Citation: YU Hui-Min, HAN Shu-Ying, DENG Hai-Shan, CHI Yu-Mei. Determination of n-Octanol/Water Partition Coefficients of Naphthalenes and Anthraquinones Using Quantitative Structure-Retention Relationship Models by Reversed Phase-High Performance Liquid Chromatography[J]. Chinese Journal of Analytical Chemistry, ;2016, 44(6): 958-964. doi: 10.11895/j.issn.0253-3820.150997 shu

Determination of n-Octanol/Water Partition Coefficients of Naphthalenes and Anthraquinones Using Quantitative Structure-Retention Relationship Models by Reversed Phase-High Performance Liquid Chromatography

College of Pharmacy, Nanjing University of Chinese Medicine, Nanjing 210023, China

Received Date: 17 December 2015
Revised Date: 21 March 2016

Fund Project: This work was supported by the National Natural Science Foundation of China (No.81303311), the Natural Science Foundation of Jiangsu, China (No.BK20130958), the Natural Science Foundation for Colleges of Jiangsu Province (No.13KJB150030), and the Priority Academic Program Development of Jiangsu Higher Education Institutions

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n-Octanol/water partition coefficients (K_ow) is an important parameter commonly used to explain toxicity, activity and transmembrane of drugs. However, it is difficult to be detected by direct experimental determination. In this work, a set of 29 neutral and acidic analogues of naphthalene and anthraquinone with reliable experimental K_ow data was chosen as model compounds for establishing linear relationship between the logarithm of apparent n-octanol/water partition coefficient (lgK_ow"), and the logarithm of reversed phase-high performance liquid chromatography (RP-HPLC) retention factor of the solutes corresponding to neat aqueous fraction of mobile phase (lgk_w) as the quantitative structure-retention relationship (QSRR) model. Methanol-water mixture was used as mobile phase at various pH, and retention time (t_R) was rectified by a dual-point retention time correction (DP-RTC) in this method. The experiment results indicated that the proposed QSRR model had good correlation coefficient R²=0.974-0.976 with satisfactory results of internal and external validation (the cross-validated correlation coefficient R²_cv of 0.970-0.973, and 1.4%≤relative error (RE) ≤7.9% for all the 6 verification compounds). In addition, this QSRR model was compared with linear solvation energy relationship (LSER) involved in different descriptors of molecular structure, showing no differences. The QSRR model was applied to measure K_ow of 11 naphthalenes and anthraquinones, and the predicted data were compared with Shake-flask method (SFM) experimental ones, as well as calculated ones obtained by software. The results suggested that the proposed method for K_ow determination in this work was more accurate, simple and fast. To the best of our knowledge, this is the first report on measuring K_ow data for these compounds. The proposed strategy provides the possibility in determining K_ow of lipophilic components in complex mixture more quickly and accurately by RP-HPLC.
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