Membrane-Targeting Perylenylethynylphenols Inactivate Medically
Important Coronaviruses via the Singlet Oxygen Photogeneration
Mechanism

J 2023

Membrane-Targeting Perylenylethynylphenols Inactivate Medically Important Coronaviruses via the Singlet Oxygen Photogeneration Mechanism

MARIEWSKAYA, Kseniya A., Daniil A. GVOZDEV, Alexey A. CHISTOV, Petra STRAKOVÁ, Ivana HUVAROVÁ et. al.

Základní údaje

Originální název

Membrane-Targeting Perylenylethynylphenols Inactivate Medically Important Coronaviruses via the Singlet Oxygen Photogeneration Mechanism

Autoři

MARIEWSKAYA, Kseniya A., Daniil A. GVOZDEV, Alexey A. CHISTOV, Petra STRAKOVÁ (203 Česká republika, domácí), Ivana HUVAROVÁ, Pavel SVOBODA (203 Česká republika, domácí), Jan KOTOUČEK, Nikita M. IVANOV, Maxim S. KRASILNIKOV, Mikhail Y. ZHITLOV, Alexandra M. PAK, Igor E. MIKHNOVETS, Timofei D. NIKITIN, Vladimir A. KORSHUN, Vera A. ALFEROVA, Josef MAŠEK, Daniel RŮŽEK (203 Česká republika, domácí), Luděk EYER (203 Česká republika, domácí) a Alexey V. USTINOV

Vydání

Molecules, MDPI, 2023, 1420-3049

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10607 Virology

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.600 v roce 2022

Kód RIV

RIV/00216224:14310/23:00132671

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.3390/molecules28176278

UT WoS

001062679500001

Klíčová slova anglicky

perylene; photosensitizers; antivirals; singlet oxygen; SARS-CoV-2

Štítky

rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 16. 1. 2024 13:32, Mgr. Marie Šípková, DiS.

Anotace

V originále

Perylenylethynyl derivatives have been recognized as broad-spectrum antivirals that target the lipid envelope of enveloped viruses. In this study, we present novel perylenylethynylphenols that exhibit nanomolar or submicromolar antiviral activity against Severe Acute Respiratory Syndrome Coronavirus-2 (SARS-CoV-2) and feline infectious peritonitis virus (FIPV) in vitro. Perylenylethynylphenols incorporate into viral and cellular membranes and block the entry of the virus into the host cell. Furthermore, these compounds demonstrate an ability to generate singlet oxygen when exposed to visible light. The rate of singlet oxygen production is positively correlated with antiviral activity, confirming that the inhibition of fusion is primarily due to singlet-oxygen-induced damage to the viral envelope. The unique combination of a shape that affords affinity to the lipid bilayer and the capacity to generate singlet oxygen makes perylenylethynylphenols highly effective scaffolds against enveloped viruses. The anticoronaviral activity of perylenylethynylphenols is strictly light-dependent and disappears in the absence of daylight (under red light). Moreover, these compounds exhibit negligible cytotoxicity, highlighting their significant potential for further exploration of the precise antiviral mechanism and the broader scope and limitations of this compound class.

Návaznosti

LM2018127, projekt VaV

Název: Česká infrastruktura pro integrativní strukturní biologii (Akronym: CIISB)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Czech Infrastructure for Integrative Structural Biology

Citovat

MARIEWSKAYA, Kseniya A., Daniil A. GVOZDEV, Alexey A. CHISTOV, Petra STRAKOVÁ, Ivana HUVAROVÁ, Pavel SVOBODA, Jan KOTOUČEK, Nikita M. IVANOV, Maxim S. KRASILNIKOV, Mikhail Y. ZHITLOV, Alexandra M. PAK, Igor E. MIKHNOVETS, Timofei D. NIKITIN, Vladimir A. KORSHUN, Vera A. ALFEROVA, Josef MAŠEK, Daniel RŮŽEK, Luděk EYER a Alexey V. USTINOV. Membrane-Targeting Perylenylethynylphenols Inactivate Medically Important Coronaviruses via the Singlet Oxygen Photogeneration Mechanism. Molecules. MDPI, 2023, roč. 28, č. 17, s. 1-19. ISSN 1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules28176278.

@article{2353805,
   author = {Mariewskaya, Kseniya A. and Gvozdev, Daniil A. and Chistov, Alexey A. and Straková, Petra and Huvarová, Ivana and Svoboda, Pavel and Kotouček, Jan and Ivanov, Nikita M. and Krasilnikov, Maxim S. and Zhitlov, Mikhail Y. and Pak, Alexandra M. and Mikhnovets, Igor E. and Nikitin, Timofei D. and Korshun, Vladimir A. and Alferova, Vera A. and Mašek, Josef and Růžek, Daniel and Eyer, Luděk and Ustinov, Alexey V.},
   article_number = {17},
   doi = {http://dx.doi.org/10.3390/molecules28176278},
   keywords = {perylene; photosensitizers; antivirals; singlet oxygen; SARS-CoV-2},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   title = {Membrane-Targeting Perylenylethynylphenols Inactivate Medically Important Coronaviruses via the Singlet Oxygen Photogeneration Mechanism},
   url = {https://www.mdpi.com/1420-3049/28/17/6278},
   volume = {28},
   year = {2023}
}

TY  - JOUR
ID  - 2353805
AU  - Mariewskaya, Kseniya A. - Gvozdev, Daniil A. - Chistov, Alexey A. - Straková, Petra - Huvarová, Ivana - Svoboda, Pavel - Kotouček, Jan - Ivanov, Nikita M. - Krasilnikov, Maxim S. - Zhitlov, Mikhail Y. - Pak, Alexandra M. - Mikhnovets, Igor E. - Nikitin, Timofei D. - Korshun, Vladimir A. - Alferova, Vera A. - Mašek, Josef - Růžek, Daniel - Eyer, Luděk - Ustinov, Alexey V.
PY  - 2023
TI  - Membrane-Targeting Perylenylethynylphenols Inactivate Medically Important Coronaviruses via the Singlet Oxygen Photogeneration Mechanism
JF  - Molecules
VL  - 28
IS  - 17
SP  - 1-19
EP  - 1-19
PB  - MDPI
SN  - 14203049
KW  - perylene
KW  - photosensitizers
KW  - antivirals
KW  - singlet oxygen
KW  - SARS-CoV-2
UR  - https://www.mdpi.com/1420-3049/28/17/6278
N2  - Perylenylethynyl derivatives have been recognized as broad-spectrum antivirals that target the lipid envelope of enveloped viruses. In this study, we present novel perylenylethynylphenols that exhibit nanomolar or submicromolar antiviral activity against Severe Acute Respiratory Syndrome Coronavirus-2 (SARS-CoV-2) and feline infectious peritonitis virus (FIPV) in vitro. Perylenylethynylphenols incorporate into viral and cellular membranes and block the entry of the virus into the host cell. Furthermore, these compounds demonstrate an ability to generate singlet oxygen when exposed to visible light. The rate of singlet oxygen production is positively correlated with antiviral activity, confirming that the inhibition of fusion is primarily due to singlet-oxygen-induced damage to the viral envelope. The unique combination of a shape that affords affinity to the lipid bilayer and the capacity to generate singlet oxygen makes perylenylethynylphenols highly effective scaffolds against enveloped viruses. The anticoronaviral activity of perylenylethynylphenols is strictly light-dependent and disappears in the absence of daylight (under red light). Moreover, these compounds exhibit negligible cytotoxicity, highlighting their significant potential for further exploration of the precise antiviral mechanism and the broader scope and limitations of this compound class.
ER  -

MARIEWSKAYA, Kseniya A., Daniil A. GVOZDEV, Alexey A. CHISTOV, Petra STRAKOVÁ, Ivana HUVAROVÁ, Pavel SVOBODA, Jan KOTOUČEK, Nikita M. IVANOV, Maxim S. KRASILNIKOV, Mikhail Y. ZHITLOV, Alexandra M. PAK, Igor E. MIKHNOVETS, Timofei D. NIKITIN, Vladimir A. KORSHUN, Vera A. ALFEROVA, Josef MAŠEK, Daniel RŮŽEK, Luděk EYER a Alexey V. USTINOV. Membrane-Targeting Perylenylethynylphenols Inactivate Medically Important Coronaviruses via the Singlet Oxygen Photogeneration Mechanism. \textit{Molecules}. MDPI, 2023, roč.~28, č.~17, s.~1-19. ISSN~1420-3049. Dostupné z: https://dx.doi.org/10.3390/molecules28176278.

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