Donor‐Acceptor (Perylenethienyl)Ethylenes as Singlet Oxygen‐Photogenerating Viral Inhibitors**

The development of broad-spectrum antiviral drugs effective against a wide range of viruses is of significant practical importance. Derivatives of perylene, a pentacyclic aromatic hydrocarbon, demonstrate pronounced antiviral activity. These compounds act primarily as membrane-active singlet oxygen photogenerators, disrupting virions and inhibiting their fusion with the host cell membrane. Modification of the perylene core allows for chemical diversification of antiviral photosensitizers. Additionally, achieving a bathochromic shift of the absorption band is crucial for effective treatment of superficial lesions, as it facilitates deeper tissue penetration of therapeutic light. In this work, donor-acceptor perylenylethylenes and (perylenethienyl)ethylenes were synthesized and evaluated for their spectral properties, singlet oxygen photogeneration, and inhibitory activity against vesicular stomatitis virus (VSV), a representative enveloped virus. Incorporation of a thiophene moiety into the molecule significantly enhanced both the singlet oxygen generation ability and the antiviral activity. These findings provide useful insights into the relationship between the structure, spectral/photochemical properties, and biological activity of perylene-based photosensitizers.

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Publication Details

Journal
ChemBioChem
Published
2025-03-11
DOI
https://doi.org/10.1002/cbic.202401019
Citations
1
Primary Topic
Photodynamic Therapy Research Studies
Type
article
Field-Weighted Citation Impact
1.52
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article

Donor‐Acceptor (Perylenethienyl)Ethylenes as Singlet Oxygen‐Photogenerating Viral Inhibitors**

Alexey V. Ustinov, Vera A. Alferova, Vladimir A. Brylev, Timofei D. Nikitin et al.
1 citations
ChemBioChem
Photodynamic Therapy Research Studies
1.52
article

Donor‐Acceptor (Perylenethienyl)Ethylenes as Singlet Oxygen‐Photogenerating Viral Inhibitors**

Alexey V. Ustinov, Vera A. Alferova, Vladimir A. Brylev, Timofei D. Nikitin, Maxim S. Krasilnikov, V. Ya. Denisov, Daniil A. Gvozdev, Vladimir A. Korshun, Evgeny L. Gulyak, Stepan Petrovich Chumakov, Roman V. Mazur, Evgeny A. Bersenev, Polina S. Orinicheva, Yan I. Nikolaenko
article en
1 citations

Abstract

The development of broad-spectrum antiviral drugs effective against a wide range of viruses is of significant practical importance. Derivatives of perylene, a pentacyclic aromatic hydrocarbon, demonstrate pronounced antiviral activity. These compounds act primarily as membrane-active singlet oxygen photogenerators, disrupting virions and inhibiting their fusion with the host cell membrane. Modification of the perylene core allows for chemical diversification of antiviral photosensitizers. Additionally, achieving a bathochromic shift of the absorption band is crucial for effective treatment of superficial lesions, as it facilitates deeper tissue penetration of therapeutic light. In this work, donor-acceptor perylenylethylenes and (perylenethienyl)ethylenes were synthesized and evaluated for their spectral properties, singlet oxygen photogeneration, and inhibitory activity against vesicular stomatitis virus (VSV), a representative enveloped virus. Incorporation of a thiophene moiety into the molecule significantly enhanced both the singlet oxygen generation ability and the antiviral activity. These findings provide useful insights into the relationship between the structure, spectral/photochemical properties, and biological activity of perylene-based photosensitizers.

ChemBioChemVol. 26(7)
Sechenov University (RU), Lomonosov Moscow State University (RU), Institute of Bioorganic Chemistry (RU), Moscow State University (TJ)
Good health and well-being
Openalex Percentile: Top 21%
Photodynamic Therapy Research Studies
1.52
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