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Electrochemical features of the interaction between (R)-/(S)-methyl-2- (5-fluorouracil-1-acetamide)-3-phenylpropionate and DNAs

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Title Electrochemical features of the interaction between (R)-/(S)-methyl-2- (5-fluorouracil-1-acetamide)-3-phenylpropionate and DNAs
 
Creator Liu, Aili
Dong, Xiaomei
Jin, Huile
Wang, Shun
Jiang, Weizhong
 
Subject Cyclic voltammetry
DNA
Gold electrode
Intercalation
(R)/(S)-5FUPPM
 
Description 398-403
Cyclic voltammetry was exploited to understand the interaction between chiral methyl-2-(5- fluorouracil-1-acetamide)-3-phenylpropionate molecules (denoted as (R)- or (S)-5FUPPM) and double-stranded (ds) or G-quadruplex (G4) DNAs. Using Fe(CN)<sub>6</sub><sup>3- </sup>as the redox mark, experiments illustrate that the anodic peak of Fe(CN)<sub>6</sub><sup>3- </sup>oxidation decreases as the concentration of 5FUPPM in the solution is increased. Calculation with the Langmuir equation yields the binding equilibrium constant of 9.1 × 10<sup>3 </sup>for the dsDNA and (S)-5FUPPM and of 3.3 × 10<sup>3</sup> for dsDNA and (R)-5FUPPM, suggesting that (S)-5FUPPM has more favorable interaction with dsDNA. On the other hand, the calculated binding constant between G4-DNA and (S)-5FUPPM is 1.6 × 10<sup>4</sup>, as opposed to 3.2 × 10<sup>4</sup> between G4-DNA and (R)-5FUPPM. The results suggest that the binding selectivity of (R)-5FUPPM with DNAs, defined with (<em>K</em><sub>G4-DNA</sub><em>/K</em><sub>dsDNA</sub>), is about 5 times larger than that of (S)-5FUPPM and DNAs, which is consistent with their inhibition rate on tumor cell. The information achieved here suggests that electrochemical characterization can provide useful information for the screening of new drug candidates.
 
Date 2018-11-29T05:45:54Z
2018-11-29T05:45:54Z
2018-12
 
Type Article
 
Identifier 0975-0959 (Online); 0301-1208 (Print)
http://nopr.niscair.res.in/handle/123456789/45455
 
Language en_US
 
Rights <img src='http://nopr.niscair.res.in/image/cc-license-sml.png'> <a href='http://creativecommons.org/licenses/by-nc-nd/2.5/in' target='_blank'>CC Attribution-Noncommercial-No Derivative Works 2.5 India</a>
 
Publisher NISCAIR-CSIR, India
 
Source IJBB Vol.55(6) [December 2018]