Synthesis of Antiviral Perfluoroalkyl Derivatives of Teicoplanin and Vancomycin.
Animals
Anti-Bacterial Agents
/ chemical synthesis
Antiviral Agents
/ chemical synthesis
Bacillus subtilis
/ drug effects
Catalysis
Cell Line
Cell Survival
/ drug effects
Coronavirus
/ drug effects
Dogs
Fluorocarbons
/ chemistry
Humans
Microbial Sensitivity Tests
Palladium
/ chemistry
Staphylococcus aureus
/ drug effects
Structure-Activity Relationship
Teicoplanin
/ chemistry
Vancomycin
/ chemistry
Zika Virus
/ drug effects
antiviral
coronavirus
glycopeptide antibiotic
influenza virus
perfluoroalkyl
Journal
ChemMedChem
ISSN: 1860-7187
Titre abrégé: ChemMedChem
Pays: Germany
ID NLM: 101259013
Informations de publication
Date de publication:
03 09 2020
03 09 2020
Historique:
received:
22
04
2020
revised:
28
06
2020
pubmed:
12
7
2020
medline:
17
12
2020
entrez:
12
7
2020
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 32652783
doi: 10.1002/cmdc.202000260
pmc: PMC7540527
doi:
Substances chimiques
Anti-Bacterial Agents
0
Antiviral Agents
0
Fluorocarbons
0
Palladium
5TWQ1V240M
Teicoplanin
61036-62-2
Vancomycin
6Q205EH1VU
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
1661-1671Subventions
Organisme : European Regional Development Fund
ID : GINOP-2.3.2-15-2016-00044
Pays : International
Organisme : European Regional Development Fund
ID : GINOP-2.3.2-15-2016-00008
Pays : International
Organisme : European Regional Development Fund
ID : GINOP-2.3.3-15-2016-00004
Pays : International
Organisme : European Social Fund
ID : EFOP-3.6.3-VEKOP-16-2017-00009
Pays : International
Organisme : National Research, Development and Innovation Office of Hungary
ID : K119509
Pays : International
Informations de copyright
© 2020 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
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