Simplistic perylene-related compounds as inhibitors of tick-borne encephalitis virus reproduction

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Abstract

Rigid amphipathic fusion inhibitors are potent broad-spectrum antivirals based on the perylene scaffold, usually decorated with a hydrophilic group linked via ethynyl or triazole. We have sequentially simplified these structures by removing sugar moiety, then converting uridine to aniline, then moving to perylenylthiophenecarboxylic acids and to perylenylcarboxylic acid. All these polyaromatic compounds, as well as antibiotic heliomycin, still showed pronounced activity against tick-borne encephalitis virus (TBEV) with limited toxicity in porcine embryo kidney (PEK) cell line. 5-(Perylen-3-yl)-2-thiophenecarboxylic acid (5a) showed the highest antiviral activity with 50% effective concentration of approx. 1.6 nM.

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Declaration of Competing Interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgments

The research was supported by the Russian Science Foundation (grant no. 15-15-00053 – synthesis of compounds), by the President Fellowship to AAC (SP-4083.2018.4), and by the State Research Funding for Chumakov FSC R&D IBP RAS (topic no. 0837-2019-0002 – antiviral activity and cytotoxicity studies). We thank Dr. Sergey N. Mikhailov (Engelhardt Institute of Molecular Biology RAS) for providing a sample of N6-(9-anthrylmethyl)-adenosine.

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