Indirect photochemical transformations of acyclovir and penciclovir in aquatic environments increase ecological risk
Acyclovir and penciclovir, 2 antiviral drugs, are increasingly detected in aquatic environments. The present study explores the natural photochemical transformation mechanisms and fate of these drugs, examining direct and indirect photochemical transformation under simulated sunlight irradiation. Th...
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| Veröffentlicht in: | Environmental toxicology and chemistry 2016-03, Vol.35 (3), p.584-592 |
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| creator | An, Jibin Li, Guiying An, Taicheng Nie, Xiangping |
| description | Acyclovir and penciclovir, 2 antiviral drugs, are increasingly detected in aquatic environments. The present study explores the natural photochemical transformation mechanisms and fate of these drugs, examining direct and indirect photochemical transformation under simulated sunlight irradiation. The 2 antiviral drugs are photostable under certain conditions but significantly degrade in the presence of chromophoric dissolved organic matter (DOM). The degradation rate associated with the drugs' indirect photochemical transformation scaled with chromophoric DOM concentration. Quenchers and sensitizers were used to identify indirect photochemical transformation mechanism. Results suggested that both pharmaceuticals could be transformed by reacting with ¹O₂, •OH, and excited chromophoric DOM. The ¹O₂ played an important role in indirect photochemical transformation. Furthermore, the reaction kinetics between their substructural molecules, guanine, isocytosine, and imidazole, with different reactive oxygen species were evaluated to determine which substrate functionalities were most susceptible to singlet oxygenation. Imidazole was identified as the reaction site for ¹O₂, and preliminary ¹O₂ oxidation mechanisms were further evaluated based on liquid chromatographic–tandem mass spectrometric results. Finally, aquatic ecotoxicity assessment of phototransformed solutions revealed that the degradation of acyclovir and penciclovir may not ultimately diminish environmental risk because of either formation of more toxic intermediates than parent pharmaceuticals or some synergistic effects existing between the intermediates. Environ Toxicol Chem 2016;35:584–592. © 2015 SETAC |
| doi_str_mv | 10.1002/etc.3238 |
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The present study explores the natural photochemical transformation mechanisms and fate of these drugs, examining direct and indirect photochemical transformation under simulated sunlight irradiation. The 2 antiviral drugs are photostable under certain conditions but significantly degrade in the presence of chromophoric dissolved organic matter (DOM). The degradation rate associated with the drugs' indirect photochemical transformation scaled with chromophoric DOM concentration. Quenchers and sensitizers were used to identify indirect photochemical transformation mechanism. Results suggested that both pharmaceuticals could be transformed by reacting with ¹O₂, •OH, and excited chromophoric DOM. The ¹O₂ played an important role in indirect photochemical transformation. Furthermore, the reaction kinetics between their substructural molecules, guanine, isocytosine, and imidazole, with different reactive oxygen species were evaluated to determine which substrate functionalities were most susceptible to singlet oxygenation. Imidazole was identified as the reaction site for ¹O₂, and preliminary ¹O₂ oxidation mechanisms were further evaluated based on liquid chromatographic–tandem mass spectrometric results. Finally, aquatic ecotoxicity assessment of phototransformed solutions revealed that the degradation of acyclovir and penciclovir may not ultimately diminish environmental risk because of either formation of more toxic intermediates than parent pharmaceuticals or some synergistic effects existing between the intermediates. Environ Toxicol Chem 2016;35:584–592. © 2015 SETAC</description><identifier>ISSN: 0730-7268</identifier><identifier>EISSN: 1552-8618</identifier><identifier>DOI: 10.1002/etc.3238</identifier><identifier>PMID: 26356329</identifier><language>eng</language><publisher>United States: Pergamon</publisher><subject>Acyclovir - analogs & derivatives ; Acyclovir - chemistry ; Acyclovir - toxicity ; Animals ; Antiviral Agents - chemistry ; Antiviral Agents - toxicity ; Antiviral drug ; Antiviral drugs ; Aquatic ecosystems ; Aquatic environment ; Chromatography, High Pressure Liquid ; Daphnia - drug effects ; Daphnia - physiology ; Dissolved organic matter ; Ecological risk assessment ; Environmental risk ; Irradiation ; Kinetics ; Microalgae - drug effects ; Microalgae - physiology ; Oxidation-Reduction ; Oxygenation ; Photobacterium - drug effects ; Photochemical transformation mechanism ; Photochemicals ; Photochemistry ; Radical reaction ; Risk Assessment ; Singlet oxygen ; Singlet Oxygen - chemistry ; Sunlight ; Synergistic effect ; Tandem Mass Spectrometry ; Toxicity</subject><ispartof>Environmental toxicology and chemistry, 2016-03, Vol.35 (3), p.584-592</ispartof><rights>2015 SETAC</rights><rights>2015 SETAC.</rights><rights>2016 SETAC</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4818-fd34cd536e570c7b88ca61f0bad41bdb52e51009a047a6b6e0f0c9b51874f9563</citedby><cites>FETCH-LOGICAL-c4818-fd34cd536e570c7b88ca61f0bad41bdb52e51009a047a6b6e0f0c9b51874f9563</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fetc.3238$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fetc.3238$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26356329$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>An, Jibin</creatorcontrib><creatorcontrib>Li, Guiying</creatorcontrib><creatorcontrib>An, Taicheng</creatorcontrib><creatorcontrib>Nie, Xiangping</creatorcontrib><title>Indirect photochemical transformations of acyclovir and penciclovir in aquatic environments increase ecological risk</title><title>Environmental toxicology and chemistry</title><addtitle>Environ Toxicol Chem</addtitle><description>Acyclovir and penciclovir, 2 antiviral drugs, are increasingly detected in aquatic environments. The present study explores the natural photochemical transformation mechanisms and fate of these drugs, examining direct and indirect photochemical transformation under simulated sunlight irradiation. The 2 antiviral drugs are photostable under certain conditions but significantly degrade in the presence of chromophoric dissolved organic matter (DOM). The degradation rate associated with the drugs' indirect photochemical transformation scaled with chromophoric DOM concentration. Quenchers and sensitizers were used to identify indirect photochemical transformation mechanism. Results suggested that both pharmaceuticals could be transformed by reacting with ¹O₂, •OH, and excited chromophoric DOM. The ¹O₂ played an important role in indirect photochemical transformation. Furthermore, the reaction kinetics between their substructural molecules, guanine, isocytosine, and imidazole, with different reactive oxygen species were evaluated to determine which substrate functionalities were most susceptible to singlet oxygenation. Imidazole was identified as the reaction site for ¹O₂, and preliminary ¹O₂ oxidation mechanisms were further evaluated based on liquid chromatographic–tandem mass spectrometric results. Finally, aquatic ecotoxicity assessment of phototransformed solutions revealed that the degradation of acyclovir and penciclovir may not ultimately diminish environmental risk because of either formation of more toxic intermediates than parent pharmaceuticals or some synergistic effects existing between the intermediates. Environ Toxicol Chem 2016;35:584–592. © 2015 SETAC</description><subject>Acyclovir - analogs & derivatives</subject><subject>Acyclovir - chemistry</subject><subject>Acyclovir - toxicity</subject><subject>Animals</subject><subject>Antiviral Agents - chemistry</subject><subject>Antiviral Agents - toxicity</subject><subject>Antiviral drug</subject><subject>Antiviral drugs</subject><subject>Aquatic ecosystems</subject><subject>Aquatic environment</subject><subject>Chromatography, High Pressure Liquid</subject><subject>Daphnia - drug effects</subject><subject>Daphnia - physiology</subject><subject>Dissolved organic matter</subject><subject>Ecological risk assessment</subject><subject>Environmental risk</subject><subject>Irradiation</subject><subject>Kinetics</subject><subject>Microalgae - drug effects</subject><subject>Microalgae - physiology</subject><subject>Oxidation-Reduction</subject><subject>Oxygenation</subject><subject>Photobacterium - drug effects</subject><subject>Photochemical transformation mechanism</subject><subject>Photochemicals</subject><subject>Photochemistry</subject><subject>Radical reaction</subject><subject>Risk Assessment</subject><subject>Singlet oxygen</subject><subject>Singlet Oxygen - chemistry</subject><subject>Sunlight</subject><subject>Synergistic effect</subject><subject>Tandem Mass Spectrometry</subject><subject>Toxicity</subject><issn>0730-7268</issn><issn>1552-8618</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp1kktv1TAQRi1ERS8FiV8AkdiwSfEjfi1RRR9SCwtagdhYjjNp3Sb2rZ0U7r-v2xuKhMTK8ujoaGa-QegNwfsEY_oRJrfPKFPP0IpwTmsliHqOVlgyXEsq1C56mfM1xkRorV-gXSoYF4zqFZpOQucTuKlaX8UpuisYvbNDNSUbch_TaCcfQ65iX1m3cUO886myoavWEJxf_j5U9nYupKsglEIMI4Qpl7pLYDNU4OIQLx_FyeebV2int0OG18u7hy4OP58fHNenX49ODj6d1q5RRNV9xxrXcSaAS-xkq5SzgvS4tV1D2q7lFHgZX1vcSCtaAbjHTrecKNn0ugy4hz5svesUb2fIkxl9djAMNkCcsyFSCsGF1Lyg7_9Br-OcQumuUEI1SjMh_wpdijkn6M06-dGmjSHYPCRhShLmIYmCvl2EcztC9wT-WX0B6i3wyw-w-a_IFGYRLrzPE_x-4m26MaUzyc33L0fm_Ez8_CGPsaGFf7flexuNvSx7NxffaDmBcgaNpFyyexnDrD8</recordid><startdate>201603</startdate><enddate>201603</enddate><creator>An, Jibin</creator><creator>Li, Guiying</creator><creator>An, Taicheng</creator><creator>Nie, Xiangping</creator><general>Pergamon</general><general>Blackwell Publishing Ltd</general><scope>FBQ</scope><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SN</scope><scope>7SS</scope><scope>7ST</scope><scope>7T7</scope><scope>7TK</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>K9.</scope><scope>P64</scope><scope>RC3</scope><scope>SOI</scope></search><sort><creationdate>201603</creationdate><title>Indirect photochemical transformations of acyclovir and penciclovir in aquatic environments increase ecological risk</title><author>An, Jibin ; Li, Guiying ; An, Taicheng ; Nie, Xiangping</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4818-fd34cd536e570c7b88ca61f0bad41bdb52e51009a047a6b6e0f0c9b51874f9563</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Acyclovir - analogs & derivatives</topic><topic>Acyclovir - chemistry</topic><topic>Acyclovir - toxicity</topic><topic>Animals</topic><topic>Antiviral Agents - chemistry</topic><topic>Antiviral Agents - toxicity</topic><topic>Antiviral drug</topic><topic>Antiviral drugs</topic><topic>Aquatic ecosystems</topic><topic>Aquatic environment</topic><topic>Chromatography, High Pressure Liquid</topic><topic>Daphnia - drug effects</topic><topic>Daphnia - physiology</topic><topic>Dissolved organic matter</topic><topic>Ecological risk assessment</topic><topic>Environmental risk</topic><topic>Irradiation</topic><topic>Kinetics</topic><topic>Microalgae - drug effects</topic><topic>Microalgae - physiology</topic><topic>Oxidation-Reduction</topic><topic>Oxygenation</topic><topic>Photobacterium - drug effects</topic><topic>Photochemical transformation mechanism</topic><topic>Photochemicals</topic><topic>Photochemistry</topic><topic>Radical reaction</topic><topic>Risk Assessment</topic><topic>Singlet oxygen</topic><topic>Singlet Oxygen - chemistry</topic><topic>Sunlight</topic><topic>Synergistic effect</topic><topic>Tandem Mass Spectrometry</topic><topic>Toxicity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>An, Jibin</creatorcontrib><creatorcontrib>Li, Guiying</creatorcontrib><creatorcontrib>An, Taicheng</creatorcontrib><creatorcontrib>Nie, Xiangping</creatorcontrib><collection>AGRIS</collection><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Ecology Abstracts</collection><collection>Entomology Abstracts (Full archive)</collection><collection>Environment Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Neurosciences Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>Genetics Abstracts</collection><collection>Environment Abstracts</collection><jtitle>Environmental toxicology and chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>An, Jibin</au><au>Li, Guiying</au><au>An, Taicheng</au><au>Nie, Xiangping</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Indirect photochemical transformations of acyclovir and penciclovir in aquatic environments increase ecological risk</atitle><jtitle>Environmental toxicology and chemistry</jtitle><addtitle>Environ Toxicol Chem</addtitle><date>2016-03</date><risdate>2016</risdate><volume>35</volume><issue>3</issue><spage>584</spage><epage>592</epage><pages>584-592</pages><issn>0730-7268</issn><eissn>1552-8618</eissn><abstract>Acyclovir and penciclovir, 2 antiviral drugs, are increasingly detected in aquatic environments. The present study explores the natural photochemical transformation mechanisms and fate of these drugs, examining direct and indirect photochemical transformation under simulated sunlight irradiation. The 2 antiviral drugs are photostable under certain conditions but significantly degrade in the presence of chromophoric dissolved organic matter (DOM). The degradation rate associated with the drugs' indirect photochemical transformation scaled with chromophoric DOM concentration. Quenchers and sensitizers were used to identify indirect photochemical transformation mechanism. Results suggested that both pharmaceuticals could be transformed by reacting with ¹O₂, •OH, and excited chromophoric DOM. The ¹O₂ played an important role in indirect photochemical transformation. Furthermore, the reaction kinetics between their substructural molecules, guanine, isocytosine, and imidazole, with different reactive oxygen species were evaluated to determine which substrate functionalities were most susceptible to singlet oxygenation. Imidazole was identified as the reaction site for ¹O₂, and preliminary ¹O₂ oxidation mechanisms were further evaluated based on liquid chromatographic–tandem mass spectrometric results. Finally, aquatic ecotoxicity assessment of phototransformed solutions revealed that the degradation of acyclovir and penciclovir may not ultimately diminish environmental risk because of either formation of more toxic intermediates than parent pharmaceuticals or some synergistic effects existing between the intermediates. Environ Toxicol Chem 2016;35:584–592. © 2015 SETAC</abstract><cop>United States</cop><pub>Pergamon</pub><pmid>26356329</pmid><doi>10.1002/etc.3238</doi><tpages>9</tpages></addata></record> |
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| ispartof | Environmental toxicology and chemistry, 2016-03, Vol.35 (3), p.584-592 |
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| subjects | Acyclovir - analogs & derivatives Acyclovir - chemistry Acyclovir - toxicity Animals Antiviral Agents - chemistry Antiviral Agents - toxicity Antiviral drug Antiviral drugs Aquatic ecosystems Aquatic environment Chromatography, High Pressure Liquid Daphnia - drug effects Daphnia - physiology Dissolved organic matter Ecological risk assessment Environmental risk Irradiation Kinetics Microalgae - drug effects Microalgae - physiology Oxidation-Reduction Oxygenation Photobacterium - drug effects Photochemical transformation mechanism Photochemicals Photochemistry Radical reaction Risk Assessment Singlet oxygen Singlet Oxygen - chemistry Sunlight Synergistic effect Tandem Mass Spectrometry Toxicity |
| title | Indirect photochemical transformations of acyclovir and penciclovir in aquatic environments increase ecological risk |
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