Skip to main content
SpringerLink
Log in

Electrochemical behavior of superoxide anion radical towards quinones: a mechanistic approach

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Among the reactive oxygen species, the superoxide anion radical (O ·−2 ) has a fundamental role in several biological functions. Consequently, its interaction with several chemical moieties is equally important both from a biological and chemical point of view. Considering this importance, the present study demonstrates the electrochemical generation of O ·−2 followed by its interaction with four different quinones. The fate of electrochemically generated O ·−2 was probed in the presence of a quinone while monitoring the changes in the shape of its voltammogram. The nature of interaction was interpreted in terms of electrochemical mechanism and the interaction moiety was identified both from voltammetric and computational data (Mullikan charges). The chemical coupled reactions of the quinones with O ·−2 were identified as hydrogen atom transfer, protonation and electron transfer in different cases. The strength of interaction was quantified in terms of association constant (Kao) and IC50 values for antiradical activity of quinones and compared with standards of vitamin C and quercetin. The kinetics of the interaction reaction was quantitated having second-order rate constant values 0.1 to 3.0 × 103 M−1 s−1.

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

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9

Similar content being viewed by others

References

  1. S.S. Ali, N. Kasoju, A. Luthra, A. Singh, H. Sharanabasava, U. Bora, Food. Res. Inter. 4, 1 (2008)

    Article  Google Scholar 

  2. S. Sen, R. Chakraborty, C. Sridhar, Y.S.R. Reddy, B. De, Inter. J. Pharm. Sci. Rev. Res. 3, 91 (2010)

    CAS  Google Scholar 

  3. M. Valkoa, C.J. Rhodesb, J. Moncola, M. Izakovica, M. Mazu, Chemico-Bio. Intera 160, 1 (2006)

    Article  CAS  Google Scholar 

  4. G.K. Ziyatdinova, H.C. Budnikov, V.I. Pogorel’tzev, Anal. Bioanal. Chem. 381, 1546 (2005)

    Article  CAS  PubMed  Google Scholar 

  5. N. Cenas, H. Nivinskas, Z. Anusevicius, J. Sarlauskas, F. Lederer, E.S.J. Arnér, J. Biol. Chem. 279, 2583 (2004)

    Article  CAS  PubMed  Google Scholar 

  6. X.C. Weng, M.H. Gordon, J. Agric. Food Chem. 40, 1331 (1992)

    Article  CAS  Google Scholar 

  7. S. Ahmed, A.Y. Khan, R. Qureshi, M.S. Subhani, Russ. J. Electrochem. 43, 811 (2007)

    Article  CAS  Google Scholar 

  8. K.P. Klinman, M. David, Annu. Rev. Biochem. 63, 299 (1994)

    Article  CAS  PubMed  Google Scholar 

  9. R. Huber, Angew. Chem. Int. Ed. Engl. 28, 848 (1989)

    Article  Google Scholar 

  10. D.C. Hanley, W.A.B. Soloman, B. Saffarn, J. Am. Podiatr. Med. Assoc. 72, 275 (1982)

    Article  CAS  Google Scholar 

  11. J.H. Zaidi, F. Naeem, K. Iqbal, M.I. Choudhary, K.M. Khan, S. Parveen, S.T.A. Shah, S. Hayat, W. Voelter, Z. Naturforsch. 56B, 689 (2001)

    Article  Google Scholar 

  12. J.A. Bautisa-Martinez, I. Gonzalez, M. Aguilar-Martinez, J. Electroanal. Chem. 573, 289 (2004)

    Article  CAS  Google Scholar 

  13. M. Gomez, F.J. Gonzalez, I. Gonzalez, J. Electroanal. Chem. 578, 193 (2005)

    Article  CAS  Google Scholar 

  14. A. Rahman, R. Qureshi, S. Ahmed, J. Chem. Soc. Pak. 30, 655 (2008)

    CAS  Google Scholar 

  15. J.F. Arambula, R. McCall, K.J. Sidoran, D. Magda, N.A. Mitchell, C.W. Bielawski, V.M. Lynch, J.L. Sesslerg, K. Arumugam, Chem. Sci. 7, 1245 (2016)

    Article  CAS  PubMed  Google Scholar 

  16. E.I. Korotkova, Y.A. Karbainov, O.A. Avramchik, Anal. Bioanal. Chem. 375, 465 (2003)

    Article  CAS  PubMed  Google Scholar 

  17. S. Ahmed, F. Shakeel, Cz. J. Food Sci. 30, 153 (2012)

    Article  CAS  Google Scholar 

  18. H. Muhammad, I.A. Tahiri, M. Muhammad, Z. Masood, M.A. Versiani, O. Khaliq, M. Latif, M. Hanif, J. Electroanal. Chem. 775, 157 (2016)

    Article  CAS  Google Scholar 

  19. E.J. Nanni, M.D. Stallings, D.T. Sawyer, J. Amer. Chem Soc. 102, 4481 (1980)

    Article  CAS  Google Scholar 

  20. K.E. Heim, A.R. Tagliaferro, D.J. Bobilya, J. Nutr. Biochem. 13, 572 (2002)

    Article  CAS  PubMed  Google Scholar 

  21. E.I. Korotkova, O.A. Avramchik, T.V. Kagiya, Y.A. Karbainov, N.V. Tcherdyntseva, Talanta 63, 729 (2004)

    Article  CAS  PubMed  Google Scholar 

  22. L. Bourvellec, D. Hauchard, A. Darchen, J.-L. Burgot, M.L. Abasq, Talanta 75, 1098 (2008)

    Article  PubMed  CAS  Google Scholar 

  23. N. Arshad, N.K. Janjua, S. Ahmed, A.Y. Khan, L.H. Skibsted, Electrochim. Acta 54, 184 (2009)

    Article  CAS  Google Scholar 

  24. G.K. Ziyatdinova, D.M. Gil’metdinova, G.K. Budnikov, J. Anal. Chem. 60, 49 (2005)

    Article  CAS  Google Scholar 

  25. N.A. Macías-Ruvalcaba, I. González, M. Aguilar-Martınez, J. Electrochem. Soc. 151, 110 (2004)

    Article  CAS  Google Scholar 

  26. M. Collins, C. Sotiriou-Leventis, M.T. Canalas, N. Leventis, Electrochim. Acta 45, 2049 (2000)

    Article  CAS  Google Scholar 

  27. R.S. Nicholson, I. Shain, J. Anal. Chem. 36, 706 (1964)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the Higher Education Commission (HEC) Govt. of Pakistan for the research work financial support through the HEC Project (project # P&D/12(156)/46/2008). One of authors, Haji Muhammad, is thankful to Hafiz Abdullah Shahid for moral support.

Author information

Authors and Affiliations

  1. Department of Chemistry, Federal Urdu University of Arts, Sciences and Technology, Gulshan-e-Iqbal, Science Campus, Karachi, 75300, Pakistan

    Haji Muhammad, Iftikhar Ahmad Tahiri, Muhammad Ali Versiani, Obaid Khaliq & Syed Tahir Ali

  2. Department of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330022, Jiangxi, People’s Republic of China

    Muddasir Hanif

  3. Department of Chemistry, COMSATS Institute of Information Technology, Abbottabad, 22060, Pakistan

    Faheem Shah

  4. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Safeer Ahmed

Authors
  1. Haji Muhammad
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Muddasir Hanif
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Iftikhar Ahmad Tahiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Muhammad Ali Versiani
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Faheem Shah
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Obaid Khaliq
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Syed Tahir Ali
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Safeer Ahmed
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Iftikhar Ahmad Tahiri or Safeer Ahmed.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Muhammad, H., Hanif, M., Tahiri, I.A. et al. Electrochemical behavior of superoxide anion radical towards quinones: a mechanistic approach. Res Chem Intermed 44, 6387–6400 (2018). https://doi.org/10.1007/s11164-018-3496-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3496-8

Keywords

Search

Navigation