Skip to main content
SpringerLink
Log in

Ion trap tandem mass spectrometry study of dexamethasone transformation products on light activated TiO2 surface

  • Published:
Journal of the American Society for Mass Spectrometry

Abstract

The photocatalytic transformation of dexamethasone and the formation of its intermediate compounds have been studied using titanium dioxide as a photocatalyst. The degradation of dexamethasone occurs easily through the formation of several hydroxy derivatives whose characterization has been made by HPLC/MS/MS. Even if both oxidative and reductive processes can be operating, only oxidative products have been identified in air saturated aqueous suspensions. A pattern of reaction pathways accounting for the observed intermediates is proposed. The obtained experimental evidence may be rationalized postulating the existence of a double initial mechanism. A single oxidation step resulting from the attack by one ·OH radical leading to the formation of five hydroxy-derivatives and a concomitant attack involving two ·OH radicals leading to the hydroxylation of the quinoid moiety of the molecule.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Gentile, D. M.; Tomlinson, E. S.; Maggs, J. L.; Park, B. K.; Back, D. J. J. Pharmacol. Exp. Ther. 1996, 277(1), 105–112.

    CAS  Google Scholar 

  2. Tomlinson, E. S.; Maggs, J. L.; Park, B. K.; Back, D. J. J. Steroid Biochem. 1997, 62(4), 345–352.

    Article  CAS  Google Scholar 

  3. Tomlinson, E. S.; Lewis, D. F. V.; Maggs, J. L.; Kroemer, H. K.; Park, B. K.; Back, D. J. Biochem. Pharmacol. 1997, 54(5), 605–611.

    Article  CAS  Google Scholar 

  4. Pruden, A. L.; Ollis, D. Environ. Sci. Technol. 1983, 17, 628.

    Article  CAS  Google Scholar 

  5. Hsiao, C. Y.; Lee, C. L.; Ollis, D. F. J. Catal. 1983, 82, 418.

    Article  CAS  Google Scholar 

  6. Hisanaga, T.; Harada, K.; Tanaka, K. J. Photochem. Photobiol. A 1990, 54, 113.

    Article  CAS  Google Scholar 

  7. Kormann, C.; Bahnemann, D.; Hoffmann, M. R. Environ. Sci. Technol. 1991, 25, 494.

    Article  CAS  Google Scholar 

  8. Sabin, F.; Tirlúk, T.; Vogler, A. J. Photochem. Photobiol. A 1992, 63, 99.

    Article  CAS  Google Scholar 

  9. Hingendorff, M.; Bahnemann, D. W. J. Adv. Oxid. Technol. 1996, 1, 35.

    Google Scholar 

  10. Choi, W.; Hoffmann, M. R. Environ. Sci. Technol. 1995, 29, 1646.

    Article  CAS  Google Scholar 

  11. Choi, W.; Hoffmann, M. R. J. Phys. Chem. 1996, 100, 2161.

    Article  CAS  Google Scholar 

  12. Minero, C.; Catozzo, F.; Pelizzetti, E. Langmuir 1992, 8, 481.

    Article  CAS  Google Scholar 

  13. Lawless, D.; Serpone, N.; Meisel, D. J. Phys. Chem. 1991, 95, 5166.

    Article  CAS  Google Scholar 

  14. Morrison, S. R. Electrochemistry at Semiconductor and Oxidized Metal Electrodes; Plenum: New York, 1980; p 163.

    Google Scholar 

  15. Bahnemann, D. W.; Cunnigham, J.; Fox, M. A.; Pelizzetti, E.; Pichat, P.; Serpone, N. In Aquatic and Surface Chemistry; Helz, G. R.; Zepp, R. G.; Crosby, D. G., Eds.; Lewis: Boca Raton, 1994; 261.

    Google Scholar 

  16. Hoffmann, M. R.; Martin, S. T.; Choi, W.; Bahnemann, D. W. Chem. Rev 1995, 95, 69.

    Article  CAS  Google Scholar 

  17. Pelizzetti, E.; Minero, C.; Maurino, V.; Sclafani, A.; Hidaka, H.; Serpone, N. Environ. Sci. Technol. 1989, 23, 1380.

    Article  CAS  Google Scholar 

  18. Minero, C.; Pelizzetti, E.; Malato, S.; Blanco, J. Chemosphere 1993, 26, 2103.

    Article  CAS  Google Scholar 

  19. Strukul, G. Catalytic Oxydations with Hydrogen Peroxyde as Oxidant; Kluwer Academic: Boston, 1992; p 127.

    Google Scholar 

  20. Buxton, G. V.; Greestock, C. L.; Helmann, W. P.; Ross, A. B. J. Phys. Chem. Ref. Data 1988, 17, 513.

    CAS  Google Scholar 

  21. Walling, C. H. Acc. Chem. Res. 1975, 8, 125–131.

    Article  CAS  Google Scholar 

  22. Walling, C.; Cleary, M. Int. J. Chem. Kinet. 1977, 9, 595–601.

    Article  CAS  Google Scholar 

  23. Markham, M. C.; Laidler, J. K. J. Phys. Chem. 1953, 57, 363.

    Article  CAS  Google Scholar 

  24. Osawa, Y. O.; Gratzel, M. J. Chem. Soc. Faraday Trans. 1 1988, 84, 197.

    Article  CAS  Google Scholar 

  25. Muraki, H.; Saji, T.; Fujihira, M.; Aoyagui, S. J. Electroanal. Chem. 1984, 169, 319.

    Article  CAS  Google Scholar 

  26. Bielski, B. H. J.; Cabelli, D. E.; Arudi, R. L.; Ross, A. B. J. Phys. Chem. Ref. Data 1985, 14, 1041–1100.

    CAS  Google Scholar 

  27. Frimer, A. A.. In Oxygen Radicals in Biology and Medicine; Simic, M. G.; et al, Eds.; Plenum Press: New York, 1988; 29–38.

    Google Scholar 

  28. Lilie, V. J.; Beck, G.; Henglein, A. Ber. Bunsen-ges Phys. Chem. 1971, 75, 458.

    CAS  Google Scholar 

  29. Micic, O.; Zhang, Y.; Cromeck, K. R.; Trifunac, A. D.; Thurnauer, M. C. J. Phys. Chem. 1993, 97, 13284.

    Article  CAS  Google Scholar 

  30. Von Sonntag, C.. In Oxygen Radicals in Biology and Medicine; Simic, M. G.; et al, Eds.; Plenum Press: New York, 1988; 47–54.

    Google Scholar 

  31. Kunai, A.; Hata, S.; Ita, S.; Sasaki, K. J. Am. Chem. Soc. 1986, 108, 6012–6016.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Dipartimento di Chimica Analitica, Università di Torino, via P. Giuria 5, 10125, Torino, Italy

    Paola Calza, Ezio Pelizzetti, Mariacarla Brussino & Claudio Baiocchi

Authors
  1. Paola Calza
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Ezio Pelizzetti
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mariacarla Brussino
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Claudio Baiocchi
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Calza, P., Pelizzetti, E., Brussino, M. et al. Ion trap tandem mass spectrometry study of dexamethasone transformation products on light activated TiO2 surface. J Am Soc Mass Spectrom 12, 1286–1295 (2001). https://doi.org/10.1016/S1044-0305(01)00319-1

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1016/S1044-0305(01)00319-1

Keywords

Search

Navigation