Identification of 3-acyl-2-phenylamino-1,4-dihydroquinolin-4-one derivatives as inhibitors of the phosphatase SerB653 in Porphyromonas gingivalis, implicated in periodontitis

Bioorg Med Chem Lett. 2012 Mar 1;22(5):2084-8. doi: 10.1016/j.bmcl.2012.01.011. Epub 2012 Jan 21.

Abstract

The serine phosphatase SerB653 plays a crucial role in the infection of Porphyromonas gingivalis, which contributes to the pathogenesis of periodontitis, an inflammatory disease of teeth-supporting tissues. Because functional loss of SerB653 eliminates the virulence of P. gingivalis, SerB653 inhibitors are considered potential periodontitis therapeutic or preventive agents. To identify SerB653 inhibitors with potent anti-periodontitis activity, we conducted a high-throughput screen of a representative 6800-compound subset of a synthetic chemical library of the Korea Chemical Bank (KCB) for compounds with activity against SerB653. The primary screening yielded 150 hits, and subsequent confirmatory studies identified eight compounds, mainly within a single cluster of 3-acyl-2-phenylamino-1,4-dihydroquinolin-4-one derivatives, that showed greater than 50% inhibition of SerB653 activity at a concentration of 50μM. A second screening with a focused library identified 10 compounds with IC(50) values less than 10μM. In antibacterial tests, three of these compounds showed a minimum inhibitory concentration against P. gingivalis growth of 5-50nM.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Bacteroidaceae Infections / drug therapy
  • Bacteroidaceae Infections / enzymology
  • Enzyme Inhibitors / chemistry
  • Enzyme Inhibitors / pharmacology*
  • Humans
  • Models, Molecular
  • Periodontitis / drug therapy
  • Periodontitis / microbiology*
  • Phosphoric Monoester Hydrolases / antagonists & inhibitors*
  • Phosphoric Monoester Hydrolases / metabolism
  • Porphyromonas gingivalis / drug effects*
  • Porphyromonas gingivalis / enzymology*
  • Porphyromonas gingivalis / growth & development
  • Quinolines / chemistry
  • Quinolines / pharmacology*
  • Structure-Activity Relationship

Substances

  • 1,4-dihydroquinoline
  • Enzyme Inhibitors
  • Quinolines
  • Phosphoric Monoester Hydrolases