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Elution behavior of drugs in high-speed counter-current chromatography using on-column complexation with metal ions

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Abstract

In this study, determination of (nitrogen containing) drugs by on-column complexation with metal ions in high-speed counter-current chromatography (HSCCC) was investigated. Bromazepam (BMP) was strongly retained in the organic upper stationary phase (UP) of the two-phase solvent system composed of tert-butyl methyl ether-acetonitrile–water (2:2:3, v/v/v) by eluting the aqueous lower mobile phase (LP) at a flow rate of 2 mL min−1. On the other hand, BMP (200 µg mL−1) was eluted faster without retention to the organic UP with the two-phase system containing 100 μg mL−1 of copper ions (CuCl2) because a very polar BMP-Cu2+ complex was immediately formed in the aqueous LP. The dramatic change in the retention behavior of BMP resulted from on-column complexation. The on-column complexation in HSCCC was further investigated for five (nitrogen containing) drugs and seven metal ions. In the result, tizanidine and phentolamine formed complexes with Al3+, Fe2+, Co2+, Ni2+, Cu2+, and Zn2+, ambroxol formed complexes with Al3+, Fe2+, and Cu2+, but voriconazole formed no complexes with all metal ions tested.

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This method is useful for investigating drug side effects based on interaction with metal ions.

References

  1. P. Fernandes, I. Sousa, L. Cunha-Silva, M. Ferreira, B. de Castro, E.F. Pereira, M.J. Feio, P. Gameiro, J. Inorg. Biochem.Biochem 131, 21 (2014)

    Article  CAS  Google Scholar 

  2. J. Nagaj, R. Starosta, M. Jezowska-Bojczuk, J. Inorg. Biochem.Biochem. 142, 68 (2015)

    Article  CAS  Google Scholar 

  3. P. Lehto, K.T. Kivisto, P.J. Neuvonen, Br. J. Clin. Pharm. 37, 82 (1994)

    Article  CAS  Google Scholar 

  4. M.W. Pletz, P. Petzold, A. Allen, O. Burkhardt, H. Lode, Antimicrob. Agents Chemother.. Agents Chemother. 47, 2158 (2003)

    Article  CAS  Google Scholar 

  5. H. Liang, B. Zhou, D. Wu, J. Li, B. Li, Adv. Colloid Interface Sci. 272, 102019 (2019)

    Article  CAS  PubMed  Google Scholar 

  6. J. Lakshmipraba, S. Arunachalam, A. Riyasdeen, R. Dhivya, M.A. Akbarsha, J. Photochem. Photobiol. B Biol. 142, 56 (2015)

    Article  Google Scholar 

  7. B.M. Polanuer, S.V. Ivanov, J. Chromatogr. AChromatogr. A 722, 311 (1996)

    Article  CAS  Google Scholar 

  8. J.A. O’Hanlon, R.D. Chapman, F. Taylor, M.A. Denecke, J. Radioanal. Nucl. Chem.Radioanal. Nucl. Chem. 322, 1915 (2019)

    Article  Google Scholar 

  9. S. Tanaka, T. Dohi, S. Aizawa, T. Kemmei, H. Terashima, A. Taga, A. Yamamoto, S. Kodama, J. Sep. Sci. 40, 4168 (2017)

    Article  CAS  PubMed  Google Scholar 

  10. T. Bertuzzi, S. Rastelli, A. Mulazzi, A. Pietri, Toxins 11, 570 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  11. S. Sotgia, A. Zinellu, E. Pisanu, G.A. Pinna, L. Deiana, C. Carru, J. Chromatogr. AChromatogr. A 1205, 90 (2008)

    Article  CAS  Google Scholar 

  12. T. Cecchi, F. Pucciarelli, P. Passamonti, J. Liq. Chromatogr. Relat. Technol.Chromatogr. Relat. Technol. 22, 2467 (1999)

    Article  CAS  Google Scholar 

  13. H. Engelhardt, T. Lobert, Anal. Chem. 71, 1885 (1999)

    Article  CAS  PubMed  Google Scholar 

  14. A. Berthod, T. Maryutina, B. Spivakov, O. Shpigun, I.A. Sutherland, Pure Appl. Chem. 81, 355 (2009)

    Article  CAS  Google Scholar 

  15. Y. Ito, J. Chromatogr. AChromatogr. A 1065, 145 (2005)

    Article  CAS  Google Scholar 

  16. M. Dembowsk, J.E. Rowley, K. Boland, J. Droessler, D.A. Hathcoat, A. Marchi, G.S. Goff, I. May, J. Chromatogr. AChromatogr. A 1682, 463528 (2022)

    Article  Google Scholar 

  17. A. Hosoda, A. Tsuyoshi, K. Akiba, Anal. Sci. 18, 897 (2002)

    Article  CAS  PubMed  Google Scholar 

  18. E. Kitazume, T. Takatsuka, N. Sato, Y. Ito, J. Liq. Chromatogr. Relat. Technol.Chromatogr. Relat. Technol. 27, 437 (2004)

    Article  CAS  Google Scholar 

  19. C. Han, W. Wang, G. Xue, D. Xu, T. Zhu, S. Wang, P. Cai, J. Luo, L. Kong, J. Chromatogr. AChromatogr. A 1532, 1 (2018)

    Article  CAS  Google Scholar 

  20. Q. Liu, S. Shi, L. Liu, H. Yang, W. Su, X. Chen, J. Chromatogr. AChromatogr. A 1304, 183 (2013)

    Article  CAS  Google Scholar 

  21. M.M. Correiados-Santos, V. Famila, M.L. Simoes Goncalves, Anal. Biochem.Biochem. 303, 111 (2022)

    Article  Google Scholar 

  22. J.A. Real, M.C. Mugoz, J. Brras, Thermochim. Acta 101, 83 (1986)

    Article  CAS  Google Scholar 

  23. H. Block, B. Maertens, A. Spriestersbach, N. Brinker, J. Kubicek, R. Fabis, J. Labahn, F. Schäfer, Methods Enzymol.Enzymol. 463, 439 (2009)

    Article  CAS  Google Scholar 

  24. J.D. Sabatino, O.W. Weber, G.R. Padmanabhan, B.Z. Senkowski, Anal. Chem. 41, 905 (1969)

    Article  CAS  Google Scholar 

  25. Q. Li, T. Wu, J. Lai, Z. Fan, W. Zhang, G. Zhang, D. Cui, Z. Gao, Eur. J. Inorg. Chem. 31, 5281 (2015)

    Article  Google Scholar 

  26. Y. Zhao, G. Tang, Y. Wang, Y. Cui, S.W. Ng, J. Solid State Chem. 259, 19 (2018)

    Article  CAS  Google Scholar 

  27. D.E. Shalev, Int. J. Mol. Sci. 23, 15957 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. T.I. Kostelnik, H. Scheiber, R. Cappai, N. Choudhary, F. Lindheimer, M.G. Jaraquemada-Peláez, C. Orvig, Inorg. Chem. 60, 5343 (2021)

    Article  CAS  PubMed  Google Scholar 

  29. E. Falcone, P. Faller, Dalton Trans. 52, 2197 (2023)

    Article  CAS  PubMed  Google Scholar 

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Acknowledgements

We would like to thank S. Takamizu and A. Nakai from alumni and alumnae of Tokyo University of Pharmacy and Life Sciences for their technical support during the experiment.

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Correspondence to Yukiko Moriiwa.

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Moriiwa, Y., Shoji, A., Shibusawa, Y. et al. Elution behavior of drugs in high-speed counter-current chromatography using on-column complexation with metal ions. ANAL. SCI. 40, 1121–1128 (2024). https://doi.org/10.1007/s44211-024-00536-4

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