Supramolecular complex of tetracationic porphyrin with acyclic cucurbituril-like container induces quantitative singlet oxygen generation. Phototoxicity studies in vitro in MCF-7 human breast cancer cells

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dc.article.number115388
dc.catalogadorjca
dc.contributor.authorDay, Skarlett
dc.contributor.authorPérez, Benjamín
dc.contributor.authorGuerra Díaz, Daniel
dc.contributor.authorMariño-Ocampo, Nory
dc.contributor.authorZúñiga-Núñez, Daniel
dc.contributor.authorFaúndez, Mario A.
dc.contributor.authorSoto-Arriaza, Marco
dc.contributor.authorPizarro, Nancy
dc.contributor.authorHeyne, Belinda
dc.contributor.authorFuentealba, Denis
dc.date.accessioned2023-12-19T18:30:06Z
dc.date.available2023-12-19T18:30:06Z
dc.date.issued2024
dc.description.abstractSinglet oxygen generation by porphyrin-based photosensitizers is one of the main strategies used in the photodynamic therapy of cancerous lesions. In this work, we report that the complexation of tetracationic 5,10,15,20-tetrakis(N-methylpiridinium-4-yl)porphyrin (TMPyP) with an acyclic cucurbituril-like container denominated M2C4 achieves quantitative generation of singlet oxygen. The complexation was studied by isothermal titration calorimetry, revealing a highly favored binding event controlled by enthalpic contributions, a stoichiometry of 1:1 and a high binding constant (K = (1.7 ± 0.2) × 107 M−1). Photophysical studies of the complex showed bathochromic shifts in the absorption bands, increased fluorescence emission quantum yield and lengthened fluorescence lifetime. Nonetheless, fluorescence emission was minor, being intersystem crossing with the consequent generation of singlet oxygen the main deactivation pathway for the excited state. All these properties were compared with the previously reported TMPyP and cucurbit[7]uril (CB[7]) complex, which showed a superiority of the acyclic complex in terms of quantum efficiencies. Phototoxicity studies in a breast cancer cell line (MCF-7) cultured in vitro, showed that the TMPyP@M2C4 complex is unable to enter the cells even after a 24 h incubation period. However, this issue could be circumvented by encapsulating the complex into liposomes which delivered the complex to the cells efficiently. Overall, this strategy showed good potential for a highly efficient photodynamic treatment using the TMPyP@M2C4 complex in liposomal formulations.
dc.fechaingreso.objetodigital2023-12-15
dc.fuente.origenORCID
dc.identifier.doi10.1016/j.jphotochem.2023.115388
dc.identifier.issn1010-6030
dc.identifier.urihttps://doi.org/10.1016/j.jphotochem.2023.115388
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/75544
dc.information.autorucEscuela de Química;Mariño Ocampo, Nory;S/I;1059618
dc.language.isoen
dc.nota.accesoContenido completo
dc.pagina.final8
dc.pagina.inicio1
dc.revistaJournal of Photochemistry & Photobiology, A: Chemistry
dc.rightsacceso abierto
dc.subjectSupramolecular complex
dc.subjectAcyclic cucurbituril
dc.subjectSinglet oxygen
dc.subjectPhotodynamic therapy
dc.subject.ddc510
dc.subject.deweyMatemática física y químicaes_ES
dc.titleSupramolecular complex of tetracationic porphyrin with acyclic cucurbituril-like container induces quantitative singlet oxygen generation. Phototoxicity studies in vitro in MCF-7 human breast cancer cells
dc.typeartículo
dc.volumen449
sipa.codpersvinculados1059618
sipa.trazabilidadORCID;2023-12-11
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