Photolysis of four β‑lactam antibiotics under simulated environmental conditions: Degradation, transformation products and antibacterial activity

Autor: Alexander Timm, Christian Zwiener, Marius Majewsky, Sylvain Merel, Stefan Bräse, Harald Horn, Ewa Borowska
Přispěvatelé: Eberhard Karls Universität Tübingen = Eberhard Karls University of Tuebingen, Institute of Organic Chemistry [Karlsruhe], Karlsruhe Institute of Technology (KIT)
Rok vydání: 2019
Předmět:
Environmental Engineering
010504 meteorology & atmospheric sciences
medicine.drug_class
Carboxylic acid
Antibiotics
Thiazolidine
Bacillus subtilis
010501 environmental sciences
beta-Lactams
Waste Disposal
Fluid
01 natural sciences
chemistry.chemical_compound
[CHIM.ANAL]Chemical Sciences/Analytical chemistry
Ampicillin
polycyclic compounds
medicine
Environmental Chemistry
Waste Management and Disposal
ComputingMilieux_MISCELLANEOUS
0105 earth and related environmental sciences
Piperacillin
chemistry.chemical_classification
Photolysis
biology
[SDE.IE]Environmental Sciences/Environmental Engineering
Chemistry
Amoxicillin
biology.organism_classification
Pollution
Anti-Bacterial Agents
3. Good health
Penicillin
Biodegradation
Environmental
Sunlight
Penicillin V
Antibacterial activity
Water Pollutants
Chemical
medicine.drug
Nuclear chemistry
Zdroj: Science of the Total Environment
Science of the Total Environment, Elsevier, 2019, 651, pp.1605-1612. ⟨10.1016/j.scitotenv.2018.09.248⟩
ISSN: 0048-9697
1879-1026
Popis: β‑Lactam antibiotics are among the most widely used antibiotics in human medicine and their effects on the aquatic environment - concerning bacterial resistance - are controversially discussed. This study focused on the photolysis of the four β‑lactam antibiotics - amoxicillin, ampicillin, penicillin V and piperacillin - under simulated environmental conditions. It was observed that all investigated β‑lactam antibiotics are photolytically degradable by simulated sunlight (1 kW/m2) with half-lives between 3.2 and 7.0 h. Structure elucidation of transformation products performed with liquid chromatography coupled to high resolution mass spectrometry showed that the hydrolysis of the β‑lactam ring is the primary transformation reaction, followed by the elimination of carboxylic and dimethyl thiazolidine carboxylic acid. Growth inhibition tests on Bacillus subtilis showed the loss of bactericide activity of irradiated solutions of amoxicillin, ampicillin and piperacillin, suggesting the transformation of the β‑lactam ring is responsible for the antibiotic effect. In contrast, the solutions of penicillin V did not show any decline of the antibacterial activity after photolytic degradation, probably due to the formation of still active epimers.
Databáze: OpenAIRE
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