Abstract
Four sets of rationally designed chalcones were prepared for evaluation of their antiobesity, antioxidant and cytotoxicity activities. These sets include nine oleoyl chalcones as mimics of oleoyl estrone, three monohydroxy chalcones (chalcone ligands), Schiff base-derived chalcones and four copper as well as zinc complexes. Oleoyl chalcones 4d, 4e and particularly 6a as an isosteric isomer of oleoyl estrone, were as active as Orlistat on weight loss and related metabolic parameters using male SD rats in vivo. Chalcone ligands 10a–c and Schiff base-derived chalcones 11 and 14a,b were weakly antioxidants, while, the copper and zinc complexes 15a–d were good antioxidants with zinc chelates 15b,d being more active than their copper analogues 15a,cin vitro. Compounds 10c and 14a showed good cytotoxicity activities as Doxorubicin against PC3 cancer cell line in vitro, while, the copper complex 15c showed promising activity with IC50 value of 5.95 μM. The estimated IC50 value for Doxorubicin was 8.7 μM. Chalcones 14a,b are bifunctional probes for potential investigations in cancer diagnosis and radiotherapy by complexation with Gd3+ or metal radioisotopes followed by posttranslation of Shiga toxin B-subunits that target globotriosyl ceramide expressing cancer cells.
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•A set of oleoyl, hydroxy, Schiff base-derived chalcones, their copper and zinc complexes were prepared.•Three oleoyl chalcones showed comparable in vivo antiobesity activity to Orlistat.•In vitro cytotoxicity assay against PC3 cell line showed a better activity for one copper complex than Doxorubicin.•All complexes displayed high in vitro antioxidant activities.