NDLI: Formation of bioactive transformation products during glucocorticoid chlorination

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Environmental Science: Water Research & Technology Vol -3

Environmental Science: Water Research & Technology Vol - 3 Issue - 3

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Formation of bioactive transformation products during glucocorticoid chlorination

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Environmental Science: Water Research & Technology Vol - 3 Issue - 2

Environmental Science: Water Research & Technology Vol - 3 Issue - 1

Environmental Science: Water Research & Technology Vol -2

Environmental Science: Water Research & Technology Vol -1

Formation of bioactive transformation products during glucocorticoid chlorination

Content Provider	Royal Society of Chemistry (RSC)
Author	Pflug, Nicholas C. Kupsco, Allison Schlenk, Daniel Kolodziej, Edward P. Cwiertny, David M. Gloer, James B. Teesch, Lynn M.
Copyright Year	2017
Abstract	Glucocorticoid (GC) release into the environment has led to widespread detection of glucocorticoid receptor (GR) activity in water resources that has been shown to persist throughout conventional and some advanced wastewater treatment processes. Here, we used high performance liquid chromatography, high resolution mass spectrometry and nuclear magnetic resonance spectroscopy to explore the reaction of natural (cortisone, cortisol) and synthetic (prednisone, prednisolone, dexamethasone) GCs with free chlorine (HOCl) to simulate their fate during chemical disinfection of water and wastewater. Generally, GCs react slowly (t1/2 ∼ 7–200 h) with HOCl when compared to other steroid classes, but they yield complex mixtures of transformation products, with at times the majority of product mass comprising structurally identifiable and likely bioactive steroids. For example, we frequently observed chlorination at the C-9 position (e.g., 9-chloro-prednisone), a reaction known to increase GC activity 4-fold. We also identified reaction products in the adrenosterone family of androgens produced via cleavage of the C-17 side-chain on many GCs. Another common transformation pathway was the conversion of endogenous GCs to their more potent synthetic analogs via oxidation at the C-1/C-2 positions, with unsaturation reported to increase GR activity 4-fold (e.g., cortisol to prednisolone). Despite identification of such products, in vitro assays generally suggest GR activity decreases with extent of parent decay during chlorination. Cortisol was the exception, with GR activity only decreasing 2-fold in product mixtures (based on measured EC50 values) despite a 95% reduction in parent concentration, a result attributable to formation of the more potent prednisolone during chlorination. Furthermore, our assay likely underestimates product bioactivity as it did not account for the activity of several identified GC byproducts that first require in vivo activation via C-11 reduction, nor did it consider androgen receptor (AR) activity associated with byproducts from the adrenosterone family. To avoid formation of product mixtures with conserved bioactivity, advanced chemical oxidation processes may represent a more promising approach; we show that GCs react much more rapidly with ozone (t1/2 ∼ 0.4–1.3 min) and produce no observable UV-active products. This suggests disruption of the GC conjugated π-electron and ring systems, thereby likely mitigating biological activity.
Starting Page	450
Ending Page	461
Page Count	12
File Format	HTM / HTML PDF
ISSN	20531400
Volume Number	3
Issue Number	3
Journal	Environmental Science: Water Research & Technology
DOI	10.1039/c7ew00033b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Glucocorticoid Glucocorticoid receptor Wastewater High-performance liquid chromatography Mass spectrometry Nuclear magnetic resonance spectroscopy Cortisol Prednisone Prednisolone Dexamethasone Chlorine Adrenosterone Boeing C-17 Globemaster III EC50 Androgen Estrogen receptor Androgen receptor Ozone
Content Type	Text
Resource Type	Article
Subject	Environmental Engineering Water Science and Technology

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1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
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3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
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Boeing C-17 Globemaster III

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Determination of unbound prednisolone, prednisone and cortisol in human serum and saliva by on-line solid-phase extraction liquid chromatography tandem mass spectrometry and potential implications for drug monitoring of prednisolone and prednisone in saliva.

High Resolution Mass Spectrometry Elucidation of Captopril’s Ozonation and Chlorination By-Products

First identification of prednisone in human hair by liquid chromatography-ionspray mass spectrometry.

Simultaneous determination of fourteen steroid hormone residues in beef samples by liquid chromatography-tandem mass spectrometry

Formation of bioactive transformation products during glucocorticoid chlorination

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