Membrane-Active Singlet Oxygen Photogenerators as a Paradigm
for Broad-Spectrum Antivirals: The Case of Halogenated
(BOron)-DIPYrromethenes

J 2025

Membrane-Active Singlet Oxygen Photogenerators as a Paradigm for Broad-Spectrum Antivirals: The Case of Halogenated (BOron)-DIPYrromethenes

MARYEWSKI, Xenia A.; Maxim S. KRASILNIKOV; Petra STRAKOVÁ; Jiří HOLOUBEK; Tereza FRČKOVÁ et al.

Základní údaje

Originální název

Membrane-Active Singlet Oxygen Photogenerators as a Paradigm for Broad-Spectrum Antivirals: The Case of Halogenated (BOron)-DIPYrromethenes

Autoři

Vydání

ACS Applied Materials and Interfaces, American Chemical Society, 2025, 1944-8244

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10607 Virology

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 8.200 v roce 2024

Označené pro přenos do RIV

Ano

Kód RIV

RIV/00216224:14310/25:00140569

Organizační jednotka

Přírodovědecká fakulta

Klíčová slova anglicky

BODIPY; enveloped viruses; membrane-targeting photosensitizer; singlet oxygen photogeneration; virus-inactivating activity

Štítky

14314010, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 27. 2. 2025 10:41, Mgr. Marie Novosadová Šípková, DiS.

Anotace

V originále

Enveloped viruses, such as flaviviruses and coronaviruses, are pathogens of significant medical concern that cause severe infections in humans. Some photosensitizers are known to possess virucidal activity against enveloped viruses, targeting their lipid bilayer. Here we report a series of halogenated difluoroboron-dipyrromethene (BODIPYs) photosensitizers with strong virus-inactivating activity. Our structure–activity relationship analysis revealed that BODIPY scaffolds with a heavy halogen atom demonstrate significant efficacy against both tick-borne encephalitis virus (TBEV; Flaviviridae family) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2; Coronaviridae family) along with high singlet oxygen quantum yields. Moreover, select compounds also inactivated other enveloped viruses, such as herpes simplex virus type 1 and monkeypox virus. The nature and length of the alkyl side chain notably influenced the virus-inactivating activity of BODIPY molecules. Furthermore, molecular dynamics studies highlighted the critical importance of the positioning of the chromophore moiety within the lipid bilayer. As membrane-targeting photosensitizers, BODIPYs interact directly with virus particles, causing damage to the viral envelope membranes. Thus, TBEV pretreated with BODIPY was completely noninfective for lab mice. Consequently, BODIPY-based photosensitizers hold potential either as broad-spectrum virus-inactivating antivirals against a variety of phylogenetically unrelated enveloped viruses or as potent inactivators of viruses for the development of vaccines for preventing life-threatening emerging viral diseases.

Citovat

MARYEWSKI, Xenia A.; Maxim S. KRASILNIKOV; Petra STRAKOVÁ; Jiří HOLOUBEK; Tereza FRČKOVÁ; Irina S. PANINA; Nikolay A. KRYLOV; Daniil A. GVOZDEV; Vladislav S. DENISOV; Alexey N. SEMENOV; Natalia Y. LOTOSH; Alla A. SELISHCHEVA; Alexey A. CHISTOV; Evgeny L. GULYAK; Grigory L. KOZHEMYAKIN; Vladimir A. KORSHUN; Roman G. EFREMOV; Alexey V. USTINOV; Daniel RŮŽEK; Luděk EYER a Vera A. ALFEROVA. Membrane-Active Singlet Oxygen Photogenerators as a Paradigm for Broad-Spectrum Antivirals: The Case of Halogenated (BOron)-DIPYrromethenes. ACS Applied Materials and Interfaces. American Chemical Society, 2025, roč. 17, č. 3, s. 4502-4528. ISSN 1944-8244. Dostupné z: https://doi.org/10.1021/acsami.4c17482.

@article{2473181,
   author = {Maryewski, Xenia A. and Krasilnikov, Maxim S. and Straková, Petra and Holoubek, Jiří and Frčková, Tereza and Panina, Irina S. and Krylov, Nikolay A. and Gvozdev, Daniil A. and Denisov, Vladislav S. and Semenov, Alexey N. and Lotosh, Natalia Y. and Selishcheva, Alla A. and Chistov, Alexey A. and Gulyak, Evgeny L. and Kozhemyakin, Grigory L. and Korshun, Vladimir A. and Efremov, Roman G. and Ustinov, Alexey V. and Růžek, Daniel and Eyer, Luděk and Alferova, Vera A.},
   article_number = {3},
   doi = {https://doi.org/10.1021/acsami.4c17482},
   keywords = {BODIPY; enveloped viruses; membrane-targeting photosensitizer; singlet oxygen photogeneration; virus-inactivating activity},
   language = {eng},
   issn = {1944-8244},
   journal = {ACS Applied Materials and Interfaces},
   title = {Membrane-Active Singlet Oxygen Photogenerators as a Paradigm for Broad-Spectrum Antivirals: The Case of Halogenated (BOron)-DIPYrromethenes},
   url = {https://doi.org/10.1021/acsami.4c17482},
   volume = {17},
   year = {2025}
}

TY  - JOUR
ID  - 2473181
AU  - Maryewski, Xenia A. - Krasilnikov, Maxim S. - Straková, Petra - Holoubek, Jiří - Frčková, Tereza - Panina, Irina S. - Krylov, Nikolay A. - Gvozdev, Daniil A. - Denisov, Vladislav S. - Semenov, Alexey N. - Lotosh, Natalia Y. - Selishcheva, Alla A. - Chistov, Alexey A. - Gulyak, Evgeny L. - Kozhemyakin, Grigory L. - Korshun, Vladimir A. - Efremov, Roman G. - Ustinov, Alexey V. - Růžek, Daniel - Eyer, Luděk - Alferova, Vera A.
PY  - 2025
TI  - Membrane-Active Singlet Oxygen Photogenerators as a Paradigm for Broad-Spectrum Antivirals: The Case of Halogenated (BOron)-DIPYrromethenes
JF  - ACS Applied Materials and Interfaces
VL  - 17
IS  - 3
SP  - 4502-4528
EP  - 4502-4528
PB  - American Chemical Society
SN  - 19448244
KW  - BODIPY
KW  - enveloped viruses
KW  - membrane-targeting photosensitizer
KW  - singlet oxygen photogeneration
KW  - virus-inactivating activity
UR  - https://doi.org/10.1021/acsami.4c17482
N2  - Enveloped viruses, such as flaviviruses and coronaviruses, are pathogens of significant medical concern that cause severe infections in humans. Some photosensitizers are known to possess virucidal activity against enveloped viruses, targeting their lipid bilayer. Here we report a series of halogenated difluoroboron-dipyrromethene (BODIPYs) photosensitizers with strong virus-inactivating activity. Our structure–activity relationship analysis revealed that BODIPY scaffolds with a heavy halogen atom demonstrate significant efficacy against both tick-borne encephalitis virus (TBEV; Flaviviridae family) and severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2; Coronaviridae family) along with high singlet oxygen quantum yields. Moreover, select compounds also inactivated other enveloped viruses, such as herpes simplex virus type 1 and monkeypox virus. The nature and length of the alkyl side chain notably influenced the virus-inactivating activity of BODIPY molecules. Furthermore, molecular dynamics studies highlighted the critical importance of the positioning of the chromophore moiety within the lipid bilayer. As membrane-targeting photosensitizers, BODIPYs interact directly with virus particles, causing damage to the viral envelope membranes. Thus, TBEV pretreated with BODIPY was completely noninfective for lab mice. Consequently, BODIPY-based photosensitizers hold potential either as broad-spectrum virus-inactivating antivirals against a variety of phylogenetically unrelated enveloped viruses or as potent inactivators of viruses for the development of vaccines for preventing life-threatening emerging viral diseases.
ER  -

MARYEWSKI, Xenia A.; Maxim S. KRASILNIKOV; Petra STRAKOVÁ; Jiří HOLOUBEK; Tereza FRČKOVÁ; Irina S. PANINA; Nikolay A. KRYLOV; Daniil A. GVOZDEV; Vladislav S. DENISOV; Alexey N. SEMENOV; Natalia Y. LOTOSH; Alla A. SELISHCHEVA; Alexey A. CHISTOV; Evgeny L. GULYAK; Grigory L. KOZHEMYAKIN; Vladimir A. KORSHUN; Roman G. EFREMOV; Alexey V. USTINOV; Daniel RŮŽEK; Luděk EYER a Vera A. ALFEROVA. Membrane-Active Singlet Oxygen Photogenerators as a Paradigm for Broad-Spectrum Antivirals: The Case of Halogenated (BOron)-DIPYrromethenes. \textit{ACS Applied Materials and Interfaces}. American Chemical Society, 2025, roč.~17, č.~3, s.~4502-4528. ISSN~1944-8244. Dostupné z: https://doi.org/10.1021/acsami.4c17482.

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