QSPR modelling with the topological substructural molecular design approach: β-cyclodextrin complexation

Journal of Pharmaceutical Sciences

Volumn 98, Issue 12, 2009, Pages 4557-4576

  Pérez Garrido, Alfonso ^a   Helguera, Aliuska Morales ^b,c   Cordeiro, M Natália D S ^c   Escudero, Amalio Garrido ^a  

^a CATHOLIC UNIVERSITY OF MURCIA   (Spain)

^b CENTRAL UNIVERSITY OF LAS VILLAS   (Cuba)

^c UNIVERSITY OF PORTO   (Portugal)

Author keywords

Complexation; Cyclodextrins; Drug design; QSAR; QSPR

Indexed keywords

BETA CYCLODEXTRIN DERIVATIVE; BROMIDE; CHLORIDE; IODIDE; ORGANIC COMPOUND;

ARTICLE; CONTROLLED STUDY; HYDROPHOBICITY; QUANTITATIVE STRUCTURE PROPERTY RELATION;

EID: 71649087406     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.21747     Document Type: Article

References (82)

1. Saenger W, Jacob J, Gessler K, Steiner T, Daniel S, Sanbe H, Koizumi K, Smith SM, Tanaka T. 1998. Structures of the common cyclodextrins and their larger analogues - Beyond the doughnut. Chem Rev 98:1787-1802. (Pubitemid 128633437)
2. Loftsson T, Brewster M, Masson M. 2004. Role of cyclodextrins in improving oral drug delivery. Am J Drug Deliv 2:261-275. (Pubitemid 40045491)
3. Davis ME, Brewster M. 2004. Cyclodextrin-based pharmaceutics: Past, present and future. Nat Rev Drug Discov 3:1023-1035. (Pubitemid 39642365)
4. Avdeef A, Bendels S, Tsinman O, Tsinman K, Kansy M. 2007. Solubility excipient classification gradient maps. Pharm Res 24:530-545. (Pubitemid 46295156)
5. Kim C, Park J. 2004. Solubility enhancers for oral drug delivery. Am J Drug Deliv 2:113-130.
6. Loftsson T, Jarho P, Masson M, Jarvinen T. 2005. Cyclodextrins in drug delivery. Expert Opin Drug Deliv 2:335-351.
7. Kola I, Landis J. 2004. Can the pharmaceutical industry reduce attrition rates? Nat Rev Drug Discov 2:711-715.
8. Liu R. 2000. Water-insoluble drug formulation. Englewood: CO Interpharm Press.
9. Irie T, Uekama K. 1997. Pharmaceutical applications of cyclodextrins. iii. Toxicological issues and safety evaluation. J Pharm Sci 86:147-162. (Pubitemid 27078377)
10. Szejtli J. 1998. Introduction and general overview of cyclodextrin chemistry. Chem Rev 98:1743-1753. (Pubitemid 128633435)
11. Lantz A, Rodriguez M, Wetterer S, Armstrong D. 2006. Estimation of association constants between oral malodor components and various native and derivatized cyclodextrins. Anal Chim Acta 557:184-190. (Pubitemid 43097294)
12. Uekama K. 1999. Cyclodextrins in drug delivery. Adv Drug Deliv Rev 36:1-2.
13. Duchêne D, editor. 1987. Cyclodextrins and their industrial uses. Paris: Editions de Santé Paris.
14. Horvath G, Premkumar T, Boztas A, Lee E, Jon S, Geckeler KE. 2008. Supramolecular nanoencapsulation as a tool: Solubilization of the anticancer drug trans-dichloro(dipyridine)platinum(ii) by complexation with beta-cyclodextrin. Mol Pharm 5:358-363. (Pubitemid 351579138)
15. Lipkowitz KB. 1998. Applications of computational chemistry to the study of cyclodextrins. Chem Rev 98:1829-1873. (Pubitemid 128633439)
16. Suzuki T. 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 Comput Sci 41:1266-1273. (Pubitemid 33663891)
17. Pérez F, Jaime C, Sánchez-Ruiz X. 1995. Mm2 calculations on cyclodextrins: Multimodel inclusion complexes. J Org Chem 60:3840-3845.
18. Matsui Y, Nishioka T, Fujita T. 1985. Quantitative structure-reactivity analysis of the inclusion mechanism by cyclodextrins. Top Curr Chem 128:61-89.
19. Davis DM, Savage JR. 1993. Correlation analysis of the host-guest interaction of α-cyclodextrin and substituted benzenes. J Chem Res-S 94-95.
20. Park JH, Nah TH. 1994. Binding forces contributing to the complexation of organic molecules with β-cyclodextrin in aqueous solution. J Chem Soc [Perkin Trans] 2:1359-1362.
21. Klein CT, Polheim D, Viernstein H, Wolschann P. 2000. A method for predicting the free energies of complexation between β-cyclodextrin and guest molecules. J Inclusion Phenom Macrocyclic Chem 36:409-423.
22. Liu L, Guo QX. 1999. Wavelet neural network and its application to the inclusion of β-cyclodextrin with benzene derivatives. J Chem Inf Comput Sci 39:133-138. (Pubitemid 129676568)
23. Suzuki T, Ishida M, Fabian WMF. 2000. Classical QSAR and comparative molecular field analyses of the host-guest interaction of organic molecules with cyclodextrins. J Comput Aided Mol Des 14:669-678. (Pubitemid 30705859)
24. Cramer IRD, Patterson DE, Bunce JD. 1988. Comparative molecular field analysis (COMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959-5967.
25. Katritzky AR, Fara DC, Yang HF, Karelson M, Suzuki T, Solov'ev VP, Varnek A. 2004. Quantitative structure-property relationship modelling of β-cyclodextrin complexation free energies. J Chem Inf Comput Sci 44:529-541.
26. Estrada E. 1996. Spectral moments of the edge adjacency matrix in molecular graphs. 1. Definition and applications to the prediction of physical properties of alkanes. J Chem Inf Comput Sci 36:844-849. (Pubitemid 126581737)
27. Estrada E. 1997. Spectral moments of the edge-adjacency matrix of molecular graphs. 2. Molecules containing heteroatoms and QSAR applications. J Chem Inf Comput Sci 37:320-328. (Pubitemid 127603533)
28. Estrada E. 1995. Edge adjacency relationships and a novel topological index related to molecular volume. J Chem Inf Comput Sci 35:31-33.
29. Estrada E, Molina E. 2006. Automatic extraction of structural alerts for predicting chromosome aberrations of organic compounds. J Mol Graph Model 25:275-288. (Pubitemid 44740067)
30. Estrada E, Patlewicz G, Gutierrez Y. 2004. From knowledge generation to knowledge archive. A general strategy using tops-mode with Derek to formulate new alerts for skin sensitization. J Chem Inf Comput Sci 44:688-698.
31. González MP, Dias L, Helguera AM. 2004. A topological sub-structural approach to the mutagenic activity in dental monomers. 2. Cycloaliphatic epoxides. Polymer 15:5353-5359.
32. González MP, Helguera AM, Molina R, Garca JR. 2004. A topological substructural approach of the mutagenic activity in dental monomers. 1. Aromatic epoxides. Polymer 45:2773-2779.
33. González MP, Helguera AM, Cabrera MA. 2005. Quantitative structureactivity relationship to predict toxicological properties of benzene derivative compounds. Bioorg Med Chem 13:1775-1781.
34. Helguera AM, Pérez MAC, Combes RD, González MP. 2006. Quantitative structure activity relationship for the computational prediction of nitrocompounds carcinogenicity. Toxicology 220:51-62. (Pubitemid 43197629)
35. Helguera AM, González MP, Cordeiro MNDS, Cabrera MA. 2007. Quantitative structure carcinogenicity relationship for detecting structural alerts in nitrosocompounds. Toxicol Appl Pharmacol 221:189-202.
36. Helguera AM, González MP, Cordeiro MNDS, Cabrera MA. 2008. Quantitative structure-carcinogenicity relationship for detecting structural alerts in nitroso compounds: Species, rat; sex, female; route of administration, gavage. Chem Res Toxicol 21:633-642.
37. González MP, Terán C, Teijeira M. 2006. A topological function based on spectral moments for predicting affinity toward a3 adenosine receptors. Bioorg Med Chem Lett 16:1291-1296. (Pubitemid 43143008)
38. González MP, Helguera AM, Collado IG. 2006. A topological substructural molecular design to predict soil sorption coefficients for pesticides. Mol Divers 10:109-118.
39. González MP, Diáz HG, Ruiz RM, Cabrera MA, Ramos de Armas R. 2003. Tops-mode based QSARs derived from heterogeneous series of compounds. Applications to the design of new herbicides. J Chem Inf Comput Sci 43:1192-1199.
40. Pérez-Garrido A, González MP, Escudero AG. 2008. Halogenated derivatives QSAR model using spectral moments to predict haloacetic acids (haa) mutagenicity. Bioorg Med Chem 16:5720-5732.
41. Helguera AM, Cordeiro MNDS, Cabrera MA, Combes RD, González MP. 2008. Quantitative structure carcinogenicity relationship for detecting structural alerts in nitroso-compounds species: Rat; sex: male; route of administration: water. Toxicol Appl Pharmacol 231:197-207.
42. Helguera AM, Pérez MAC, Gonzá lez MP, Ruiz RM, Díaz HG. 2005. A topological substructural approach applied to the computational prediction of rodent carcinogenicity. Bioorg Med Chem 13:2477-2488.
43. Environment Directorate OECD. 2007. Guidance Document of the Validation of (Quantitative) Structure-Activity Relationships (Q)SAR Models. Enviromental Health and Safety Publications, Series on Testing and Assessment No. 69.
44. Estrada E, Uriarte E, Gutierrez Y, Gonzá lez H. 2003. Quantitative structure-toxicity relationships using tops-mode. 3. Structural factors influencing the permeability of commercial solvents through living human skin. SAR QSAR Environ Res 14:145-163.
45. Gutierrez Y, Estrada E. 2002. Modes Lab, Version 1.0.
46. Weininger D. 1988. Smiles, a chemical language and information system. 1. Introduction to methodology and encoding rules. J Chem Inf Comput Sci 28:31-36. (Pubitemid 18574254)
47. Goldberg D. 1989. Genetic algorithms in search, optimization, and machine learning. USA: Addison-Wesley.
48. Todeschini R, Ballabio D, Consonni V, Mauri A, Pavan M. 2004. Mobydigs Computer Software. Milano: TALLETE SRL.
49. Pérez-Garrido A, Helguera AM, Cordeiro MNDS, Abellán A, Escudero AG. 2008. Convenient QSAR model for predicting the complexation of structurally diverse compounds with β-cyclodextrins. Bioorg Med Chem 17:896-904.
50. Garcia-Domenech R, Julian-Ortiz JV. 1998. Antimicrobial activity characterization in a heterogeneous group of compounds. J Chem Inf Comput Sci 38:445-449. (Pubitemid 128594457)
51. Kubinyi H. 1994. Variable selection in QSAR studies. 1. An evolutionary algorithm. Quant Struct Act Relat 13:285-294.
52. Kubinyi H. 1994. Variable selection in QSAR studies. 2. A highly efficient combination of systematic search and evolution. Quant Struct Act Relat 13:393-401.
53. Akaike H. 1973. Information theory and an extension of the maximum likelihood principle. In Proceedings of the Second International Symposium on Information Theory. Budapest: Akademiai Kiado, pp 267-281.
54. Akaike H. 1974. New look at statistical-model identification. IEEE Trans Automat Control AC-19:716-723.
55. Lučić B, Nikolić S, Trinajstić N, Jurić D. 1995. The structure-property models can be improved using the orthogonalized descriptors. J Chem Inf Comput Sci 35:532-538.
56. Todeschini R, Consonni V. 2000. Handbook of molecular descriptors. Mannheim: Wiley-VCH, 667p.
57. Klein D, Randić M, Babić D, Lučić B, Nikolić S, Trinajstić N. 1997. Hierarchical orthogonalization of descriptors. Int J Quantum Chem 63:215-222.
58. Randić M. 1991. Orthogonal molecular descriptors. N J Chem 15:517-525.
59. Randić M. 1991. Resolution of ambiguities in structure-property studies by use of orthogonal descriptors. J Chem Inf Comput Sci 31:311-320.
60. Randić M. 1991. Correlation of enthalpy of octanes with orthogonal connectivity indices. J Mol Struct (Theochem) 233:45-59.
61. Eriksson L, Jaworska J, Worth AP, Cronin MTD, McDowell RM, Gramatica P. 2003. Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ Health Perspect 111:1361-1375. (Pubitemid 37021142)
62. Netzeva TI, Worth AP, Aldenberg T, Benigni R, Cronin MTD, Gramatica P, Jaworska JS, Kahn S, Klopman P, Marchant CA, Myatt G, Nikolova-Jeliazkova N, Patlewicz GY, Perkins R, Roberts DW, Schultz TW, Stanton DT, van de Sandt JJH, Tong W, Veith G, Yang C. 2005. Current status of methods for defining the applicability domain of (quantitative) structure activity relationships. ATLA 33:155-173.
63. Gramatica P. 2007. Principles of QSAR models validation: Internal and external. QSAR Comb Sci 26:1-9. (Pubitemid 46932857)
64. Vighi M, Gramatica P, Consolaro F, Todeschini R. 2001. QSAR and chemometrics approaches for setting water quality objectives for dangerous chemicals. Ecotoxicol Environ Saf 49:206-220. (Pubitemid 32662274)
65. Hansch C, Leo A, Hoekman DH. 1995. Exploring QSAR fundamentals and applications in chemistry and biology. In ACS professional reference book. Washington, DC: American Chemical Society, p 580.
66. Free SM, Wilson JW. 1964. A mathematical contribution to structure-activity studies. J Med Chem 7:395-399.
67. Estrada E. 2008. How the parts organize in the whole? A top-down view of molecular descriptors and properties for QSAR and drug design. Mini Rev Med Chem 8:213-221. (Pubitemid 351611824)
68. Benigni R, Giuliani A. 2003. Putting the predictive toxicology challenge into perspective: Reflections on the results. Bioinformatics 19:1194-1200. (Pubitemid 36850211)
69. Seo H, Tsuruoka M, Hashimoto T, Fujinaga T, Otagiri M, Uekama K. 1983. Enhancement of oral bioavailability of spironolactone by betacyclodextrin and gamma-cyclodextrin complexations. Chem Pharm Bull 31:286-291.
70. Pitha J, Harman SM, Michel ME. 1986. Hydrophilic cyclodextrin derivatives enable effective oraladministration of steroidal hormones. J Pharm Sci 75:165-167. (Pubitemid 16162540)
71. Uekama K, Fujinaga T, Otagiri M, Seo H, Tsuruoka M. 1981. Enhanced bioavailability of digoxin by gamma-cyclodextrin complexation. J Pharmacobiodyn 4:735-737. (Pubitemid 12234250)
72. Uekama K, Fujinaga T, Hirayama F, Otagiri M, Yamasaki M, Seo H, Hashimoto T, Tsuruoka M. 1983. Improvement of the oral bioavailability of digitalis glycosides by cyclodextrin complexation. J Pharm Sci 72:1338-1341. (Pubitemid 14229750)
73. Taylor GT, Weiss J, Pitha J. 1989. Testosterone in a cyclodextrin containing formulation - Behavioral and physiological-effects of episode like pulses in rats. Pharm Res 6:641-646.
74. Loftsson T, Olafsdottir BJ, Bodor N. 1991. The effects of cyclodextrins on transdermal delivery of drugs. Eur J Pharm Biopharm 37:30-33.
75. Uekama K, Arimori K, Sakai A, Masaki K, Irie T, Otagiri M. 1987. Improvement in percutaneous-absorption of prednisolone by betacyclodextrin and gamma-cyclodextrin complexations. Chem Pharm Bull 35:2910-2913. (Pubitemid 17135849)
76. Rekharsky MV, Inoue Y. 1998. Complexation thermodynamics of cyclodextrins. Chem Rev 98:1875-1917.
77. Liu L, Guo QX. 2002. The driving forces in the inclusion complexation of cyclodextrins. J Inclusion Phenom Macrocyclic Chem 42:1-14. (Pubitemid 38075810)
78. Sutherland JJ, O'Brien LA, Boztas A, Weaver DF. 2003. Spline-fitting with a genetic algorithm: A method for developing classification structure-activity relationships. J Chem Inf Comput Sci 43:1906-1915.
79. Inoue Y, Hakushi T, Liu Y, Tong LH, Shen BJ, Jin DS. 1993. Thermodynamics of molecular recognition by cyclodextrins. 1. Calorimetric titration of inclusion complexation of naphthalenesulfonates with α-, β-, and γ-cyclodextrins: Enthalpy-entropy compensation. J Am Chem Soc 115:475-481. (Pubitemid 23961262)
80. Carpignano R, Marzona M, Cattaneo E, Quaranta S. 1997. QSAR study of inclusion complexes of heterocyclic compounds with β-cyclodextrin. Anal Chim Acta 348:489-493. (Pubitemid 27397452)
81. Rekharsky MV, Goldberg RN, Schwarz FP, Tewari YB, Ross PD, Yamashoji Y, Inoue Y. 1995. Thermodynamic and nuclear magnetic resonance study of the interactions of α- and β-cyclodextrin with model substances: Phenethylamine, ephedrines, and related substances. J Am Chem Soc 117:8830-8840.
82. Wallimann P, Marti T, Fürer A, Diederich F. 1997. Steroids in molecular recognition. Chem Rev 97:1567-1608.