Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: Synthesis and antiviral studies

Ilona Bereczki, Máté Kicsák, Laura Dobray, Anikó Borbás, Gyula Batta, Sándor Kéki, Éva Nemes Nikodém, Eszter Ostorházi, Ferenc Rozgonyi, Evelien Vanderlinden, Lieve Naesens, Pál Herczegh

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

In order to obtain new, cluster-forming antibiotic compounds, teicoplanin pseudoaglycone derivatives containing two lipophilic n-octyl chains have been synthesized. The compounds proved to be poor antibacterials, but, surprisingly, they exhibited potent anti-influenza virus activity against influenza A strains. This antiviral action was related to inhibition of the binding interaction between the virus and the host cell. Related analogs bearing methyl substituents in lieu of the octyl chains, displayed no anti-influenza virus activity. Hence, an interaction between the active, dually n-octylated compounds and the lipid bilayer of the host cell can be postulated, to explain the observed inhibition of influenza virus attachment.

Original languageEnglish
Pages (from-to)3251-3254
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number15
DOIs
Publication statusPublished - Aug 1 2014

Keywords

  • Aggregation
  • Influenza virus binding inhibitor
  • Lipophilic substituents
  • Teicoplanin pseudoaglycone

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: Synthesis and antiviral studies'. Together they form a unique fingerprint.

  • Cite this