Evidencing generation of persistent ozonation products of antibiotics roxithromycin and trimethoprim
J Radjenović1, M Godehardt, M Petrović
1Department of Environmental Chemistry, IDAEA-CSIC, c/Jordi irona 18-26, 08034 Barcelona, Spain.
Abstract:
The mechanism of product formation during ozonation of two widely used antimicrobial agents, macrolide roxithromycin and inhibitor of dihydrofolate reductase (DHFR) trimethoprim was studied in laboratory-scale experiments with two types of matrix: distilled water and secondary wastewater effluent The structures ofthe primary and secondary reaction intermediates were elucidated byquadrupole-time-of-flight (QqToF) instrument, showing that in spite of their high ozone affinity both roxithromycin and trimethoprim oxidation pathway involve to a great degree the *OH radical chain reactions. In total nine ozonation products were detected, whereas two products of roxithromycin exhibited high refractoriness to ozonation, especially in the case of distilled water. Furthermore, the intact tertiary amine moiety of roxithromycin in these products suggests that the antimicrobial activity of the parent compound will be preserved.
Insights
Ozonation of roxithromycin and trimethoprim involves hydroxyl radical reactions, forming nine products. Some roxithromycin products resist ozonation, potentially retaining antimicrobial activity.
Area of Science:
- Environmental Chemistry
- Organic Chemistry
- Pharmaceutical Chemistry
Background:
- Roxithromycin and trimethoprim are widely used antimicrobial agents.
- Understanding their transformation products during water treatment is crucial for environmental safety and efficacy.
Purpose of the Study:
- To elucidate the reaction mechanisms and identify products formed during the ozonation of roxithromycin and trimethoprim.
- To investigate the influence of water matrix (distilled water vs. wastewater effluent) on ozonation pathways.
Main Methods:
- Laboratory-scale ozonation experiments were conducted.
- Product identification and structural elucidation were performed using quadrupole-time-of-flight (QqToF) mass spectrometry.
Main Results:
- Nine ozonation products were identified for both roxithromycin and trimethoprim.
- Ozonation pathways were significantly influenced by hydroxyl radical (*OH) chain reactions, despite the compounds' high ozone affinity.
- Two roxithromycin ozonation products showed high refractoriness to further degradation, particularly in distilled water.
Conclusions:
- The ozonation of roxithromycin and trimethoprim proceeds via complex pathways involving *OH radicals.
- The persistence of certain roxithromycin products suggests potential preservation of antimicrobial activity.
- Further research is needed to assess the environmental fate and biological activity of these transformation products.
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