Electrochemical studies of quercetin interacting with DNA

Zhu, Zhiwei; Li, Can; Li, Nanqiang

doi:10.1016/s0026-265x(01)00118-7

Cited by 84 publications

(49 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Moreover, the low abundances of product ions resulted from base loss are indicative of weaker DNA-binding affinities of the flavonoid aglycones than those conventional intercalators previously studied [5,29,39]. The intercalative binding mode and weak binding affinities of the flavonoid aglycones toward DNA deduced from the tandem mass spectrometry are in fairly good agreements with the results obtained using solution-phase techniques [20,22,24].…”

Section: Esi-ms/ms Of the Flavonoid/dna Complexessupporting

confidence: 78%

“…Meanwhile, the binding of flavonoids to nucleic acid structures has also been recognized as one important mechanism of their actions [11-19[. The noncovalent interactions between flavonoids and DNA have been elucidated using several solution-phase techniques including absorption [20,21], fluorescence [21], linear dichroism [22], and nuclear magnetic resonance [23J spectroscopies, as well as electrochemical [24] and surface plasmon resonance [25] techniques. However, these methods are laborintensive or require large quantities of materials.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Evaluation of flavonoids binding to DNA duplexes by electrospray ionization mass spectrometry

Zhaofu

Cui

Song

et al. 2008

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

In this study, electrospray ionization mass spectrometry (ESI·I\tIS) was Llsed to investigate the binding interactions of ten flavonoid aglycones and ten flavonoid glycosides with DNA duplexes. Relative binding affinities of the flavonoids toward DNA duplexes were estimated based on the fraction of bound DNA. The results revealed that the 4'-OH group of flavonoid aglycones was essential for their DNA-binding properties. Flavonoid glycosides with sugar chain linked on ring A or ring B showed enhanced binding toward the duplexes over their aglycone counterparts, whereas glycosylation of the flavonol quercetin on ring C exhibited a less pronounced effect. The aglycone skeletons and other hydroxyl substitutions on the aglycone also have an effect on the fractions of bound DNA. Upon collision-induced dissociation, the complexes containing flavonoid aglycones underwent the predominant ejection of a neutral ligand molecule, suggesting an intercalative DNA-binding mode. . These drugs may bind to certain DNA sequences, prevent the specific recognition of these sequences with their trans-acting factors, and interfere with the replication or transcription of certain genes, and thus exert their pharmacological activities [2]. Among the various organic molecules, natural products have attracted considerable interest given that many clinical anticancer drugs are natural products (or their derivatives) and most of them exert their effects by acting on DNA [1]. In this context, studies of the binding of natural products with DNA are helpful for better understanding the molecular basis of their bioac· tivities as well as providing useful guidance for further deSign of more efficient anticancer drugs [1, 3-7J.As an important class of natural products, flavonoids have received considerable attention because of their health benefits and chemopreventive properties [8]. Flavonoids consist of a diverse group of compounds derived from 2-phenolchromotome and can be categorized into several subgroups according to the structure (Table 1). Flavonoid aglycones and their modified forms are widely found in the roots, stalks, and fruits of many natural plants and act as the major functional components in many herb medicines [8,9]. Many studies have demonstrated that flavonoids possess a wide range of biological activities, such as anticancer, antiviral, antibacterial, antiOXidants, and anti~inflammatory effects [8J. These biological activities are considered to be related to their interaction with several enzymes in the human body as well as their notable antioxidant activity [8, 1OJ. Meanwhile, the binding of flavonoids to nucleic acid structures has also been recognized as one important mechanism of their actions [11-19[. The noncovalent interactions between flavonoids and DNA have been elucidated using several solution-phase techniques including absorption [20,21], fluorescence [21], linear dichroism [22], and nuclear magnetic resonance [23J spectroscopies, as well as electrochemical [24] and surface plasmon resonance [25] techniques. Ho...

show abstract

Section: Esi-ms/ms Of the Flavonoid/dna Complexessupporting

confidence: 78%

mentioning

confidence: 99%

Evaluation of flavonoids binding to DNA duplexes by electrospray ionization mass spectrometry

Zhaofu

Cui

Song

et al. 2008

J. Am. Soc. Mass Spectrom.

View full text Add to dashboard Cite

show abstract

“…Cyclic voltammograms showed irreversible one step oxidation process for three flavonoids with the involvement of two electrons and two protons [10][11][12]. Since pure DNA is electrochemically inactive in the potential range of -0.2 V to -1.6 V [10,11], the interaction flavonoids with DNA can be inferred from the shift in peak potential and decrease in peak heights in the cyclic voltammograms. Addition of different concentration of DNA to the fixed concentration of quercetin and rutin (1 mM) caused a gradual decrease in both the oxidation and reduction peak currents with no shift in both peak potentials, Figure 2 (A and B).…”

Section: Voltammetric Studies Of Dna-flavonoid Interactionsmentioning

confidence: 98%

“…Concentration of chicken blood ds.DNA in distilled water was determined spectrophotometrically at 260 nm using molar extinction coefficient ε260 = 6600 cm -1 M -1 [9]. The ratio of the absorbance at 260 nm to that at 280 nm, A260/A280> 1.8, indicated that DNA was sufficiently pure and free from protein [10].…”

Section: Reagents and Chemicalsmentioning

confidence: 99%

Voltammetric and viscometric studies of flavonoids interactions with DNA at physiological conditions

Hussain

Siddiqa

2011

Eur. J. Chem.

View full text Add to dashboard Cite

KEYWORDSCyclic voltammetric behaviour of three flavonoids: quercetin, morin and rutin was investigated for their interaction with DNA at pH = 4.7 and pH = 7.4 at body temperature (310 K), using glassy carbon electrode. The diffusion coefficients of the free and DNA bound forms of the flavonoids were evaluated using Randles-Sevcik equation. The binding parameters like binding constant, binding site size and binding free energy were also determined from voltammetric data. Moreover, the binding modes of flavonoids with DNA were evaluated from viscommetric analysis. A comparatively high value of binding constant, binding site size and diffusion coefficients for quercetin reveals its stronger binding with DNA under physiological conditions. The negative values of ∆G indicate the spontaneity of binding of flavonoids with DNA.

show abstract

“…Quercetin is known to bind to DNA through intercalation and external binding, and prevent DNA from free radical damage [5]. For quercetin, the intercalation was conceivably facilitated by its planar molecular conformation [6][7][8]. The strong interaction of quercetin with DNA is responsible in part for its strong biological activity (in Chinese hamster V79 cells) since its dihydro counterpart (dihydroquercetin) with non-planar conformation did not bind to DNA and showed a weaker activity [9,10].…”

Section: Introductionmentioning

confidence: 99%

Molecular Modeling Studies of Interaction Between Plasmid DNA (pBR322) and Dendritic Antioxidants

Chhetri

Lee²,

Rakesh³

2011

JCST

View full text Add to dashboard Cite

It is known that oxidative stress leads to aging and pathogenesis of many ailments. Antioxidants are considered to be one of the effective solutions for the oxidative stress and are used in the prevention and treatment of numerous diseases including inflammatory and infectious diseases, pre and post cancer therapy. In one of the authors' previous experimental study, potent antioxidant activities were observed from dendritic antioxidant (zero generation -G0) derived from syringaldehyde [1]. In this study, we also designed its analogs derived from vanillin and 5-iodovanillin. The aim of our present study was to characterize and understand the molecular interaction of the dendritic antioxidants with pBR322 plasmid DNA using computer simulations, in the hope that only the chemical structures with promising results would be synthesized in the laboratory experiments for further investigation. Towards this undertaking, we investigated the effects of various non-covalent interactions of the dendritic antioxidants with double stranded (dsDNA) 20-and 80-base pairs of pBR322 and compared with those of commonly used small antioxidant molecules, like quercetin, and vitamins C. Molecular dynamics (MD) simulation has been adopted to generate binding site of the compound with pBR322 DNA after the conformational search. This study revealed that the nature of the diverse binding free energy components obtained via computational methodology. Based on interaction and binding energy, syringaldehyde-derivatized G0 dendrimer was found to be the most favorable entity for pBR322 DNA, followed by quercetin.

show abstract

Electrochemical studies of quercetin interacting with DNA

Cited by 84 publications

References 31 publications

Evaluation of flavonoids binding to DNA duplexes by electrospray ionization mass spectrometry

Evaluation of flavonoids binding to DNA duplexes by electrospray ionization mass spectrometry

Voltammetric and viscometric studies of flavonoids interactions with DNA at physiological conditions

Molecular Modeling Studies of Interaction Between Plasmid DNA (pBR322) and Dendritic Antioxidants

Contact Info

Product

Resources

About