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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 11\u03b2-OMe-estradiol-BODIPY 2 and 7\u03b1-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 7\u03b1-Me-19-nortestosterone-BODIPY 4 induced cell death, suggesting their potential for use as PDT agents.<\/jats:p>","DOI":"10.3390\/ijms24043600","type":"journal-article","created":{"date-parts":[[2023,2,13]],"date-time":"2023-02-13T03:28:46Z","timestamp":1676258926000},"page":"3600","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":6,"title":["Cell Uptake of Steroid-BODIPY Conjugates and Their Internalization Mechanisms: Cancer Theranostic Dyes"],"prefix":"10.3390","volume":"24","author":[{"given":"Ana F.","family":"Amendoeira","sequence":"first","affiliation":[{"name":"Associate Laboratory i4HB, Institute for Health and Bioeconomy, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"},{"name":"UCIBIO\u2014Applied Molecular Biosciences Unit, Department of Life Sciences, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7764-9033","authenticated-orcid":false,"given":"Andr\u00e9","family":"Luz","sequence":"additional","affiliation":[{"name":"Associate Laboratory i4HB, Institute for Health and Bioeconomy, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"},{"name":"UCIBIO\u2014Applied Molecular Biosciences Unit, Department of Life Sciences, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6534-4128","authenticated-orcid":false,"given":"Ruben","family":"Valente","sequence":"additional","affiliation":[{"name":"Associate Laboratory i4HB, Institute for Health and Bioeconomy, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"},{"name":"UCIBIO\u2014Applied Molecular Biosciences Unit, Department of Life Sciences, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8676-6562","authenticated-orcid":false,"given":"Catarina","family":"Roma-Rodrigues","sequence":"additional","affiliation":[{"name":"Associate Laboratory i4HB, Institute for Health and Bioeconomy, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"},{"name":"UCIBIO\u2014Applied Molecular Biosciences Unit, Department of Life Sciences, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"}]},{"given":"Hasrat","family":"Ali","sequence":"additional","affiliation":[{"name":"Department of Nuclear Medicine and Radiobiology, Faculty of Medicine and Health Sciences, University of Sherbrooke, Sherbrooke, QC J1H5N4, Canada"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2190-4557","authenticated-orcid":false,"given":"Johan E.","family":"van Lier","sequence":"additional","affiliation":[{"name":"Department of Nuclear Medicine and Radiobiology, Faculty of Medicine and Health Sciences, University of Sherbrooke, Sherbrooke, QC J1H5N4, Canada"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8440-5299","authenticated-orcid":false,"given":"Fernanda","family":"Marques","sequence":"additional","affiliation":[{"name":"Centro de Ci\u00eancias e Tecnologias Nucleares, Departamento de Engenharia e Ci\u00eancias Nucleares, Instituto Superior T\u00e9cnico, Universidade de Lisboa, Estrada Nacional 10, km 139.7, 2695-066 Bobadela, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5255-7095","authenticated-orcid":false,"given":"Pedro V.","family":"Baptista","sequence":"additional","affiliation":[{"name":"Associate Laboratory i4HB, Institute for Health and Bioeconomy, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"},{"name":"UCIBIO\u2014Applied Molecular Biosciences Unit, Department of Life Sciences, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2054-4438","authenticated-orcid":false,"given":"Alexandra R.","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Associate Laboratory i4HB, Institute for Health and Bioeconomy, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"},{"name":"UCIBIO\u2014Applied Molecular Biosciences Unit, Department of Life Sciences, NOVA School of Science and Technology, 2819-516 Caparica, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,2,10]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4891","DOI":"10.1021\/cr078381n","article-title":"BODIPY Dyes and Their Derivatives: Syntheses and Spectroscopic Properties","volume":"107","author":"Loudet","year":"2007","journal-title":"Chem. 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