Synthesis and biological evaluation of hydroxyl-substituted Schiff-bases containing ferrocenyl moieties

Abstract

Three new hydroxyl-substituted Schiff-bases containing ferrocenyl moieties were synthesized, and their antioxidant and anticancer activities were evaluated. Among the synthesized hydroxyl-substituted Schiff-bases, compound 1 containing both ferrocenyl and o-dihydroxyl groups exhibits the highest antioxidant and anticancer activities. Flow cytometric analysis showed that compound 1 is capable of disturbing the cancer cell cycle and inducing more cells to be arrested in G2 phase. The excellent biological activities of compound 1 are attributed to the presence of both ferrocenyl and o-dihydroxyl groups. The ferrocenyl moiety has dual functions in compound 1, i.e., increasing the lipophilicity and lowering the redox potentials of o-dihydroxyl groups. In addition, compound 1 could reversibly bind with HSA mainly via a mechanism involving the formation of complexes, in which hydrophobic interaction is the main acting force. Thus, compound 1 containing both ferrocenyl and o-dihydroxyl groups is a potential antioxidant with anticancer activity.