Prediction of octanol-water partition coefficient for polychlorinated naphthalenes through three-dimensional QSAR models

References

• Bidleman TF, Helm PA, Braune BM, et al. 2010. Polychlorinated naphthalenes in polar environments—a review. Sci Total Environ 408:2919–35
   PubMed Web of Science ®Google Scholar
• Canada Environment. 2011. Ecological screening assessment polychlorinated naphththalenes. Secondary ecological screening assessment polychlorinated naphththalenes. Available at http://www.ec.gc.ca/ese-ees/835522FE-AE6C-405A-A729-7BC4B7C794BF/CNs_SAR_En.pdf
   Google Scholar
• Castillo-Garit JA, Marrero-Ponce Y, Escobar J, et al. 2008. A novel approach to predict aquatic toxicity from molecular structure. Chemosphere 73:415–27
   PubMed Web of Science ®Google Scholar
• Chen Y, Cai XY, and Jiang L. 2016. Prediction of octanol-air partition coefficients for Polychlorinated biphenyls (PCBs) using 3D-QSAR models. Ecotoxicol Environ Saf 124:202–12
   PubMed Web of Science ®Google Scholar
• Clark RD. 2003. Boosted leave-many-out cross-validation: the effect of training and test set diversity on PLS statistics. J Comput-Aided Mol Des 17:265–75
   PubMed Web of Science ®Google Scholar
• Clark M, Cramer RD, and Vanopdenbosch N. 1989. Validation of the general purpose tripos 5.2 force field. J Comput Chem 10:982–1012
   Web of Science ®Google Scholar
• Clark RD and Fox PC. 2004. Statistical variation in progressive scrambling. J Comput-Aided Mol Des 18:563–76
   PubMed Web of Science ®Google Scholar
• Falandysz J, Strandberg B, Strandberg L, et al. 1997. Concentrations and biomagnification of polychlorinated naphthalenes in black cormorants Phalacrocorax carbo sinensis from the Gulf of Gdansk, Baltic Sea. Sci Total Environ 204:97–106
   PubMed Web of Science ®Google Scholar
• Gasteiger J and Marsili M. 1980. Iterative partial equalization of orbital electronegativity a rapid access to atomic charges. Tetrahedron 36:3219–28
   Web of Science ®Google Scholar
• Golbraikh A and Tropsha A. 2002. Beware of q2 !. J Mol Graph Modell 20:269–76
   PubMed Web of Science ®Google Scholar
• Guo L, Ba T, and Zheng MH. 2009. Study of sources and distribution characteristics of polychlorinated naphthalenes. Prog Chem 21:377–88
   Web of Science ®Google Scholar
• Hanari N, Kannan K, Horii Y, et al. 2004. Polychlorinated naphthalenes and polychlorinated biphenyls in benthic organisms of a Great Lakes food chain. Arch Environ Con Tox 47:84–93
   PubMed Web of Science ®Google Scholar
• Hu SQ, Mi SQ, Jia XL, et al. 2011. 3D-QSAR study and molecular design of benzimidazole derivatives as corrosion inhibitors. Chem J Chinese Univ 32:2402–9
   Web of Science ®Google Scholar
• Iván PR, Mastromichalib A, Tyrovolab K, et al. 2014. Rapid determination of octanol-water partition coefficient using vortex-assisted liquid-liquid microextraction. J Chromatogr A 1330:1–5
   PubMed Web of Science ®Google Scholar
• Jackson SH, Cowan-Ellsberry CE, and Thomas G. 2009. Use of quantitative structural analysis to predict fish bioconcentration factors for pesticides. J Agri Food Chem 57(3):958–67
   PubMed Web of Science ®Google Scholar
• Jiang L, Li Y. 2016. 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 307:202–12
   PubMed Web of Science ®Google Scholar
• Kilanowicz A, Skrzypinska-Gawrysiak M. 2010. Toxicity of hexachloronaphthalene (HxCN) and induction of CYP 1A in rats. Ecotox Environ Safe 73:196–205
   PubMed Web of Science ®Google Scholar
• Kilanowicz A, Wiaderna D, Lutz P, et al. 2012. Behavioral effects following repeated exposure to hexachloronaphthalene in rats. Neurotoxicology 33:361–9
   PubMed Web of Science ®Google Scholar
• Kruger U, Zhou Y, Wang X, et al. 2008. Robust partial least squares regression: Part I, algorithmic developments. J Chemom 22:1–13
   Web of Science ®Google Scholar
• Kunisue T, Johnson-Restrepo B, Hilker DR, et al. 2009. Polychlorinated naphthalenes in human adipose tissue from New York, USA. Environ Pollut 157(3):910–5
   PubMed Web of Science ®Google Scholar
• Leach AR. 2001. Molecular Modelling: Principles and Applications. Person Education Limited, Harlow, UK
   Google Scholar
• Li M, Wei DB, Zhao HM, et al. 2014. Genotoxicity of quinolones: substituents contribution and transformation products QSAR evaluation using 2D and 3D models. Chemosphere 95(1):220–6
   PubMed Web of Science ®Google Scholar
• Li XL, Ye L, Shi W, et al. 2013. In silico study on hydroxylated polychlorinated biphenyls as androgen receptor antagonists. Ecotoxicol Environ Saf 92(1):258–64
   PubMed Web of Science ®Google Scholar
• Li XL, Ye L, Wang XX, et al. 2012a. Molecular docking, molecular dynamics simulation, and structure-based 3D-QSAR studies on estrogenic activity of hydroxylated polychlorinated biphenyls. Sci Total Environ 441:230–8
   PubMed Web of Science ®Google Scholar
• Li XL, Ye L, Wang XX, et al. 2012b. Combined 3D-QSAR, molecular docking and molecular dynamics study on thyroid hormone activity of hydroxylated polybrominated diphenyl ethers to thyroid receptors β. Toxicol Appl Pharm 265:300–7
   PubMed Web of Science ®Google Scholar
• Liao SY, Qian L, Miao TF, et al. 2009. CoMFA and docking studies of 2-phenylindole derivatives with anticancer activity. Eur J Med Chem 44:2822–7
   PubMed Web of Science ®Google Scholar
• Liu GR, Cai ZW, Zheng MH, et al. 2015. Identification of indicator congeners and evaluation of emission pattern of polychlorinated naphthalenes in industrial stack gas emissions by statistical analyses. Chemosphere 118:194–200
   PubMed Web of Science ®Google Scholar
• Lundén Å and Noren K. 1998. Polychlorinated naphthalenes and other organochlorine contaminants in Swedish human milk, 1972–1992. Arch Environ Contam Toxicol 34(4):414–23
   PubMed Web of Science ®Google Scholar
• Lundgren K, Tysklind M, Ishaq R, et al. 2003. Flux estimates and seimentation of polychlorinated naphthalenes in the northern part of the Baltic Sea. Environ Pollut 126:93–105
   PubMed Web of Science ®Google Scholar
• Lv YY, Yin CS, Liu HY, et al. 2008. 3D-QSAR study on atmospheric half-lives of POPs using CoMFA and CoMSIA. J Environ Sci-China 20(12):1433–8
   PubMedGoogle Scholar
• Park H, Kang JH, Baek SY, et al. 2010. Relative importance of polychlorinated naphthalenes compared to dioxins, and polychlorinated biphenyls in human serum from Korea: contribution to TEQs and potential sources. Environ Pollut 158(5):1420–7
   PubMed Web of Science ®Google Scholar
• Puzyn T and Falandysz J. 2005. Octanol/water partition coefficients of chloronaphthalenes. J Environ Sci Health A 40(9):1651–63
   Web of Science ®Google Scholar
• Puzyn T and Falandysz J. 2007. QSPR modeling of partition coefficients and henry's law constants for 75 chloronaphthalene congeners by means of six chemometric approaches-a comparative study. J Phys Chem Ref Data 36:203–14
   Web of Science ®Google Scholar
• Stephan K, Saab J, Mokbel I, et al. 2014. Continuous-flow microfluidic method for octanol-water partition coefficient measurement. Fluid Phase Equilibr 380:116–20
   Web of Science ®Google Scholar
• Vikas C. 2015. Externally predictive single-descriptor based QSPRs for physico-chemical properties of polychlorinated-naphthalenes: exploring relationships of logSW logKOA, and logKOW with electron-correlation. J Hazard Mater 296:68–81
   PubMed Web of Science ®Google Scholar
• Wang C, Lu GH, Tang ZY, et al. 2008. Quantitative structure-activity relationships for joint toxicity of substituted phenols and anilines to (Scenedesmus obliquus). J Environ Sci 20(1):115–9
   Web of Science ®Google Scholar
• Wattanasin P, Saetear P, Wilairat P, et al. 2015. Zone fluidics for measurement of octanol-water partition coefficient of drugs. Analytica Chimica Acta 860:1–7
   PubMed Web of Science ®Google Scholar
• Wold S, Sjostrom M, and Eriksson L. 2001. PLS-regression: a basic tool of chemometrics. Chemom Intell Lab Syst 58:109–30
   Web of Science ®Google Scholar
• Xu Z, Chen Y, Qiu YL, et al. 2016. Prediction of stability for polychlorinated biphenyls in transformer insulation oil through three-dimensional quantitative structure-activity relationship pharmacophore model and full factor experimental design. Chen Res Chinese U 32:348–56
   Web of Science ®Google Scholar
• Xu M, Zhang AQ, Han SK, et al. 2002. Studies of 3D-quantitative structure-activity relationships on a set of nitroaromatic compounds: CoMFA, advanced CoMFA and CoMSIA. Chemosphere 48:707–15
   PubMed Web of Science ®Google Scholar
• Zhang AQ, Chen EQ, Wei DB, et al. 2000. QSAR research of chlorinated aromatic compounds toxicity to (Selenastrum capricornuturn). China Environ Sci 20(2):102–5
   Google Scholar
• Zhang LL, Zhang LF, Dong L, et al. 2015. Concentrations and patterns of polychlorinated naphthalenes in surface sediment samples from Wuxi, Suzhou, and Nantong, in East China. Chemosphere 138:668–74
   PubMed Web of Science ®Google Scholar
• Zhao BZ, Han TR, Hao XR, et al. 2004. Theoretical calculation of the solubility for polycyclic aromatic hydrocarbons. J Mol Sci 20(2):1–4
   Google Scholar