Red haloBODIPYs as theragnostic agents: The role of the substitution at meso position

Three different molecular designs based on BODIPY dye have been proposed as photosensitizers (PSs) for photodynamic therapy (PDT) by the inclusion of halogen atoms (Iodine) at 2,6-positions and with extended conjugation at 3, 5-positions and varying the substitution at meso position. The synthesis i...

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Bibliographic Details
Authors: Prieto Montero, Ruth, Prieto Castañeda, Alejandro, Katsumiti, Alberto, Sola Llano, Rebeca, Rodríguez Agarrabeitia, Antonia, Cajaraville, Miren P., Ortiz García, María Josefa, Martínez Martínez, Virginia
Format: article
Publication Date:2021
Country:España
Institution:Universidad Complutense de Madrid (UCM)
Repository:Docta Complutense
Language:English
OAI Identifier:oai:docta.ucm.es:20.500.14352/4603
Online Access:https://hdl.handle.net/20.500.14352/4603
Access Level:Open access
Keyword:547.1:615.8
543.426
615.8
BODIPY photosensitizer
Singlet oxygen
Photodynamic therapy
HeLa cells
Theragnosis
Química física (Física)
Química orgánica (Química)
2210 Química Física
2306 Química Orgánica
Description
Summary:Three different molecular designs based on BODIPY dye have been proposed as photosensitizers (PSs) for photodynamic therapy (PDT) by the inclusion of halogen atoms (Iodine) at 2,6-positions and with extended conjugation at 3, 5-positions and varying the substitution at meso position. The synthesis is described and their main photophysical features including singlet oxygen production and triplet states were characterized by absorption and fluorescence spectroscopy (steady-state and time-correlated) and nanosecond transient absorption spectroscopy. The results were compared with the commercial Chlorin e6. The three new red-halogen-BODIPYs showed a great balance between singlet oxygen generation (ΦΔ≥0.40) and fluorescence (Φfl≥0.22) for potential application on PDT, and particularly in theragnosis. In vitro experiments in HeLa cells were done to study their performance and to elucidate the best potential candidate for PDT.