Electrochemistry-coupled to liquid chromatography-mass spectrometry-density functional theory as a new tool to mimic the environmental degradation of selected phenylurea herbicides
In vitro and in vivo experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways. However, time, cost, and matrix complexity often hinder the success of these methods. In this study, we propose an...
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| Veröffentlicht in: | Environmental science--processes & impacts 2021-10, Vol.23 (1), p.16-1611 |
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| creator | Tonleu Temgoua, Ranil Clément Bussy, Ugo Alvarez-Dorta, Dimitri Galland, Nicolas Njanja, Evangeline Hémez, Julie Thobie-Gautier, Christine Tonlé, Ignas Kenfack Boujtita, Mohammed |
| description | In vitro
and
in vivo
experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways. However, time, cost, and matrix complexity often hinder the success of these methods. In this study, we propose an alternative non-enzymatic method, using electrochemistry (EC) coupled to liquid chromatography (LC) - high resolution mass spectrometry (HRMS) - DFT theoretical calculations (EC/LC-MS/DFT) for the mimicry/simulation of the environmental degradation of phenylurea herbicides, and for the mechanism elucidation of this class of herbicides. Fenuron, monuron, isoproturon, linuron, monolinuron, metoxuron and chlortoluron were selected as relevant model compounds. The intended compounds are oxidized by EC, separated by LC and detected using electrospray ionization HRMS. The main oxidation products were hydroxylated compounds obtained by substitution and addition reactions. Unstable quinone imines/methines, rarely observed by conventional methods, have been identified during the oxidative degradation of phenylurea herbicides for the first time in this study. Some were directly observed and the others were trapped by glutathione GSH. Reactions such as hydrolytic substitutions (−Cl/+OH and −C
3
H
7
/+OH and −CH
3
/+OH and −OCH
3
/+OH), aromatic hydroxylation, alkyl carbon hydroxylation, dehydrochlorination/dehydromethylation/dehydromethoxylation and conjugation have been successfully mimicked. The obtained results, supported by theoretical calculations, are useful for simulating/understanding and predicting the oxidative degradation pathways of pesticides in the environment.
In vitro
and
in vivo
experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways. |
| doi_str_mv | 10.1039/d1em00351h |
| format | Article |
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and
in vivo
experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways. However, time, cost, and matrix complexity often hinder the success of these methods. In this study, we propose an alternative non-enzymatic method, using electrochemistry (EC) coupled to liquid chromatography (LC) - high resolution mass spectrometry (HRMS) - DFT theoretical calculations (EC/LC-MS/DFT) for the mimicry/simulation of the environmental degradation of phenylurea herbicides, and for the mechanism elucidation of this class of herbicides. Fenuron, monuron, isoproturon, linuron, monolinuron, metoxuron and chlortoluron were selected as relevant model compounds. The intended compounds are oxidized by EC, separated by LC and detected using electrospray ionization HRMS. The main oxidation products were hydroxylated compounds obtained by substitution and addition reactions. Unstable quinone imines/methines, rarely observed by conventional methods, have been identified during the oxidative degradation of phenylurea herbicides for the first time in this study. Some were directly observed and the others were trapped by glutathione GSH. Reactions such as hydrolytic substitutions (−Cl/+OH and −C
3
H
7
/+OH and −CH
3
/+OH and −OCH
3
/+OH), aromatic hydroxylation, alkyl carbon hydroxylation, dehydrochlorination/dehydromethylation/dehydromethoxylation and conjugation have been successfully mimicked. The obtained results, supported by theoretical calculations, are useful for simulating/understanding and predicting the oxidative degradation pathways of pesticides in the environment.
In vitro
and
in vivo
experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways.</description><identifier>ISSN: 2050-7887</identifier><identifier>EISSN: 2050-7895</identifier><identifier>DOI: 10.1039/d1em00351h</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Cell culture ; Chromatography ; Clinical trials ; Conjugation ; Dehydrochlorination ; Density functional theory ; Electrochemistry ; Environmental degradation ; Glutathione ; Herbicides ; Hydroxylation ; Imines ; Ionization ; Isoproturon ; Linuron ; Liquid chromatography ; Mass spectrometry ; Mass spectroscopy ; Metabolic pathways ; Mimicry ; Monuron ; Oxidation ; Pesticides ; Phenylurea ; Quinones ; Scientific imaging ; Spectroscopy</subject><ispartof>Environmental science--processes & impacts, 2021-10, Vol.23 (1), p.16-1611</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c314t-277272027595d256703754cb6a8190157e31ce11e3166451d588419a9e4640063</citedby><cites>FETCH-LOGICAL-c314t-277272027595d256703754cb6a8190157e31ce11e3166451d588419a9e4640063</cites><orcidid>0000-0001-5618-226X ; 0000-0003-1876-2962 ; 0000-0003-1852-4905 ; 0000-0003-4782-6232</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Tonleu Temgoua, Ranil Clément</creatorcontrib><creatorcontrib>Bussy, Ugo</creatorcontrib><creatorcontrib>Alvarez-Dorta, Dimitri</creatorcontrib><creatorcontrib>Galland, Nicolas</creatorcontrib><creatorcontrib>Njanja, Evangeline</creatorcontrib><creatorcontrib>Hémez, Julie</creatorcontrib><creatorcontrib>Thobie-Gautier, Christine</creatorcontrib><creatorcontrib>Tonlé, Ignas Kenfack</creatorcontrib><creatorcontrib>Boujtita, Mohammed</creatorcontrib><title>Electrochemistry-coupled to liquid chromatography-mass spectrometry-density functional theory as a new tool to mimic the environmental degradation of selected phenylurea herbicides</title><title>Environmental science--processes & impacts</title><description>In vitro
and
in vivo
experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways. However, time, cost, and matrix complexity often hinder the success of these methods. In this study, we propose an alternative non-enzymatic method, using electrochemistry (EC) coupled to liquid chromatography (LC) - high resolution mass spectrometry (HRMS) - DFT theoretical calculations (EC/LC-MS/DFT) for the mimicry/simulation of the environmental degradation of phenylurea herbicides, and for the mechanism elucidation of this class of herbicides. Fenuron, monuron, isoproturon, linuron, monolinuron, metoxuron and chlortoluron were selected as relevant model compounds. The intended compounds are oxidized by EC, separated by LC and detected using electrospray ionization HRMS. The main oxidation products were hydroxylated compounds obtained by substitution and addition reactions. Unstable quinone imines/methines, rarely observed by conventional methods, have been identified during the oxidative degradation of phenylurea herbicides for the first time in this study. Some were directly observed and the others were trapped by glutathione GSH. Reactions such as hydrolytic substitutions (−Cl/+OH and −C
3
H
7
/+OH and −CH
3
/+OH and −OCH
3
/+OH), aromatic hydroxylation, alkyl carbon hydroxylation, dehydrochlorination/dehydromethylation/dehydromethoxylation and conjugation have been successfully mimicked. The obtained results, supported by theoretical calculations, are useful for simulating/understanding and predicting the oxidative degradation pathways of pesticides in the environment.
In vitro
and
in vivo
experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways.</description><subject>Cell culture</subject><subject>Chromatography</subject><subject>Clinical trials</subject><subject>Conjugation</subject><subject>Dehydrochlorination</subject><subject>Density functional theory</subject><subject>Electrochemistry</subject><subject>Environmental degradation</subject><subject>Glutathione</subject><subject>Herbicides</subject><subject>Hydroxylation</subject><subject>Imines</subject><subject>Ionization</subject><subject>Isoproturon</subject><subject>Linuron</subject><subject>Liquid chromatography</subject><subject>Mass spectrometry</subject><subject>Mass spectroscopy</subject><subject>Metabolic pathways</subject><subject>Mimicry</subject><subject>Monuron</subject><subject>Oxidation</subject><subject>Pesticides</subject><subject>Phenylurea</subject><subject>Quinones</subject><subject>Scientific imaging</subject><subject>Spectroscopy</subject><issn>2050-7887</issn><issn>2050-7895</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkc1q3TAQhU1JoSHNJvuAIJsScKuxLUteluS2KaR0066NIs2NFfTjSHKD36sPWDm3JNDZzMB85zDMqaozoB-BtsMnDegobRlMb6rjhjJaczGwo5dZ8HfVaUoPtJRgIFh_XP3ZWVQ5BjWhMynHtVZhmS1qkgOx5nExmqgpBidzuI9yntbayZRImp9lDjeJRp9MXsl-8Sqb4KUlecIQVyITkcTjU3ELdrN0xhm1bQn63yYG79Dnwmss7lpuahL2JOF2VrlintCvdokoyYTxziijMb2v3u6lTXj6r59Uv77sfl7d1Lc_vn67-nxbqxa6XDecN7yhDWcD0w3rOW0569RdLwUMFBjHFhQClNb3HQPNhOhgkAN2fUdp355UHw6-cwyPC6Y8lh8ptFZ6DEsaG8YFFw0HVtCL_9CHsMTyiY0SbccE9LRQlwdKxZBSxP04R-NkXEeg45bheA27788Z3hT4_ADHpF6414zbv4Ltm3s</recordid><startdate>20211020</startdate><enddate>20211020</enddate><creator>Tonleu Temgoua, Ranil Clément</creator><creator>Bussy, Ugo</creator><creator>Alvarez-Dorta, Dimitri</creator><creator>Galland, Nicolas</creator><creator>Njanja, Evangeline</creator><creator>Hémez, Julie</creator><creator>Thobie-Gautier, Christine</creator><creator>Tonlé, Ignas Kenfack</creator><creator>Boujtita, Mohammed</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7ST</scope><scope>C1K</scope><scope>SOI</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-5618-226X</orcidid><orcidid>https://orcid.org/0000-0003-1876-2962</orcidid><orcidid>https://orcid.org/0000-0003-1852-4905</orcidid><orcidid>https://orcid.org/0000-0003-4782-6232</orcidid></search><sort><creationdate>20211020</creationdate><title>Electrochemistry-coupled to liquid chromatography-mass spectrometry-density functional theory as a new tool to mimic the environmental degradation of selected phenylurea herbicides</title><author>Tonleu Temgoua, Ranil Clément ; Bussy, Ugo ; Alvarez-Dorta, Dimitri ; Galland, Nicolas ; Njanja, Evangeline ; Hémez, Julie ; Thobie-Gautier, Christine ; Tonlé, Ignas Kenfack ; Boujtita, Mohammed</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c314t-277272027595d256703754cb6a8190157e31ce11e3166451d588419a9e4640063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Cell culture</topic><topic>Chromatography</topic><topic>Clinical trials</topic><topic>Conjugation</topic><topic>Dehydrochlorination</topic><topic>Density functional theory</topic><topic>Electrochemistry</topic><topic>Environmental degradation</topic><topic>Glutathione</topic><topic>Herbicides</topic><topic>Hydroxylation</topic><topic>Imines</topic><topic>Ionization</topic><topic>Isoproturon</topic><topic>Linuron</topic><topic>Liquid chromatography</topic><topic>Mass spectrometry</topic><topic>Mass spectroscopy</topic><topic>Metabolic pathways</topic><topic>Mimicry</topic><topic>Monuron</topic><topic>Oxidation</topic><topic>Pesticides</topic><topic>Phenylurea</topic><topic>Quinones</topic><topic>Scientific imaging</topic><topic>Spectroscopy</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tonleu Temgoua, Ranil Clément</creatorcontrib><creatorcontrib>Bussy, Ugo</creatorcontrib><creatorcontrib>Alvarez-Dorta, Dimitri</creatorcontrib><creatorcontrib>Galland, Nicolas</creatorcontrib><creatorcontrib>Njanja, Evangeline</creatorcontrib><creatorcontrib>Hémez, Julie</creatorcontrib><creatorcontrib>Thobie-Gautier, Christine</creatorcontrib><creatorcontrib>Tonlé, Ignas Kenfack</creatorcontrib><creatorcontrib>Boujtita, Mohammed</creatorcontrib><collection>CrossRef</collection><collection>Environment Abstracts</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Environment Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Environmental science--processes & impacts</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tonleu Temgoua, Ranil Clément</au><au>Bussy, Ugo</au><au>Alvarez-Dorta, Dimitri</au><au>Galland, Nicolas</au><au>Njanja, Evangeline</au><au>Hémez, Julie</au><au>Thobie-Gautier, Christine</au><au>Tonlé, Ignas Kenfack</au><au>Boujtita, Mohammed</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Electrochemistry-coupled to liquid chromatography-mass spectrometry-density functional theory as a new tool to mimic the environmental degradation of selected phenylurea herbicides</atitle><jtitle>Environmental science--processes & impacts</jtitle><date>2021-10-20</date><risdate>2021</risdate><volume>23</volume><issue>1</issue><spage>16</spage><epage>1611</epage><pages>16-1611</pages><issn>2050-7887</issn><eissn>2050-7895</eissn><abstract>In vitro
and
in vivo
experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways. However, time, cost, and matrix complexity often hinder the success of these methods. In this study, we propose an alternative non-enzymatic method, using electrochemistry (EC) coupled to liquid chromatography (LC) - high resolution mass spectrometry (HRMS) - DFT theoretical calculations (EC/LC-MS/DFT) for the mimicry/simulation of the environmental degradation of phenylurea herbicides, and for the mechanism elucidation of this class of herbicides. Fenuron, monuron, isoproturon, linuron, monolinuron, metoxuron and chlortoluron were selected as relevant model compounds. The intended compounds are oxidized by EC, separated by LC and detected using electrospray ionization HRMS. The main oxidation products were hydroxylated compounds obtained by substitution and addition reactions. Unstable quinone imines/methines, rarely observed by conventional methods, have been identified during the oxidative degradation of phenylurea herbicides for the first time in this study. Some were directly observed and the others were trapped by glutathione GSH. Reactions such as hydrolytic substitutions (−Cl/+OH and −C
3
H
7
/+OH and −CH
3
/+OH and −OCH
3
/+OH), aromatic hydroxylation, alkyl carbon hydroxylation, dehydrochlorination/dehydromethylation/dehydromethoxylation and conjugation have been successfully mimicked. The obtained results, supported by theoretical calculations, are useful for simulating/understanding and predicting the oxidative degradation pathways of pesticides in the environment.
In vitro
and
in vivo
experimental models, mainly based on cell cultures, animals, healthy humans and clinical trials, are useful approaches for identifying the main metabolic pathways.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1em00351h</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0001-5618-226X</orcidid><orcidid>https://orcid.org/0000-0003-1876-2962</orcidid><orcidid>https://orcid.org/0000-0003-1852-4905</orcidid><orcidid>https://orcid.org/0000-0003-4782-6232</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2050-7887 |
| ispartof | Environmental science--processes & impacts, 2021-10, Vol.23 (1), p.16-1611 |
| issn | 2050-7887 2050-7895 |
| language | eng |
| recordid | cdi_proquest_journals_2583458160 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Cell culture Chromatography Clinical trials Conjugation Dehydrochlorination Density functional theory Electrochemistry Environmental degradation Glutathione Herbicides Hydroxylation Imines Ionization Isoproturon Linuron Liquid chromatography Mass spectrometry Mass spectroscopy Metabolic pathways Mimicry Monuron Oxidation Pesticides Phenylurea Quinones Scientific imaging Spectroscopy |
| title | Electrochemistry-coupled to liquid chromatography-mass spectrometry-density functional theory as a new tool to mimic the environmental degradation of selected phenylurea herbicides |
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