2026-06-29T07:26:02Zhttps://docta.ucm.es/rest/oai/request

oai:docta.ucm.es:20.500.14352/732342025-04-23T00:02:58Zcom_20.500.14352_14col_20.500.14352_15

Halogen-free photosensitizers based on meso-enamine-BODIPYs for bioimaging and photodynamic therapy Prieto Montero, Ruth Díaz Andrés, Aitor Prieto Castañeda, Alejandro Tabero Truchado, Andrea Longarte Aldama, Asier Rodríguez Agarrabeitia, Antonia Villanueva Oroquieta, Ángeles Ortiz García, María Josefa Montero Santos, Raul Casanova, David Martínez Martínez, Virginia 543.426 547 Photosensitizers PSs Photodynamic therapy PDT BODIPYs Bioimaging Química orgánica (Química) Técnicas de la imagen 2306 Química Orgánica This work was funded by MCIN/AEI/10.13039/501100011033 (projects no. PID2020-114347RB-C32, PID2020-114755GB-C31, PID2019-109555GB-I00 and RED2018-102815-T) and Gobierno Vasco (project no. IT1639-22 and PIBA19-0004). R. P.-M. and A. D. A. thank UPV/EHU, MIU and NGEU for their respective postdoctoral (MARSA21/71) and predoctoral (PRE2020-092036) fellowships. We also thank the SGIker Laser Facility of the UPV/ EHU for technical support. The search for efficient heavy atom free photosensitizers (PSs) for photodynamic therapy (PDT) is a very active field. We describe herein a simple and easily accessible molecular design based on the attachment of an enamine group as an electron-donor moiety at the meso position of the BODIPY core with different alkylation patterns. The effect of the alkylation degree and solvent polarity on the photophysical properties in terms of splitting absorption bands, fluorescence efficiencies and singlet oxygen production is analyzed in depth experimentally using spectroscopic techniques, including femtosecond and nanosecond transient absorption (fs- and ns-TA) and using computational simulations based on time-dependent density functional theory. The correlation between the theoretical/experimental results permits the rationalization of the observed photophysical behavior exhibited by meso-enamine-BODIPY compounds and the determination of mechanistic details, which rule the population of the triplet state manifold. The potential applicability as a theragnostic agent for the most promising compound is demonstrated through in vitro assays in HeLa cells by analyzing the internalization, localization and phototoxic action. Ministerio de Ciencia, Innovación y Universidades (España) Gobierno vasco (España) Sección Deptal. de Química Orgánica (Óptica y Optometría) Fac. de Óptica y Optometría TRUE pub 2023-06-22T12:50:02Z 2023-06-22T12:50:02Z 2022-11-23 journal article https://hdl.handle.net/20.500.14352/73234 2050-750X 10.1039/D2TB01515C eng info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-114347RB-C32/ES/DISEÑO, SINTESIS, PROPIEDADES FOTOFISICAS Y ACTIVIDAD ANTIMICROBIANA DE NANOPARTICULAS ORGANO%2FINORGANICA FOTOSENSIBILIZADAS/ info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2020-114755GB-C31/ES/CARACTERIZACION FOTONICA MULTI-PARAMETRICA Y APLICACIONES BIO-MEDICAS DE SONDAS MOLECULARES INTELIGENTES / info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-109555GB-I00/ES/PROCESOS FOTOFISICOS EN MOLECULAS, AGREGADOS MOLECULARES Y SOLIDOS MOLECULARES/ restricted access application/pdf application/pdf The Royal Society of Chemistry