Skip to Content
MilliporeSigma
  • Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure--comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives.

Novel vitamin D receptor ligands bearing a spherical hydrophobic core structure--comparison of bicyclic hydrocarbon derivatives with boron cluster derivatives.

Bioorganic & medicinal chemistry letters (2012-01-31)
Angsuma Wongmayura, Shinya Fujii, Shigeru Ito, Atsushi Kano, Yoshiyuki Taoda, Emiko Kawachi, Hiroyuki Kagechika, Aya Tanatani
ABSTRACT

Vitamin D receptor (VDR) is a nuclear receptor for 1α,25-dihydroxyvitamin D(3) (1α,25(OH)(2)D(3)), and is an attractive target for multiple clinical applications. We recently developed novel non-secosteroidal VDR ligands bearing a hydrophobic p-carborane cage, thereby establishing the utility of this spherical hydrophobic core structure for development of VDR ligands. Here, we synthesized two series of novel non-secosteroidal VDR ligands with different spherical hydrophobic cores, that is, bicyclo[2.2.2]octane derivatives and p-carborane derivatives, and compared their biological activities in order to examine the difference between the interactions of the C-H hydrocarbon surface and the B-H carborane surface with the receptor. Carborane derivatives exhibited more potent differentiation-inducing activity toward HL-60 cells than did the corresponding bicyclo[2.2.2]octane derivatives. These results suggest that the hydrophobic carborane cage may interact more efficiently than the hydrocarbons with the hydrophobic surface of VDR. This finding further supports the view that carborane structure is a promising option for drug development.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1α,25-Dihydroxyvitamin D3, ≥99% (HPLC)
Sigma-Aldrich
1α,25-Dihydroxyvitamin D3, ≥97.0% (HPLC)
Sigma-Aldrich
1α,25-Dihydroxyvitamin D2 solution, 50 μg/mL in ethanol, 95% (CP)
Sigma-Aldrich
1α,25-Dihydroxyvitamin D2 solution, 100 μg/mL in ethanol, 95% (CP)