Stereoselective metabolism of chloramphenicol by bacteria isolated from wastewater, and the importance of stereochemistry in environmental risk assessments for antibiotics

Felicity C T Elder, Ben Pascoe, Stephen Wells, Samuel K Sheppard, Jason Snape, William H. Gaze, Edward J Feil, Barbara Kasprzyk-Hordern

Research output: Contribution to journalArticlepeer-review

3 Citations (SciVal)

Abstract

Wastewater treatment plants have been highlighted as a potential hotspot for the development and spread of antibiotic resistance. Although antibiotic resistant bacteria in wastewater present a public health threat, it is also possible that these bacteria play an important role in the bioremediation through the metabolism of antibiotics before they reach the wider environment. Here we address this possibility with a particular emphasis on stereochemistry using a combination of microbiology and analytical chemistry tools including the use of supercritical-fluid chromatography coupled with mass spectrometry for chiral analysis and high-resolution mass spectrometry to investigate metabolites. Due to the complexities around chiral analysis the antibiotic chloramphenicol was used as a proof of concept to demonstrate stereoselective metabolism due to its relatively simple chemical structure and availability over the counter in the U.K. The results presented here demonstrate the chloramphenicol can be stereoselectively transformed by the chloramphenicol acetyltransferase enzyme with the orientation around the first stereocentre being key for this process, meaning that accumulation of two isomers may occur within the environment with potential impacts on ecotoxicity and emergence of bacterial antibiotic resistance within the environment.
Original languageEnglish
Article number118415
JournalWater Research
Volume217
Early online date6 Apr 2022
DOIs
Publication statusPublished - 15 Jun 2022

Bibliographical note

Funding Information:
Support from Engineering and Physical Sciences Research Council (EP/N509589/1, EP/P028403/1), Natural Environment Research Council (NE/N019261/1), and AstraZeneca Global Safety, Health and Environment is greatly appreciated. The authors would like to thank Waters for support and provision of ACQUITY UPC2 System for the study. MC2 for support and provision of UPLC-QTOF for this study.

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