4.7 Article

Electrochemical characterization of cefadroxil β-lactam antibiotic and Cu(II) complex formation

Journal

JOURNAL OF ELECTROANALYTICAL CHEMISTRY
Volume 844, Issue -, Pages 124-131

Publisher

ELSEVIER SCIENCE SA
DOI: 10.1016/j.jelechem.2019.04.077

Keywords

beta-Lactam antibiotic; Cefadroxil; Amoxicillin; Cu(II) complex; Electrochemical characterization

Funding

  1. Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brasil (CAPES) [001]
  2. Fundacao para a Ciencia e a Tecnologia (FCT), Portugal [PTDC/QEQ-QAN/2201/2014]
  3. European Community Fund FEDER [3599-PPCDT, UID/EMS/00285/2013]

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The electrochemical behaviour of cefadroxil, a first-generation beta-lactam antibiotic, was studied at glassy carbon electrodes in aqueous media over a wide range of pH. The first oxidation process is of the phenol moiety and follows an ECE mechanism, generating catechol and resorcinol derivatives as sub-products, which are then reduced and oxidized in subsequent cycles. The sulphur heteroatom present in the cyclic structure close to the beta-lactam moiety is oxidized in two steps generating sulphoxide and sulphone. This process was identified from direct comparison with amoxicillin, which has a similar molecular structure, although they belong to different classes of beta-lactam antibiotics. For amoxicillin, oxidation of the sulphur heteroatom occurred at more positive potentials, most likely due to structural difficulties in stabilizing the charged oxidized species. Formation of a complex between copper (II) and each of the antibiotics was studied by cyclic voltammetry. Finally, determination of cefadroxil in commercial samples was successfully carried out.

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