Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog
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/10216/143704 |
Resumo: | Chemiluminescence is a remarkable process in which light is emitted due to a chemical reaction, without the need for photoexcitation. Among some of the most well-known chemiluminescent systems is that of marine Coelenterazine. Herein, we report the synthesis of a novel halogenated Coelenterazine analog, as well as the characterization of its potential anticancer activity and chemiluminescence. We have found that this analog is capable of significantly enhanced emission in aqueous solution when triggered by superoxide anion while being compatible with human cell lines. So, this compound presents great potential for the sensitive and dynamic sensing of a molecule of interest in biological media. Furthermore, the analysis of its cytotoxicity provided structural insight into the properties of brominated Coelenterazines, which were previously found to possess selective anticancer activity. Namely, the introduction of bromine heteroatoms is not enough to provide cyto-toxicity, while the introduction of electro-withdrawing groups eliminates all previously reported anticancer activity. Finally, while this compound is not active, its use in a combination approach allowed to improve the profile of a known chemotherapeutic agent. These results should be useful to guide future optimizations of halogenated Coelenterazine analogs. |
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Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analogChemiluminescence is a remarkable process in which light is emitted due to a chemical reaction, without the need for photoexcitation. Among some of the most well-known chemiluminescent systems is that of marine Coelenterazine. Herein, we report the synthesis of a novel halogenated Coelenterazine analog, as well as the characterization of its potential anticancer activity and chemiluminescence. We have found that this analog is capable of significantly enhanced emission in aqueous solution when triggered by superoxide anion while being compatible with human cell lines. So, this compound presents great potential for the sensitive and dynamic sensing of a molecule of interest in biological media. Furthermore, the analysis of its cytotoxicity provided structural insight into the properties of brominated Coelenterazines, which were previously found to possess selective anticancer activity. Namely, the introduction of bromine heteroatoms is not enough to provide cyto-toxicity, while the introduction of electro-withdrawing groups eliminates all previously reported anticancer activity. Finally, while this compound is not active, its use in a combination approach allowed to improve the profile of a known chemotherapeutic agent. These results should be useful to guide future optimizations of halogenated Coelenterazine analogs.2023-08-292023-08-29T00:00:00Z2024-08-29T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/10216/143704eng1010-603010.1016/j.jphotochem.2022.114228Luís Pinto da SilvaJosé Pedro SilvaPatricia González-BerdullasMariana PereiraDiana DuarteRodriguez Borges, JENuno ValeJoaquim C G E Esteves da Silvainfo:eu-repo/semantics/embargoedAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-11-29T13:40:21Zoai:repositorio-aberto.up.pt:10216/143704Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T23:45:18.032461Repositório 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 |
Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog |
title |
Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog |
spellingShingle |
Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog Luís Pinto da Silva |
title_short |
Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog |
title_full |
Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog |
title_fullStr |
Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog |
title_full_unstemmed |
Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog |
title_sort |
Evaluation of the anticancer activity and chemiluminescence of a halogenated coelenterazine analog |
author |
Luís Pinto da Silva |
author_facet |
Luís Pinto da Silva José Pedro Silva Patricia González-Berdullas Mariana Pereira Diana Duarte Rodriguez Borges, JE Nuno Vale Joaquim C G E Esteves da Silva |
author_role |
author |
author2 |
José Pedro Silva Patricia González-Berdullas Mariana Pereira Diana Duarte Rodriguez Borges, JE Nuno Vale Joaquim C G E Esteves da Silva |
author2_role |
author author author author author author author |
dc.contributor.author.fl_str_mv |
Luís Pinto da Silva José Pedro Silva Patricia González-Berdullas Mariana Pereira Diana Duarte Rodriguez Borges, JE Nuno Vale Joaquim C G E Esteves da Silva |
description |
Chemiluminescence is a remarkable process in which light is emitted due to a chemical reaction, without the need for photoexcitation. Among some of the most well-known chemiluminescent systems is that of marine Coelenterazine. Herein, we report the synthesis of a novel halogenated Coelenterazine analog, as well as the characterization of its potential anticancer activity and chemiluminescence. We have found that this analog is capable of significantly enhanced emission in aqueous solution when triggered by superoxide anion while being compatible with human cell lines. So, this compound presents great potential for the sensitive and dynamic sensing of a molecule of interest in biological media. Furthermore, the analysis of its cytotoxicity provided structural insight into the properties of brominated Coelenterazines, which were previously found to possess selective anticancer activity. Namely, the introduction of bromine heteroatoms is not enough to provide cyto-toxicity, while the introduction of electro-withdrawing groups eliminates all previously reported anticancer activity. Finally, while this compound is not active, its use in a combination approach allowed to improve the profile of a known chemotherapeutic agent. These results should be useful to guide future optimizations of halogenated Coelenterazine analogs. |
publishDate |
2023 |
dc.date.none.fl_str_mv |
2023-08-29 2023-08-29T00:00:00Z 2024-08-29T00:00:00Z |
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/10216/143704 |
url |
https://hdl.handle.net/10216/143704 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
1010-6030 10.1016/j.jphotochem.2022.114228 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/embargoedAccess |
eu_rights_str_mv |
embargoedAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.source.none.fl_str_mv |
reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação instacron:RCAAP |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
reponame_str |
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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