Fast Imaging of Mitochondria and Efficient Generation of Singlet Oxygen by Red Fluorescent BODIPY Photosensitizers

Analytical Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 9, 2025

The biomedical applications of BODIPY fluorophores are limited by challenges such as short-wavelength emission, high hydrophobicity, and poor selectivity. To address these issues, two water-soluble red-emitting derivatives, namely, PSPyBDP I-PSPyBDP, were synthesized conjugating pyridine units to the core, followed ring-opening reactions with 1,3-propanesulfonate. Notably, showed fast mitochondrial imaging capability (∼5 min), indicating its potential an alternative mitochondria tracker. heavy-atom effect, could effectively produce singlet oxygen (1O2) under irradiation at 660 nm in a short time (∼1 min) 1O2 quantum yield 0.89. Cytotoxicity assays revealed that derivatives exhibited phototoxicity HeLa cells while maintaining low dark toxicity. Interestingly, they had toxicity against normal COS-7 cells. Confocal flow cytometry confirmed increase intracellular reactive species (ROS), reduce membrane potential, induce apoptosis upon irradiation. These findings suggest their promising application photodynamic therapy (PDT) for tumors.

Language: Английский

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Thieno[3,2-b]thiophene based-bridged BODIPY dimer: synthesis, e-chem, one- and two-photon photophysical properties

Dalton Transactions, Journal Year: 2024, Volume and Issue: 54(2), P. 674 - 682

Published: Nov. 12, 2024

Four BODIPY dyes (6a-6d) with electron-donating or electron-withdrawing groups at the meso-position were synthesized by Sonogashira coupling reaction of 2,5-diethynylthieno[3,2-b]thiophene mono-iodo-BODIPY moieties. All compounds fully characterized 1H NMR and MALDI-TOF MS. Their photophysical electrochemical properties studied UV-visible absorption spectroscopy, steady-state time-resolved fluorescence two-photon excitation spectroscopy cyclic voltammetry. These conjugated exhibit interesting such as a high molar extinction coefficient, large Stokes shift cross section σ2.

Language: Английский

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Palladium catalyzed homocoupling reactions of gem-dibromo BODIPYs: Formation of dimer and trimer products

Dyes and Pigments, Journal Year: 2024, Volume and Issue: 233, P. 112537 - 112537

Published: Nov. 12, 2024

Language: Английский

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