Electrochemical and Spectroscopic Study on the Interaction Between G-Quadruplex DNA and (R)-/(S)-2-(5-Fluorouracil-1-Acetyl) Amido-1, 5-Dimethyl Glutarate

The cyclic voltammetry and ultraviolet-visible absorption spectrometry have proved to be powerful electrochemical means for the research of interactions between G-quadruplex DNA (G4-DNA) and chemical anti-carcinogens. In this study, the electrochemical behavior of (R)-/(S)-2-(5-fluorouracil-1-acetyl) amido-1,5-dimethyl glutarate (i.e., (R)-5FUGlu and (S)-5FUGlu) and the interaction of (R)/(S)-2-(5-fluorouracil-1-acetyl) amido-1,5-dimethyl glutarate with DNA using Fe(CN)(6)(3-/4-) as electroactive indicator were investigated, and the compounds were assayed for anticancer activities in HL-60 cells. The experiment showed that the interaction between (R)-/(S)-2-(5-fluorouracil-1-acetyl) amido-1,5-dimethyl glutarate and DNA were electrostatic, and the binding equilibrium constant KG4-DNA of the compounds is closely related to the configuration. It was observed that the binding equilibrium constant KG4-DNA of (R)-5FUGlu was about 2 times larger than that of (S)-5FUGlu. The inhibition rates of the different concentration of (R)-5FUGlu in tumor cell line HL-60 cells were larger than those of (S)-5FUGlu, which gave a good agreement with the above-mentioned electrochemical results.