Differential interactions of antiretroviral agents with LXR, ER and GR nuclear receptors: potential contributing factors to adverse events

Br J Pharmacol. 2014 Jan;171(2):480-97. doi: 10.1111/bph.12480.

Abstract

Background and purpose: Antiretroviral (ARV) drugs activate pregnane X receptors and constitutive androstane receptors, increasing the risk of drug interactions due to altered drug metabolism and disposition. The closely related liver X receptors (LXRα/β), oestrogen receptors (ERα/β) and glucocorticoid receptor (GR) regulate many endogenous processes such as lipid/cholesterol homeostasis, cellular differentiation and inflammation. However, ARV drug activation of these nuclear receptors has not been thoroughly investigated.

Experimental approach: The ability of an ARV drug library to activate LXRα/β, ERα/β and GR was assessed using a combined in silico and in vitro approach encompassing computational docking and molecular descriptor filtering, cell-free time-resolved fluorescence resonance energy transfer co-activator assays to assess direct binding to ligand-binding domains (LBDs), cell-based reporter assays and target gene expression.

Key results: Direct LBD interactions with LXRα and/or LXRβ were predicted in silico and confirmed in vitro for darunavir, efavirenz, flavopiridol, maraviroc and tipranavir. Likewise, efavirenz was also predicted and confirmed as a ligand of ERα-LBD. Interestingly, atazanavir and ritonavir also activated LXRα/β in reporter assays, while tipranavir enhanced transcriptional activity of ERα. Effects on ER and LXR target gene expression were confirmed for efavirenz and tipranavir.

Conclusions and implications: There was good agreement between in silico predictions and in vitro results. However, some nuclear receptor interactions identified in vitro were probably due to allosteric effects or nuclear receptor cross-talk, rather than direct LBD binding. This study indicates that some of the adverse effects associated with ARV use may be mediated through 'off-target' effects involving nuclear receptor activation.

Keywords: HIV protease inhibitor; TR-FRET co-activator assay; antiretroviral drug; efavirenz; glucocorticoid receptor; ligand-binding domain; liver X receptor; luciferase reporter assay; molecular modelling; nuclear receptor; oestrogen receptor.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Retroviral Agents / pharmacology*
  • Benzoates / pharmacology
  • Benzylamines / pharmacology
  • Cell Line
  • Computer Simulation
  • Dexamethasone / pharmacology
  • Estradiol / pharmacology
  • Fluorescence Resonance Energy Transfer
  • Gene Expression / drug effects
  • Gene Library
  • Humans
  • Liver X Receptors
  • Luciferases / genetics
  • Models, Molecular
  • Orphan Nuclear Receptors / drug effects*
  • Receptors, Cytoplasmic and Nuclear / drug effects
  • Receptors, Cytoplasmic and Nuclear / metabolism*
  • Receptors, Estrogen / drug effects*
  • Receptors, Glucocorticoid / drug effects*
  • Transfection
  • X-Ray Diffraction

Substances

  • Anti-Retroviral Agents
  • Benzoates
  • Benzylamines
  • GW 3965
  • Liver X Receptors
  • NR1H3 protein, human
  • Orphan Nuclear Receptors
  • Receptors, Cytoplasmic and Nuclear
  • Receptors, Estrogen
  • Receptors, Glucocorticoid
  • Estradiol
  • Dexamethasone
  • Luciferases