Enhanced anti-influenza agents conjugated with anti-inflammatory activity

J Med Chem. 2012 Oct 11;55(19):8493-501. doi: 10.1021/jm3009844. Epub 2012 Sep 20.

Abstract

Influenza therapy with a single targeted compound is often limited in efficacy due to the rapidly developed drug resistance. Moreover, the uncontrolled virus-induced cytokines could cause the high mortality of human infected by H5N1 avian influenza virus. In this study, we explored the novel dual-targeted bifunctional anti-influenza drugs formed by conjugation with anti-inflammatory agents. In particular, the caffeic acid (CA)-bearing zanamivir (ZA) conjugates ZA-7-CA (1) and ZA-7-CA-amide (7) showed simultaneous inhibition of influenza virus neuraminidase and suppression of pro-inflammatory cytokines. These ZA conjugates provided remarkable protection of cells and mice against influenza infections. Intranasal administration of low dosage (<1.2 μmol/kg/day) of ZA conjugates exhibited much greater effect than the combination therapy with ZA and the anti-inflammatory agents in protection of the lethally infected mice by H1N1 or H5N1 influenza viruses.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Inflammatory Agents, Non-Steroidal / chemical synthesis*
  • Anti-Inflammatory Agents, Non-Steroidal / chemistry
  • Anti-Inflammatory Agents, Non-Steroidal / pharmacology
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Antiviral Agents / pharmacology
  • Caffeic Acids / chemical synthesis*
  • Caffeic Acids / pharmacology
  • Cell Line
  • Dogs
  • Female
  • Influenza A Virus, H1N1 Subtype
  • Influenza A Virus, H5N1 Subtype
  • Interferon-gamma / blood
  • Interleukin-6 / blood
  • Lipopolysaccharides / pharmacology
  • Mice
  • Mice, Inbred BALB C
  • Neuraminidase / antagonists & inhibitors
  • Orthomyxoviridae Infections / drug therapy
  • Orthomyxoviridae Infections / virology
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Tumor Necrosis Factor-alpha / blood
  • Zanamivir / analogs & derivatives*
  • Zanamivir / chemical synthesis*
  • Zanamivir / pharmacology

Substances

  • Anti-Inflammatory Agents, Non-Steroidal
  • Antiviral Agents
  • Caffeic Acids
  • Interleukin-6
  • Lipopolysaccharides
  • Tumor Necrosis Factor-alpha
  • Interferon-gamma
  • Neuraminidase
  • Zanamivir