The novel antibacterial compound walrycin A induces human PXR transcriptional activity

Toxicol Sci. 2012 May;127(1):225-35. doi: 10.1093/toxsci/kfs073. Epub 2012 Feb 7.

Abstract

The human pregnane X receptor (PXR) is a ligand-regulated transcription factor belonging to the nuclear receptor superfamily. PXR is activated by a large, structurally diverse, set of endogenous and xenobiotic compounds and coordinates the expression of genes central to metabolism and excretion of potentially harmful chemicals and therapeutic drugs in humans. Walrycin A is a novel antibacterial compound targeting the WalK/WalR two-component signal transduction system of Gram (+) bacteria. Here, we report that, in hepatoma cells, walrycin A potently activates a gene set known to be regulated by the xenobiotic sensor PXR. Walrycin A was as efficient as the reference PXR agonist rifampicin to activate PXR in a transactivation assay at noncytotoxic concentrations. Using a limited proteolysis assay, we show that walrycin A induces conformational changes at a concentration which correlates with walrycin A ability to enhance the expression of prototypic target genes, suggesting that walrycin A interacts with PXR. The activation of the canonical human PXR target gene CYP3A4 by walrycin A is dose and PXR dependent. Finally, in silico docking experiments suggest that the walrycin A oxidation product Russig's blue is the actual ligand for PXR. Taken together, these results identify walrycin A as a novel human PXR activator.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / toxicity*
  • Cell Line, Transformed
  • Cell Survival / drug effects
  • Computational Biology
  • Computer Simulation
  • Cytochrome P-450 CYP3A / biosynthesis*
  • Cytochrome P-450 CYP3A / genetics
  • Gene Expression / drug effects*
  • Hepatocytes / drug effects*
  • Hepatocytes / metabolism
  • Humans
  • Naphthols / toxicity*
  • Oligonucleotide Array Sequence Analysis
  • Pregnane X Receptor
  • Protein Binding
  • Quantitative Structure-Activity Relationship
  • RNA, Small Interfering / administration & dosage
  • RNA, Small Interfering / genetics
  • Real-Time Polymerase Chain Reaction
  • Receptors, Steroid / drug effects*
  • Receptors, Steroid / genetics
  • Rifampin / pharmacology
  • Transfection

Substances

  • Anti-Bacterial Agents
  • Naphthols
  • Pregnane X Receptor
  • RNA, Small Interfering
  • Receptors, Steroid
  • walrycin A
  • Cytochrome P-450 CYP3A
  • CYP3A4 protein, human
  • Rifampin