Assessment of Long-range Transport Potential of Polychlorinated Naphthalenes Based on Three-dimensional QSAR Models

Overview

Journal Environ Sci Pollut Res Int

Publisher Springer

Specialties Environmental Health
Toxicology

Date 2017 May 5

PMID 28470501

Citations 8

Authors

Xiaolei Wang

Wenen Gu

Ermin Guo

Chunyue Cui

Yu Li

Affiliations

Soon will be listed here.

Abstract

Experimentally determined octanol-air partition coefficients (K ) for 43 polychlorinated naphthalene (PCN) congeners and experimentally determined subcooled liquid vapor pressures (P ) for 17 PCN congeners were used with comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) to generate three-dimensional quantitative structure-activity relationship (3D-QSAR) models. The data were used to predict K values for the other 32 congeners and P values for the other 58 congeners. The CoMFA and CoMSIA model contour maps showed that the electrostatic fields of the PCN molecules are the most important factors affecting the K and P values. The long-range transport potentials of several PCN homologs were assessed using the following grading system: high mobility (MoCNs), relatively high mobility (DiCNs to TeCNs), relatively low mobility (PeCNs to HeCNs) and low mobility (HeCNs and OCN). The PCN-2 molecule was modified using the contour maps of the two models, and the results showed that introducing an electronegative R substituent increased the K value but introducing an electropositive R substituent decreased the P value. PCN-2 was in the high mobility class, but introducing these substituents moved the long-range transport potentials of the modified molecules to the relatively high mobility class.

Citing Articles

Unveiling the Photodegradation Mechanism of Monochlorinated Naphthalenes under UV-C Irradiation: Affecting Factors Analysis, the Roles of Hydroxyl Radicals, and DFT Calculation.

Yu Y, Liu M, Wang S, Zhang C, Zhang X, Liu L Molecules. 2024; 29(19).

PMID: 39407464 PMC: 11477601. DOI: 10.3390/molecules29194535.

Triazine Herbicides Risk Management Strategies on Environmental and Human Health Aspects Using In-Silico Methods.

Yao T, Sun P, Zhao W Int J Mol Sci. 2023; 24(6).

PMID: 36982765 PMC: 10052965. DOI: 10.3390/ijms24065691.

Strategies to Control Human Health Risks Arising from Antibiotics in the Environment: Molecular Modification of QNs for Enhanced Plant-Microbial Synergistic Degradation.

Sun P, Zhao W Int J Environ Res Public Health. 2021; 18(20).

PMID: 34682354 PMC: 8536065. DOI: 10.3390/ijerph182010610.

Environmentally Friendly Quinolones Design for a Two-Way Choice between Biotoxicity and Genotoxicity through Double-Activity 3D-QSAR Model Coupled with the Variation Weighting Method.

Sun P, Zhao Y, Yang L, Ren Z, Zhao W Int J Environ Res Public Health. 2020; 17(24).

PMID: 33333906 PMC: 7765274. DOI: 10.3390/ijerph17249398.

A Double-Activity (Green Algae Toxicity and Bacterial Genotoxicity) 3D-QSAR Model Based on the Comprehensive Index Method and Its Application in Fluoroquinolones' Modification.

Yang L, Liu M Int J Environ Res Public Health. 2020; 17(3).

PMID: 32028728 PMC: 7037916. DOI: 10.3390/ijerph17030942.

References

Klebe G, Abraham U, Mietzner T . Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem. 1994; 37(24):4130-46. DOI: 10.1021/jm00050a010. View

Crippen G . Quantitative structure-activity relationships by distance geometry: systematic analysis of dihydrofolate reductase inhibitors. J Med Chem. 1980; 23(6):599-606. DOI: 10.1021/jm00180a004. View

Bidleman T, Helm P, Braune B, Gabrielsen G . Polychlorinated naphthalenes in polar environments--a review. Sci Total Environ. 2009; 408(15):2919-35. DOI: 10.1016/j.scitotenv.2009.09.013. View

Lee S, Harner T, Pozo K, Shoeib M, Wania F, Muir D . Polychlorinated naphthalenes in the Global Atmospheric Passive sampling (GAPS) study. Environ Sci Technol. 2007; 41(8):2680-7. DOI: 10.1021/es062352x. View

Jiang L, Li Y . Modification of PBDEs (BDE-15, BDE-47, BDE-85 and BDE-126) biological toxicity, bio-concentration, persistence and atmospheric long-range transport potential based on the pharmacophore modeling assistant with the full factor experimental design. J Hazard Mater. 2016; 307:202-12. DOI: 10.1016/j.jhazmat.2015.12.031. View

Helm P, Bidleman T, Li H, Fellin P . Seasonal and spatial variation of polychlorinated naphthalenes and non-/mono-ortho-substituted polychlorinated biphenyls in arctic air. Environ Sci Technol. 2004; 38(21):5514-21. DOI: 10.1021/es049619h. View

Helm P, Bidleman T . Gas-particle partitioning of polychlorinated naphthalenes and non- and mono-ortho-substituted polychlorinated biphenyls in arctic air. Sci Total Environ. 2005; 342(1-3):161-73. DOI: 10.1016/j.scitotenv.2004.12.030. View

Chayawan , Vikas . Externally predictive single-descriptor based QSPRs for physico-chemical properties of polychlorinated-naphthalenes: Exploring relationships of logS(W), logK(OA), and logK(OW) with electron-correlation. J Hazard Mater. 2015; 296:68-81. DOI: 10.1016/j.jhazmat.2015.04.028. View

Hung H, Katsoyiannis A, Brorstrom-Lunden E, Olafsdottir K, Aas W, Breivik K . Temporal trends of Persistent Organic Pollutants (POPs) in arctic air: 20 years of monitoring under the Arctic Monitoring and Assessment Programme (AMAP). Environ Pollut. 2016; 217:52-61. DOI: 10.1016/j.envpol.2016.01.079. View

10.

Herbert B, Halsall C, Villa S, Fitzpatrick L, Jones K, Lee R . Polychlorinated naphthalenes in air and snow in the Norwegian Arctic: a local source or an Eastern Arctic phenomenon?. Sci Total Environ. 2005; 342(1-3):145-60. DOI: 10.1016/j.scitotenv.2004.12.029. View

11.

Lv Y, Yin C, Liu H, Yi Z, Wang Y . 3D-QSAR study on atmospheric half-lives of POPs using CoMFA and CoMSIA. J Environ Sci (China). 2009; 20(12):1433-8. DOI: 10.1016/s1001-0742(08)62545-0. View

12.

Odabasi M, Cetin B . Determination of octanol-air partition coefficients of organochlorine pesticides (OCPs) as a function of temperature: application to air-soil exchange. J Environ Manage. 2012; 113:432-9. DOI: 10.1016/j.jenvman.2012.10.010. View

13.

Cramer R, Patterson D, Bunce J . Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc. 2011; 110(18):5959-67. DOI: 10.1021/ja00226a005. View

14.

Chen Y, Cai X, Jiang L, Li Y . Prediction of octanol-air partition coefficients for polychlorinated biphenyls (PCBs) using 3D-QSAR models. Ecotoxicol Environ Saf. 2015; 124:202-212. DOI: 10.1016/j.ecoenv.2015.10.024. View

15.

Chen J, Yang P, Chen S, Quan X, Yuan X, Schramm K . Quantitative structure-property relationships for vapor pressures of polybrominated diphenyl ethers. SAR QSAR Environ Res. 2003; 14(2):97-111. DOI: 10.1080/1062936031000073135. View

16.

Wania F, Mackay D . Peer reviewed: tracking the distribution of persistent organic pollutants. Environ Sci Technol. 2011; 30(9):390A-6A. DOI: 10.1021/es962399q. View

17.

Pegoraro C, Chiappero M, Montejano H . Measurements of octanol-air partition coefficients, vapor pressures and vaporization enthalpies of the (E) and (Z) isomers of the 2-ethylhexyl 4-methoxycinnamate as parameters of environmental impact assessment. Chemosphere. 2015; 138:546-52. DOI: 10.1016/j.chemosphere.2015.07.035. View

18.

Yamamoto T, Noma Y, Sakai S . Thermal destruction of wastes containing polychlorinated naphthalenes in an industrial waste incinerator. Environ Sci Pollut Res Int. 2016; 25(32):31819-31827. DOI: 10.1007/s11356-016-7100-8. View

19.

da Cunha E, Sippl W, Ramalho T, Antunes O, Alencastro R, Albuquerque M . 3D-QSAR CoMFA/CoMSIA models based on theoretical active conformers of HOE/BAY-793 analogs derived from HIV-1 protease inhibitor complexes. Eur J Med Chem. 2009; 44(11):4344-52. DOI: 10.1016/j.ejmech.2009.05.016. View

20.

Huang J, Yu G, Yamauchi M, Matsumura T, Yamazaki N, Weber R . Congener-specific analysis of polychlorinated naphthalenes (PCNs) in the major Chinese technical PCB formulation from a stored Chinese electrical capacitor. Environ Sci Pollut Res Int. 2014; 22(19):14471-7. DOI: 10.1007/s11356-014-3677-y. View