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Study on the binding interaction between perfluoroalkyl acids and DNA

  • Contaminated Land, Ecological Assessment and Remediation Conference Series (CLEAR 2012): Environmental Pollution and Risk Assessments
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An Erratum to this article was published on 14 June 2014

Abstract

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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Acknowledgments

This study was supported by the National Natural Science Foundation of China (20907068 and 21077124), the Science and Technology Program of the General Administration of Quality Supervision, Inspection and Quarantine of the P.R.C. (2012IK219), and the National Natural Science Foundation of Fujian Province (2011J05015).

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Authors and Affiliations

  1. AQSIQ Key Laboratory of Drug Detection, Fujian International Travel Healthcare Center, Fujian Entry–Exit Inspection and Quarantine Bureau of P.R.C., Fujian, 350001, China

    Jie Cao

  2. State Key Laboratory of Environmental Chemistry and Ecotoxicology, Research Center for Eco-environmental Sciences, Chinese Academy of Sciences, P.O. Box 2871, Beijing, 100085, China

    Yin Wei

  3. Chinese Academy of Inspection & Quarantine, No. 3A, North Gaobeidian Road, Beijing, 100123, China

    Yan Cheng

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  1. Jie Cao
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  2. Yin Wei
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  3. Yan Cheng
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Correspondence to Yin Wei.

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Responsible editor: Henner Hollert

Jie Cao and Yin Wei contributed equally to this work.

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Cao, J., Wei, Y. & Cheng, Y. Study on the binding interaction between perfluoroalkyl acids and DNA. Environ Sci Pollut Res 20, 8355–8363 (2013). https://doi.org/10.1007/s11356-013-1760-4

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  • DOI: https://doi.org/10.1007/s11356-013-1760-4

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