Measurement of hydrolysis decay time constants of monoarylimino derivatives of β-lapachone through cyclic voltammetry

Rosana I. Misico, Erica S. Forzani

Research output: Contribution to journalArticle

6 Scopus citations

Abstract

The stability of monoarylimino o-quinones derived from β-lapachone (1) was studied by cyclic voltammetry in buffer solutions of different pH values. Experiments performed on glassy carbon electrodes demonstrated not only that β-lapachone derivatives (2-6) are electroactive compounds but also that β-lapachone is one of the hydrolysis products. Decreasing concentrations of β-lapachone derivatives and increasing concentrations of β-lapachone were electrochemically evaluated and decay time constants were determined. All the studied compounds showed hydrolysis kinetics more rapid in acidic media than in neutral solutions, resulting the p-nitrophenylimine (5) and p-bromophenylimine (6) the most stable compounds at pH 4.5 and 7.4, respectively. Stability of the monoarylimino derivatives and their correlation with biological activity tests were analysed in order to propose some of the studied compounds as prodrugs of cancer therapy.

Original languageEnglish (US)
Pages (from-to)449-454
Number of pages6
JournalElectrochemistry Communications
Volume5
Issue number6
DOIs
StatePublished - Jun 1 2003
Externally publishedYes

Keywords

  • Biological activity
  • Electrochemical response
  • Hydrolysis process
  • β-Lapachone derivatives

ASJC Scopus subject areas

  • Electrochemistry

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