Optimal Lipophilicity of Sulfonium <i>p</i>-Toluenesulfonate as Anti-allergic Drug

Abstract

In the development of the anti-allergic drug Suplatast Tosilate (IPD-1151T) we have reported the QSAR analysis using only the calculated values, because the few logK values of sulfonium compounds had been measured till then. In this study, we measured the logK TLC value of sulfonium compounds by using octylsililated silicagel plate (Merck HPTLC RP-8 F 254S ). The logK TLC values of the optimized compounds 52 and 67 (Suplatast Tosilate) of dimethylsulfonium p-toluenesulfonates derivatives were 0.07 and 0.06, respectively. Therefore, it was found that the desirable logK TLC value of the sulfonium compound was approximately zero as the anti-allergic drug.

Development of antitumor biguanides targeting energy metabolism and stress responses in the tumor microenvironment

“…d Calculated by IC 50 (Glc +)/IC 50 (Glc −). e Rm , hydrophobic parameter 34 , 35 calculated as described in the “ Experimental section ” section. f Calculated by Accord for Excel ver.…”

“…We evaluated hydrophobicity for biguanides by Rm values calculated from TLC-relation factor (Rf) by using octylsililated silicagel plate 34 , 35 and calculated log D (clog D), distribution coefficients at physiological pH. According to the regression analyses of the homologation series data (Figure S2 A), there was a very good positive correlation between the methylene number of the alkylene linker and the hydrophobicity parameters (Rm; R 2 = 0.9758, clog D; R 2 = 0.9971) and between Rm and clog D values (R 2 = 0.9699).…”

Improving the Solubility of Artificial Ligands of Streptavidin to Enable More Practical Reversible Switching of Protein Localization in Cells

“…In particular, water solubility was evaluated over the concentration range where linearity of absorbance was maintained (Figure S3) . Log P was measured by reversed‐phase thin layer chromatography . ALiS‐3 and ALiS‐4 had higher solubility than ALiS‐1 (Table ), in accordance with their lower log P values; no significant improvement was seen for ALiS‐5 and ALiS‐6, presumably because of their high planarity .…”