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.
authors: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.
authors: Ilona
authors: I
authors: Bereczki
authors: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.
authors: Máté
authors: M
authors: Kicsák
authors: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.
authors: Laura
authors: L
authors: Dobray
authors: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary.
authors: Anikó
authors: A
authors: Borbás
authors: Department of Organic Chemistry, University of Debrecen, H-4032 Debrecen, Hungary.
authors: Gyula
authors: G
authors: Batta
authors: Department of Applied Chemistry, University of Debrecen, H-4032 Debrecen, Hungary.
authors: Sándor
authors: S
authors: Kéki
authors: Microbiology Laboratory, Department of Dermatology, Venerology and Dermatooncology, Semmelweis University, Mária u. 41, H-1085 Budapest, Hungary.
authors: Éva Nemes
authors: ÉN
authors: Nikodém
authors: Microbiology Laboratory, Department of Dermatology, Venerology and Dermatooncology, Semmelweis University, Mária u. 41, H-1085 Budapest, Hungary.
authors: Eszter
authors: E
authors: Ostorházi
authors: Microbiology Laboratory, Department of Dermatology, Venerology and Dermatooncology, Semmelweis University, Mária u. 41, H-1085 Budapest, Hungary.
authors: Ferenc
authors: F
authors: Rozgonyi
authors: Rega Institute for Medical Research, KU Leuven, B-3000 Leuven, Belgium.
authors: Evelien
authors: E
authors: Vanderlinden
authors: Rega Institute for Medical Research, KU Leuven, B-3000 Leuven, Belgium. Electronic address: lieve.naesens@rega.kuleuven.be.
authors: Lieve
authors: L
authors: Naesens
authors: Department of Pharmaceutical Chemistry, University of Debrecen, Egyetem tér 1, H-4032 Debrecen, Hungary. Electronic address: herczeghp@gmail.com.
authors: Pál
authors: P
authors: Herczegh
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D001665:Binding Sites / Q000187:drug effects; D004285:Dogs; D004305:Dose-Response Relationship, Drug; D008051:Lipid Bilayers / Q000378:metabolism; D061985:Madin Darby Canine Kidney Cells / Q000187:drug effects / Q000378:metabolism / Q000821:virology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009975:Orthomyxoviridae / Q000187:drug effects*; D013329:Structure-Activity Relationship; D017334:Teicoplanin / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000998:Antiviral Agents; D008051:Lipid Bilayers; D017334:Teicoplanin
keywords: Aggregation; Influenza virus binding inhibitor; Lipophilic substituents; Teicoplanin pseudoaglycone