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Neoechinulin B and its analogues as potential entry inhibitors of influenza viruses, targeting viral hemagglutinin.

Abstract
A class of prenylated indole diketopiperazine alkaloids including 15 new compounds namely rubrumlines A-O obtained from marine-derived fungus Eurotium rubrum, were tested against influenza A/WSN/33 virus. Neoechinulin B (18) exerted potent inhibition against H1N1 virus infected in MDCK cells, and is able to inhibit a panel of influenza virus strains including amantadine- and oseltamivir-resistant clinical isolates. Mechanism of action studies indicated that neoechinulin B binds to influenza envelope hemagglutinin, disrupting its interaction with the sialic acid receptor and the attachment of viruses to host cells. In addition, neoechinulin B was still efficient in inhibiting influenza A/WSN/33 virus propagation even after a fifth passage. The high potency and broad-spectrum activities against influenza viruses with less drug resistance make neoechinulin B as a new lead for the development of potential inhibitor of influenza viruses.
AuthorsXueqing Chen, Longlong Si, Dong Liu, Peter Proksch, Lihe Zhang, Demin Zhou, Wenhan Lin
JournalEuropean journal of medicinal chemistry (Eur J Med Chem) Vol. 93 Pg. 182-95 (Mar 26 2015) ISSN: 1768-3254 [Electronic] France
PMID25681711 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
CopyrightCopyright © 2015 Elsevier Masson SAS. All rights reserved.
Chemical References
  • Alkaloids
  • Antiviral Agents
  • H1N1 virus hemagglutinin
  • Hemagglutinin Glycoproteins, Influenza Virus
  • Piperazines
  • neoechinulin
Topics
  • Alkaloids (chemical synthesis, chemistry, isolation & purification, pharmacology)
  • Animals
  • Antiviral Agents (chemical synthesis, chemistry, isolation & purification, pharmacology)
  • Cell Line, Tumor
  • Cell Survival (drug effects)
  • Cytopathogenic Effect, Viral
  • Dogs
  • Dose-Response Relationship, Drug
  • Drug Resistance, Viral (drug effects)
  • Eurotium (chemistry)
  • HEK293 Cells
  • Hemagglutinin Glycoproteins, Influenza Virus (metabolism)
  • Humans
  • Influenza A Virus, H1N1 Subtype (drug effects, growth & development, metabolism)
  • Madin Darby Canine Kidney Cells
  • Molecular Structure
  • Piperazines (chemical synthesis, chemistry, isolation & purification, pharmacology)
  • Structure-Activity Relationship
  • Viral Plaque Assay

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