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

Ilona Bereczki, Máté Kicsák, Laura Dobray, A. Borbás, G. Batta, S. Kéki, Éva Nemes Nikodém, Eszter Ostorházi, F. Rozgonyi, Evelien Vanderlinden, Lieve Naesens, P. Herczegh

Research output: Contribution to journalArticle

11 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

Fingerprint

Teicoplanin
Virus Attachment
Orthomyxoviridae
Viruses
Antiviral Agents
Derivatives
Bearings (structural)
Lipid Bilayers
Human Influenza
Lipid bilayers
Anti-Bacterial Agents

Keywords

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

ASJC Scopus subject areas

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

Cite this

Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors : Synthesis and antiviral studies. / Bereczki, Ilona; Kicsák, Máté; Dobray, Laura; Borbás, A.; Batta, G.; Kéki, S.; Nikodém, Éva Nemes; Ostorházi, Eszter; Rozgonyi, F.; Vanderlinden, Evelien; Naesens, Lieve; Herczegh, P.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 24, No. 15, 01.08.2014, p. 3251-3254.

Research output: Contribution to journalArticle

Bereczki, Ilona ; Kicsák, Máté ; Dobray, Laura ; Borbás, A. ; Batta, G. ; Kéki, S. ; Nikodém, Éva Nemes ; Ostorházi, Eszter ; Rozgonyi, F. ; Vanderlinden, Evelien ; Naesens, Lieve ; Herczegh, P. / Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors : Synthesis and antiviral studies. In: Bioorganic and Medicinal Chemistry Letters. 2014 ; Vol. 24, No. 15. pp. 3251-3254.
@article{2386c07ff9984f6fbf36a270a467b7fe,
title = "Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors: Synthesis and antiviral studies",
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",
author = "Ilona Bereczki and M{\'a}t{\'e} Kics{\'a}k and Laura Dobray and A. Borb{\'a}s and G. Batta and S. K{\'e}ki and Nikod{\'e}m, {{\'E}va Nemes} and Eszter Ostorh{\'a}zi and F. Rozgonyi and Evelien Vanderlinden and Lieve Naesens and P. Herczegh",
year = "2014",
month = "8",
day = "1",
doi = "10.1016/j.bmcl.2014.06.018",
language = "English",
volume = "24",
pages = "3251--3254",
journal = "Bioorganic and Medicinal Chemistry Letters",
issn = "0960-894X",
publisher = "Elsevier Limited",
number = "15",

}

TY - JOUR

T1 - Semisynthetic teicoplanin derivatives as new influenza virus binding inhibitors

T2 - Synthesis and antiviral studies

AU - Bereczki, Ilona

AU - Kicsák, Máté

AU - Dobray, Laura

AU - Borbás, A.

AU - Batta, G.

AU - Kéki, S.

AU - Nikodém, Éva Nemes

AU - Ostorházi, Eszter

AU - Rozgonyi, F.

AU - Vanderlinden, Evelien

AU - Naesens, Lieve

AU - Herczegh, P.

PY - 2014/8/1

Y1 - 2014/8/1

N2 - 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.

AB - 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.

KW - Aggregation

KW - Influenza virus binding inhibitor

KW - Lipophilic substituents

KW - Teicoplanin pseudoaglycone

UR - http://www.scopus.com/inward/record.url?scp=84904068586&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84904068586&partnerID=8YFLogxK

U2 - 10.1016/j.bmcl.2014.06.018

DO - 10.1016/j.bmcl.2014.06.018

M3 - Article

C2 - 24974341

AN - SCOPUS:84904068586

VL - 24

SP - 3251

EP - 3254

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 15

ER -