Inhibitors of DNA polymerase III as novel antimicrobial agents against gram-positive eubacteria
Tarantino, Paul M. Jr. ; Zhi, Chengxin ; Wright, George E. ; Brown, Neal C.
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Keywords
Animals
Anti-Bacterial Agents
Bacillus subtilis
Bacterial Proteins
Cattle
DNA Polymerase III
Enterococcus faecalis
Enterococcus faecium
Enzyme Inhibitors
Female
Gram-Positive Bacteria
Kinetics
Mice
Microbial Sensitivity Tests
Staphylococcal Infections
Staphylococcus aureus
Structure-Activity Relationship
Uracil
Medical Molecular Biology
Pharmacology
Toxicology
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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.
Source
Antimicrob Agents Chemother. 1999 Aug;43(8):1982-7.