Halogen-free photosensitizers based on meso -enamine-BODIPYs for bioimaging and photodynamic therapy.
Ruth Prieto-MonteroAitor Díaz AndresAlejandro Prieto-CastañedaAndrea TaberoAsier LongarteAntonia R AgarrabeitiaAngeles VillanuevaMaria J OrtizRaúl MonteroDavid CasanovaVirginia Martínez-MartínezPublished in: Journal of materials chemistry. B (2022)
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.
Keyphrases
- photodynamic therapy
- density functional theory
- molecular dynamics
- fluorescent probe
- living cells
- cell cycle arrest
- single molecule
- energy transfer
- fluorescence imaging
- induced apoptosis
- cell death
- quantum dots
- molecular docking
- dengue virus
- high throughput
- pi k akt
- optical coherence tomography
- solar cells
- solid phase extraction
- ionic liquid
- endoplasmic reticulum stress
- electron transfer
- zika virus
- molecularly imprinted
- risk assessment
- aedes aegypti
- liquid chromatography
- mass spectrometry
- monte carlo
- electron microscopy