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Synthesis of Antiviral Perfluoroalkyl Derivatives of Teicoplanin and Vancomycin
Author(s) -
Bereczki Ilona,
Csávás Magdolna,
Szűcs Zsolt,
Rőth Erzsébet,
Batta Gyula,
Ostorházi Eszter,
Naesens Lieve,
Borbás Anikó,
Herczegh Pál
Publication year - 2020
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.202000260
Subject(s) - teicoplanin , glycopeptide , vancomycin , glycopeptide antibiotic , herpes simplex virus , chemistry , virus , antibiotics , combinatorial chemistry , microbiology and biotechnology , biology , virology , biochemistry , bacteria , staphylococcus aureus , genetics
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 linkers of different length 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 nontoxic 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.