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《Acta Chimica Sinica》 2011-10
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Electrochemical Study on the Interactions between Enantiomer of 2-(5-Fluorouracil-1-acetyl)amido-1,5-dimethyl Glutarate and Double-stranded/G-quadruplex DNA

Meng,Chenpeng Wang,Shun* Zhang,Kejun Jin,Huile* Chen,Xian Hu,Maolin Xiong,Jing(Nano-materials & Chemistry Key Laboratory,Wenzhou University,Wenzhou 325027)  
The interaction between 2-(5-fluorouracil-1-acetyl) amido-1,5-dimethyl glutarate enantiomer and DNA have been investigated via cyclic and differential pulse voltammetry,in which double-stranded DNA(ds-DNA) or G-quadruplex DNA(G4-DNA) modified Au electrode was used as the working electrode while was employed as the electroactive indicator.Our investigation indicates that:(1) As opposed to the influence of 5-fluorouracil(5-FU),(S)-5FUGlu and(R)-5FUGlu caused the peak potential of at Au/ds-DNA and Au/G4-DNA electrodes shift negatively;(2) 5-FU,(S)-5FUGlu and(R)-5FUGlu all caused the peak current of at the above modified electrodes to decrease,in which the inverse of current change exhibited a linear relationship with the inverse of reagent concentration;(3) Utilizing Langmuir equation the binding constants of 5-FU,(S)-and(R)-5FUGlu with ds-DNA are found to be 6.16×103,0.42×103 and 0.58×103 L?mol-1,respectively,whereas the binding constants of 5-FU,(S)-and(R)-5FUGlu with G4-DNA are 0.78×103,2.60×103 and 5.29×103 L?mol-1;and(4) the inhibition rates of(R)-and(S)-5FUGlu on tumor cell line HL-60 are,respectively,55.8 and 2.8,12.8 and 1.5,and 5.9 and 0.6 at the concentrations of 10-4,10-6 and 10-8 mol?L-1,which is consistent with the observed tendency that(R)-5FUGlu and G4-DNA have a stronger binding affinity than that of(S)-5FUGlu.
【Fund】: 国家自然科学基金(No.21073133);; 浙江省自然科学基金(Nos.Y4090248 Y4080177)
【CateGory Index】: O646
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