Acta Phys. -Chim. Sin. ›› 2015, Vol. 31 ›› Issue (5): 893-898.doi: 10.3866/PKU.WHXB201503193

• THEORETICAL AND COMPUTATIONAL CHEMISTRY • Previous Articles     Next Articles

Norm Index-Based Quantitative Structure-Activity Relationship to Predict β-Cyclodextrin Complex Binding Constants

QIAN Hai-Cheng1, KANWAL Shahid1, JIA Qing-Zhu2, WANG Qiang1, JI Hui-Fen1, ZHU Zhi-Chen3, XIA Shu-Qian4, MA Pei-Sheng4   

  1. 1 School of Material Science and Chemical Engineering, Tianjin University of Science and Technology, Tianjin 300457, P. R. China;
    2 School of Marine Science and Engineering, Tianjin University of Science and Technology, Tianjin 300457, P. R. China;
    3 School of Science, Tianjin University of Urban Construction, Tianjin 300384, P. R. China;
    4 School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072, P. R. China
  • Received:2015-02-09 Revised:2015-03-19 Published:2015-05-08
  • Contact: WANG Qiang E-mail:wang_q@tust.edu.cn
  • Supported by:

    The project was supported by the National Natural Science Foundation of China (21306137, U1162104).

Abstract:

Cyclodextrins (CDs) are widely used in the pharmaceutical industry, and the complex stability constant (logK) is an important evaluation target for CD inclusion complexes. In this work, the structures of the inclusion complexes of 233 compounds with β-cyclodextrin (β-CD) were investigated by the quantitative structure-activity relationship (QSAR) method based on a new set of norm indexes proposed by our group. Here, using several arithmetic approaches, a set of QSAR models based on these new norm indexes were developed to predict the logK values of the β-CD complexes. The results showed that all of the norm indexbased- QSAR models could predict logK well, and the best QSAR model was obtained using the least-squares support vector machine method with correlation coefficient (R), leave-one/ten-out validation correlation coefficient (QLOO and QLTO) values of 0.9587, 0.8775, and 0.8732, respectively. Comparison with other methods suggested that our method performed better for predicting the logK values of β-CD complexes in terms of both accuracy and stability, especially for the discrimination of isomer structures. The results of this and previous studies demonstrate that it might be possible to use the norm index-based model to predict not only the basic physical-chemical properties, but also the chemical reaction-related constants of organic compounds.

Key words: β-cyclodextrin, Norm index, Complex stability constant, Ab initio method, Structure-activity relationship

MSC2000: 

  • O641