Several attempts were then made to synthesize organotin compounds with enhanced water solubility. The lipophilic/hydrophilic characteristics of the compounds are very important; their lipophilic properties being essential to allow for the crossing of the cell membrane and their hydrophilic character for being accepted by the water-rich cell.67
First, the hydrogen atoms of phenyl rings of benzoato ligands were replaced by hydroxyl groups.68 This did not significantly affect the water solubility or the cytotoxicity of the resultant organotin compounds. A more successful strategy to improve water solubility was to incorporate fluorine in the molecules.
As early as 1984, such fluoride-substituted organotin compounds were synthesized to determine whether the replacement of hydrogen by fluorine improved cytotoxicity.69 Indeed, a peculiar property of the fluorine-substituted compounds is that they are more soluble in water than their hydrogen analogues and yet still retain their solubility in non-polar solvents. Unfortunately, the fluorine-containing organotin compounds were not significantly more potent than their unfluorinated analogues as may be seen from the data in Table 22.5.70 74
Organotin salts, for instance stannates, were also synthesized by adding an anionic ligand to diorganotin derivatives.75 79 Their cytotoxicities were not better than those of the starting compounds and this line of investigation was abandoned.
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