Skip to main content
Log in

Determination of Cyclohexylmethylfluorophosphonate Metabolites in Human Blood Plasma Using High-Resolution Liquid Chromatography–Mass Spectrometry

  • ARTICLES
  • Published:
Journal of Analytical Chemistry Aims and scope Submit manuscript

Abstract

Conditions for the extraction of a phosphonylated nonapeptide, phosphonylated tyrosine, and cyclohexylmethylphosphonic acid from human blood plasma followed by HPLC determination with detection by high-resolution tandem mass spectrometry were optimized. Conditions for human blood plasma sample preparation, mass-spectrometric detection in selected reaction monitoring mode, and gradient elution were chosen to determine the above markers of exposure to cyclohexylmethylfluorophosphonate. The detection limit of the initial substance introduced into blood plasma was 0.05–0.1 ng/mL depending on the test marker.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1.
Fig. 2.
Fig. 3.

Similar content being viewed by others

REFERENCES

  1. Convention on the Prohibition of the Development, Production, Stockpiling and Use of Chemical Weapons and Their Destruction, 1997. www.opcw.org. Accessed March 17, 2019.

  2. Pan, H., Hu, XZ., Jacobowitz, D.M., Chen, C., McDonough, J., Van Shura, K., Lyman, M., and Marini, A.M., Neurotoxicology, 2012, vol. 33, no. 5, p. 1219.

    Article  CAS  Google Scholar 

  3. Perkins, M.W., Pierre, Z., Sabnekar, P., Sciuto, A.M., Song, J., Soojhawon, I., Oguntayo, S., Doctor, B.P., and Nambiar, M.P., Inhalation Toxicol., 2012, vol. 24, no. 9, p. 539.

    Article  CAS  Google Scholar 

  4. Black, R.M., Clarke, R.J., Read, R.W., and Reid, M.T.J., J. Chromatogr. A, 1994, vol. 662, no. 2, p. 301.

    Article  CAS  Google Scholar 

  5. Black, R.M. and Read, R.W., J. Chromatogr. A, 1999, vol. 862, no. 2, p. 169.

    Article  Google Scholar 

  6. Driskell, W.J., Shih, M., Needham, L.L., and Barr, D.B., J. Anal. Toxicol., 2002, vol. 26, no. 1, p. 6.

    Article  CAS  Google Scholar 

  7. Matsuda, Y., Nagao, M., Takatori, T., Niijima, H., Nakajima, M., Iwase, H., Kobayashi, M., and Iwadate, K., Toxicol. Appl. Pharmacol., 1998, vol. 150, no. 2, p. 310.

    Article  CAS  Google Scholar 

  8. Minami, M., Hui, D., Katsumata, M., Inagaki, H., and Boulet, C.A., J. Chromatogr. B: Biomed. Sci. Appl., 1997, vol. 695, no. 2, p. 237.

    Article  CAS  Google Scholar 

  9. Shih, M.L., Smith, J.R., McMonagle, J.D., Dolzine, T.W., and Gresham, V.C., Biol. Mass Spectrom., 1991, vol. 20, no. 11, p. 717.

    Article  CAS  Google Scholar 

  10. Barr, J.R., Driskell, W.J., Aston, L.S., and Mar-tinez, R.A., J. Anal. Toxicol., 2004, vol. 28, no. 5, p. 372.

    Article  CAS  Google Scholar 

  11. Ciner, F.L., McCord, C.E., Plunkett, R.W., Martin, M.F., and Croley, T.R., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2007, vol. 846, nos. 1–2, p. 42.

    Article  CAS  Google Scholar 

  12. Kanamori-Katoaoka, M. and Seto, Y., Jpn. J. Forensic Toxicol., 2005, vol. 23, p. 21.

    Google Scholar 

  13. Liu, Q., Hu, X., and Xie, J., Anal. Chim. Acta, 2004, vol. 512, no. 1, p. 93.

    Article  CAS  Google Scholar 

  14. Hayes, T.L., Kenny, D.V., and Hernon-Kenny, L., J. Med. Chem. Def., 2004, vol. 2, p. 1.

    Google Scholar 

  15. D’Agostino, P.A., Chenier, C.L., and Hancock, J.R., J. Chromatogr. A, 2002, vol. 950, nos. 1–2, p. 149.

    Article  Google Scholar 

  16. Evans, R.A., Jakubowski, E.M., Muse, W.T., Matson, K., Hulet, S.W., Mioduszewski, R.J., Thomson, S.A., Totura, A.L., Renner, J.A., and Crouse, C.L., J. Anal. Toxicol., 2008, vol. 32, no. 1, p. 78.

    Article  CAS  Google Scholar 

  17. Riches, J., Morton, I., Read, R.W., and Black, R.M., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2005, vol. 816, nos. 1–2, p. 251.

    Article  CAS  Google Scholar 

  18. Mawhinney, D.B., Hamelin, E.I., Fraser, R., Silva, S.S., Pavlopoulos, A.J., and Kobelski, R.J.J., J. Chromatogr. B: Anal. Technol. Biomed. Life Sci., 2007, vol. 852, nos. 1–2, p. 235.

    Article  CAS  Google Scholar 

  19. Sporty, J.L., Lemire, S.W., Jakubowski, E.M., Renner, J.A., Evans, R.A., Williams, R.F., Schmidt, J.G., van der Schans, M.J., Noort, D., and Johnson, R.C., Anal. Chem., 2010, vol. 82, no. 15, p. 6593.

    Article  CAS  Google Scholar 

  20. Fidder, A., Hulst, A.G., Noort, D., de Ruiter, R., van der Schans, M.J., Benschop, H.P., and Langenberg, J.P., Chem. Res. Toxicol., 2002, vol. 15, no. 4, p. 582.

    Article  CAS  Google Scholar 

  21. Knaack, J.S., Zhou, Y., Abney, C.W., Jacob, J.T., Prezioso, S.M., Hardy, K., Lemire, S.W., Thomas, J., and Johnson, R.C., Anal. Chem., 2012, vol. 84, no. 21, p. 9470.

    Article  CAS  Google Scholar 

  22. Noort, D., Fidder, A., van der Schans, M.J., and Hulst, A.G., Anal. Chem., 2006, vol. 78, no. 18, p. 6640.

    Article  CAS  Google Scholar 

  23. Adams, T.K., Capacio, B.R., Smith, J.R., Whalley, C.E., and Korte, W.D., Drug Chem. Toxicol., 2005, vol. 27, no. 1, p. 77.

    Article  Google Scholar 

  24. Williams, N.H., Harrison, J.M., Read, R.W., and Black, R.M., Arch. Toxicol., 2007, vol. 81, no. 9, p. 627.

    Article  CAS  Google Scholar 

  25. Black, R.M., Harrison, J.M., and Read, R.W., Arch. Toxicol., 1999, vol. 73, no. 2, p. 123.

    Article  CAS  Google Scholar 

  26. Peeples, E.S., Schopfer, L.M., Duysen, E.G., Spaulding, R., Voelker, T., Thompson, C.M., and Lockridge, O., Toxicol. Sci., 2005, vol. 83, no. 2, p. 303.

    Article  CAS  Google Scholar 

  27. Bao, Y., Liu, Q., Chen, J., Lin, Y., Wu, B., and Xie, J., J. Chromatogr. A, 2012, vol. 1229, p. 164.

    Article  CAS  Google Scholar 

  28. Crow, B.S., Pantazides, B.G., Quiñones-González, J., Garton, J.W., Carter, M.D., Perez, J.W., Watson, C.M., Tomcik, D.J., Crenshaw, M.D., Brewer, B.N., Riches, J.R., Stubbs, S.J., Read, R.W., Evans, R.A., Thomas, J.D., Blake, T.A., and Johnson, R.C., Anal. Chem., 2014, vol. 86, no. 20, p. 10397.

    Article  CAS  Google Scholar 

  29. Williams, N.H., Harrison, J.M., Read, R.W., and Black, R.M., Arch. Toxicol., 2007, vol. 81, no. 9, p. 627.

    Article  CAS  Google Scholar 

  30. Koryagina, N.L., Savel’eva, E.I., Karakashev, G.V., Babakov, V.N., Dubrovskii, Ya.A., Ukolova, E.S., Khlebnikova, N.S., Murashko, E.A., Koneva, V.Yu., Ukolov, A.I., Kopeikin, V.A., and Radilov, A.S., J. Anal. Chem., 2016, vol. 71, no. 8, p. 849.

    Article  CAS  Google Scholar 

  31. Jiang, W., Murashko, E.A., Dubrovskii, Y.A., Podolskaya, E.P., Babakov, V.N., Mikler, J., Nachon, F., Masson, P., Schopfer, L.M., and Lockridge, O., Anal. Biochem., 2013, vol. 439, no. 2, p. 132.

    Article  CAS  Google Scholar 

  32. Mathews, T.P., Carter, M.D., Johnson, D., Isenberg, S.L., Graham, L.A., Thomas, J.D., and Johnson, R.C., Anal. Chem., 2017, vol. 89, no. 3, p. 1955.

    Article  CAS  Google Scholar 

  33. Hamelin, E.I., Schulze, N.D., Shaner, R.L., Coleman, R.M., Lawrence, R.J., Crow, B.S., Jakubowski, E.M., and Johnson, R.C., Anal. Bioanal. Chem., 2014, vol. 406, no. 21, p. 5195.

    Article  CAS  Google Scholar 

Download references

Funding

This study was supported by the Russian Foundation for Basic Research (project no. 18-33-20068 mol_a_ved).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. V. Braun.

Additional information

Translated by V. Makhlyarchuk

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Braun, A.V., Stavitskaya, Y.V., Baigil’diev, T.M. et al. Determination of Cyclohexylmethylfluorophosphonate Metabolites in Human Blood Plasma Using High-Resolution Liquid Chromatography–Mass Spectrometry. J Anal Chem 75, 783–791 (2020). https://doi.org/10.1134/S1061934820060027

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1061934820060027

Keywords:

Navigation