A set of structurally diverse curcuminoids (CC) were synthesized by the reaction of 2,5-pentanedione with the appropriate aldehyde in the presence of tributylborate as a drying agent and n-butylamine as catalyst. The aldehydes used include 9-anthraldehyde, thiophene-2-carbaldehyde, ferrocenecarbaldehyde and indole-3-carbaldehyde. These curcuminoids were used as ligands in the synthesis of zinc and vanadium complexes best formulated as Zn(CC)2 and VO(CC)2 though there was some structural variation amongst the complexes. The complexes have been characterized by a variety of spectroscopic techniques and initial investigations of reactions with DNA have been carried out. A number of the complexes show a weak ability to uncoil pBR322 plasmid DNA. Spectroscopic, viscometric, fluorescence, and electrochemical experiments suggest that the complexes interact with DNA via intercalation. For the Zn(dmabCC)2 the binding constants are on the order of 104 M-1 (ΔH = 32.5 kJ) and for VO(phenCC)2 it was 105 M-1 (ΔH = 40.6 kJ). On the other hand the interaction, as measured by the binding constant, with human serum albumin is strong with binding constants on the order of 105 M-1.

Curcuminoids as ligands in zinc and vanadium complexes: Synthesis and biophysical reactivity

249th National Meeting (2015)

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