Exploring the photophysics of cinnamoyl-coumarin derivatives in cucurbit [7]uril complexes and assessing phototoxicity in HeLa cells

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dc.contributor.authorZuniga-Nunez, Daniel
dc.contributor.authorMura, Francisco
dc.contributor.authorMarino-Ocampo, Nory
dc.contributor.authorZuniga, Benjamin
dc.contributor.authorRobinson-Duggon, Jose
dc.contributor.authorZamora, Ricardo A.
dc.contributor.authorPoblete, Horacio
dc.contributor.authorAspee, Alexis
dc.contributor.authorFuentealba, Denis
dc.date.accessioned2025-01-20T16:14:27Z
dc.date.available2025-01-20T16:14:27Z
dc.date.issued2024
dc.description.abstractCinnamoyl-coumarin derivatives containing 5 or 12 carbon aliphatic chains were evaluated as photosensitizers and their photophysical properties were studied in detail. Moreover, these compounds were encapsulated in cucurbit[7]uril macrocycle with relatively high binding affinities in aqueous media. Fluorescence quantum yields, fluorescence lifetimes and singlet oxygen quantum yields were measured upon encapsulation. Computational DFT calculations and molecular dynamics simulations allowed the visualization of the binding modes of both derivatives inside the macrocycle. In particular, the free energy profiles for the insertion of the molecules into the macrocycle were determined to assess the most probable conformations of the complexes in water. In vitro phototoxicity assays were carried out in HeLa cells showed significant decreases in cell viability upon illumination of the 5 carbon aliphatic chain derivative at 460 nm with an LED source at different concentrations and enhanced by cucurbit[7]uril. However, the one with 12 carbon aliphatic chain did not display any phototoxicity regardless of the presence of cucurbit[7]uril. This behavior is related to the high lipophilicity introduced by a 12 carbon aliphatic chain conditioning its distribution on hydrophobic compartments and decreasing its phototoxicity. The enhanced phototoxicity elicited by cucurbit[7]uril on the 5 carbon aliphatic chain derivative but not in the 12 carbon derivative remark that there is a balance between hydrophobicity of these probes with the carrier properties of cucurbit[7]uril to be reach for effective phototoxicity properties.
dc.fuente.origenWOS
dc.identifier.doi10.1016/j.dyepig.2024.112290
dc.identifier.eissn1873-3743
dc.identifier.issn0143-7208
dc.identifier.urihttps://doi.org/10.1016/j.dyepig.2024.112290
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/90441
dc.identifier.wosidWOS:001258563800001
dc.language.isoen
dc.revistaDyes and pigments
dc.rightsacceso restringido
dc.subjectCinnamoyl-coumarin
dc.subjectCucurbit[7]uril
dc.subjectExcited state
dc.subjectSinglet oxygen
dc.subjectPhototoxicity
dc.subjectComplex
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleExploring the photophysics of cinnamoyl-coumarin derivatives in cucurbit [7]uril complexes and assessing phototoxicity in HeLa cells
dc.typeartículo
dc.volumen229
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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