Bifunctional ferrocene derivatives for molecular recognition of DNA duplexes

Using 1,1'-bis(chlorocarbonyl)ferrocene as the starting material the novel amide derivative 1,1'-bis(carbamoylmethylcarbamoyl)ferrocene has been isola ted. Furthermore, the in situ reaction of 1,1'-di(bromomethyl)ferrocene wit h several amines led to the formation of salt-like and tertiary amine ferro cene compounds. These compounds are all very stable in air and exhibit inte resting hydrogen bonding patterns that can complement those of the DNA nucl eobases. Differential pulse voltammetry was used to monitor the interaction s of the water soluble ferrocene derivatives with DNA oligomers. The three compounds tested bind strongly to the DNA oligomers and the binding constan ts calculated are similar to those obtained for the [Fe(phen)(3)](3+/2+) io ns. The interaction results from a combination of hydrogen bonding, electro static, hydrophobic and pi-stacking interactions.