Structure-activity relationship of nonsecosteroidal vitamin D receptor modulators

Trends Pharmacol Sci. 2014 Jul;35(7):324-37. doi: 10.1016/j.tips.2014.04.008. Epub 2014 May 25.

Abstract

The vitamin D receptor (VDR), a receptor for the secosteroid 1α,25-dihydroxyvitamin D3 [1,25(OH)2D3], is a promising drug target in the treatment of bone and mineral disorders, cancer, autoimmune disease, infection, and cardiovascular disease. Indeed, approximately 100 nonsecosteroidal VDR modulators (VDRMs) have been developed. Analysis of X-ray crystal structures reveals: (i) nonsecosteroidal VDRMs bind to VDR in a position similar to 1,25(OH)2D3; (ii) hydrogen bond interactions between ligands and VDR are the most important for VDR binding; (iii) hydrophobic interactions and CH-π interactions in aromatic ligands are also important for VDR binding; and (iv) exchange of C-O-C linkage to C-CH2-C linkage in VDRMs increases transactivation activity, probably as a result of an entropic effect of solvation/desolvation of molecules. Several VDRMs have better therapeutic efficacy when compared to 1,25(OH)2D3 in experimental models of cancer and osteoporosis with less induction of hypercalcemia, a major potential adverse effect in the clinical application of VDR ligands.

Keywords: cancer; crystal structures; hypercalcemia; nuclear receptors; selective VDR modulators; vitamin D receptor.

Publication types

  • Review

MeSH terms

  • Acetates / chemistry
  • Acetates / pharmacology
  • Animals
  • Arylsulfonates / chemistry
  • Arylsulfonates / pharmacology
  • Benzene Derivatives / chemistry*
  • Benzene Derivatives / pharmacology*
  • Biphenyl Compounds / chemistry
  • Biphenyl Compounds / pharmacology
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology
  • Crystallography, X-Ray
  • Humans
  • Ligands
  • Models, Molecular
  • Receptors, Calcitriol / chemistry*
  • Receptors, Calcitriol / metabolism*
  • Structure-Activity Relationship
  • Thiophenes / chemistry
  • Thiophenes / pharmacology

Substances

  • Acetates
  • Arylsulfonates
  • Benzene Derivatives
  • Biphenyl Compounds
  • Carboxylic Acids
  • LY 2108491
  • LY 2109866
  • Ligands
  • Receptors, Calcitriol
  • Thiophenes
  • YR301