem mass spectrometry. Journal of Chromatography B, 878(9–10), 725–737. https://doi.org/10.1016/j.jchromb.2009.12.018.

    Article  Google Scholar 

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Acknowledgments

The work was performed according to the Russian Government Program of Competitive Growth of Kazan Federal University using the equipment of the Interdisciplinary Center for Collective Use of Kazan Federal University.

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Authors and Affiliations

  1. Institute of Fundamental Medicine and Biology, Kazan Federal University, Kazan, Russian Federation

    L. V. Lopukhov, A. V. Laikov, V. A. Romanova, D. Z. Gatina, V. L. Lopukhov, S. R. Abdulkhakov, I. I. Salafutdinov & T. V. Grigoryeva

  2. Federal State Budget Scientific Institution All-Russian Scientific Research Institute of Tobacco, Makhorka and Tobacco Products, Krasnodar, Russian Federation

    T. A. Zaitseva, S. N. Medvedeva & E. V. Gnuchikh

Authors
  1. L. V. Lopukhov
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  2. A. V. Laikov
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  3. V. A. Romanova
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  4. D. Z. Gatina
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  5. V. L. Lopukhov
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  6. S. R. Abdulkhakov
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  7. T. A. Zaitseva
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  8. S. N. Medvedeva
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  9. E. V. Gnuchikh
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  10. I. I. Salafutdinov
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  11. T. V. Grigoryeva
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Correspondence to L. V. Lopukhov.

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Lopukhov, L.V., Laikov, A.V., Romanova, V.A. et al. LC-MS Method Development for Simultaneous Determination of Trans-3′-hydroxycotinine and Three Mercapturic Acids in Urine. BioNanoSci. 8, 924–929 (2018). https://doi.org/10.1007/s12668-018-0528-1

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  • DOI: https://doi.org/10.1007/s12668-018-0528-1

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