LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment

The discovery of various sartans, which are among the most used antihypertensive drugs in the world, is increasingly frequent not only in wastewater but also in surface water and, in some cases, even in drinking or groundwater. In this paper, the degradation pathway of olmesartan acid, one of the mo...

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Main Authors: Giovanni Luongo, Antonietta Siciliano, Giovanni Libralato, Sara Serafini, Lorenzo Saviano, Lucio Previtera, Giovanni Di Fabio, Armando Zarrelli
Format: Article
Language:English
Published: MDPI AG 2021-03-01
Series:Molecules
Subjects:
Online Access:https://www.mdpi.com/1420-3049/26/6/1769
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author Giovanni Luongo
Antonietta Siciliano
Giovanni Libralato
Sara Serafini
Lorenzo Saviano
Lucio Previtera
Giovanni Di Fabio
Armando Zarrelli
author_facet Giovanni Luongo
Antonietta Siciliano
Giovanni Libralato
Sara Serafini
Lorenzo Saviano
Lucio Previtera
Giovanni Di Fabio
Armando Zarrelli
author_sort Giovanni Luongo
collection DOAJ
description The discovery of various sartans, which are among the most used antihypertensive drugs in the world, is increasingly frequent not only in wastewater but also in surface water and, in some cases, even in drinking or groundwater. In this paper, the degradation pathway of olmesartan acid, one of the most used sartans, was investigated by simulating the chlorination process normally used in a wastewater treatment plant to reduce similar emerging pollutants. The structures of nine isolated degradation byproducts (DPs), eight of which were isolated for the first time, were separated via chromatography column and HPLC methods, identified by combining nuclear magnetic resonance and mass spectrometry, and justified by a proposed mechanism of formation beginning from the parent drug. Ecotoxicity tests on olmesartan acid and its nine DPs showed that 50% of the investigated byproducts inhibited the target species <i>Aliivibrio fischeri</i> and <i>Raphidocelis subcapitata</i>, causing functional decreases of 18% and 53%, respectively.
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spelling doaj.art-c4b6f5fb700e4b02b2079085bfc2ec842023-11-21T11:27:38ZengMDPI AGMolecules1420-30492021-03-01266176910.3390/molecules26061769LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity AssessmentGiovanni Luongo0Antonietta Siciliano1Giovanni Libralato2Sara Serafini3Lorenzo Saviano4Lucio Previtera5Giovanni Di Fabio6Armando Zarrelli7Department of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Biology, University of Naples Federico II, 80126 Naples, ItalyDepartment of Biology, University of Naples Federico II, 80126 Naples, ItalyDepartment of Biology, University of Naples Federico II, 80126 Naples, ItalyDepartment of Biology, University of Naples Federico II, 80126 Naples, ItalyAssociazione Italiana per la Promozione delle Ricerche su Ambiente e Salute Umana, 82030 Dugenta, ItalyDepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyDepartment of Chemical Sciences, University of Naples Federico II, 80126 Naples, ItalyThe discovery of various sartans, which are among the most used antihypertensive drugs in the world, is increasingly frequent not only in wastewater but also in surface water and, in some cases, even in drinking or groundwater. In this paper, the degradation pathway of olmesartan acid, one of the most used sartans, was investigated by simulating the chlorination process normally used in a wastewater treatment plant to reduce similar emerging pollutants. The structures of nine isolated degradation byproducts (DPs), eight of which were isolated for the first time, were separated via chromatography column and HPLC methods, identified by combining nuclear magnetic resonance and mass spectrometry, and justified by a proposed mechanism of formation beginning from the parent drug. Ecotoxicity tests on olmesartan acid and its nine DPs showed that 50% of the investigated byproducts inhibited the target species <i>Aliivibrio fischeri</i> and <i>Raphidocelis subcapitata</i>, causing functional decreases of 18% and 53%, respectively.https://www.mdpi.com/1420-3049/26/6/1769olmesartan acidchlorinationhypochloritedegradation byproductswater treatment<i>Aliivibrio fischeri</i>
spellingShingle Giovanni Luongo
Antonietta Siciliano
Giovanni Libralato
Sara Serafini
Lorenzo Saviano
Lucio Previtera
Giovanni Di Fabio
Armando Zarrelli
LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment
Molecules
olmesartan acid
chlorination
hypochlorite
degradation byproducts
water treatment
<i>Aliivibrio fischeri</i>
title LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment
title_full LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment
title_fullStr LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment
title_full_unstemmed LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment
title_short LC and NMR Studies for Identification and Characterization of Degradation Byproducts of Olmesartan Acid, Elucidation of Their Degradation Pathway and Ecotoxicity Assessment
title_sort lc and nmr studies for identification and characterization of degradation byproducts of olmesartan acid elucidation of their degradation pathway and ecotoxicity assessment
topic olmesartan acid
chlorination
hypochlorite
degradation byproducts
water treatment
<i>Aliivibrio fischeri</i>
url https://www.mdpi.com/1420-3049/26/6/1769
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