RT Journal Article
T1 Halogen-free photosensitizers based on meso-enamine-BODIPYs for bioimaging and photodynamic therapy
A1 Prieto  Montero, Ruth
A1 Díaz Andrés, Aitor
A1 Prieto Castañeda, Alejandro
A1 Tabero Truchado, Andrea
A1 Longarte Aldama, Asier
A1 Rodríguez Agarrabeitia, Antonia
A1 Villanueva Oroquieta, Ángeles
A1 Ortiz García, María Josefa
A1 Montero Santos, Raul
A1 Casanova, David
A1 Martínez Martínez, Virginia
AB 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.
PB The Royal Society of Chemistry
SN 2050-750X
YR 2022
FD 2022-11-23
LK https://hdl.handle.net/20.500.14352/73234
UL https://hdl.handle.net/20.500.14352/73234
LA eng
NO 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 GobiernoVasco (project no. IT1639-22 and PIBA19-0004). R. P.-M. andA. D. A. thank UPV/EHU, MIU and NGEU for their respectivepostdoctoral (MARSA21/71) and predoctoral (PRE2020-092036)fellowships. We also thank the SGIker Laser Facility of the UPV/EHU for technical support.
NO Ministerio de Ciencia, Innovación y Universidades (España)
NO Gobierno vasco (España)
DS Docta Complutense
RD 13 abr 2025