BODIPY-labeled estrogens for fluorescence analysis of environmental microbial degradation

Felion, C., Lopez-Gonzalez, R., Sewell, A. L., Marquez, R. and Gauchotte-Lindsay, C. (2022) BODIPY-labeled estrogens for fluorescence analysis of environmental microbial degradation. ACS Omega, 7(45), pp. 41284-41295. (doi: 10.1021/acsomega.2c05002) (PMID:36406552) (PMCID:PMC9670910)

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Biodegradation of estrogen hormone micropollutants is a well-established approach toward their remediation. Fluorescently labeled substrates are used extensively for rapid, near-real-time analysis of biological processes and are a potential tool for studying biodegradation processes faster and more efficiently than conventional approaches. However, it is important to understand how the fluorescently tagged surrogates compare with the natural substrate in terms of chemical analysis and the intended application. We derivatized three natural estrogens with BODIPY fluorophores by azide–alkyne cycloaddition click reaction and developed an analytical workflow based on simple liquid–liquid extraction and HPLC-PDA analysis. The developed methods allow for concurrent analysis of both fluorescent and natural estrogens with comparable recovery, accuracy, and precision. We then evaluated the use of BODIPY-labeled estrogens as surrogate substrates for studying biodegradation using a model bacterium for estrogen metabolism. The developed analytical methods were successfully employed to compare the biological transformation of 17β-estradiol (E2), with and without the BODIPY fluorescent tag. Through measuring the complete degradation of E2 and the transformation of BODIPY-estradiol to BODIPY-estrone in the presence of a co-substrate, we found that BODIPY-labeled estrogens are biologically viable surrogates for investigating biodegradation in environmental bacteria.

Item Type:Articles
Glasgow Author(s) Enlighten ID:Sewell, Mr Alan and Felion, Ms Celeste Marie and Gauchotte-Lindsay, Dr Caroline
Authors: Felion, C., Lopez-Gonzalez, R., Sewell, A. L., Marquez, R., and Gauchotte-Lindsay, C.
College/School:College of Science and Engineering > School of Chemistry
College of Science and Engineering > School of Engineering > Infrastructure and Environment
Journal Name:ACS Omega
Publisher:American Chemical Society
ISSN (Online):2470-1343
Published Online:03 November 2022
Copyright Holders:Copyright © 2022 The Authors
First Published:First published in ACS Omega 7(45): 41284-41295
Publisher Policy:Reproduced under a Creative Commons License

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
314985Microbiofilters fluorescent assay for organic micropollutants biodegradation.Caroline Gauchotte-LindsayBiotechnology and Biological Sciences Research Council (BBSRC)POC202113ENG - Infrastructure & Environment
309846Decentralised water technologiesWilliam SloanEngineering and Physical Sciences Research Council (EPSRC)EP/V030515/1ENG - Infrastructure & Environment