Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography
Autor(a) principal: | |
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Data de Publicação: | 2023 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | https://hdl.handle.net/1822/85301 |
Resumo: | MDMA (3,4-methylenedioxymethamphetamine) is a chiral psychoactive recreational drug sold in illicit markets as racemate. Studies on the impact of MDMA on aquatic organisms are scarce. While enantioselectivity in toxicity in animals and humans has been reported, none is reported on aquatic organisms. This study aimed to investigate the ecotoxicological effects of MDMA and its enantiomers in <i>Daphnia magna</i>. For that, enantiomers (enantiomeric purity > 97%) were separated by liquid chromatography using a homemade semipreparative chiral column. Daphnids were exposed to three concentrations of (<i>R</i>,<i>S</i>)-MDMA (0.1, 1.0 and 10.0 µg L<sup>−1</sup>) and two concentrations of (<i>R</i>)- and (<i>S</i>)-enantiomers (0.1 and 1.0 µg L<sup>−1</sup>) over the course of 8 days. Morphophysiological responses were dependent on the substance form and daphnia development stage, and they were overall not affected by the (<i>R</i>)-enantiomer. Changes in swimming behaviour were observed for both the racemate and its enantiomers, but enantioselective effects were not observed. Reproductive or biochemical changes were not observed for enantiomers whereas a significant decrease in acetylcholinesterase and catalase activity was noted at the highest concentration of (<i>R</i>,<i>S</i>)-MDMA (10 µg L<sup>−1</sup>). Overall, this study showed that sub-chronic exposure to MDMA racemate and its enantiomers can interfere with morphophysiological and swimming behaviour of <i>D. magna</i>. In general, the (<i>R</i>)-enantiomer demonstrated less toxicity than the (<i>S</i>)-enantiomer. |
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Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatographyAquatic organismsChiralityEcotoxicityEnantioselectivityPsychoactive drugsScience & TechnologyMDMA (3,4-methylenedioxymethamphetamine) is a chiral psychoactive recreational drug sold in illicit markets as racemate. Studies on the impact of MDMA on aquatic organisms are scarce. While enantioselectivity in toxicity in animals and humans has been reported, none is reported on aquatic organisms. This study aimed to investigate the ecotoxicological effects of MDMA and its enantiomers in <i>Daphnia magna</i>. For that, enantiomers (enantiomeric purity > 97%) were separated by liquid chromatography using a homemade semipreparative chiral column. Daphnids were exposed to three concentrations of (<i>R</i>,<i>S</i>)-MDMA (0.1, 1.0 and 10.0 µg L<sup>−1</sup>) and two concentrations of (<i>R</i>)- and (<i>S</i>)-enantiomers (0.1 and 1.0 µg L<sup>−1</sup>) over the course of 8 days. Morphophysiological responses were dependent on the substance form and daphnia development stage, and they were overall not affected by the (<i>R</i>)-enantiomer. Changes in swimming behaviour were observed for both the racemate and its enantiomers, but enantioselective effects were not observed. Reproductive or biochemical changes were not observed for enantiomers whereas a significant decrease in acetylcholinesterase and catalase activity was noted at the highest concentration of (<i>R</i>,<i>S</i>)-MDMA (10 µg L<sup>−1</sup>). Overall, this study showed that sub-chronic exposure to MDMA racemate and its enantiomers can interfere with morphophysiological and swimming behaviour of <i>D. magna</i>. In general, the (<i>R</i>)-enantiomer demonstrated less toxicity than the (<i>S</i>)-enantiomer.This work was financially supported by national funds through the FCT/MCTES (PIDDAC), under the project PTDC/CTA-AMB/6686/2020, and partially supported through the projects UIDB/04423/2020 and UIDP/04423/2020 (Group of Natural Products and Medicinal ChemistryCIIMAR).Multidisciplinary Digital Publishing Institute (MDPI)Universidade do MinhoCosta, Ana RitaGonçalves, Virgínia M. F.Castro, Bruno B.Carrola, João SoaresLanga, IvanPereira, ArianaCarvalho, Ana RitaTiritan, Maria ElizabethRibeiro, Cláudia2023-02-022023-02-02T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/85301engCosta, A.R.; Gonçalves, V.M.F.; Castro, B.B.; Carrola, J.S.; Langa, I.; Pereira, A.; Carvalho, A.R.; Tiritan, M.E.; Ribeiro, C. Toxicity of the 3,4-Methylenedioxymethamphetamine and Its Enantiomers to Daphnia magna after Isolation by Semipreparative Chromatography. Molecules 2023, 28, 1457. https://doi.org/10.3390/molecules280314571420-304910.3390/molecules28031457367711191457https://www.mdpi.com/1420-3049/28/3/1457info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-07-21T12:26:41Zoai:repositorium.sdum.uminho.pt:1822/85301Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:21:10.078871Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse |
dc.title.none.fl_str_mv |
Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography |
title |
Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography |
spellingShingle |
Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography Costa, Ana Rita Aquatic organisms Chirality Ecotoxicity Enantioselectivity Psychoactive drugs Science & Technology |
title_short |
Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography |
title_full |
Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography |
title_fullStr |
Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography |
title_full_unstemmed |
Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography |
title_sort |
Toxicity of the 3,4-methylenedioxymethamphetamine and its enantiomers to Daphnia magna after isolation by semipreparative chromatography |
author |
Costa, Ana Rita |
author_facet |
Costa, Ana Rita Gonçalves, Virgínia M. F. Castro, Bruno B. Carrola, João Soares Langa, Ivan Pereira, Ariana Carvalho, Ana Rita Tiritan, Maria Elizabeth Ribeiro, Cláudia |
author_role |
author |
author2 |
Gonçalves, Virgínia M. F. Castro, Bruno B. Carrola, João Soares Langa, Ivan Pereira, Ariana Carvalho, Ana Rita Tiritan, Maria Elizabeth Ribeiro, Cláudia |
author2_role |
author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Costa, Ana Rita Gonçalves, Virgínia M. F. Castro, Bruno B. Carrola, João Soares Langa, Ivan Pereira, Ariana Carvalho, Ana Rita Tiritan, Maria Elizabeth Ribeiro, Cláudia |
dc.subject.por.fl_str_mv |
Aquatic organisms Chirality Ecotoxicity Enantioselectivity Psychoactive drugs Science & Technology |
topic |
Aquatic organisms Chirality Ecotoxicity Enantioselectivity Psychoactive drugs Science & Technology |
description |
MDMA (3,4-methylenedioxymethamphetamine) is a chiral psychoactive recreational drug sold in illicit markets as racemate. Studies on the impact of MDMA on aquatic organisms are scarce. While enantioselectivity in toxicity in animals and humans has been reported, none is reported on aquatic organisms. This study aimed to investigate the ecotoxicological effects of MDMA and its enantiomers in <i>Daphnia magna</i>. For that, enantiomers (enantiomeric purity > 97%) were separated by liquid chromatography using a homemade semipreparative chiral column. Daphnids were exposed to three concentrations of (<i>R</i>,<i>S</i>)-MDMA (0.1, 1.0 and 10.0 µg L<sup>−1</sup>) and two concentrations of (<i>R</i>)- and (<i>S</i>)-enantiomers (0.1 and 1.0 µg L<sup>−1</sup>) over the course of 8 days. Morphophysiological responses were dependent on the substance form and daphnia development stage, and they were overall not affected by the (<i>R</i>)-enantiomer. Changes in swimming behaviour were observed for both the racemate and its enantiomers, but enantioselective effects were not observed. Reproductive or biochemical changes were not observed for enantiomers whereas a significant decrease in acetylcholinesterase and catalase activity was noted at the highest concentration of (<i>R</i>,<i>S</i>)-MDMA (10 µg L<sup>−1</sup>). Overall, this study showed that sub-chronic exposure to MDMA racemate and its enantiomers can interfere with morphophysiological and swimming behaviour of <i>D. magna</i>. In general, the (<i>R</i>)-enantiomer demonstrated less toxicity than the (<i>S</i>)-enantiomer. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-02-02 2023-02-02T00:00:00Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
https://hdl.handle.net/1822/85301 |
url |
https://hdl.handle.net/1822/85301 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Costa, A.R.; Gonçalves, V.M.F.; Castro, B.B.; Carrola, J.S.; Langa, I.; Pereira, A.; Carvalho, A.R.; Tiritan, M.E.; Ribeiro, C. Toxicity of the 3,4-Methylenedioxymethamphetamine and Its Enantiomers to Daphnia magna after Isolation by Semipreparative Chromatography. Molecules 2023, 28, 1457. https://doi.org/10.3390/molecules28031457 1420-3049 10.3390/molecules28031457 36771119 1457 https://www.mdpi.com/1420-3049/28/3/1457 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Multidisciplinary Digital Publishing Institute (MDPI) |
publisher.none.fl_str_mv |
Multidisciplinary Digital Publishing Institute (MDPI) |
dc.source.none.fl_str_mv |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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