Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms

Detalhes bibliográficos
Autor(a) principal: Amendoeira, Ana F.
Data de Publicação: 2023
Outros Autores: Luz, André, Valente, Ruben, Roma-Rodrigues, Catarina, Ali, Hasrat, van Lier, Johan E., Marques, Fernanda, Baptista, Pedro V., Fernandes, Alexandra R.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/154838
Resumo: Funding Information: This work was financed by national funds from FCT—Fundação para a Ciência e a Tecnologia, I.P., within the scope of the projects of the Ministry of Science Technology and Higher Education: the project of the Associate Laboratory Institute for Health and Bioeconomy—i4HB and, in part, by the Jeanne and J.-Louis Lévesque foundation, Montreal, QC, Canada (J.E.v.L.). J.E.v.L. is a member of the Research Center of the CHUS (CRCHUS), Sherbrooke, QC, Canada, supported by the Fonds de la Recherche du Québec—Santé. C.R.R., A.L. and R.V. were funded by FCT/MCTES, grant numbers SFRH/BD/12161/2022, and SFRH/BD/09845/2022, respectively. Publisher Copyright: © 2023 by the authors.
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spelling Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization MechanismsCancer Theranostic Dyesandrogen-BODIPY conjugatesestradiol-BODIPY conjugatesfluorescence imagingphotodynamic therapyphotosensitizersreceptor-mediated cell uptakeCatalysisMolecular BiologySpectroscopyComputer Science ApplicationsPhysical and Theoretical ChemistryOrganic ChemistryInorganic ChemistrySDG 3 - Good Health and Well-beingFunding Information: This work was financed by national funds from FCT—Fundação para a Ciência e a Tecnologia, I.P., within the scope of the projects of the Ministry of Science Technology and Higher Education: the project of the Associate Laboratory Institute for Health and Bioeconomy—i4HB and, in part, by the Jeanne and J.-Louis Lévesque foundation, Montreal, QC, Canada (J.E.v.L.). J.E.v.L. is a member of the Research Center of the CHUS (CRCHUS), Sherbrooke, QC, Canada, supported by the Fonds de la Recherche du Québec—Santé. C.R.R., A.L. and R.V. were funded by FCT/MCTES, grant numbers SFRH/BD/12161/2022, and SFRH/BD/09845/2022, respectively. Publisher Copyright: © 2023 by the authors.Estradiol-BODIPY linked via an 8-carbon spacer chain and 19-nortestosterone- and testosterone-BODIPY linked via an ethynyl spacer group were evaluated for cell uptake in the breast cancer cell lines MCF-7 and MDA-MB-231 and prostate cancer cell lines PC-3 and LNCaP, as well as in normal dermal fibroblasts, using fluorescence microscopy. The highest level of internalization was observed with 11β-OMe-estradiol-BODIPY 2 and 7α-Me-19-nortestosterone-BODIPY 4 towards cells expressing their specific receptors. Blocking experiments showed changes in non-specific cell uptake in the cancer and normal cells, which likely reflect differences in the lipophilicity of the conjugates. The internalization of the conjugates was shown to be an energy-dependent process that is likely mediated by clathrin- and caveolae-endocytosis. Studies using 2D co-cultures of cancer cells and normal fibroblasts showed that the conjugates are more selective towards cancer cells. Cell viability assays showed that the conjugates are non-toxic for cancer and/or normal cells. Visible light irradiation of cells incubated with estradiol-BODIPYs 1 and 2 and 7α-Me-19-nortestosterone-BODIPY 4 induced cell death, suggesting their potential for use as PDT agents.DCV - Departamento de Ciências da VidaUCIBIO - Applied Molecular Biosciences UnitRUNAmendoeira, Ana F.Luz, AndréValente, RubenRoma-Rodrigues, CatarinaAli, Hasratvan Lier, Johan E.Marques, FernandaBaptista, Pedro V.Fernandes, Alexandra R.2023-07-04T22:16:56Z2023-02-102023-02-10T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article22application/pdfhttp://hdl.handle.net/10362/154838eng1661-6596PURE: 65198394https://doi.org/10.3390/ijms24043600info: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:RCAAP2024-03-11T05:37:17Zoai:run.unl.pt:10362/154838Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:55:46.983797Repositório 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 Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms
Cancer Theranostic Dyes
title Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms
spellingShingle Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms
Amendoeira, Ana F.
androgen-BODIPY conjugates
estradiol-BODIPY conjugates
fluorescence imaging
photodynamic therapy
photosensitizers
receptor-mediated cell uptake
Catalysis
Molecular Biology
Spectroscopy
Computer Science Applications
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
SDG 3 - Good Health and Well-being
title_short Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms
title_full Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms
title_fullStr Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms
title_full_unstemmed Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms
title_sort Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms
author Amendoeira, Ana F.
author_facet Amendoeira, Ana F.
Luz, André
Valente, Ruben
Roma-Rodrigues, Catarina
Ali, Hasrat
van Lier, Johan E.
Marques, Fernanda
Baptista, Pedro V.
Fernandes, Alexandra R.
author_role author
author2 Luz, André
Valente, Ruben
Roma-Rodrigues, Catarina
Ali, Hasrat
van Lier, Johan E.
Marques, Fernanda
Baptista, Pedro V.
Fernandes, Alexandra R.
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv DCV - Departamento de Ciências da Vida
UCIBIO - Applied Molecular Biosciences Unit
RUN
dc.contributor.author.fl_str_mv Amendoeira, Ana F.
Luz, André
Valente, Ruben
Roma-Rodrigues, Catarina
Ali, Hasrat
van Lier, Johan E.
Marques, Fernanda
Baptista, Pedro V.
Fernandes, Alexandra R.
dc.subject.por.fl_str_mv androgen-BODIPY conjugates
estradiol-BODIPY conjugates
fluorescence imaging
photodynamic therapy
photosensitizers
receptor-mediated cell uptake
Catalysis
Molecular Biology
Spectroscopy
Computer Science Applications
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
SDG 3 - Good Health and Well-being
topic androgen-BODIPY conjugates
estradiol-BODIPY conjugates
fluorescence imaging
photodynamic therapy
photosensitizers
receptor-mediated cell uptake
Catalysis
Molecular Biology
Spectroscopy
Computer Science Applications
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry
SDG 3 - Good Health and Well-being
description Funding Information: This work was financed by national funds from FCT—Fundação para a Ciência e a Tecnologia, I.P., within the scope of the projects of the Ministry of Science Technology and Higher Education: the project of the Associate Laboratory Institute for Health and Bioeconomy—i4HB and, in part, by the Jeanne and J.-Louis Lévesque foundation, Montreal, QC, Canada (J.E.v.L.). J.E.v.L. is a member of the Research Center of the CHUS (CRCHUS), Sherbrooke, QC, Canada, supported by the Fonds de la Recherche du Québec—Santé. C.R.R., A.L. and R.V. were funded by FCT/MCTES, grant numbers SFRH/BD/12161/2022, and SFRH/BD/09845/2022, respectively. Publisher Copyright: © 2023 by the authors.
publishDate 2023
dc.date.none.fl_str_mv 2023-07-04T22:16:56Z
2023-02-10
2023-02-10T00:00:00Z
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/10362/154838
url http://hdl.handle.net/10362/154838
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1661-6596
PURE: 65198394
https://doi.org/10.3390/ijms24043600
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 22
application/pdf
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
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instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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