基于范数指数定量构效关系预测β-环糊精络合常数

doi:10.3866/PKU.WHXB201503193

Abstract

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 (Q_LOO and Q_LTO) 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

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QIAN Hai-Cheng, KANWAL Shahid, JIA Qing-Zhu, WANG Qiang, JI Hui-Fen, ZHU Zhi-Chen, XIA Shu-Qian, MA Pei-Sheng. Norm Index-Based Quantitative Structure-Activity Relationship to Predict β-Cyclodextrin Complex Binding Constants[J].Acta Phys. -Chim. Sin., 2015, 31(5): 893-898.

References

(1) Loftsson, T.; Ducheêne, D. Int. J. Pharm. 2007, 329, 1. doi: 10.1016/j.ijpharm.2006.10.044
(2) Brewster, M. E.; Loftsson, T. Adv. Drug Deliver Rev. 2007, 59, 645. doi: 10.1016/j.addr.2007.05.012
(3) Freudenberg, K.; Jacobi, R. Ann. Chem. 1935, 518, 102.
(4) Larsen, K. L. J. Incl. Phenom. Macrocycl. Chem. 2002, 43, 1. doi: 10.1023/A:1020494503684
(5) Hsu, C. M.; Tsai, F. J.; Tsai, Y. Carbohyd. Polym. 2014, 114, 115. doi: 10.1016/j.carbpol.2014.07.042
(6) Vyas, A.; Saraf, S. J. Incl. Phenom. Macrocycl. Chem. 2008, 62, 23. doi: 10.1007/s10847-008-9456-y
(7) Yang, S. G.; Chen, Q. D.; Shi, J. F.; Shen, X. H. Acta Phys. -Chim. Sin. 2010, 26 (4), 805. [杨士国, 陈庆德, 施建峰, 沈兴海. 物理化学学报, 2010, 26 (4), 805.] doi: 10.3866/PKU.WHXB20100407
(8) Avdeef, A.; Bendels, S.; Tsinman, O.; Tsinman, K.; Kansy, M. Pharm. Res. 2007, 24, 530. doi: 10.1007/s11095-006-9169-0
(9) Kim, C.; Park, J. Am. J. Drug Deliv. 2004, 2, 113. doi: 10.2165/00137696-200402020-00004
(10) Loftsson, T.; Jarho, P.; Masson, M.; Jarvinen, T. Expert Opin. Drug Deliv. 2005, 2, 335. doi: 10.1517/edd.2005.2.issue-2
(11) Szejtli, J.; Szente, L. Eur. J. Pharm. Biopharm. 2005, 61, 115. doi: 10.1016/j.ejpb.2005.05.006
(12) Lantz, A.; Rodriguez, M.; Wetterer, S.; Armstrong, D. Anal. Chim. Acta 2006, 557, 184. doi: 10.1016/j.aca.2005.10.005
(13) Loukas, Y. L. J. Pharm. Biomed. 1997, 275.
(14) Ogwu, S. O.; Alcala, M. J.; Bhardwaj, R.; Blanchard, J. J. Pharm. Biomed. Anal. 1999, 19, 391. doi: 10.1016/S0731-7085(98)00139-3
(15) Chen, J.; Ohnmacht, C. M.; Hage, D. S. J. Chromatogr. A 2004, 1033, 115. doi: 10.1016/j.chroma.2004.01.032
(16) Rundlett, K. L.; Armstrong, D.W. J. Chromatogr. A 1996, 721, 173. doi: 10.1016/0021-9673(95)00774-1
(17) Berglund, J.; Cedergren, L.; Andersson, S. B. Int. J. Pharm. 1997, 156, 195. doi: 10.1016/S0378-5173(97)00203-2
(18) Bellini, M. S.; Deyl, Z.; Manetto, G.; Kohlìcková, M. J. Chromatogr. A 2001, 924, 483. doi: 10.1016/S0021-9673(01)00775-0
(19) Junquera, E.; Aicart, E. J. Phys. Chem. B 1997, 101, 7163. doi: 10.1021/jp963977s
(20) Ono, N.; Hirayama, F.; Uekama, K. Eur. J. Pharm. Sci. 1999, 8, 133. doi: 10.1016/S0928-0987(99)00002-0
(21) Cirri, M.; Maestrelli, F.; Orlandini, S.; Furlanetto, S.; Pinzauti, S.; Mura, P. J. Pharm. Biomed. Anal. 2005, 37, 995. doi: 10.1016/j.jpba.2004.09.044
(22) Faucci, M. T.; Melani, F.; Mura, P. Chem. Phys. Lett. 2002, 358, 383. doi: 10.1016/S0009-2614(02)00410-4
(23) Melani, F.; Mura, P.; Adamo, M.; Maestrelli, F.; Gratteri, P.; Bonaccini, C. Chem. Phys. Lett. 2003, 370, 280. doi: 10.1016/S0009-2614(03)00126-X
(24) Loukas, Y. L.; Vraka, V.; Gregoriadis, G. Int. J. Pharm. 1996, 144, 225. doi: 10.1016/S0378-5173(96)04759-X
(25) Pérez-Garrido, A.; Helguera, A. M.; Guillén, A. A.; Cordeiro, M. N. D. S.; Escudero, A. G. Bioorg. Med. Chem. 2009, 17, 896. doi: 10.1016/j.bmc.2008.11.040
(26) Wang, Q.; Jia, Q. Z.; Yan, L. H.; Xia, S. Q.; Ma, P. S. Chemosphere 2014, 2, 30.
(27) Zhu, Z. C.; Wang, Q.; Jia, Q. Z.; Xia, S. Q.; Ma, P. S. Acta Phys. -Chim. Sin. 2014, 30 (6), 1086. [朱志臣, 王强, 贾青竹, 夏淑倩, 马沛生. 物理化学学报, 2014, 30 (6), 1086.] doi: 10.3866/PKU.WHXB201404161
(28) Zhu, Z. C.; Wang, Q.; Jia, Q. Z.; Tang, H. M.; Ma, P. S. Acta Phys. -Chim. Sin. 2013, 29 (1), 30. [朱志臣, 王强, 贾青竹, 汤红梅, 马沛生. 物理化学学报, 2013, 29 (1), 30.] doi: 10.3866/PKU.WHXB201210265
(29) Hyperchem. 7.0. Hypercube, Inc.: Gainesville, Florida. http://www.hyper.com.

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

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