Naphthalimides Selectively Inhibit the Activity of Bacterial, Replicative DNA Ligases and Display Bactericidal Effects against Tubercle Bacilli

Molecules. 2017 Jan 17;22(1):154. doi: 10.3390/molecules22010154.

Abstract

The DNA ligases, enzymes that seal breaks in the backbones of DNA, are essential for all organisms, however bacterial ligases essential for DNA replication use β-nicotinamide adenine dinucleotide as their co-factor, whereas those that are essential in eukaryotes and viruses use adenosine-5'-triphosphate. This fact leads to the conclusion that NAD⁺-dependent DNA ligases in bacteria could be targeted by their co-factor specific inhibitors. The development of novel alternative medical strategies, including new drugs, are a top priority focus areas for tuberculosis research due to an increase in the number of multi-drug resistant as well as totally drug resistant tubercle bacilli strains. Here, through the use of a virtual high-throughput screen and manual inspection of the top 200 records, 23 compounds were selected for in vitro studies. The selected compounds were evaluated in respect to their Mycobacterium tuberculosis NAD⁺ DNA ligase inhibitory effect by a newly developed assay based on Genetic Analyzer 3500 Sequencer. The most effective agents (e.g., pinafide, mitonafide) inhibited the activity of M. tuberculosis NAD⁺-dependent DNA ligase A at concentrations of 50 µM. At the same time, the ATP-dependent (phage) DNA LigT₄ was unaffected by the agents at concentrations up to 2 mM. The selected compounds appeared to also be active against actively growing tubercle bacilli in concentrations as low as 15 µM.

Keywords: DNA ligase A; Mycobacterium tuberculosis; antituberculosis drugs; naphthalimides.

MeSH terms

  • Antitubercular Agents / pharmacology*
  • Bacterial Proteins / antagonists & inhibitors
  • DNA Ligases / antagonists & inhibitors*
  • Enzyme Inhibitors / pharmacology
  • High-Throughput Screening Assays
  • Isoquinolines / pharmacology
  • Molecular Docking Simulation
  • Mycobacterium tuberculosis / drug effects*
  • NAD
  • Naphthalimides / pharmacology*

Substances

  • Antitubercular Agents
  • Bacterial Proteins
  • Enzyme Inhibitors
  • Isoquinolines
  • Naphthalimides
  • mitonafide
  • NAD
  • pinafide
  • DNA Ligases