Development of derivatives of 3, 3'-diindolylmethane as potent Leishmania donovani bi-subunit topoisomerase IB poisons

PLoS One. 2011;6(12):e28493. doi: 10.1371/journal.pone.0028493. Epub 2011 Dec 12.

Abstract

Background: The development of 3, 3'-diindolyl methane (DIM) resistant parasite Leishmania donovani (LdDR50) by adaptation with increasing concentrations of the drug generates random mutations in the large and small subunits of heterodimeric DNA topoisomerase I of Leishmania (LdTOP1LS). Mutation of large subunit of LdTOP1LS at F270L is responsible for resistance to DIM up to 50 µM concentration.

Methodology/principal findings: In search of compounds that inhibit the growth of the DIM resistant parasite and inhibit the catalytic activity of mutated topoisomerase I (F270L), we have prepared three derivatives of DIM namely DPDIM (2,2'-diphenyl 3,3'-diindolyl methane), DMDIM (2,2'-dimethyl 3,3'-diindolyl methane) and DMODIM (5,5'-dimethoxy 3,3'-diindolyl methane) from parent compound DIM. All the compounds inhibit the growth of DIM resistant parasites, induce DNA fragmentation and stabilize topo1-DNA cleavable complex with the wild type and mutant enzyme.

Conclusion: The results suggest that the three derivatives of DIM can act as promising lead molecules for the generation of new anti-leishmanial agents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Cell Death / drug effects
  • Cells, Cultured
  • DNA / metabolism
  • DNA Cleavage / drug effects
  • DNA Fragmentation / drug effects
  • DNA Topoisomerases, Type I / metabolism
  • DNA-Binding Proteins / chemistry
  • DNA-Binding Proteins / metabolism
  • Drug Resistance / drug effects
  • Endocytosis / drug effects
  • Fluorescence
  • Genome / genetics
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Leishmania donovani / cytology
  • Leishmania donovani / drug effects*
  • Leishmania donovani / enzymology*
  • Leishmania donovani / growth & development
  • Life Cycle Stages / drug effects
  • Macrophages / drug effects
  • Macrophages / parasitology
  • Mice
  • Mice, Inbred BALB C
  • Models, Molecular
  • Parasites / cytology
  • Parasites / drug effects
  • Parasites / growth & development
  • Protein Subunits / antagonists & inhibitors*
  • Protein Subunits / metabolism
  • Topoisomerase I Inhibitors / chemistry
  • Topoisomerase I Inhibitors / pharmacology*

Substances

  • DNA-Binding Proteins
  • Indoles
  • Protein Subunits
  • Topoisomerase I Inhibitors
  • DNA
  • DNA Topoisomerases, Type I
  • 3,3'-diindolylmethane