Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines
Autor(a) principal: | |
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Data de Publicação: | 2020 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/65640 |
Resumo: | Photodynamic therapy is an innovative treatment approach broadly directed towards oncological diseases. Its applicability and efficiency are closely related to the interaction of three main components, namely a photosensitizer, light and molecular triplet oxygen, which should drive cell death. Recently, several studies have demonstrated that squaraine cyanine dyes have a set of photophysical and photochemical properties that have made of these compounds’ potential photosensitizers for this therapeutic modality. In the present research work, we describe the synthesis and characterization of four quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes. Except for the precursor of aminosquaraine dyes, i.e., O-methylated derivative, all dyes were evaluated for their behavior and absorption capacity in different organic and aqueous solvents, their ability to form singlet oxygen, their light-stability, and in vitro phototherapeutic effects against two human breast cancer cell cultures (BT-474 and MCF-7). Regardless of the nature of the used solvents, the synthesized dyes showed intense absorption in the red and near-infrared spectral regions, despite the formation of aggregates in aqueous media. Dyes showed high light-stability against light exposure. Despite the low ability to produce singlet oxygen, aminosquaraine dyes demonstrated worthy in vitro phototherapeutic activity. |
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Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell linesbreast cancerphototherapeutic effectssinglet oxygenlight-stabilityquinolinebenzoselenazoleunsymmetrical squaraine dyesScience & TechnologyPhotodynamic therapy is an innovative treatment approach broadly directed towards oncological diseases. Its applicability and efficiency are closely related to the interaction of three main components, namely a photosensitizer, light and molecular triplet oxygen, which should drive cell death. Recently, several studies have demonstrated that squaraine cyanine dyes have a set of photophysical and photochemical properties that have made of these compounds’ potential photosensitizers for this therapeutic modality. In the present research work, we describe the synthesis and characterization of four quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes. Except for the precursor of aminosquaraine dyes, i.e., O-methylated derivative, all dyes were evaluated for their behavior and absorption capacity in different organic and aqueous solvents, their ability to form singlet oxygen, their light-stability, and in vitro phototherapeutic effects against two human breast cancer cell cultures (BT-474 and MCF-7). Regardless of the nature of the used solvents, the synthesized dyes showed intense absorption in the red and near-infrared spectral regions, despite the formation of aggregates in aqueous media. Dyes showed high light-stability against light exposure. Despite the low ability to produce singlet oxygen, aminosquaraine dyes demonstrated worthy in vitro phototherapeutic activity.This research was funded by the European Investment Funds by FEDER/COMPETE/POCI under projects POCI-01-0145-FEDER-006958 (CITAB) and POCI-01-0145-FEDER-007491 (CICS-UBI) and Funds by FCT—Portuguese Foundation for Science and technology, under the projects UIDB/ 04033/2020 (CITAB) and UIDB/ 00616/2020 (CQ-VR). This work was also supported by funds from the Health Sciences Research Center (CICS-UBI) through National Funds by FCT—Foundation for Science and Technology (UID/Multi/00709/2019).The research at iBB was supported by Project UID/NAN/50024/2019 and M-ERA-NET/0002/2015 from FCT. E.L. was supported by the FCT PhD grant SFRH/BD/147645/2019.info:eu-repo/semantics/publishedVersionMDPI PublishingUniversidade do MinhoLima, EuricoBoto, Renato E.Ferreira, DianaFernandes, José R.Almeida, PauloFerreira, Luis F. V.Souto, Eliana B.Silva, Amélia M.Reis, Lucinda V.2020-06-102020-06-10T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/65640engLima, Eurico; Boto, Renato E.; Ferreira, Diana; Fernandes, José R.; Almeida, Paulo; Ferreira, Luis F. V.; Souto, Eliana; Silva, Amélia M.; Reis, Lucinda V., Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines. Materials, 13(11), 2646, 20201996-194410.3390/ma13112646http://www.mdpi.com/journal/materialsinfo: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:RCAAP2023-07-21T12:26:15Zoai:repositorium.sdum.uminho.pt:1822/65640Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:20:38.169429Repositório 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 |
Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines |
title |
Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines |
spellingShingle |
Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines Lima, Eurico breast cancer phototherapeutic effects singlet oxygen light-stability quinoline benzoselenazole unsymmetrical squaraine dyes Science & Technology |
title_short |
Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines |
title_full |
Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines |
title_fullStr |
Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines |
title_full_unstemmed |
Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines |
title_sort |
Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines |
author |
Lima, Eurico |
author_facet |
Lima, Eurico Boto, Renato E. Ferreira, Diana Fernandes, José R. Almeida, Paulo Ferreira, Luis F. V. Souto, Eliana B. Silva, Amélia M. Reis, Lucinda V. |
author_role |
author |
author2 |
Boto, Renato E. Ferreira, Diana Fernandes, José R. Almeida, Paulo Ferreira, Luis F. V. Souto, Eliana B. Silva, Amélia M. Reis, Lucinda V. |
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 |
Lima, Eurico Boto, Renato E. Ferreira, Diana Fernandes, José R. Almeida, Paulo Ferreira, Luis F. V. Souto, Eliana B. Silva, Amélia M. Reis, Lucinda V. |
dc.subject.por.fl_str_mv |
breast cancer phototherapeutic effects singlet oxygen light-stability quinoline benzoselenazole unsymmetrical squaraine dyes Science & Technology |
topic |
breast cancer phototherapeutic effects singlet oxygen light-stability quinoline benzoselenazole unsymmetrical squaraine dyes Science & Technology |
description |
Photodynamic therapy is an innovative treatment approach broadly directed towards oncological diseases. Its applicability and efficiency are closely related to the interaction of three main components, namely a photosensitizer, light and molecular triplet oxygen, which should drive cell death. Recently, several studies have demonstrated that squaraine cyanine dyes have a set of photophysical and photochemical properties that have made of these compounds’ potential photosensitizers for this therapeutic modality. In the present research work, we describe the synthesis and characterization of four quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes. Except for the precursor of aminosquaraine dyes, i.e., O-methylated derivative, all dyes were evaluated for their behavior and absorption capacity in different organic and aqueous solvents, their ability to form singlet oxygen, their light-stability, and in vitro phototherapeutic effects against two human breast cancer cell cultures (BT-474 and MCF-7). Regardless of the nature of the used solvents, the synthesized dyes showed intense absorption in the red and near-infrared spectral regions, despite the formation of aggregates in aqueous media. Dyes showed high light-stability against light exposure. Despite the low ability to produce singlet oxygen, aminosquaraine dyes demonstrated worthy in vitro phototherapeutic activity. |
publishDate |
2020 |
dc.date.none.fl_str_mv |
2020-06-10 2020-06-10T00:00:00Z |
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 |
http://hdl.handle.net/1822/65640 |
url |
http://hdl.handle.net/1822/65640 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Lima, Eurico; Boto, Renato E.; Ferreira, Diana; Fernandes, José R.; Almeida, Paulo; Ferreira, Luis F. V.; Souto, Eliana; Silva, Amélia M.; Reis, Lucinda V., Quinoline- and benzoselenazole-derived unsymmetrical squaraine cyanine dyes: design, synthesis, photophysicochemical features and light-triggerable antiproliferative effects against breast cancer cell lines. Materials, 13(11), 2646, 2020 1996-1944 10.3390/ma13112646 http://www.mdpi.com/journal/materials |
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 |
MDPI Publishing |
publisher.none.fl_str_mv |
MDPI Publishing |
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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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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