Methyl thiophanate as a DNA minor groove binder produces MT–Cu(II)–DNA ternary complex preferably with AT rich region for initiation of DNA damage

Saquib, Quaiser; Al-Khedhairy, Abdulaziz A.; Alarifi, Saud; Dutta, Sansa; Dasgupta, Swagata; Musarrat, Javed

doi:10.1016/j.ijbiomac.2010.03.017

Cited by 29 publications

(10 citation statements)

References 37 publications

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“…The other symbols have the same meanings as in eqn (3). The values of K a were calculated to be in the order of 10 4 L mol À1 , which corresponds to DNA groove binders, such as methyl thiophanate 39 and carmoisine. The values of K a were calculated to be in the order of 10 4 L mol À1 , which corresponds to DNA groove binders, such as methyl thiophanate 39 and carmoisine.…”

Section: Fluorescence Quenching Of Res By Ctdnamentioning

confidence: 99%

Characterization of the interaction between resmethrin and calf thymus DNA in vitro

et al. 2015

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Resmethrin (RES) is a synthetic pyrethroid insecticide widely used to control pests in agriculture, but it may cause potential hazards to human health. The characteristics of the binding of RES with calf thymus DNA (ctDNA) were investigated in a physiological buffer (pH 7.4) by multiple spectroscopic methods combined with ctDNA melting and viscosity measurements, multivariate curve resolution-alternating least-squares (MCR-ALS) chemometrics and the molecular docking technique. The concentration profiles and the pure spectra for the reactive species (RES, ctDNA and RES-ctDNA complex), obtained through decomposing the augmented UV-vis spectral data matrix by the MCR-ALS approach, indicated that RES could bind to ctDNA and the reaction process could be quantitatively monitored. The RES molecules bound to ctDNA by groove binding, as evidenced by the negligible changes in the ctDNA melting temperature, viscosity and iodide quenching effect and the increase in the single-stranded DNA quenching effect. Fluorescence titration data indicated that the complexation of RES with ctDNA was mainly driven by hydrogen bonds and van der Waals forces, and had strong affinity. The changes in the Fourier transform infrared spectra of ctDNA suggested that RES molecules preferentially bound to the G-C region of ctDNA, which was consistent with the prediction of the molecular docking. The circular dichroism spectral analysis indicated that RES induced a decrease in the right-handed helicity of ctDNA.The DNA cleavage assay showed that RES did not cleave the pUC18 plasmid DNA. This study offers a comprehensive picture of RES-ctDNA interaction, which may provide insights into the toxicological effect of the insecticide.

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Section: Fluorescence Quenching Of Res By Ctdnamentioning

confidence: 99%

Characterization of the interaction between resmethrin and calf thymus DNA in vitro

et al. 2015

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“…Furthermore, similar fluorescence quenching effects of EtBr bound to DNA have been observed for the addition of several groove-binding compounds, including distamycin A, methyl thiophanate, and amsacrine. [24][25][26] This observation leads us to suggest that the cadmium complex may interact with DNA through the groove-binding mode. 27 …”

Section: Fluorescence Spectroscopymentioning

confidence: 98%

“…24,26,32 Therefore, DNA containing higher contents of AT could receive more damage from the groove-binding compounds. To examine whether the Cd-MAA complex is a groove-binding compound, experiments evaluating the biological damage to plasmids with different GC percentage (41.5%, 59.55%) were performed.…”

Section: Genotoxicities Of Different Nanoparticles Residual Transformmentioning

confidence: 99%

The cadmium–mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots

Tang¹,

Fan²,

He³

et al. 2012

IJN

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Quantum dots (QDs) have many potential clinical and biological applications because of their advantages over traditional fluorescent dyes. However, the genotoxicity potential of QDs still remains unclear. In this paper, a plasmid-based system was designed to explore the genotoxic mechanism of QDs by detecting changes in DNA configuration and biological activities. The direct chemicobiological interactions between DNA and mercaptoacetic acid-coated CdSecore QDs (MAA-QDs) were investigated. After incubation with different concentrations of MAA-QDs (0.043, 0.13, 0.4, 1.2, and 3.6 µmol/L) in the dark, the DNA conversion of the covalently closed circular (CCC) DNA to the open circular (OC) DNA was significantly enhanced (from 13.9% ± 2.2% to 59.9% ± 12.8%) while the residual transformation activity of plasmid DNA was greatly decreased (from 80.7% ± 12.8% to 13.6% ± 0.8%), which indicated that the damages to the DNA structure and biological activities induced by MAA-QDs were concentration-dependent. The electrospray ionization mass spectrometry data suggested that the observed genotoxicity might be correlated with the cadmium-mercaptoacetic acid complex (Cd-MAA) that is formed in the solution of MAA-QDs. Circular dichroism spectroscopy and transformation assay results indicated that the Cd-MAA complex might interact with DNA through the groove-binding mode and prefer binding to DNA fragments with high adenine and thymine content. Furthermore, the plasmid transformation assay could be used as an effective method to evaluate the genotoxicities of nanoparticles.

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“…Docking methods can provide visual representations of the interactions between the macromolecule and ligand, which can complement and substantiate the experimental results [29]. In recent years, this method has provided insight into the interactions between macromolecules and ligands with the help of docking programs such as Dock, AutoDock, Glide, and Surflexn [30][31][32][33][34].…”

Section: Molecular Modeling Studiesmentioning

confidence: 99%

Investigation on the toxic interaction of typical plasticizers with calf thymus DNA

Sun

Zong

Liu

et al. 2015

Journal of Luminescence

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Methyl thiophanate as a DNA minor groove binder produces MT–Cu(II)–DNA ternary complex preferably with AT rich region for initiation of DNA damage

Cited by 29 publications

References 37 publications

Characterization of the interaction between resmethrin and calf thymus DNA in vitro

Characterization of the interaction between resmethrin and calf thymus DNA in vitro

The cadmium–mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots

Investigation on the toxic interaction of typical plasticizers with calf thymus DNA

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Methyl thiophanate as a DNA minor groove binder produces MT–Cu(II)–DNA ternary complex preferably with AT rich region for initiation of DNA damage

Cited by 29 publications

References 37 publications

Characterization of the interaction between resmethrin and calf thymus DNA in vitro

Characterization of the interaction between resmethrin and calf thymus DNA in vitro

The cadmium&ndash;mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots

Investigation on the toxic interaction of typical plasticizers with calf thymus DNA

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The cadmium–mercaptoacetic acid complex contributes to the genotoxicity of mercaptoacetic acid-coated CdSe-core quantum dots