Non‐covalent Interaction of Perfluorooctanoic Acid with DNA

Zhang, Xian; Shen, Rongkun; Chen, Ling

doi:10.1002/cjoc.200990380

Cited by 6 publications

(4 citation statements)

References 49 publications

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“…Although both PFAAs and PAHs preferentially intercalate into DNA rather than bind to grooves, the tested PFAAs did bind into the minor groove with varying affinities. Intercalation of PFOS and groove binding of PFOA with DNA were reported previously (Li et al 2010;Zhang et al 2009a). In contrast, no groove binding was observed for PAHs.…”

Section: Resultssupporting

confidence: 61%

“…Different to the fluorescence displacement data, we observed that PFAAs containing shorter carbon chain lengths give rise to larger DNA conformational changes. Zhang et al studied conformational changes to DNA upon binding PFOA (Zhang et al 2009a). An enhancement in the CD signal at both 245 and 275 nm in the presence of PFOA was observed.…”

Section: Conformational Changes To Dna Upon Interaction With Pfaasmentioning

confidence: 99%

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Study on the binding interaction between perfluoroalkyl acids and DNA

Cao

Wei

Cheng

2013

Environ Sci Pollut Res

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Perfluoroalkyl acids (PFAAs) are carcinogens, and elucidating their DNA binding properties is crucial for understanding PFAA genotoxicity. We have investigated the binding mode and affinity of five PFAAs to seven DNA molecules using fluorescence displacement and molecular docking analysis. DNA conformational changes upon PFAA binding were also examined by circular dichroism (CD). The data revealed that DNA intercalation was the dominant interaction mode of the PFAAs; however, these molecules also bound to grooves. The dissociation constants for the PFAAs ranged between 0.11 and 1,217.14 μM, and between 3.46 and 2,141.21 μM for DNA intercalation and groove binding, respectively. PFAAs that contain longer carbon chains had stronger DNA intercalation affinities. Binding to DNA was stronger for perfluoroalkyl sulfonates than for perfluorcarboxyl acids that contain the same number of carbons. This observation is postulated to arise from the presence of more fluorine and oxygen atoms in perfluoroalkyl sulfonates acting as hydrogen bond donors that facilitate stronger DNA intercalation. The binding of the PFAAs to DNA showed some CT-DNA sequence selectivity. Molecular docking analysis confirmed the DNA binding mode and affinities of the PFAAs. CD analysis revealed that the PFAAs weakened DNA base stacking and loosened DNA helicity. The present study has improved our understanding of the formation of PFAA-DNA adducts.

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Section: Resultssupporting

confidence: 61%

Section: Conformational Changes To Dna Upon Interaction With Pfaasmentioning

confidence: 99%

Study on the binding interaction between perfluoroalkyl acids and DNA

Cao

Wei

Cheng

2013

Environ Sci Pollut Res

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“…In 2009 we identified more than 400 articles after searching Web of Science, PubMed, SciDir and OVID databases using ‘isothermal AND titration AND calorimetry’ or ITC or ‘Isothermal Titration Calorimetry’ search terms. These have been classified into the following categories: Pre‐2009 references cited in the text and review articles 1–43 Protein‐protein and protein‐peptide interactions 44–124 Protein/peptide‐small molecule interactions 125–218 Protein/peptide‐metal ion interactions 219–253 Protein/peptide‐nucleic acid interactions 254–273 Protein/peptide‐lipid interactions 274–292 Protein/peptide‐polysaccharide interactions 293–316 Nucleic acid‐small molecule interactions 317–348 Small molecule interactions …”

Section: Introductionmentioning

confidence: 99%

Survey of the year 2009: applications of isothermal titration calorimetry

Falconer

Collins

2010

J. Mol. Recognit.

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Isothermal titration calorimetry (ITC) is now an established and invaluable method for determining the thermodynamic constants, association constant and stoichiometry of molecular interactions in aqueous solutions. The technique has become widely used by biochemists to study protein interaction with other proteins, small molecules, metal ions, lipids, nucleic acids and carbohydrates; and nucleic acid interaction with small molecules. The drug discovery industry has utilized this approach to measure protein (or nucleic acid) interaction with drug candidates. ITC has been used to screen candidates, guide the design of potential drugs and validate the modelling used in structure-based drug design. Emerging disciplines including nanotechnology and drug delivery could benefit greatly from ITC in enhancing their understanding and control of nano-particle assembly, and drug binding and controlled release.

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“…Neither is PFOA a planar molecule capable of intercalation into DNA. Interactions of PFOA with DNA using circular dichroism indicated a change in DNA conformation with the binding to DNA being non-covalent in which PFOA aligned along the backbones and interacted with the homolateral bases via hydrophobic interactions [42] . DNA binding was not found when tested at either 50 (21 μg/mL) or 500 μM (210 μg/mL) concentrations [43] .…”

Section: Discussionmentioning

confidence: 99%

Evaluation of perfluorooctanoate for potential genotoxicity

Butenhoff

Kennedy

Jung³

et al. 2014

Toxicology Reports

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Perfluorooctanoate (PFOA) is a fully fluorinated eight-carbon fatty acid analog with exceptional stability toward degradation that has been used as an industrial surfactant and has been detected in environmental and biological matrices. Exposures to PFOA in the workplace and in the environment have continuously stimulated investigations into its potential human health hazards. In this article, the results of fifteen unpublished genotoxicity assays conducted with perfluorooctanoate (as either the linear or linear/branched ammonium salt (APFO) or the linear/branched sodium salt) are reported and include: seven mutation assays (three in vitro reverse mutation assays with histidine auxotrophic strains of Salmonella typhimurium, two in vitro reverse mutation assays with the tryptophan auxotrophic Escherichia coli WP2uvr strain, one in vitro mitotic recombination (gene conversion) assay with Saccharomyces cerevisiae D4, and an in vitro Chinese hamster ovary (CHO) HGPRT forward mutation assay); seven studies to assess potential for chromosomal damage (three in vitro CHO chromosomal aberration studies, an in vitro human whole blood lymphocyte chromosomal aberration study, and three in vivo mouse micronucleus assays); and an in vitro C3H 10T1/2 cell transformation assay. Although PFOA has not been demonstrated to be metabolized, all in vitro assays were conducted both in the presence and in the absence of a mammalian hepatic microsomal activation system. These assays were originally described in twelve contract laboratory reports which have been available via the United States Environmental Protection Agency public docket (Administrative Record 226) for over a decade; however, the details of these assays have not been published previously in the open scientific literature. With the exception of limited positive findings at high and cytotoxic concentrations in some assay trials which reflected the likely consequence of cytotoxic disruption of normal cellular processes and not a specific genotoxic effect, the results of the studies presented in this paper and other published results clearly demonstrate the absence of direct mutagenic or genotoxic risk associated with PFOA. This finding is consistent with the physical/chemical characteristics of PFOA and is supported by other published genotoxicity studies.

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Non‐covalent Interaction of Perfluorooctanoic Acid with DNA

Cited by 6 publications

References 49 publications

Study on the binding interaction between perfluoroalkyl acids and DNA

Study on the binding interaction between perfluoroalkyl acids and DNA

Survey of the year 2009: applications of isothermal titration calorimetry

Evaluation of perfluorooctanoate for potential genotoxicity

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