The β-lactam antibiotics such as penicillins and cephalosporins are among the most widely used antibiotics and frequently detected in the environment. Owing to the O- and N-containing functional groups of their structures, β-lactam antibiotics complex favorably with transition metal ions such as copper. This metal complexation tendency not only influences the environmental fate of β-lactam antibiotics but also can be harnessed in treatment technologies to promote their removal. Our recent in-depth studies have identified two new reaction mechanisms that were previously overlooked for β-lactam antibiotics and copper under environmentally relevant conditions. First, while Cu(II) ions are known to promote hydrolysis of β-lactams, we discovered that Cu(II) ions can promote hydrolysis and/or oxidation of β-lactam antibiotics, depending on β-lactams’ structural characteristics and solution pH. Most significantly, β-lactam antibiotics that contain a phenylglycine primary amine group on the side chain can undergo oxidation by Cu(II) via this functional group, and this transformation involves cycling of Cu(II)/Cu(I). Second, while free Cu(II) ion is known to be ineffective to activate peroxydisulfate (PDS) for advanced oxidation, we discovered that Cu(II) complexed with β-lactam antibiotics are effective activators for PDS which generates Cu(III) and radicals. The generated Cu(III) (major contributor) and radicals in turn can quickly degrade the β-lactam antibiotics, resulting in cycling of Cu(II)/Cu(III) in this system. Further studies show that this novel activation mechanism of PDS is much less influenced by water matrix components, and is common with a wide range of contaminants and ligands, with N-containing functional groups (i.e. amines) identified to be critical ligand characteristics. Overall, these new findings mark important contributions to a more accurate mechanistic understanding of the reactions between β-lactam antibiotics and copper species, as well as activation of PDS by copper.

Enhanced degradation of β-lactam antibiotics: Roles of reactive copper species in the absence and presence of peroxydisulfate

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.