Teicoplanin and vancomycin derivatives with perfluorilated alkyl groups are active against influenza and coronavirus

ABSTRACT

Background: As we have seen in the last six months, emerging and re-emerging viruses could be the biggest threat for the human population nowadays in our modern, accelerated and globalized world. Both of influenza and coronaviruses have the potential to cause serious pandemics worldwide. Unfortunately, there are no effective enough medications against most of these viruses. Aims: As some glycopeptide antibiotics and their derivatives proved to be effective against several viruses1, therefore we planned to synthesize some new derivatives equipped with highly fluorinated lipophilic groups. Methods: Perfluorobutyl and perfluorooctyl groups were conjugated to the N-terminus of teicoplanin pseudoaglycone and vancomycin aglycone derivatives through ethylene glycol and tetraethylene glycol linkers by means of photoinitiated addition and azide-alkyne click reaction. The effect of the derivatives were evaluated against several viruses including influenza and human coronavirus. Results: Vancomycin aglycone derivatives were inactive against all of the studied influenza strains, while 3 out of the 4 perfluorobutyl and perfluorooctyl derivatives of teicoplanin pseudoaglycone displayed very good activity against influenza H1N1, H3N2 and B strains. Two of the derivatives were active against human coronavirus as well. Conclusion: We hope that these results can open a new way in finding more effective antivirals based on glycopeptide antibiotics.