tetracycline and 1-hydroxybenzotriazole

Enzyme-based catalyzed oxidative coupling reactions (E-COCRs) are considered as viable technologies to transform a variety of pharmaceutical antibiotics. This study indicated that the extracellular fungal laccase from Pleurotus ostreatus was effective in transforming tetracycline (TC) with 1-hydroxybenzotriazole (HBT) present at varying conditions during E-COCRs. The presence of humic acid (HA) showed suppressive effect on the transformation rate constants (k) of TC, and the k values for TC decreased as HA concentration increased. It was ascribed primarily to the covalent binding between TC and HA, which reduced the apparent concentration and availability of TC in water. It is noted that TC molecules from the cross-coupling products were likely re-released under extreme conditions (pH<2.0). The intermediate products were identified regardless of HA presence by high-resolution mass spectrometry (HRMS). A possible reaction pathway of TC in HA solution including electron transfer, hydroxylation, dehydrogenation, oxidation, radical reaction, decomposition, and covalent binding was proposed. The growth inhibition assays of Escherichia coli (E. coli) confirmed that the antimicrobial activity of TC was remarkably reduced with an increasing reaction time. These findings provide novel insights into the decomposition and cross-coupling of TC in a multi-solute natural aquatic environment by laccase-based catalyzed oxidative processes.

Topics: Biotransformation; Escherichia coli; Humic Substances; Laccase; Pleurotus; Tetracycline; Triazoles

Tetracycline antibiotics are widely used in human and veterinary medicine; however, residual amounts of these antibiotics in the environment are of concern since they could contribute to selection of resistant bacteria. In this study, tetracycline (TC), chlortetracycline (CTC), doxycycline (DC) and oxytetracycline (OTC) were treated with laccase from the white rot fungus Trametes versicolor in the presence of the redox mediator 1-hydroxybenzotriazole (HBT). High performance liquid chromatography demonstrated that DC and CTC were completely eliminated after 15 min, while TC and CTC were eliminated after 1 h. This system also resulted in a complete loss of inhibition of growth of Escherichia coli and Bacillus subtilis and the green alga Pseudokirchneriella subcapitata with decreasing tetracycline antibiotic concentration. These results suggest that the laccase-HBT system is effective in eliminating tetracycline antibiotics and removing their ecotoxicity.

Topics: Anti-Bacterial Agents; Bacillus subtilis; Chlorophyta; Escherichia coli; Humans; Laccase; Lignin; Tetracycline; Triazoles