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

Analytical Chemistry, Год журнала: 2025, Номер unknown

Опубликована: Апрель 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.

Язык: Английский

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Effect of Iodine, and Polar Group Substitutions at α,β,$$ \alpha, \beta, $$ and meso$$ meso $$‐Positions on Some Photophysical Properties of BODIPY‐Based Photosensitizers Relevant to Photodynamic Therapy

Journal of Computational Chemistry, Год журнала: 2025, Номер 46(15)

Опубликована: Июнь 4, 2025

ABSTRACT BODIPY‐based photosensitizers are well‐known for their two‐photon (TP) activity. The BODIPY core can be substituted at three distinct positions: , and . Current literature suggests that substitutions the position most commonly preferred due to labile nature, which makes synthesis easier. However, there has been no systematic study investigating how of impacts TP activity systems. Furthermore, we found reports addressing effects heavy atoms, such as iodine, on this property. To fill these gaps, work presents a investigation substitution iodine position, along with few polar groups other positions in core, affects For purpose, 36 systems were designed one‐ activities studied computationally using state‐of‐the‐art resolution‐of‐identity coupled cluster doubles method. explain effect nature activity, used three‐state model. Further, also performed molecular docking dynamics simulations interaction molecules Human Serum Albumin (HSA) protein. Our findings suggest substituting increases Additionally, observed results larger compared positions. Molecular simulation revealed interact HSA, complexes formed stable throughout period.

Язык: 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, Год журнала: 2024, Номер 54(2), С. 674 - 682

Опубликована: Ноя. 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.

Язык: Английский

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

Dyes and Pigments, Год журнала: 2024, Номер 233, С. 112537 - 112537

Опубликована: Ноя. 12, 2024

Язык: Английский

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