A series of three ruthenium complexes containing ferrocene curcuminoid ligands were synthesized: [(arene)Ru(FeCC)Cl] where arene = benzene, p-cymene and 9aneS3. These complexes were characterized by elemental analyses and spectroscopic methods. The complexes were interacted with both dsDNA and quadruplex DNA in order to determine if they had a binding preference for quadruplex DNA. The methodologies used include electronic absorption titrations, competition experiments using ethidium bromide for dsDNA and thiazole orange for quadruplex DNA, and cyclic voltammetry. The kinetics of the complexes in pure water and in 50 mM NaCl solutions were also studied using UV-Vis spectroscopy. The first order rate constants for [(cymene)Ru(FeCC)Cl] (in 50 mM NaCl solution) and [(ben)Ru(FeCC)Cl] (in pure water) were 4.542 x 10.5 s-1 and 3.334 x 10-5 s-1, respectively. In addition, molecular modeling was utilized for this project. The geometry of the complexes were optimized by DFT: wb97x-D/6-31G*. A binding energy of -7.56 kJ/mol and dissociation constant of 2.85 μM was calculated for binding of [(arene)Ru(FeCC)Cl] with 1BNA via this method. Various types of intermolecular interactions with 1BNA were observed. These include a pi-lone pair interaction between the cyclopentadienyl ring and the sugar of Gua4, pi-pi interactions between Ade5 and Ade6 and the other cyclopentadienyl ring, and interaction of the phosphate group on Ade6 with the chloride on the complex. Initial results (experimental and calculated) of the interaction of the complexes with other biological targets, such as topoisomerase and HSA will be reported.

Synthesis, characterization, and DNA reactivity of half-sandwich ruthenium complexes containing ferrocene curcuminoid ligands

251st National Meeting (2016)

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