A structure-based investigation on the binding interaction of hydroxylated polycyclic aromatic hydrocarbons with DNA

Wang, Lirong; Wang, Ying; Chen, Jingwen; Guo, Liang

doi:10.1016/j.tox.2009.06.015

Cited by 47 publications

(27 citation statements)

References 30 publications

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“…The K b values of 24 HO-PAHs with CT-DNA were taken from Wang et al (2009a), and then converted into the form of log K b ( Table 2). The K b values were determined by a previously established electrochemical displacement method.…”

Section: Data Compilation and The Chemical Domainmentioning

confidence: 99%

“…The K b values were determined by a previously established electrochemical displacement method. More details can be found in the previous study (Wang et al, 2009a).…”

Section: Data Compilation and The Chemical Domainmentioning

confidence: 99%

“…Ohura et al (2010) reported that HO-PAHs showed AhR-ligand binding activities by a recombinant yeast assay system, especially the hydroxylated derivatives of naphthalene. Additionally, a clear morphological change of calf thymus DNA (CT-DNA) from linear type to condensation form was observed after binding with 9-hydroxyfluorene in atomic force microscopy (Wang et al, 2009a). Recently, Wei et al (2010) also reported that 11 PAHs metabolites predominantly interacted with human p53 DNA by intercalation instead of groove binding.…”

Section: Introductionmentioning

confidence: 99%

“…Most recently, hydroxylated PAHs (HO-PAHs) have emerged and are causing increasing concern due to their detection in human hair (Schummer et al, 2009), urine (Campo et al, 2010Li et al, 2010c), and expired air samples (Li et al, 2010c); these agents have even been found in the bile of deep-sea fish (Escartin and Porte, 1999). Previous studies have shown that certain HO-PAHs can affect hormone homeostasis, as they act as potent ligands for binding to the aryl hydrocarbon receptor (AhR) and even interact with DNA (Wang et al, 2009a;Wenger et al, 2009;Ohura et al, 2010;Wei et al, 2010). For instance, it was reported that 5 HO-PAHs (2-hydroxychrysene, 2-hydroxyphenanthrene, 1-hydroxypyrene, 2-hydroxynaphthalene and 1-hydroxynaphthalene), which showed structural similarities to 17␤-estrodiol, exhibit estrogenic activities (Wenger et al, 2009).…”

Section: Introductionmentioning

confidence: 99%

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Noncovalent interactions between hydroxylated polycyclic aromatic hydrocarbon and DNA: Molecular docking and QSAR study

Liu

et al. 2011

Environmental Toxicology and Pharmacology

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Section: Data Compilation and The Chemical Domainmentioning

confidence: 99%

“…The K b values were determined by a previously established electrochemical displacement method. More details can be found in the previous study (Wang et al, 2009a).…”

Section: Data Compilation and The Chemical Domainmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Noncovalent interactions between hydroxylated polycyclic aromatic hydrocarbon and DNA: Molecular docking and QSAR study

Liu

et al. 2011

Environmental Toxicology and Pharmacology

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“…obtained, and the binding constant is calculated accordingly. Using this method, 21 hydroxylated polycyclic aromatic hydrocarbons (OH-PAHs) were investigated [15]. It was found that IC 50 value of eight of the OH-PAHs was higher than the solubility of these compounds in aqueous solutions.…”

Section: Introductionmentioning

confidence: 99%

Highly sensitive electrochemiluminescence displacement method for the study of DNA/small molecule binding interactions

Huang¹,

Wang²,

Guo³

2010

Analytica Chimica Acta

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a b s t r a c tNon-covalent binding interactions of small molecules with DNA play important roles in regulating gene expression and gene function. In this work, a highly sensitive electrochemiluminescence (ECL) displacement method has been developed to investigate such interactions, particularly for weak DNA binders. This ECL method relies on a double-stranded DNA film deposited on an indium tin oxide electrode (ITO) surface by layer-by-layer self-assembly. A DNA intercalator, [Ru(bpy) 2 (dppz)] 2+ (bpy = 2,2 -bipyridine, dppz = dipyrido[3,2-a:2 3 -c]phenazine), is employed as the ECL signal indicator. If a test compound competes with the indicator for the same binding sites in DNA, it would displace the indicator from the film and reduce ECL signal. The new method was validated by measuring five well-known DNA-binding organic molecules including quinacrine, H33258, thiazole orange, ethidium bromide and 4,6-diamidine-2-phenylindole dihydrochloride. Due to high ECL sensitivity, only 0.4 mol L −1 [Ru(bpy) 2 (dppz)] 2+ was needed in the ECL displacement measurement, which is about 75-fold less than the concentration in the voltammetric measurement. The lowered concentration permitted direct measurement of IC 50 values of eight hydroxylated polycyclic aromatic hydrocarbons in their ECL displacement curves and subsequent calculation of their binding constants with DNA. The ECL displacement method is particularly useful for investigating weak DNA binders with limited aqueous solubility.

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The determination of polycyclic aromatic hydrocarbons in human urine by high‐resolution gas chromatography–mass spectrometry

Cho

Lee

Kim

2018

Biomedical Chromatography

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Polycyclic aromatic hydrocarbons (PAHs), organic compounds formed by at least two condensed aromatic rings, are ubiquitous environmental pollutants that are produced by incomplete combustion of organic materials. PAHs have been classified as carcinogenIC to humans by the International Agency for Research on Cancer, because they can bind to DNA, causing mutations. Therefore, the levels of PAHs in human urine can be used as an indicator for potential carcinogenesis and cell mutation. An analytical method was developed for the accurate measurement of PAHs in urine using high-resolution gas chromatography-mass spectrometry. Urine samples were extracted by an Oasis HLB extraction cartridge after enzymatic hydrolysis with a β-glucuronidase/arylsulfatase cocktail. The 18 PAHs were separated using an Agilent DB-5 MS capillary column (30 m × 0.25 mm, 0.25 μm) and monitored by time-of-flight mass spectrometry. Under the optimized method, the linearity of calibration curves was >0.994. The limits of detection at a signal-to-noise ratio of 3 were 10-100 ng/L. The coefficients of variation were in the range of 0.4-9.0%. The present method was highly accurate for simultaneous determination of 18 PAHs in human urine and could be applied to monitoring and biomedical investigations to check exposure of PAHs.

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A structure-based investigation on the binding interaction of hydroxylated polycyclic aromatic hydrocarbons with DNA

Cited by 47 publications

References 30 publications

Noncovalent interactions between hydroxylated polycyclic aromatic hydrocarbon and DNA: Molecular docking and QSAR study

Noncovalent interactions between hydroxylated polycyclic aromatic hydrocarbon and DNA: Molecular docking and QSAR study

Highly sensitive electrochemiluminescence displacement method for the study of DNA/small molecule binding interactions

The determination of polycyclic aromatic hydrocarbons in human urine by high‐resolution gas chromatography–mass spectrometry

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