Collect. Czech. Chem. Commun. 1985, 50, 538-550

Lipophilic-hydrophilic properties and retention of phenylhydrazonopropanedinitriles by biological systems

Ernest Šturdík, Štefan Baláž, Marián Antalík and Pavol Sulo

Department of Biochemical Technology, Slovak Institute of Technology, 812 37 Bratislava


Apparent partition coefficients in n-octanol-buffer system, solubility in the buffers, and retention by mitochondria from rat liver, by Mycobacterium phlei and by Saccharomyces cerevisiae (after 10 min incubation) have been characterized for 13 arylsubstituted phenylhydrazonopropanedinitrile derivatives. Regression analysis has shown linear dependence of logarithms of the apparent partition coefficients on the published π parameters characterizing lipophilicity of the substituents. The apparent partition coefficients are inversely proportional to the solubility of the phenylhydrazonopropanedinitriles. The retention by the biosystems studied increases linearly with increasing lipophilicity, being independent of reactivity of the phenylhydrazonopropanedinitriles. The non-linear dependence of concentration of the phenylhydrazonopropanedinitriles remaining in the medium on the lipophilicity indicates that a lipophilic-hydrophilic equilibrium is established in the given time. The retained amount of the derivatives tested decreases with increasing pH values. The dependences are Z-shaped and have been described by the equations derived from the model presented by application of non-linear regression analysis.