Skip to main content
SpringerLink
Log in

Combined QSAR/QSPR, Molecular Docking, and Molecular Dynamics Study of Environmentally Friendly PBDEs with Improved Insulating Properties

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

To improve the insulating properties of polybrominated diphenyl ethers(PBDEs), we studied the molecular structures and energy gap(Eg) values of 209 PBDEs using a three-dimensional quantitative structure-activity relationship(3D-QSAR) model, molecular docking, and molecular dynamics. We also analyzed the interaction mechanisms of PBDEs using a 2D-QSAR model, molecular substitution characteristics, and molecular docking. The 3D-QSAR model showed that the 2-, 4-, 5-, and 6-positions significantly influenced the PBDE insulating properties. Using BDE-34 as a template molecule, we designed six derivatives with 0.47%—28.44% higher insulation than BDE-34. Compared with BDE-34, the stability and flame retardancy of the above six derivatives were not adversely affected. These derivatives, except for 2,6-cyanomethyl-BDE, 2-cyanomethyl-BDE, and 2-aminomethyl-BDE, were more toxic and biodegradable than BDE-34, but showed weaker bioaccumulation and migration abilities than BDE-34. Mechanism analysis showed that the highest occupied orbital energy, the most negative charge, and the dipole moment were the main quantitative parameters that affected the PBDE insulating properties. PBDE insulation gradually decreased as the number of Br atoms increased. The level of similarity between the substitution patterns on the two benzene rings was significantly correlated with PBDE insulation, with hydrophobic groups having a more significant effect on PBDE insulation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Zhou J., Chen Q. S., Huang S. X., Wang Y., Zou P. Y., National Symposium on Insulation Materials and Insulation Technology, 2010

    Google Scholar 

  2. Liu X., Science and Technology Innovation, 2010, 27, 30

    Google Scholar 

  3. Stiborova H., Vrkoslavova J., Lovecka P., Pulkrabova J., Hradkova P., Hajslova J., Demnerova K., Chemosphere, 2015, 118, 315

    Article  CAS  PubMed  Google Scholar 

  4. Zhang X., Gao Y. J., Yan C. Z., Ecology and Environmental Sciences, 2009, 18, 761

    Google Scholar 

  5. Aznar-Alemany Ò., Aminot Y., Vilà-Cano J., Köck-Schulmeyer M., Readman W., Marques A., Godinho L., Botteon E., Ferrari F., Boti V., Albanis T., Eljarrat E., Barceló D., Science of the Total Environment, 2018, 612, 492

    Article  CAS  PubMed  Google Scholar 

  6. McDonald T. A., Chemosphere, 2002, 46, 745

    Article  CAS  PubMed  Google Scholar 

  7. Schecter A., Pavuk M., Päpke O., Ryan J., Birnbaum L., Rosen R., Environmental Health Perspectives, 2003, 111, 1723

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  8. Christensen H., Glasius M., Pécseli M., Platz J., Pritzl G., Chemosphere, 2002, 47, 631

    Article  CAS  PubMed  Google Scholar 

  9. Parolini M., Guazzoni N., Binelli A., Tremolada P., Archives of Environmental Contamination & Toxicology, 2012, 63, 29

    Article  CAS  Google Scholar 

  10. Stoker T. E., Cooper R. L., Lambright C. S., Wilson V. S., Furr J., Gray L. E., Toxicology & Applied Pharmacology, 2005, 207, 78

    Article  CAS  Google Scholar 

  11. Eriksson P., Fischer C., Fredriksson A., Toxicological Sciences, 2006, 94, 302

    Article  CAS  PubMed  Google Scholar 

  12. Wu W., Nie F. Q., Zhai J. H., Ecology and Environmental Sciences, 2009, 18, 408

    Google Scholar 

  13. Usenko C. Y., Robinson E. M., Usenko S., Brooks B. W., Bruce E. D., Environmental Toxicology & Chemistry, 2011, 30, 1865

    Article  CAS  Google Scholar 

  14. Gu W. W., Chen Y., Li Y., Bulletin of Environmental Contamination & Toxicology, 2017, 99, 276

    Article  CAS  Google Scholar 

  15. Frisch M. J., Trucks G. W., Schlegel H. B., Scuseria G. E., Robb M. A., Cheeseman J. R., Scalmani G., Barone V., Mennucci B., Petersson G. A., Nakatsuji H., Caricato M., Li X., Hratchian H. P., Izmaylov A. F., Bloino J., Zheng G., Sonnenberg J. L., Hada M., Ehara M., Toyota K., Fukuta R., Hasegawa J., Ishida M., Nakajima T., Honda Y., Kitao O., Nakai H., Vreven T., Montgomery J. A. Jr., Peralta J. E., Ogliaro F., Bearpark M., Heyd J. J., Brothers E., Kudin K. N., Staroverov V. N., Kobayashi R., Normand J., Raghavachari K., Rendell A., Burant J. C., Iyengar S. S., Tomasi J., Cossi M., Rega N., Millam J. M., Klene M., Knox J. E., Cross J. B., Bakken V., Adamo C., Jaramillo J., Gomperts R., Stratmann R. E., Yazyev O., Austin A. J., Cammi R., Pomelli C., Ochterski J. W., Martin R. L., Morokuma K., Zakrzewski V. G., Voth J. A., Salvador P., Dannenberg J. J., Dapprich S., Daniels A. D., Farkas Ö., Foresman J. B., Ortiz J. V., Cioslowski J., Fox D. J., Gaussian 09, Revision A.1, Gaussian Inc., Wallingford CT, 2009

    Google Scholar 

  16. Shi J. Q., Qu R. J., Feng M. B., Wang X. H., Wang L. S., Yang S. G., Wang Z. Y., Environmental Science & Technology, 2015, 49, 4209

    Article  CAS  Google Scholar 

  17. Wang X. L., Gu W. W., Guo E., Cai C., Li Y., Environmental Science & Pollution Research, 2017, 24, 14802

    Article  CAS  Google Scholar 

  18. Jiang L., Li Y., Journal of Hazardous Materials, 2016, 307, 202

    Article  CAS  PubMed  Google Scholar 

  19. Qu R. J., Liu H. X., Feng M. B., Yang X., Wang Z. Y., Journal of Chemical and Engineering Data, 2012, 57, 2442

    Article  CAS  Google Scholar 

  20. Li W. L., Si H. Z., Li Y., Ge C. Z., Song F. C., Ma X. T., Duan Y. B., Zhai H. L., Journal of Molecular Structure, 2016, 1117, 227

    Article  CAS  Google Scholar 

  21. Holt P. A., Chaires J. B., Trent J. O., ChemInform, 2010, 39, 1602

    Google Scholar 

  22. Yang M., Zhou L., Zuo Z. L., Tang X. Y., Liu J., M X., Molecular Simulation, 2008, 34, 849

    Article  CAS  Google Scholar 

  23. Li X., Fu J., Shi W., Luo Y., Zhang X., Zhu H., Yu H., Bull. Korean Chem. Soc., 2013, 34,2387

    Google Scholar 

  24. Zhang L. Z., Ren Z. J., Lu A., Zhao Z., Xu W., Bao Q. Q., Ding W. J., Yang C. L., Chem. Res. Chinese Universities, 2015, 31(2), 228

    Article  CAS  Google Scholar 

  25. Yang G. F., Ding Y., Yang H. Z., Wu X. J., Chem. J. Chinese Universities, 2004, 25(1), 71

    CAS  Google Scholar 

  26. Brinkman W., Brinkman W., Briels J., Verweij H., Chemical Physics Letters, 2017, 247, 386

    Article  Google Scholar 

  27. Chu Z. H., Li Y., Journal of Hazardous Materials, 2019, 364, 151

    Article  CAS  PubMed  Google Scholar 

  28. Zhang S. J., Qiu Y. L., Li Y., Current Analytical Chemistry, 2018, 14, 1

    Google Scholar 

  29. Robrock K. R., Mohn W. W., Eltis L. D., Alvarezcohen L., Biotechnology & Bioengineering, 2011, 108, 313

    Article  CAS  Google Scholar 

  30. Li X. L., Ye L., Wang X. X., Wang X. Z., Liu H. L., Zhu Y. L., Yu H. X., Toxicology & Applied Pharmacology, 2012, 265, 300

    Article  CAS  Google Scholar 

  31. Wang X. L., Chu Z. H., Yang J. W., Li Y., Environmental Science & Pollution Research, 2017, 24, 1

    Article  Google Scholar 

  32. Meerts I. A., Letcher R. J., Hoving S., Marsh G., Bergman A., Lemmen J. G., Burg B., Brouwer A., Environmental Health Perspectives, 2001, 109, 399

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  33. Hamers T., Kamstra J. H., Sonneveld E., Murk A. J., Kester M. H., Andersson P. L., Legler J., Brouwer A., Toxicological Sciences, 2006, 92, 157

    Article  CAS  PubMed  Google Scholar 

  34. Minerva M. F., Bigsby R. M., Environmental Health Perspectives, 2008, 116, 1315

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Environment, Northeast Normal University, Changchun, 130117, P. R. China

    Sicheng Liu & Shijun Sun

Authors
  1. Sicheng Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Shijun Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Shijun Sun.

Electronic supplementary material

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Liu, S., Sun, S. Combined QSAR/QSPR, Molecular Docking, and Molecular Dynamics Study of Environmentally Friendly PBDEs with Improved Insulating Properties. Chem. Res. Chin. Univ. 35, 478–484 (2019). https://doi.org/10.1007/s40242-019-8353-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-019-8353-9

Keywords

Search

Navigation