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In this work series new theobromine derivatives containing an arylpiperazine moiety at N with established antioxidant and antiproliferative activities were evaluated for their hepatotoxic effects on cellular and sub-cellular level. On isolated rat hepatocytes, 3c and 4c expressed lowest toxicity, while 3f and 4f showed highest toxicity. The same compounds 3f and 4f showed the most evident pro-oxidant effect in a lipid peroxidation model on rat liver microsomes, followed by 3b and 4b, while the other compounds didn’t reveal statistically significant pro-oxidant effects. The performed quantitative structuretoxicity relationship (QSTR) analysis show that increased lipophilicity of the tested compounds positively correlates to their hepatotoxicity. Opposite, the presence in the structure of highly positive H-atoms and strongly negative oxygen, possibly originating from hydrogen bond donor groups, are associated with reduced hepatotoxicity.

QUANTITATIVE STRUCTURE-HEPATOTOXICITY ASSESSMENT OF SERIES ARYLPIPERAZINE-N1-SUBSTITUTED THEOBROMINE DERIVATIVES