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Anodic behavior of clioquinol at a glassy carbon electrode.
Bioelectrochemistry. 2011 Feb; 80(2):175-81.B

Abstract

Clioquinol is an antifungal, antiprotozoal and an Alzheimer's disease drug with cytotoxic activity toward human cancer cells. The electrochemical behavior of clioquinol and its oxidation product was studied using cyclic, differential pulse and square-wave voltammetry over a wide pH range on a glassy carbon electrode. The results revealed that the oxidation of clioquinol is an irreversible pH-dependent process that proceeds with the transfer of one electron and one proton in an adsorption-controlled mechanism and results in the formation of a main oxidation product, which adsorbs very strongly on the glassy carbon surface. The charge transfer coefficient was calculated as 0.64. The adsorbed oxidation product presented reversible redox behavior, with two electron and two proton transfer. The electrochemical oxidation of clioquinol as a phenolic compound involves the formation of a phenoxy radical which reacts in at least two ways: in one pathway the radical initiates polymerization, the products remaining at the electrode surface, and in the other the radical is oxidized to a quinone-like structure. A mechanism for the oxidation of clioquinol is proposed.

Authors+Show Affiliations

Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade de Coimbra, 3004-535 Coimbra, Portugal.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

21111689

Citation

Ghalkhani, Masoumeh, et al. "Anodic Behavior of Clioquinol at a Glassy Carbon Electrode." Bioelectrochemistry (Amsterdam, Netherlands), vol. 80, no. 2, 2011, pp. 175-81.
Ghalkhani M, Fernandes IP, Oliveira SC, et al. Anodic behavior of clioquinol at a glassy carbon electrode. Bioelectrochemistry. 2011;80(2):175-81.
Ghalkhani, M., Fernandes, I. P., Oliveira, S. C., Shahrokhian, S., & Oliveira-Brett, A. M. (2011). Anodic behavior of clioquinol at a glassy carbon electrode. Bioelectrochemistry (Amsterdam, Netherlands), 80(2), 175-81. https://doi.org/10.1016/j.bioelechem.2010.10.001
Ghalkhani M, et al. Anodic Behavior of Clioquinol at a Glassy Carbon Electrode. Bioelectrochemistry. 2011;80(2):175-81. PubMed PMID: 21111689.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Anodic behavior of clioquinol at a glassy carbon electrode. AU - Ghalkhani,Masoumeh, AU - Fernandes,Isabel P G, AU - Oliveira,Severino Carlos B, AU - Shahrokhian,Saeed, AU - Oliveira-Brett,Ana Maria, Y1 - 2010/10/16/ PY - 2010/07/28/received PY - 2010/10/08/revised PY - 2010/10/10/accepted PY - 2010/11/30/entrez PY - 2010/11/30/pubmed PY - 2011/3/25/medline SP - 175 EP - 81 JF - Bioelectrochemistry (Amsterdam, Netherlands) JO - Bioelectrochemistry VL - 80 IS - 2 N2 - Clioquinol is an antifungal, antiprotozoal and an Alzheimer's disease drug with cytotoxic activity toward human cancer cells. The electrochemical behavior of clioquinol and its oxidation product was studied using cyclic, differential pulse and square-wave voltammetry over a wide pH range on a glassy carbon electrode. The results revealed that the oxidation of clioquinol is an irreversible pH-dependent process that proceeds with the transfer of one electron and one proton in an adsorption-controlled mechanism and results in the formation of a main oxidation product, which adsorbs very strongly on the glassy carbon surface. The charge transfer coefficient was calculated as 0.64. The adsorbed oxidation product presented reversible redox behavior, with two electron and two proton transfer. The electrochemical oxidation of clioquinol as a phenolic compound involves the formation of a phenoxy radical which reacts in at least two ways: in one pathway the radical initiates polymerization, the products remaining at the electrode surface, and in the other the radical is oxidized to a quinone-like structure. A mechanism for the oxidation of clioquinol is proposed. SN - 1878-562X UR - https://www.unboundmedicine.com/medline/citation/21111689/Anodic_behavior_of_clioquinol_at_a_glassy_carbon_electrode_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S1567-5394(10)00155-6 DB - PRIME DP - Unbound Medicine ER -