Insights into the reaction of beta-lactam antibiotics with copper(II) ions in aqueous and micellar media: kinetic and spectrometric studies.
Degradation of beta-lactam antibiotics by means of metallic cations seems to have a very complex chemistry, involving not only the catalytic effect of the metal ion but also complex formation. Many different compounds, such as methylpyrazines, oxazolones, penicilloic, penicillenic, and penicillonic acids, have been reported as degradation products of such antibiotics, although not many details about the progress of the reaction can be found in the literature. Two novel fluorimetric and spectrophotometric methods previously published by the authors, as well as kinetic studies, have been used to propose a possible reaction mechanism for the ampicillin degradation in the presence of copper(II) ions. Likewise, we have proposed the chemical structure required by the beta-lactam antibiotics to develop absorption or fluorescence properties. Kinetics in micellar and aqueous media shows that the copper-ampicillin reaction proceeds through different pathways depending on the reaction medium.
Fernández-González
Alfonso
A
Department of Physical and Analytical Chemistry, Faculty of Chemistry, University of Oviedo, Av. Julián Clavería, 8 33006-Oviedo, Spain.
Badía
Rosana
R
Díaz-García
Marta Elena
ME
D000667:Ampicillin / Q000378:metabolism; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000378:metabolism*; D003300:Copper / Q000737:chemistry / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D007700:Kinetics; D008823:Micelles; D013050:Spectrometry, Fluorescence; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014867:Water; D047090:beta-Lactams / Q000737:chemistry / Q000378:metabolism*
D000900:Anti-Bacterial Agents; D008823:Micelles; D047090:beta-Lactams; D014867:Water; D003300:Copper; D000667:Ampicillin