Study of interactions of flavonoids with DNA using acridine orange as a fluorescence probe

Bi, Shuyun; Qiao, Chunyu; Song, Daqian; Tian, Yuan; Gao, Dejiang; Sun, Ying; Zhang, Hanqi

doi:10.1016/j.snb.2005.12.014

Cited by 225 publications

(90 citation statements)

References 37 publications

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“…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.…”

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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.

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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...

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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.

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“…[31] It is well known that intercalation of complexes into DNA base pairs can stabilise the double helix structure and T m increases by ,5 to 88C, but that non-intercalative binding causes no obvious increase in T m . [32] Based on the experimental conditions of this work, thermal denaturation experimental results showed that ctDNA had a T m of 80 AE 0.58C, but T m of 82.5 AE 0.58C when complexed with ADNRS (Fig. 9).…”

Section: Dna Melting Studiesmentioning

confidence: 75%

Spectroscopic and Modelling Analysis on the Interaction of 3'-Azidodaunorubicin Semicarbazone with ctDNA

et al. 2014

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The synthesis and characterisation of a new anthracycline, 3 0 -azidodaunorubicin semicarbazone (ADNRS) is reported. The interaction between ADNRS and calf thymus DNA (ctDNA) was investigated by absorption and fluorescence spectroscopy in combination with melting temperature (T m ) curves and molecular modelling in physiological buffer (pH 7.4). Evidence indicates that ADNRS binds in the groove of ctDNA and the fluorescence quenching mechanism is a static quenching type. Calculated thermodynamic parameters show that hydrophobic interactions may play a predominant role in the binding. Furthermore, molecular modelling results corroborate the spectroscopic investigations.

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“…Flavonols, in particular, interacted with DNA as a target site [27]. Under exceptional ageing conditions under heat and water stress the blue colored flavanols of Taxus nuclei disappeared, whereas the yellow nuclear flavonoids became more pronounced [5,10].…”

Section: Growth-modifying Balance Of Flavanols and Flavonols In Nucleimentioning

confidence: 99%

Flavanols and Flavonols in the Nuclei of Conifer Genotypes with Different Growth

Feucht

Schmid

Treutter

2014

Forests

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Flavanols and flavonols of mitotic and post-mitotic nuclei in needles of Taxus baccata L., Tsuga canadensis L., and slow growing dwarf genotypes of both genera are investigated histochemically. The flavanols of nuclear chromatins and in the vacuoles stain blue with the p-dimethylamino-cinnamaldehyde (DMACA) reagent. Flavonols do not react with the reagent but owing to their UV absorbance they can be seen as bright yellow pigments. The nuclei in the photomicrographs obtained by microscopy were measured for flavanols at 640 nm. The vigorously sprouting Taxus baccata L. displays the most rapid cell cycling of the needles and the nuclei reveal clear blue and white mosaic structures. The flavanol component of Taxus baccata nuclei remains relatively stable most of the growing season. The dwarf genotypes also display fairly blue stained meristematic nuclei during the intense spring flush. However, after the spring flush and towards mid-summer the nuclear flavanols slowly decrease in parallel with a gradual increase in yellow staining nuclear flavonols. A mixture of blue stained flavanols and yellow flavonols results in greenish coloration of the nuclei. The greenish tint becomes more pronounced when the parenchyma cells mature and age. At the same time, the cytoplasm of the dwarf genotypes also begins to attain a more yellow tint. This trend continues towards mid-summer and autumn, particularly in the nana genotypes. It would appear that the yellow staining flavonols are linked to restricted growth conditions. In the present study, it becomes evident that the OPEN ACCESSForests 2014, 5 2123 species-typical endogenous growth potential is related to both flavanol and flavonol allocation into the nuclei. The vigorously growing species of Taxus and Tsuga have a higher capacity for recruitment of flavanols into the nuclei than the very slow growing dwarf species.

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Study of interactions of flavonoids with DNA using acridine orange as a fluorescence probe

Cited by 225 publications

References 37 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

Spectroscopic and Modelling Analysis on the Interaction of 3'-Azidodaunorubicin Semicarbazone with ctDNA

Flavanols and Flavonols in the Nuclei of Conifer Genotypes with Different Growth

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