Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents
Autor(a) principal: | |
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Data de Publicação: | 2022 |
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/1822/86830 |
Resumo: | Four squaraine dyes derived from 2,3,3-trimethylindolenine and 1,1,2-trimethyl-1H-benzo[e]indole with different combinations of barbituric groups attach to the central ring, having ester groups and alkyl chains in the nitrogen atoms of heterocyclic rings were synthesized. These dyes were fully characterized and their photophysical behavior was studied in ethanol and phosphate-buffered saline solution. Absorption and emission bands between 631 and 712 nm were detected, with the formation of aggregates in aqueous media, which is typical of this class of dyes. Tests carried out with 1,3-diphenylisobenzofuran allowed us to verify the ability of the dyes to produce singlet oxygen. The interaction of synthesized dyes with human serum albumin (HSA) was also evaluated, being demonstrated a linear correlation between fluorescence intensity and protein concentration. The antifungal potential of the dyes against the yeast Saccharomyces cerevisiae was evaluated using a broth microdilution assay. In order to test the photosensitizing capacity of the synthesized dyes, tests were carried out in the dark and with irradiation, using a custom-built light-emitting diode that emits close to the absorption wavelength of the studied dyes. The results showed that the interaction of dyes with HSA and the antifungal activity depends on the different structural modifications of the dyes. |
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Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agentsSquaraine dyesPhotostabilityPhotodynamic activityFluorescence probesHuman Serum AlbuminCiências Naturais::Ciências QuímicasScience & TechnologyFour squaraine dyes derived from 2,3,3-trimethylindolenine and 1,1,2-trimethyl-1H-benzo[e]indole with different combinations of barbituric groups attach to the central ring, having ester groups and alkyl chains in the nitrogen atoms of heterocyclic rings were synthesized. These dyes were fully characterized and their photophysical behavior was studied in ethanol and phosphate-buffered saline solution. Absorption and emission bands between 631 and 712 nm were detected, with the formation of aggregates in aqueous media, which is typical of this class of dyes. Tests carried out with 1,3-diphenylisobenzofuran allowed us to verify the ability of the dyes to produce singlet oxygen. The interaction of synthesized dyes with human serum albumin (HSA) was also evaluated, being demonstrated a linear correlation between fluorescence intensity and protein concentration. The antifungal potential of the dyes against the yeast Saccharomyces cerevisiae was evaluated using a broth microdilution assay. In order to test the photosensitizing capacity of the synthesized dyes, tests were carried out in the dark and with irradiation, using a custom-built light-emitting diode that emits close to the absorption wavelength of the studied dyes. The results showed that the interaction of dyes with HSA and the antifungal activity depends on the different structural modifications of the dyes.We thanks to Fundação para a Ciência e Tecnologia (FCT), Comissão de Coordenação e Desenvolvimento Regional do Norte (CCDR-N) and FEDER (European Fund for Regional Development)-COMPETEQREN-EU for financial support to the research centers CQ/UM (UIDB/00686/2020), CBMA (UID/BIA/04050/2020), CQ/VR (UID/QUI/UI0616/2019) and CICSUBI (POCI-01-0145-FEDER-007491), as well as PhD grants to V.S.D.G. (UMINHO/BD/43/2016) and J.C.C.F. (SFRH/BD/133207/2017).American Society for PhotobiologyUniversidade do MinhoGomes, Vanessa Sofia DiasFerreira, João C. C.Boto, Renato E. F.Almeida, PauloFernandes, Jose R.Sousa, Maria JoãoGonçalves, M. Sameiro T.Reis, Lucinda V.20222022-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/86830engV. S. D. Gomes, J. C. C. Ferreira, R E. F. Boto, P. Almeida, J. R. Fernandes, M. J. Sousa, M. S. T. Gonçalves, L. V. Reis, "Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents”, Photochemistry and Photobiology, 2022, 98(6), 1402–1417.0031-86551751-109710.1111/php.1362435348226https://onlinelibrary.wiley.com/doi/full/10.1111/php.13624info: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:RCAAP2023-10-14T01:22:45Zoai:repositorium.sdum.uminho.pt:1822/86830Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:35:32.577537Repositório 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 |
Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents |
title |
Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents |
spellingShingle |
Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents Gomes, Vanessa Sofia Dias Squaraine dyes Photostability Photodynamic activity Fluorescence probes Human Serum Albumin Ciências Naturais::Ciências Químicas Science & Technology |
title_short |
Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents |
title_full |
Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents |
title_fullStr |
Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents |
title_full_unstemmed |
Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents |
title_sort |
Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents |
author |
Gomes, Vanessa Sofia Dias |
author_facet |
Gomes, Vanessa Sofia Dias Ferreira, João C. C. Boto, Renato E. F. Almeida, Paulo Fernandes, Jose R. Sousa, Maria João Gonçalves, M. Sameiro T. Reis, Lucinda V. |
author_role |
author |
author2 |
Ferreira, João C. C. Boto, Renato E. F. Almeida, Paulo Fernandes, Jose R. Sousa, Maria João Gonçalves, M. Sameiro T. Reis, Lucinda V. |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Gomes, Vanessa Sofia Dias Ferreira, João C. C. Boto, Renato E. F. Almeida, Paulo Fernandes, Jose R. Sousa, Maria João Gonçalves, M. Sameiro T. Reis, Lucinda V. |
dc.subject.por.fl_str_mv |
Squaraine dyes Photostability Photodynamic activity Fluorescence probes Human Serum Albumin Ciências Naturais::Ciências Químicas Science & Technology |
topic |
Squaraine dyes Photostability Photodynamic activity Fluorescence probes Human Serum Albumin Ciências Naturais::Ciências Químicas Science & Technology |
description |
Four squaraine dyes derived from 2,3,3-trimethylindolenine and 1,1,2-trimethyl-1H-benzo[e]indole with different combinations of barbituric groups attach to the central ring, having ester groups and alkyl chains in the nitrogen atoms of heterocyclic rings were synthesized. These dyes were fully characterized and their photophysical behavior was studied in ethanol and phosphate-buffered saline solution. Absorption and emission bands between 631 and 712 nm were detected, with the formation of aggregates in aqueous media, which is typical of this class of dyes. Tests carried out with 1,3-diphenylisobenzofuran allowed us to verify the ability of the dyes to produce singlet oxygen. The interaction of synthesized dyes with human serum albumin (HSA) was also evaluated, being demonstrated a linear correlation between fluorescence intensity and protein concentration. The antifungal potential of the dyes against the yeast Saccharomyces cerevisiae was evaluated using a broth microdilution assay. In order to test the photosensitizing capacity of the synthesized dyes, tests were carried out in the dark and with irradiation, using a custom-built light-emitting diode that emits close to the absorption wavelength of the studied dyes. The results showed that the interaction of dyes with HSA and the antifungal activity depends on the different structural modifications of the dyes. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022 2022-01-01T00:00:00Z |
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/1822/86830 |
url |
https://hdl.handle.net/1822/86830 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
V. S. D. Gomes, J. C. C. Ferreira, R E. F. Boto, P. Almeida, J. R. Fernandes, M. J. Sousa, M. S. T. Gonçalves, L. V. Reis, "Squaraine dyes derived from indolenine and benzo[e]indole as potential fluorescent probes for HSA detection and antifungal agents”, Photochemistry and Photobiology, 2022, 98(6), 1402–1417. 0031-8655 1751-1097 10.1111/php.13624 35348226 https://onlinelibrary.wiley.com/doi/full/10.1111/php.13624 |
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 |
American Society for Photobiology |
publisher.none.fl_str_mv |
American Society for Photobiology |
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 |
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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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