Bifunctional ferrocene derivatives for molecular recognition of DNA duplexes

Abstract

Using 1,1′-bis(chlorocarbonyl)ferrocene as the starting material the novel amide derivative 1,1′-bis(carbamoylmethylcarbamoyl)ferrocene has been isolated. Furthermore, the in situ reaction of 1,1′-di(bromomethyl)ferrocene with several amines led to the formation of salt-like and tertiary amine ferrocene compounds. These compounds are all very stable in air and exhibit interesting hydrogen bonding patterns that can complement those of the DNA nucleobases. Differential pulse voltammetry was used to monitor the interactions of the water soluble ferrocene derivatives with DNA oligomers. The three compounds tested bind strongly to the DNA oligomers and the binding constants calculated are similar to those obtained for the [Fe(phen)₃]^3+/2+ ions. The interaction results from a combination of hydrogen bonding, electrostatic, hydrophobic and π-stacking interactions.