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Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms

dc.contributor.authorAmendoeira, Ana F.
dc.contributor.authorLuz, André
dc.contributor.authorValente, Ruben
dc.contributor.authorRoma-Rodrigues, Catarina
dc.contributor.authorAli, Hasrat
dc.contributor.authorvan Lier, Johan E.
dc.contributor.authorMarques, Fernanda
dc.contributor.authorBaptista, Pedro V.
dc.contributor.authorFernandes, Alexandra R.
dc.contributor.institutionDCV - Departamento de Ciências da Vida
dc.contributor.institutionUCIBIO - Applied Molecular Biosciences Unit
dc.contributor.pblMDPI - Multidisciplinary Digital Publishing Institute
dc.date.accessioned2023-07-04T22:16:56Z
dc.date.available2023-07-04T22:16:56Z
dc.date.issued2023-02-10
dc.descriptionFunding 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.
dc.description.abstractEstradiol-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.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent22
dc.format.extent4710418
dc.identifier.doi10.3390/ijms24043600
dc.identifier.issn1661-6596
dc.identifier.otherPURE: 65198394
dc.identifier.otherPURE UUID: 16cbbf10-b17f-49b4-8690-3c9b54d9c627
dc.identifier.otherScopus: 85149017122
dc.identifier.otherWOS: 000945171300001
dc.identifier.otherPubMed: 36835012
dc.identifier.otherPubMedCentral: PMC9963437
dc.identifier.otherORCID: /0000-0001-5255-7095/work/151383880
dc.identifier.otherORCID: /0000-0003-2054-4438/work/151392207
dc.identifier.urihttp://hdl.handle.net/10362/154838
dc.identifier.urlhttps://www.scopus.com/pages/publications/85149017122
dc.language.isoeng
dc.peerreviewedyes
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04378%2F2020/PT
dc.relationApplied Molecular Biosciences Unit
dc.relationApplied Molecular Biosciences Unit
dc.relationInstitute for Health and Bioeconomy
dc.relationExoNANOsi - Exosomes as mediators of inter and intra-cellular trafficking of therapeutic gold nanoparticles as vectors for gene silencing
dc.relationinfo:eu-repo/grantAgreement/FCT/OE/SFRH%2FBPD%2F124612%2F2016/PT
dc.subjectandrogen-BODIPY conjugates
dc.subjectestradiol-BODIPY conjugates
dc.subjectfluorescence imaging
dc.subjectphotodynamic therapy
dc.subjectphotosensitizers
dc.subjectreceptor-mediated cell uptake
dc.subjectCatalysis
dc.subjectMolecular Biology
dc.subjectSpectroscopy
dc.subjectComputer Science Applications
dc.subjectPhysical and Theoretical Chemistry
dc.subjectOrganic Chemistry
dc.subjectInorganic Chemistry
dc.subjectSDG 3 - Good Health and Well-being
dc.titleCell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanismsen
dc.title.subtitleCancer Theranostic Dyesen
dc.typejournal article
degois.publication.issue4
degois.publication.titleInternational Journal of Molecular Sciences
degois.publication.volume24
dspace.entity.typePublication
oaire.awardNumberUIDP/04378/2020
oaire.awardNumberUIDB/04378/2020
oaire.awardNumberLA/P/0140/2020
oaire.awardNumberSFRH/BPD/124612/2016
oaire.awardTitleApplied Molecular Biosciences Unit
oaire.awardTitleApplied Molecular Biosciences Unit
oaire.awardTitleInstitute for Health and Bioeconomy
oaire.awardTitleExoNANOsi - Exosomes as mediators of inter and intra-cellular trafficking of therapeutic gold nanoparticles as vectors for gene silencing
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F04378%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F04378%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/LA%2FP%2F0140%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/OE/SFRH%2FBPD%2F124612%2F2016/PT
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStreamOE
project.funder.identifierhttp://doi.org/10.13039/501100001871
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project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccess
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