Perylene as a controversial antiviral scaffold

Alferova, Vera A.; Mikhnovets, Igor E.; Chistov, Alexey A.; Korshun, Vladimir A.; Tyurin, Anton P.; Ustinov, A. V.

doi:10.1016/bs.armc.2022.08.001

Cited by 4 publications

(4 citation statements)

References 115 publications

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“…Nonetheless, 7b has a bulky hydrophobic perylene moiety and acts in a nonselective manner, binding to cell membranes and envelopes of viruses, where it acts as a photosensitizer. [ 40,41 ] On the other hand, a significant reduction of the infectious virus titer in the post‐treatment experiment, but not in pre‐treatment and simultaneous treatment conditions, was observed for compounds 1d , 2 , and 3d .…”

Section: Resultsmentioning

confidence: 94%

Tetrahydroquinazoline N‐oxide derivatives inhibit reproduction of tick‐borne and mosquito‐borne flaviviruses

Sedenkova

Uvarova

Назарова

et al. 2023

Archiv der Pharmazie

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Tick‐borne encephalitis virus (TBEV), yellow fever virus (YFV), and West Nile virus (WNV) are flaviviruses causing emerging arthropod‐borne infections of a great public health concern. Clinically approved drugs are not available to complement or replace the existing vaccines, which do not provide sufficient coverage. Thus, the discovery and characterization of new antiflaviviral chemotypes would advance studies in this field. In this study, a series of tetrahydroquinazoline N‐oxides was synthesized, and the antiviral activity of the compounds was assessed against TBEV, YFV, and WNV using the plaque reduction assay along with the cytotoxicity to the corresponding cell lines (porcine embryo kidney and Vero). Most of the studied compounds were active against TBEV (EC50 2 to 33 μM) and WNV (EC50 0.15 to 34 μM) and a few also demonstrated inhibitory activity against YFV (EC50 0.18 to 41 μM). To investigate the potential mechanism of action of the synthesized compounds, time‐of‐addition (TOA) experiments and virus yield reduction assays were performed for TBEV. The TOA studies suggested that the antiviral activity of the compounds should affect the early stages of the viral replication cycle after cell entry. Compounds with tetrahydroquinazoline N‐oxide scaffold show a broad spectrum of activity against flaviviruses and represent a promising chemotype for antiviral drug discovery.

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Section: Resultsmentioning

confidence: 94%

Tetrahydroquinazoline N‐oxide derivatives inhibit reproduction of tick‐borne and mosquito‐borne flaviviruses

Sedenkova

Uvarova

Назарова

et al. 2023

Archiv der Pharmazie

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“…Further development of antiviral compounds based on these scaffolds is attractive for several reasons. First, photosensitizers generally have a wide spectrum of antiviral activity, as demonstrated by photosensitizers based on perylene, hypericin [7], phenothiazine, porphyrin, and phthalocyanine [9]. Secondly, dyes with an absorption maximum falling within the "therapeutic window" require electromagnetic radiation capable of penetrating tissues for their excitation.…”

Section: Discussionmentioning

confidence: 99%

“…Their characteristic feature is the presence of an outer lipid envelope decorated with membrane proteins. Organic dye-photosensitizers capable of the photogeneration of singlet oxygen ( 1 O 2 ) and other reactive oxygen species (ROS) often show activity against enveloped viruses [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

“…However, in the case of the internal localization of viral replication foci, light delivery is difficult. The main types of chromophores of such compounds are shown in Figure 2; these are porphyrins and phthalocyanines (usually as metal complexes) [10,23], hypericin [7], perylene compounds [6,7], compound LJ001 and congeners [20], and methylene blue [24]. They are lipophilic aromatic compounds, capable of penetrating into the lipid bilayer.…”

Section: Introductionmentioning

confidence: 99%

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Near-Infrared Dyes: Towards Broad-Spectrum Antivirals

Mariewskaya

Krasilnikov

Korshun

et al. 2022

IJMS

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Broad antiviral activity in vitro is known for many organic photosensitizers generating reactive oxygen species under irradiation with visible light. Low tissue penetration of visible light prevents further development of antiviral therapeutics based on these compounds. One possible solution to this problem is the development of photosensitizers with near-infrared absorption (NIR dyes). These compounds found diverse applications in the photodynamic therapy of tumors and bacterial infections, but they are scarcely mentioned as antivirals. In this account, we aimed to evaluate the therapeutic prospects of various NIR-absorbing and singlet oxygen-generating chromophores for the development of broad-spectrum photosensitizing antivirals.

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