title: An electrochemical evidence of free radicals formation from flutamide and its reactivity with endo/xenobiotics of pharmacological relevance.
abstract: This paper reports the feasibility of free radicals formation from flutamide by using cyclic voltammetry. The electrochemical characteristics and the reactivity of the one-electron reduction product from flutamide in mixed media with thiol compounds and the nuclei acid bases are characterized. Results from this paper show the thermodynamic feasibility of free radical formation expressed for both the cathodic peak potential and the second-order rate constant values. The reactivity of the radical towards thiol compounds (glutathione, cysteamine, N-acetylcysteine) and the nuclei acid base, adenine, thymine and uracil were quantitatively assessed through the calculation of the respective interaction rate constants. Based on these results, the following tentative order of reactivity towards the xeno/endobiotics is as follows: cysteamine > uracil > glutathione > adenine > N-acetylcysteine > thymine. The stability of the nitro radical anion electrochemically generated from flutamide showed a linear dependence with pH.
authors.affiliation: Laboratory of Bioelectrochemistry, Faculty of Chemical and Pharmaceutical Sciences, University of Chile, Santiago. lununez@abello.dic.uchile.cl
authors.forename: L J
authors.initials: LJ
authors.lastname: Núñez-Vergara
authors.forename: D
authors.initials: D
authors.lastname: Farias
authors.forename: S
authors.initials: S
authors.lastname: Bollo
authors.forename: J A
authors.initials: JA
authors.lastname: Squella
mesh_terms: D000111:Acetylcysteine / Q000737:chemistry / Q000378:metabolism; D000225:Adenine / Q000737:chemistry / Q000378:metabolism; D000726:Androgen Antagonists / Q000737:chemistry; D003543:Cysteamine / Q000737:chemistry / Q000378:metabolism; D004563:Electrochemistry; D005485:Flutamide / Q000737:chemistry*; D016166:Free Radical Scavengers; D005609:Free Radicals / Q000737:chemistry*; D005978:Glutathione / Q000737:chemistry / Q000378:metabolism; D007700:Kinetics; D013816:Thermodynamics; D013941:Thymine / Q000737:chemistry / Q000378:metabolism; D014498:Uracil / Q000737:chemistry / Q000378:metabolism; D015262:Xenobiotics
chemical_list: D000726:Androgen Antagonists; D016166:Free Radical Scavengers; D005609:Free Radicals; D015262:Xenobiotics; D014498:Uracil; D003543:Cysteamine; D005485:Flutamide; D005978:Glutathione; D000225:Adenine; D013941:Thymine; D000111:Acetylcysteine