Novel nonsecosteroidal VDR agonists with phenyl-pyrrolyl pentane skeleton

Eur J Med Chem. 2013 Nov:69:768-78. doi: 10.1016/j.ejmech.2013.09.015. Epub 2013 Sep 18.

Abstract

In order to find the vitamin D receptor (VDR) ligand whose VDR agonistic activity is separated from the calcemic activity sufficiently, novel nonsecosteroidal analogs with phenyl-pyrrolyl pentane skeleton were synthesized and evaluated for the VDR binding affinity, antiproliferative activity in vitro and serum calcium raising ability in vivo (tacalcitol used as control). Among them, several compounds showed varying degrees of VDR agonistic and growth inhibition activities of the tested cell lines. The most effective compound 2g (EC₅₀: 1.06 nM) exhibited stronger VDR agonistic activity than tacalcitol (EC₅₀: 7.05 nM), inhibited the proliferations of HaCaT and MCF-7 cells with IC₅₀ of 2.06 μM and 0.307 μM (tacalcitol: 2.07 μM and 0.057 μM) and showed no significant effect on serum calcium.

Keywords: Calcemic activity; Docking study; Phenyl-pyrrolyl pentane skeleton; VDR; VDR agonistic activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology*
  • Butanones / chemical synthesis
  • Butanones / chemistry
  • Butanones / pharmacology*
  • Calcium / metabolism
  • Cell Line
  • Cell Proliferation / drug effects
  • Dose-Response Relationship, Drug
  • Drug Screening Assays, Antitumor
  • HL-60 Cells
  • Humans
  • Ligands
  • MCF-7 Cells
  • Mice
  • Mice, Inbred ICR
  • Models, Molecular
  • Molecular Structure
  • Pyrroles / chemical synthesis
  • Pyrroles / chemistry
  • Pyrroles / pharmacology*
  • Receptors, Calcitriol / agonists*
  • Structure-Activity Relationship

Substances

  • 5-(3-(4-(2-hydroxy-3,3-dimethylbutoxy)-3-methylphenyl)pentan-3-yl)-N-(1-hydroxypropan-2-yl)-1-ethylpyrrole-2-carboxamide
  • Antineoplastic Agents
  • Butanones
  • Ligands
  • Pyrroles
  • Receptors, Calcitriol
  • Calcium