2. Academic Validation
  3. Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: synthesis and antiviral studies

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

  • Bioorg Med Chem Lett. 2014 Aug 1;24(15):3251-4. doi: 10.1016/j.bmcl.2014.06.018.
Ilona Bereczki 1,  Máté Kicsák 1,  Laura Dobray 1,  Anikó Borbás 1,  Gyula Batta 2,  Sándor Kéki 3,  Éva Nemes Nikodém 4,  Eszter Ostorházi 4,  Ferenc Rozgonyi 4,  Evelien Vanderlinden 5,  Lieve Naesens 6,  Pál Herczegh 7
Affiliations

Affiliations

  • 1 Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.
  • 2 Department of Organic Chemistry, University of Debrecen, H-4032 Debrecen, Hungary.
  • 3 Department of Applied Chemistry, University of Debrecen, H-4032 Debrecen, Hungary.
  • 4 Microbiology Laboratory, Department of Dermatology, Venerology and Dermatooncology, Semmelweis University, Mária u. 41, H-1085 Budapest, Hungary.
  • 5 Rega Institute for Medical Research, KU Leuven, B-3000 Leuven, Belgium.
  • 6 Rega Institute for Medical Research, KU Leuven, B-3000 Leuven, Belgium. Electronic address: lieve.naesens@rega.kuleuven.be.
  • 7 Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary. Electronic address: herczeghp@gmail.com.
PMID: 24974341 DOI: 10.1016/j.bmcl.2014.06.018
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.

Keywords

Aggregation; Influenza virus binding inhibitor; Lipophilic substituents; Teicoplanin pseudoaglycone.

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