Dicarba-closo-dodecaboranes as a pharmacophore. Novel potent retinoidal agonists

Chem Pharm Bull (Tokyo). 1999 Apr;47(4):585-7. doi: 10.1248/cpb.47.585.


The synthesis and biological evaluation of the dicarba-closo-dodecaborane (carborane) derivatives of retinoids are described. Retinoidal activity was examined in terms of the differentiation-inducing ability toward human promyelocytic leukemia HL-60 cells. High retinoidal activity (agonist or antagonist for the retinoid receptor RAR) requires a carboxylic acid moiety and an appropriate hydrophobic group located at a suitable position on the molecule. 4-[4-(1,2-Dicarba-closo-dodecaboran-1-yl)phenylamino]b enzoic acids and 4-[3-(1,2-dicarba-closo-dodecaboran-1-yl)phenylamino]b enzoic acids showed potent agonistic activity at concentrations of 10(-8)-10(-9) M. The results indicate that carboranes are applicable as the hydrophobic moiety of biologically active molecules.

MeSH terms

  • Boron Compounds / chemical synthesis*
  • Boron Compounds / pharmacology*
  • Cell Differentiation / drug effects
  • HL-60 Cells / drug effects
  • Humans
  • Molecular Structure
  • Receptors, Retinoic Acid / agonists*
  • Retinoids / antagonists & inhibitors*
  • Structure-Activity Relationship


  • Boron Compounds
  • Receptors, Retinoic Acid
  • Retinoids