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Quercetin-Iron Complex: Synthesis, Characterization, Antioxidant, DNA Binding, DNA Cleavage, and Antibacterial Activity Studies

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Abstract

Quercetin-iron (II) complex was synthesized and characterized by elemental analysis, ultraviolet-visible spectrophotometry, fourier transform infrared spectroscopy, mass spectrometry, proton nuclear magnetic resonance spectroscopy, thermogravimetry and differential scanning calorimetry, scanning electron micrography and molar conductivity. The low molar conductivity value investigates the non-electrolyte nature of the complex. The elemental analysis and other physical and spectroscopic methods reveal the 1:2 stoichiometric ratio (metal:ligand) of the complex. Antioxidant study of the quercetin and its metal complex against 2, 2-di-phenyl-1-picryl hydrazyl radical showed that the complex has much more radical scavenging activity than free quercetin. The interaction of quercetin-iron (II) complex with DNA was determined using ultraviolet visible spectra, fluorescence spectra and agarose gel electrophoresis. The results showed that quercetin-iron (II) complex can intercalate moderately with DNA, quench a strong intercalator ethidium bromide and compete for the intercalative binding sites. The complex showed significant cleavage of pBR 322 DNA from supercoiled form to nicked circular form and these cleavage effects were dose-dependent. Moreover, the mechanism of DNA cleavage indicated that it was an oxidative cleavage pathway. These results revealed the potential nuclease activity of complex to cleave DNA. In addition, antibacterial activity of complex on E.coli and S. aureus was also investigated. The results showed that complex has higher antibacterial activity than ligand.

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Abbreviations

CT-DNA:

Calf-thymus deoxyribonucleic acid

DPPH:

2, 2-di-phenyl-1-picryl hydrazyl

EB:

Ethidium bromide

ESI-MS:

Electrospray ionization mass spectra

FT-IR:

Fourier transform Infrared spectra

1H-NMR:

Proton Nuclear magnetic resonance

MTT:

3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide

NC DNA:

Nicked circular deoxyribonucleic acid

ROS:

Reactive oxidative species

SC DNA:

Supercoiled deoxyribonucleic acid

SEM:

Scanning electron micrography

SOD:

Superoxide dismutase

TG-DSC:

Thermogravimetry and differential scanning calorimetry

UV-Vis:

Ultraviolet Visible

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Acknowledgments

This work was partly supported by National Natural Science Foundation of China (81373480, 81573529, 21372056), Chinese Government Scholarship (CSC No: 2014DFH792), Natural Science Foundation of Jiangsu Province (BK20130526), Sci. & Tech. Project from Traditional Chinese Medicine Bureau of Jiangsu Province (YB2015186), Zhenjiang Social Development Project (SH2014062).

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Authors and Affiliations

  1. School of pharmacy, Jiangsu University, Zhenjiang, 212013, China

    Aun Raza, Xiuquan Xu, Jian Tang & Zhen Ouyang

  2. School of Chemistry & Chemical Engineering, Jiangsu University, Zhenjiang, 212013, China

    Li Xia & Changkun Xia

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  1. Aun Raza
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  2. Xiuquan Xu
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  3. Li Xia
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  4. Changkun Xia
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  5. Jian Tang
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  6. Zhen Ouyang
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Correspondence to Jian Tang.

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Raza, A., Xu, X., Xia, L. et al. Quercetin-Iron Complex: Synthesis, Characterization, Antioxidant, DNA Binding, DNA Cleavage, and Antibacterial Activity Studies. J Fluoresc 26, 2023–2031 (2016). https://doi.org/10.1007/s10895-016-1896-y

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  • DOI: https://doi.org/10.1007/s10895-016-1896-y

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