Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1
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-<i>n</i>-propan...
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| Format: | Article |
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MDPI AG
2021-03-01
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| Series: | Pharmaceuticals |
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| Online Access: | https://www.mdpi.com/1424-8247/14/3/242 |
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| author | Kseniya A. Zhdanova Inga O. Savelyeva Artem V. Ezhov Andrey P. Zhdanov Konstantin Yu. Zhizhin Andrey F. Mironov Natal’ya A. Bragina Alla A. Babayants Irina S. Frolova Nadezhda I. Filippova Nadezhda N. Scliankina Olga N. Scheglovitova |
| author_facet | Kseniya A. Zhdanova Inga O. Savelyeva Artem V. Ezhov Andrey P. Zhdanov Konstantin Yu. Zhizhin Andrey F. Mironov Natal’ya A. Bragina Alla A. Babayants Irina S. Frolova Nadezhda I. Filippova Nadezhda N. Scliankina Olga N. Scheglovitova |
| author_sort | Kseniya A. Zhdanova |
| collection | DOAJ |
| description | 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-<i>n</i>-propanoyl)oxyphenyl)porphyrin tetrabromide (<b>3a</b>), 5,10,15,20-tetrakis(4-(6-pyridyl-<i>n</i>-hexanoyl)oxyphenyl)porphyrin tetrabromide (<b>3b</b>) and known 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin tetraiodide (<b>TMePyP</b>) 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 <b>3a</b>, <b>3b</b> and <b>TMePyP</b> showed virucidal efficiency and had an effect on viral replication stages. The new compound <b>3b</b> showed the highest antiviral activity, close to 100%, with the lowest concentration, while the maximum <b>TMePyP</b> activity was observed with a high concentration; porphyrin <b>3a</b> 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 <b>3a</b> and <b>TMePyP</b> acted on all stages of the viral replication cycle, porphyrin <b>3b</b> 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. |
| first_indexed | 2024-03-10T13:26:33Z |
| format | Article |
| id | doaj.art-d8069de05cfe4d25a40d9765138efdf7 |
| institution | Directory Open Access Journal |
| issn | 1424-8247 |
| language | English |
| last_indexed | 2024-03-10T13:26:33Z |
| publishDate | 2021-03-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceuticals |
| spelling | doaj.art-d8069de05cfe4d25a40d9765138efdf72023-11-21T09:37:53ZengMDPI AGPharmaceuticals1424-82472021-03-0114324210.3390/ph14030242Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1Kseniya A. Zhdanova0Inga O. Savelyeva1Artem V. Ezhov2Andrey P. Zhdanov3Konstantin Yu. Zhizhin4Andrey F. Mironov5Natal’ya A. Bragina6Alla A. Babayants7Irina S. Frolova8Nadezhda I. Filippova9Nadezhda N. Scliankina10Olga N. Scheglovitova11MIREA—Russian Technological University, Vernadsky Prospect 86, Moscow 119571, RussiaMIREA—Russian Technological University, Vernadsky Prospect 86, Moscow 119571, RussiaMIREA—Russian Technological University, Vernadsky Prospect 86, Moscow 119571, RussiaKurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences, Leninskii Pr. 31, Moscow 117907, RussiaMIREA—Russian Technological University, Vernadsky Prospect 86, Moscow 119571, RussiaMIREA—Russian Technological University, Vernadsky Prospect 86, Moscow 119571, RussiaMIREA—Russian Technological University, Vernadsky Prospect 86, Moscow 119571, RussiaGamaleya Research Center of Epidemiology and Microbiology, Gamaleya Str. 18, Moscow 123098, RussiaGamaleya Research Center of Epidemiology and Microbiology, Gamaleya Str. 18, Moscow 123098, RussiaGamaleya Research Center of Epidemiology and Microbiology, Gamaleya Str. 18, Moscow 123098, RussiaGamaleya Research Center of Epidemiology and Microbiology, Gamaleya Str. 18, Moscow 123098, RussiaGamaleya Research Center of Epidemiology and Microbiology, Gamaleya Str. 18, Moscow 123098, RussiaThis 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-<i>n</i>-propanoyl)oxyphenyl)porphyrin tetrabromide (<b>3a</b>), 5,10,15,20-tetrakis(4-(6-pyridyl-<i>n</i>-hexanoyl)oxyphenyl)porphyrin tetrabromide (<b>3b</b>) and known 5,10,15,20-tetrakis(1-methyl-4-pyridinio)porphyrin tetraiodide (<b>TMePyP</b>) 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 <b>3a</b>, <b>3b</b> and <b>TMePyP</b> showed virucidal efficiency and had an effect on viral replication stages. The new compound <b>3b</b> showed the highest antiviral activity, close to 100%, with the lowest concentration, while the maximum <b>TMePyP</b> activity was observed with a high concentration; porphyrin <b>3a</b> 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 <b>3a</b> and <b>TMePyP</b> acted on all stages of the viral replication cycle, porphyrin <b>3b</b> 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.https://www.mdpi.com/1424-8247/14/3/242virusesantiviral activitysynthesiscationic porphyrinsanti-HSV-1dark antiviral activity of porphyrins |
| spellingShingle | Kseniya A. Zhdanova Inga O. Savelyeva Artem V. Ezhov Andrey P. Zhdanov Konstantin Yu. Zhizhin Andrey F. Mironov Natal’ya A. Bragina Alla A. Babayants Irina S. Frolova Nadezhda I. Filippova Nadezhda N. Scliankina Olga N. Scheglovitova Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1 Pharmaceuticals viruses antiviral activity synthesis cationic porphyrins anti-HSV-1 dark antiviral activity of porphyrins |
| title | Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1 |
| title_full | Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1 |
| title_fullStr | Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1 |
| title_full_unstemmed | Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1 |
| title_short | Novel Cationic Meso-Arylporphyrins and Their Antiviral Activity against HSV-1 |
| title_sort | novel cationic meso arylporphyrins and their antiviral activity against hsv 1 |
| topic | viruses antiviral activity synthesis cationic porphyrins anti-HSV-1 dark antiviral activity of porphyrins |
| url | https://www.mdpi.com/1424-8247/14/3/242 |
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