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Synthesis of antiviral perfluoroalkyl derivatives of teicoplanin and vancomycin.


ABSTRACT: The limited scope of antiviral drugs and increasing problem of antiviral drug resistance represent a global health threat. Glycopeptide antibiotics and their lipophilic derivatives have emerged as relevant inhibitors of diverse viruses. Here, we describe a new strategy for the synthesis of dual hydrophobic and lipophobic derivatives of glycopeptides, to produce selective antiviral agents without membrane-disrupting activity. Perfluorobutyl and perfluorooctyl moieties through linkers of different length were attached to azido derivatives of vancomycin aglycone and teicoplanin pseudoaglycone, and the new derivatives were evaluated against a diverse panel of viruses. The teicoplanin derivatives displayed strong anti-influenza virus activity at non-toxic concentrations. Some of the perfluoroalkylated glycopeptides were also active against a few other viruses such as herpes simplex virus or coronavirus. These data encourage further exploration of glycopeptide analogues for broad antiviral application.

SUBMITTER: Bereczki I 

PROVIDER: S-EPMC7540527 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Synthesis of Antiviral Perfluoroalkyl Derivatives of Teicoplanin and Vancomycin.

Bereczki Ilona I   Csávás Magdolna M   Szűcs Zsolt Z   Rőth Erzsébet E   Batta Gyula G   Ostorházi Eszter E   Naesens Lieve L   Borbás Anikó A   Herczegh Pál P  

ChemMedChem 20200730 17


The limited scope of antiviral drugs and increasing problem of antiviral drug resistance represent a global health threat. Glycopeptide antibiotics and their lipophilic derivatives have emerged as relevant inhibitors of diverse viruses. Herein, we describe a new strategy for the synthesis of dual hydrophobic and lipophobic derivatives of glycopeptides to produce selective antiviral agents without membrane-disrupting activity. Perfluorobutyl and perfluorooctyl moieties were attached through linke  ...[more]

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