Design, synthesis, and evaluation of WC5 analogues as inhibitors of human cytomegalovirus Immediate-Early 2 protein, a promising target for anti-HCMV treatment

ChemMedChem. 2013 Aug;8(8):1403-14. doi: 10.1002/cmdc.201300106. Epub 2013 Jun 11.

Abstract

Although human cytomegalovirus (HCMV) infection is mostly asymptomatic for immunocompetent individuals, it remains a serious threat for those who are immunocompromised, in whom it is associated with various clinical manifestations. The therapeutic utility of the few available anti-HCMV drugs is limited by several drawbacks, including cross-resistance due to their common mechanism of action, i.e., inhibition of viral DNA polymerase. Therefore, compounds that target other essential viral events could overcome this problem. One example of this is the 6-aminoquinolone WC5, which acts by directly blocking the transactivation of essential viral Early genes by the Immediate-Early 2 (IE2) protein. In this study, the quinolone scaffold of the lead compound WC5 was investigated in depth, defining more suitable substituents for each of the scaffold positions explored and identifying novel, potent and nontoxic compounds. Some compounds showed potent anti-HCMV activity by interfering with IE2-dependent viral E gene expression. Among them, naphthyridone 1 was also endowed with potent anti-HIV activity in latently infected cells. Their antiviral profile along with their innovative mechanism of action make these anti-HCMV quinolones a very promising class of compounds to be exploited for more effective antiviral therapeutic treatment.

Keywords: 6-aminoquinolones; HCMV; antiviral agents; immediate-early 2 protein; inhibitors.

Publication types

  • Evaluation Study
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoquinolines / chemistry*
  • Aminoquinolines / therapeutic use
  • Aminoquinolines / toxicity
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / therapeutic use
  • Antiviral Agents / toxicity
  • Cell Line
  • Cell Survival / drug effects
  • Cytomegalovirus / drug effects
  • Cytomegalovirus / metabolism*
  • Cytomegalovirus Infections / drug therapy
  • Drug Design*
  • HEK293 Cells
  • HIV-1 / drug effects
  • Humans
  • Immediate-Early Proteins / antagonists & inhibitors*
  • Immediate-Early Proteins / metabolism
  • Quinolones / chemistry*
  • Quinolones / therapeutic use
  • Quinolones / toxicity
  • Structure-Activity Relationship
  • Trans-Activators / antagonists & inhibitors*
  • Trans-Activators / metabolism
  • Virus Replication / drug effects

Substances

  • Aminoquinolines
  • Antiviral Agents
  • IE2 protein, Cytomegalovirus
  • Immediate-Early Proteins
  • Quinolones
  • Trans-Activators
  • WC5 compound