An alignment independent 3D-QSAR study for predicting the stability constants of structurally diverse compounds with β-cyclodextrin

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 71, Issue 1-2, 2011, Pages 195-206

  Ghasemi, Jahan B ^a   Salahinejad, M ^b   Rofouei, M K ^b  

^a K N TOOSI UNIVERSITY OF TECHNOLOGY   (Iran)

^b KHARAZMI UNIVERSITY   (Iran)

Author keywords

cyclodextrin; 3D QSAR; GRIND descriptors; Stability constant

Indexed keywords

EID: 80054944454     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-011-9927-4     Document Type: Article

References (30)

1. J Szejtli 1998 Introduction and general overview of cyclodextrin chemistry Chem. Rev. 98 1743 1753 10.1021/cr970022c 1:CAS:528:DyaK1cXksV2itrw%3D (Pubitemid 128633435)
2. DO Thompson 1997 Cyclodextrins-enabling excipients: their present and future use in pharmaceuticals Criti. Rev. Ther. Drug. Carr. Syst. 14 1 104 1:CAS:528:DyaK2sXhtlems7g%3D (Pubitemid 27079973)
3. AH Hedges 1998 Industrial Applications of Cyclodextrins Chem. Rev. 98 2035 2044 10.1021/cr970014w 1:CAS:528:DyaK1cXksV2iurw%3D
4. J Szejtli 2004 Past, present, and future of cyclodextrin research Pure. App. Chem. 76 1825 1845 10.1351/pac200476101825 1:CAS:528:DC%2BD2cXhtVSntr3P
5. J Szejtli 1997 Utilization of cyclodextrins in industrial products andprocesses J. Mater. Chem. 7 575 587 10.1039/a605235e 1:CAS:528: DyaK2sXis1yjtb0%3D (Pubitemid 127730026)
6. A Vyas S Saraf 2008 Cyclodextrin based novel drug delivery systems J. Incl. Phenom. Macrocycl. Chem. 62 23 42 10.1007/s10847-008-9456-y 1:CAS:528:DC%2BD1cXhtVOmtbnL
7. Beck, M.T., Nagypal, I.: Chemistry of Complex Equilibria, Chap. 1. Horwood, Chichester. ISBN 0853121435. (1990)
8. KA Connors 1997 The Stability of Cyclodextrin Complexes in Solution Chem. Rev. 97 1325 1357 10.1021/cr960371r 1:CAS:528:DyaK2sXksV2kurs%3D (Pubitemid 127659601)
9. T Loftsson E Stefansson 2007 Cyclodextrins in ocular drug delivery: theoretical basis with dexamethasone as a sample drug J. Drug. Del. Sci. Tech. 17 3 9 1:CAS:528:DC%2BD2sXksVCqur8%3D (Pubitemid 46347809)
10. KB Lipkowitz 1998 Applications of Computational Chemistry to the Study of Cyclodextrins Chem. Rev. 98 1829 1873 10.1021/cr9700179 1:CAS:528: DyaK1cXksFSksLg%3D (Pubitemid 128633439)
11. Hansch, C., Leo, A.: Exploring QSAR: Fundamentals and Applications in Chemistry and Biology. American Chemical Society, Washington, DC (1995)
12. E Estrada I Perdomo-Lopez JJ Torres-Labandeira 2001 Combination of 2D-, 3D-Connectivity and Quantum Chemical Descriptors in QSPR. Complexation of α- and β-Cyclodextrin with Benzene Derivatives J. Chem. Inf. Comput. Sci. 41 1561 1568 10.1021/ci0100402 1:CAS:528:DC%2BD3MXntVyntr4%3D (Pubitemid 35445296)
13. A Perez-Garrido AM Helguera AA Guillen NDS Cordeiro AG Escudero 2009 Convenient QSAR model for predicting the complexation of structurally diverse compounds with b-cyclodextrins Bioorg. Med. Chem. 17 896 904 10.1016/j.bmc.2008.11.040 1:CAS:528:DC%2BD1MXhtFeqs7c%3D
14. T Suzukia M Ishidaa WMF Fabian 2000 Classical QSAR and comparative molecular field analyses of the host-guest interaction of organic molecules with cyclodextrins J. Comp. Aid. Mol. Des. 14 669 678 10.1023/A:1008103122313
15. VR Nayak GE Kellogg 1994 Cyclodextrin-barbiturate inclusion complexes: A CoMFA/HINT 3-D QSAR study Med. Chem. Res. 3 491 502 1:CAS:528:DyaK2cXlsVWgt7w%3D
16. JB Ghasemi S Saaidpour 2008 QSPR modeling of stability constants of diverse 15-crown-5 ethers complexes using best multiple linear regression J. Incl. Phenom. Macrocycl. Chem. 60 339 351 10.1007/s10847-007-9383-3 1:CAS:528:DC%2BD1cXktVCnsrk%3D
17. Ghasemi, J.B., Rofouei, M.K., Salahinejad, M.: A QSPR Study of the Stability Constant of Crown Ethers by Molecular Modelling: New Descriptors for Lariat Effect. J. Incl. Phenom. Macrocycl. Chem. In Press (2010)
18. T Suzuki 2001 A Nonlinear Group Contribution Method for Predicting the Free Energies of Inclusion Complexation of Organic Molecules with α- and β-Cyclodextrins J. Chem. Inf. Comp. Sci. 41 1266 1273 10.1021/ci010295f 1:CAS:528:DC%2BD3MXlvVagt74%3D (Pubitemid 35445318)
19. SB Hudson MR Hyde E Rahr J Wood 1996 Parameter based methods for compound selection from chemical databases Quant. Struct. Act. Relat. 15 285 289 10.1002/qsar.19960150402 1:CAS:528:DyaK28XmtFaitL8%3D (Pubitemid 26283514)
20. RD Clark PC Foz 2004 Statistical variation in progressive scrambling J. Com. Aid. Mol. Des. 18 563 576 10.1007/s10822-004-4077-z 1:CAS:528: DC%2BD2MXltVaktg%3D%3D
21. RD Clark 2003 Boosted leave-many-out cross-validation: the effect of training and test set diversity on PLS statistics J. Com. Aid. Mol. Des. 17 265 275 10.1023/A:1025366721142 1:CAS:528:DC%2BD3sXmsVGnsLs%3D (Pubitemid 37062787)
22. Duran, A., Martinez, G.C., Pastor, M.: Development and validation of AMANDA, a new algorithm for selecting highly relevant regions in Molecular Interaction Fields. J. Chem. Inf. Model. 48,1813-1823(2008); Pentacle 1.0.3; http://cadd.imim.es/grib-cadd/projects/pentacle ; http://www.moldiscovery.com (accessed on 29/09/2009)
23. P Cratteri MN Romanelli G Cruciani CB Melani F Melani 2004 GRIND-derived pharmacophore model for a series of α-tropanyl derivative ligands of the sigma-2 receptor J. Com. Aid. Mol. Des. 18 361 374 10.1023/B:JCAM.0000047815. 22931.3b 1:CAS:528:DC%2BD2cXhtFakurfF (Pubitemid 41449168)
24. M Pastor G Cruciani I McLay S Pickett S Clementi 2000 GRid-INdependent descriptors (GRIND): a novel class of alignment-independent three-dimensional molecular descriptors J. Med. Chem. 43 3233 3243 10.1021/jm000941m 1:CAS:528:DC%2BD3cXltlOrur8%3D
25. Cruciani, G.: Molecular interaction fields, Applications in Drug Discovery and ADME Prediction, vol. 27. Wiley-VCH publication, Weinheim (2006)
26. S Wold K Esbensen P Geladi 1987 Principal Component analysis Chem. Intell. Lab. Syst. 2 37 52 10.1016/0169-7439(87)80084-9 1:CAS:528: DyaL1cXjtVyjsw%3D%3D
27. H Dragos M Gilles V Alexandre 2009 Predicting the predictability: a unified approach to the applicability domain problem of QSAR models J. Chem. Inf. Model. 49 1762 1776 10.1021/ci9000579 1:CAS:528:DC%2BD1MXnt1Cmsrs%3D
28. S Dimitrov G Dimitrova T Pavlov N Dimitrova G Patlewicz J Niemela O Mekenyan 2005 A Stepwise Approach for Defining the Applicability Domain of SAR and QSAR Models J.Chem. Inf. Model. 45 839 849 10.1021/ci0500381 1:CAS:528:DC%2BD2MXltlGht78%3D (Pubitemid 41156682)
29. J Canceill L Lacombe A Collet 1987 Water-soluble cryptophane binding lipophilic guests in aqueous solution J. Chem. Soc. Chem. Commun. 3 219 221 10.1039/c39870000219
30. Hirayama, F., Uekama, K.: In: Duchene, D. (ed.) Cyclodextrin and Their Industrial Uses, pp. 131-172. Editions De Sant′e, Paris (1987)