Photogeneration of Singlet Oxygen by Tetra(p-Hydroxyphenyl)porphyrins Modified with Oligo- and Polyalkylene Oxides

Соловьева, А. Б.; Savko, M. A.; Глаголев, Н. Н.; Aksenova, N. P.; Timashev, Peter; Брагина, Н. А.; Zhdanova, Kseniya A.; Миронов, А. Ф.

doi:10.1134/s0036024418080277

Cited by 7 publications

(9 citation statements)

References 20 publications

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“…The ability of porphyrins to directly inactivate microorganisms may depend on their degree of solubility [ 50 ]. Therefore, in this work, the anti-HSV-1 activity of compounds 3a,b and TMePyP was compared in PBS (pH = 7) and Pluronic F-127 micelles.…”

Section: Resultsmentioning

confidence: 99%

“…Pluronics have found a broad application in PDT due to the ease of solution preparation, their nontoxicity, targeted delivery and the effective solubilization of hydrophobic tetrapyrroles. We have previously shown successful solubilization of tetraphenylporphyrin derivatives by Pluronic F-127 [ 48 , 49 , 50 ]. In this regard, another task of this work was to estimate the effect of Pluronic F-127 micelles on the porphyrins’ anti-HSV-1 activity.…”

Section: Introductionmentioning

confidence: 99%

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Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1

et al. 2021

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This work is devoted to the search for new antiherpes simplex virus type 1 (HSV-1) drugs among synthetic tetrapyrroles and to an investigation of their antiviral properties under nonphotodynamic conditions. In this study, novel amphiphilic 5,10,15,20-tetrakis(4-(3-pyridyl-n-propanoyl)oxyphenyl)porphyrin tetrabromide (3a), 5,10,15,20-tetrakis(4-(6-pyridyl-n-hexanoyl)oxyphenyl)porphyrin tetrabromide (3b) and known 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin tetraiodide (TMePyP) were synthesized, and their dark antiviral activity in vitro against HSV-1 was studied. The influence of porphyrin’s nanosized delivery vehicles based on Pluronic F127 on anti-HSV-1 activity was estimated. All the received compounds 3a, 3b and TMePyP showed virucidal efficiency and had an effect on viral replication stages. The new compound 3b showed the highest antiviral activity, close to 100%, with the lowest concentration, while the maximum TMePyP activity was observed with a high concentration; porphyrin 3a was the least active. The inclusion of the synthesized compounds in Pluronic F-127 polymeric micelles had a noticeable effect on antiviral activity only at higher porphyrin concentrations. Action of the received compounds differs by influence on the early or later reproduction stages. While 3a and TMePyP acted on all stages of the viral replication cycle, porphyrin 3b inhibited viral replication during the early stages of infection. The resulting compounds are promising for the development of utilitarian antiviral agents and, possibly, medical antiviral drugs.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1

et al. 2021

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“…Photosensitizing double systems (PS-AP and PS-CT100) with water-soluble PSs were prepared by mixing solutions of porphyrin and polymer or chitosan (in 0.2% acetic acid) for 10 min. [24]. To obtain ternary systems (PS-AP-CT100), porphyrin solutions were first mixed with an amphiphilic polymer for 10 min at room temperature, then a chitosan solution was added and mixed for another 10 min [24].…”

Section: Kinetics Of Tryptophan Photo-oxidationmentioning

confidence: 99%

“…[24]. To obtain ternary systems (PS-AP-CT100), porphyrin solutions were first mixed with an amphiphilic polymer for 10 min at room temperature, then a chitosan solution was added and mixed for another 10 min [24]. Solubilization of hydrophobic porphyrins was carried out according to the procedure described in [25].…”

Section: Kinetics Of Tryptophan Photo-oxidationmentioning

confidence: 99%

“…To obtain ternary systems (PS-AP-CT 100 ), porphyrin solutions were first mixed with an amphiphilic polymer for 10 min at room temperature, then a chitosan solution was added and mixed for another 10 min [23]. Solubilization of hydrophobic porphyrins was carried out according to the procedure described in [24]. The PS concentration is 5 × 10 −6 M. The AP concentrations varied from 5 × 10 −6 M to 5 × 10 −4 M; the concentration of CT 100 varied from 1 × 10 −4 M to 6 × 10 −3 M (given per unit).…”

Section: Kinetics Of Tryptophan Photo-oxidationmentioning

confidence: 99%

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Effect of Chitosan on the Activity of Water-Soluble and Hydrophobic Porphyrin Photosensitizers Solubilized by Amphiphilic Polymers

et al. 2021

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In this work, we studied the photocatalytic activity of photosensitizers (PSs) of various natures solubilized with polyvinylpyrrolidone (PVP) and ternary block copolymer ethylene and propylene oxide Pluronic F127 (F127) in a model reaction of tryptophan photo-oxidation in water in the presence of chitosan (CT). Water-soluble compounds (dimegin and trisodium salt of chlorin e6 (Ce6)) and hydrophobic porphyrins (tetraphenylporphyrin (TPP) and its fluorine derivative (TPPF20)) were used as PSs. It was shown that the use of chitosan (Mw ~100 kDa) makes it possible to obtain a system whose activity is comparable to that of the photosensitizer-amphiphilic polymer systems. Thus, the previously observed drop in the photosensitizing activity of PS in the presence of a polysaccharide and amphiphilic polymers (AP) was absent in this case. At the same time, chitosan had practically no inhibitory effect on hydrophobic porphyrins solubilized by Pluronic F127.

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