Journal
HUMAN AND ECOLOGICAL RISK ASSESSMENT
Volume 23, Issue 1, Pages 40-55Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/10807039.2016.1219650
Keywords
3D-QSAR; biological enrichment; K-ow; molecule modification; PCNs
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Funding
- Fundamental Research Funds for the Central Universities [JB2013146]
- Key Projects in the National Science and Technology Pillar Program in the Eleventh Five-Year Plan Period [2008BAC43B01]
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Based on experimental data for the octanol-water partition coefficient (K-ow) of 21 polychlorinated naphthalenes (PCNs) congeners, two types of three-dimensional QSAR (3D-QSAR) models comparative molecular field analysis (CoMFA) and comparative molecular similarity indices analysis (CoMSIA) were established with Sybyl software. This was established to predict the K-ow values of 54 additional PCN congeners and carry out a modification of CN-73 to lower its K-ow significantly, simultaneously maintaining the stability and insulativity of CN-73. The contour maps of two models showed that the electrostatic field plays a dominating role in the logK(ow) values of PCNs, and the bioconcentration of PCN decreased when -Cl atoms on the 1-, 3-, 4-, 6-, and 7-positions of PCNs were replaced with electropositive groups. Moreover, there was a positive correlation between the number of -Cl atoms on PCNs and the average logK(ow) values of PCNs. After modification of CN-73 through the electrostatic contour maps, six types of new modified CN-73 compounds were obtained with logK(ow) values two orders of magnitude lower than that of CN-73. Meanwhile, there was not a significant difference observed between the calculated total energy (representing stability) and energy gap (representing insulativity) of the new modified compounds when compared with those of CN-73.
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