Specific features of the interaction between chemical traps and phthalocyanine dyes affecting the measurement of the yield of reactive oxygen species

Gvozdev, D.A.; Ramonova, Alla A.; Maksimov, Eugene G.; Paschenko, V.Z.

doi:10.1016/j.dyepig.2020.108538

Cited by 7 publications

(3 citation statements)

References 14 publications

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“…In the inset of Figure 4, the change in the fluorescence intensity of AlPc8 and ZnPc8 is shown. Previously, we revealed that ZnPc8 is significantly less resistant to photobleaching than AlPc8 [24]. It can be seen that AlPc8 is photostable when a 1 µM solution is irradiated with monochromatic light (660 nm) in picosecond mode (50 MHz) for 20 min, while ZnPc8 is photobleached by ~4% under the same conditions.…”

Section: Temperature Dependence Of the Pcl Effectmentioning

confidence: 90%

The Role of the Photon Counting Loss Effect in Time-Resolved Measurements of Fluorescence Anisotropy

et al. 2023

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Determining the rate of rotation of molecules from their fluorescence anisotropy decay curves is a powerful method for studying molecular systems in biological applications. The single photon count detection systems used for this have a nonlinear dependence of the photon counting rate on the fluorescence intensity flux (photon counting loss effect), which can lead to a number of artifacts. Using metal complexes of phthalocyanines as a test sample, we have shown that such a nonlinearity can cause distortions in the determination of the fluorescence anisotropy lifetime and the asymptotic fluorescence anisotropy. We also assessed the dependence of the described phenomena on temperature and estimated the manifestations of the photon counting loss effect in the case of photobleaching of the fluorophores.

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Section: Temperature Dependence Of the Pcl Effectmentioning

confidence: 90%

The Role of the Photon Counting Loss Effect in Time-Resolved Measurements of Fluorescence Anisotropy

et al. 2023

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“…S5A), with 1 s of illumination followed by 5 s of dark adaptation, during which the absorption spectrum of the PS-DPBF solution was recorded. Data processing was performed as previously described ( Gvozdev et al., 2020 ).…”

Section: Methodsmentioning

confidence: 99%

Antiviral activity of singlet oxygen-photogenerating perylene compounds against SARS-CoV-2: Interaction with the viral envelope and photodynamic virion inactivation

et al. 2023

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“…where r is the rate of DPBF bleaching in solution of the photosensitizer (PS), A is the PS absorbance in the region of illumination, and index 0 represents reference PS (we used riboflavin with ϕ 0 ∆ = 0.51 in methanol [73]. The data processing procedure was performed as described earlier [74].…”

Section: Quantum Yields Of Singlet Oxygen Photogenerationmentioning

confidence: 99%

Alkyl Derivatives of Perylene Photosensitizing Antivirals: Towards Understanding the Influence of Lipophilicity

Mikhnovets,

Holoubek,

Panina

et al. 2023

IJMS

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Amphipathic perylene derivatives are broad-spectrum antivirals against enveloped viruses that act as fusion inhibitors in a light-dependent manner. The compounds target the lipid bilayer of the viral envelope using the lipophilic perylene moiety and photogenerating singlet oxygen, thereby causing damage to unsaturated lipids. Previous studies show that variation of the polar part of the molecule is important for antiviral activity. Here, we report modification of the lipophilic part of the molecule, perylene, by the introduction of 4-, 8-, and 12-carbon alkyls into position 9(10) of the perylene residue. Using Friedel–Crafts acylation and Wolff–Kishner reduction, three 3-acetyl-9(10)-alkylperylenes were synthesized from perylene and used to prepare 9 nucleoside and 12 non-nucleoside amphipathic derivatives. These compounds were characterized as fluorophores and singlet oxygen generators, as well as tested as antivirals against herpes virus-1 (HSV-1) and vesicular stomatitis virus (VSV), both known for causing superficial skin/mucosa lesions and thus serving as suitable candidates for photodynamic therapy. The results suggest that derivatives with a short alkyl chain (butyl) have strong antiviral activity, whereas the introduction of longer alkyl substituents (n = 8 and 12) to the perylenyethynyl scaffold results in a dramatic reduction of antiviral activity. This phenomenon is likely attributable to the increased lipophilicity of the compounds and their ability to form insoluble aggregates. Moreover, molecular dynamic studies revealed that alkylated perylene derivatives are predominately located closer to the middle of the bilayer compared to non-alkylated derivatives. The predicted probability of superficial positioning correlated with antiviral activity, suggesting that singlet oxygen generation is achieved in the subsurface layer of the membrane, where the perylene group is more accessible to dissolved oxygen.

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Specific features of the interaction between chemical traps and phthalocyanine dyes affecting the measurement of the yield of reactive oxygen species

Cited by 7 publications

References 14 publications

The Role of the Photon Counting Loss Effect in Time-Resolved Measurements of Fluorescence Anisotropy

The Role of the Photon Counting Loss Effect in Time-Resolved Measurements of Fluorescence Anisotropy

Antiviral activity of singlet oxygen-photogenerating perylene compounds against SARS-CoV-2: Interaction with the viral envelope and photodynamic virion inactivation

Alkyl Derivatives of Perylene Photosensitizing Antivirals: Towards Understanding the Influence of Lipophilicity

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