The work described in this thesis concerns the design, synthesis and DNA binding activity of functionalised iron(II) supramolecular helicates. DNA and the ways that organic and metallo-molecules recognise and bind to it are reviewed. The field of supramolecular chemistry and particularly supramolecular helicates is considered, including those developed as anticancer agents. The design of a novel functionalisation route for the development of functionalised helicates is presented. The synthesis and characterisation of several metallo-helicates functionalised with simple chemical groups, such as hydroxyl and phenyl moieties, is described. Studies reveal that this functionalisation does not inhibit the inherent DNA binding activity of these types of cylinders. The development of steroid-hormone functionalised iron(II) helicates for targeted delivery to cancerous tissues is also detailed, including their synthesis and characterisation. These steroid functionalised complexes bind to DNA, inducing changes in the DNA conformation. The design, synthesis and characterisation of several metallo-helicates functionalised with targeting sugar vectors, is also presented. These sugar-conjugates can bind to DNA, causing intramolecular coiling and unwinding of the DNA helix.