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.

Department of Biology Lomonosov Moscow State University Leninskie Gory 1 12 119234 Moscow Russia

Department of Chemistry Lomonosov Moscow State University Leninskie Gory 1 3 119991 Moscow Russia

Department of Experimental Biology Faculty of Science Masaryk University Kamenice 753 5 CZ 625 00 Brno Czech Republic

Department of Pharmacology and Pharmacy Faculty of Veterinary Medicine University of Veterinary Sciences Brno Palackého tř 1946 1 CZ 612 42 Brno Czech Republic

Department of Pharmacology and Toxicology Veterinary Research Institute Hudcova 296 70 CZ 621 00 Brno Czech Republic

Institute of Parasitology Biology Centre of the Czech Academy of Sciences Branišovská 1160 31 CZ 370 05 České Budějovice Czech Republic

Laboratory of Emerging Viral Diseases Veterinary Research Institute Hudcova 296 70 CZ 621 00 Brno Czech Republic

Shemyakin Ovchinnikov Institute of Bioorganic Chemistry Miklukho Maklaya 16 10 117997 Moscow Russia

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Alkyl Derivatives of Perylene Photosensitizing Antivirals: Towards Understanding the Influence of Lipophilicity