Inhibitors of DNA polymerase III as novel antimicrobial agents against gram-positive eubacteria

Antimicrob Agents Chemother. 1999 Aug;43(8):1982-7. doi: 10.1128/AAC.43.8.1982.

Abstract

6-Anilinouracils are selective inhibitors of DNA polymerase III, the enzyme required for the replication of chromosomal DNA in gram-positive bacteria (N. C. Brown, L. W. Dudycz, and G. E. Wright, Drugs Exp. Clin. Res. 12:555-564, 1986). A new class of 6-anilinouracils based on N-3 alkyl substitution of the uracil ring was synthesized and analyzed for activity as inhibitors of the gram-positive bacterial DNA polymerase III and the growth of gram-positive bacterial pathogens. Favorable in vitro properties of N-3-alkyl derivatives prompted the synthesis of derivatives in which the R group at N-3 was replaced with more-hydrophilic methoxyalkyl and hydroxyalkyl groups. These hydroxyalkyl and methoxyalkyl derivatives displayed K(i) values in the range from 0.4 to 2.8 microM against relevant gram-positive bacterial DNA polymerase IIIs and antimicrobial activity with MICs in the range from 0.5 to 15 microg/ml against a broad spectrum of gram-positive bacteria, including methicillin-resistant staphylococci and vancomycin-resistant enterococci. Two of these hydrophilic derivatives displayed protective activity in a simple mouse model of lethal staphylococcal infection.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Aniline Compounds / pharmacology
  • Animals
  • Anti-Bacterial Agents / pharmacology*
  • Bacillus subtilis / drug effects
  • Bacillus subtilis / enzymology
  • Bacterial Proteins / antagonists & inhibitors*
  • Cattle
  • DNA Polymerase III / antagonists & inhibitors*
  • Enterococcus faecalis / drug effects
  • Enterococcus faecalis / enzymology
  • Enterococcus faecium / drug effects
  • Enterococcus faecium / enzymology
  • Enzyme Inhibitors / pharmacology*
  • Female
  • Gram-Positive Bacteria / drug effects*
  • Gram-Positive Bacteria / enzymology*
  • Kinetics
  • Mice
  • Microbial Sensitivity Tests
  • Staphylococcal Infections / drug therapy
  • Staphylococcus aureus / drug effects
  • Staphylococcus aureus / enzymology
  • Structure-Activity Relationship
  • Uracil / analogs & derivatives*
  • Uracil / pharmacology

Substances

  • Aniline Compounds
  • Anti-Bacterial Agents
  • Bacterial Proteins
  • Enzyme Inhibitors
  • Uracil
  • DNA Polymerase III