Synthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones

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dc.contributor.authorInsuasty, Daniel
dc.contributor.authorMutis, Mario
dc.contributor.authorTrilleras, Jorge
dc.contributor.authorIllicachi, Luis A.
dc.contributor.authorRodriguez, Juan D.
dc.contributor.authorRamos-Hernandez, Andrea
dc.contributor.authorSan-Juan-Vergara, Homero G.
dc.contributor.authorCadena-Cruz, Christian
dc.contributor.authorMora, Jose R.
dc.contributor.authorPaz, Jose L.
dc.contributor.authorMendez-Lopez, Maximiliano
dc.contributor.authorPerez, Edwin G.
dc.contributor.authorAliaga, Margarita E.
dc.contributor.authorValencia, Jhesua
dc.contributor.authorMarquez, Edgar
dc.date.accessioned2025-01-20T17:06:05Z
dc.date.available2025-01-20T17:06:05Z
dc.date.issued2024
dc.description.abstractIn this article, three unsymmetrical 7-(diethylamino)quinolone chalcones with D-pi-A-D and D-pi-A-pi-D type push-pull molecular arrangements were synthesized via a Claisen-Schmidt reaction. Using 7-(diethylamino)quinolone and vanillin as electron donor (D) moieties, these were linked together through the alpha,beta-unsaturated carbonyl system acting as a linker and an electron acceptor (A). The photophysical properties were studied, revealing significant Stokes shifts and strong solvatofluorochromism caused by the ICT and TICT behavior produced by the push-pull effect. Moreover, quenching caused by the population of the TICT state in THF-H2O mixtures was observed, and the emission in the solid state evidenced a red shift compared to the emission in solution. These findings were corroborated by density functional theory (DFT) calculations employing the wb97xd/6-311G(d,p) method. The cytotoxic activity of the synthesized compounds was assessed on BHK-21, PC3, and LNCaP cell lines, revealing moderate activity across all compounds. Notably, compound 5b exhibited the highest activity against LNCaP cells, with an LC50 value of 10.89 mu M. Furthermore, the compounds were evaluated for their potential as imaging agents in living prostate cells. The results demonstrated their favorable cell permeability and strong emission at 488 nm, positioning them as promising candidates for cancer cell imaging applications.
dc.fuente.origenWOS
dc.identifier.doi10.1021/acsomega.3c07242
dc.identifier.issn2470-1343
dc.identifier.urihttps://doi.org/10.1021/acsomega.3c07242
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/90753
dc.identifier.wosidWOS:001203655300001
dc.issue.numero17
dc.language.isoen
dc.pagina.final18800
dc.pagina.inicio18786
dc.revistaAcs omega
dc.rightsacceso restringido
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleSynthesis, Photophysical Properties, Theoretical Studies, and Living Cancer Cell Imaging Applications of New 7-(Diethylamino)quinolone Chalcones
dc.typeartículo
dc.volumen9
sipa.indexWOS
sipa.trazabilidadWOS;2025-01-12
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