Utility of boron clusters for drug design. Relation between estrogen receptor binding affinity and hydrophobicity of phenols bearing various types of carboranyl groups

Complexation of .ALPHA.-Cyclodextrin with Carborane Derivatives in Aqueous Solution

“…In the development of carborane-containing estrogen ligands, we have investigated the hydrophobicity of carboranes by measuring the partition coefficients, log P values, and the hydrophobicity parameter p. 14,15) Cyclodextrins (CDs) are widely used as host molecules in a number of areas of chemistry where molecular recognition is required, such as material sciences, supramolecular chemistry, molecular-sensing, and artificial enzymes (Fig. 1).…”

“…13) It was suggested that the carborane cage works as a hydrophobic group for binding to the hydrophobic cavity of the ligand-binding domain (LBD) on the nuclear receptors, and that hydrophobic van der Waals contacts along the spherical carborane cage produce a stronger interaction than that in the case of the native ligand. In the development of carborane-containing estrogen ligands, we have investigated the hydrophobicity of carboranes by measuring the partition coefficients, log P values, and the hydrophobicity parameter p. 14,15) Cyclodextrins (CDs) are widely used as host molecules in a number of areas of chemistry where molecular recognition is required, such as material sciences, supramolecular chemistry, molecular-sensing, and artificial enzymes (Fig. 1).…”

Ab initio quantum chemical study of electron transfer in carboranes

“…Carboranes are an important class of boron-containing rigid structures that have potential applications in medicinal drug design as hydrophobic pharmacophores [1], as antisense agents for antisense oligonucleotide therapy (AOT) [2], as boron carriers for boron neutron capture therapy (BNCT) [3][4][5], and as molecular probes for molecular medical diagnostics [6], among others. Recently, heteroisomeric diodes, based upon the chemical vapor deposition of different isomers of closo-dicarbadodecaborane, namely closo-1,2-dicarbadodecaborane (orthocarborane, C 2 B 10 H 12 ) and closo-1,7-dicarbadodecaborane (metacarborane, C 2 B 10 H 12 ), which have important applications as solid state neutron detectors have also been fabricated [7].…”

Aliphatic Substitution of <i>o</i>-Carboranyl Phenols Enhances Estrogen Receptor Beta Selectivity

“…[11][12][13][14][15][16][17][18] In addition, our quantitative structure-activity relationship (QSAR) studies of very simple carboranyl phenols showed that the hydrophobicity of the carborane cage is significantly correlated with ERα-binding affinity. 30,31) Although carboraNote * To whom correspondence should be addressed. e-mail: yendo@tohoku-pharm.ac.jp…”