Improvement of water solubility of non-competitive AMPA receptor antagonists by complexation with β-cyclodextrin

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8706-8712

  Stancanelli, Rosanna ^a   Crupi, Vincenza ^a   De Luca, Laura ^a   Ficarra, Paola ^a   Ficarra, Rita ^a   Gitto, Rosaria ^a   Guardo, Marta ^a   Iraci, Nunzio ^a   Majolino, Domenico ^a   Tommasini, Silvana ^a   Venuti, Valentina ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

Cyclodextrin; FTIR ATR spectroscopy; Molecular modelling; Tetrahydroisoquinoline derivatives; UV vis spectroscopy

Indexed keywords

2 ACETYL 1 (4' CHLOROPHENYL) 6,7 DIMETHOXY 1,2,3,4 TETRAHYDROISOQUINOLINE; AMPA RECEPTOR ANTAGONIST; BETA CYCLODEXTRIN; TETRAHYDROISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; DRUG SOLUBILITY; ELECTROPHYSIOLOGY; ENANTIOMER; INFRARED SPECTROSCOPY; MEASUREMENT; MOLECULAR DYNAMICS; MOLECULAR MODEL; PRECIPITATION; QUANTITATIVE ANALYSIS; RACEMIC MIXTURE; ULTRAVIOLET SPECTROSCOPY;

ALGORITHMS; BETA-CYCLODEXTRINS; BINDING SITES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MODELS, MOLECULAR; RECEPTORS, AMPA; SOLUBILITY; SPECTROPHOTOMETRY, ULTRAVIOLET; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STEREOISOMERISM; WATER;

EID: 51649119237     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.085     Document Type: Article

References (48)

1. Sudhakar Y., Kuotsu K., and Bandyopadhyay A.K. J. Control. Release 114 (2006) 15-40
2. George M., and Abraham T.E. J. Control. Release 114 (2006) 1-14
3. Couvreur P., Gref R., Andrieux K., and Malvy C. Prog. Solid State Chem. 34 (2006) 231-235
4. Sajeesh S., and Sharma C.P. Int. J. Pharm. 325 (2006) 147-154
5. Rajendrakumar K., Madhusudan S., and Pralhad T. Eur. J. Pharm. Biopharm. 60 (2005) 39-46
6. Shen Y., Yang S., Wu L., and Ma X. Spectrochim. Acta A 61 (2005) 1025-1028
7. Huang M.J., Watts J.D., and Bodor N. Int. J. Quant. Chem. 64 (1997) 711-719
8. Kew J.N., and Kemp J.A. Psychopharmacology 179 (2005) 4-29
9. Wollmuth L.P., and Sobolevsky A.I. Trends Neurosci. 27 (2004) 321-328
10. Gitto R., Barreca M.L., De Luca L., and Chimirri A. Exp. Opin. Ther. Patents 14 (2004) 1199-1213
11. Catarzi D., Colotta V., and Varano F. Med. Res. Rev. 27 (2007) 239-278
12. Gitto R., Barreca M.L., De Luca L., De Sarro G., Ferreri G., Quartarone S., Russo E., Constanti A., and Chimirri A. J. Med. Chem. 46 (2003) 197-200
13. Barreca M.L., Gitto R., Quartarone S., De Luca L., De Sarro G., and Chimirri A. J. Chem. Inf. Comput. Sci. 43 (2003) 651-655
14. Chimirri A., De Sarro G., Quartarone S., Barreca M.L., Caruso R., De Luca L., and Gitto R. Pure Appl. Chem. 76 (2004) 931-939
15. De Sarro G., Russo E., Ferreri G., Gallelli L., Gitto R., Barreca M.L., and Chimirri A. Naunyn-Schmiedebergs Arch. Pharmacol. 369 (2004) R167
16. Gitto R., Barreca M.L., Francica E., Caruso R., De Luca L., Russo E., De Sarro G., and Chimirri A. Arkivoc (2004) 170-180
17. Arstad E., Gitto R., Chimirri A., Caruso R., Constanti A., Turton D., Hume S.P., Ahmad R., Pilowsky L.S., and Luthra S.K. Bioorg. Med. Chem. 14 (2006) 4712-4717
18. De Luca L., Gitto R., Barreca M.L., Caruso R., Quartarone S., Citraro R., De Sarro G., and Chimirri A. Arch. Pharm. (Weinheim) 339 (2006) 388-400
19. Gitto R., Caruso R., Pagano B., De Luca L., Citraro R., Russo E., De Sarro G., and Chimirri A. J. Med. Chem. 49 (2006) 5618-5622
20. Gitto R., Ficarra R., Stancanelli R., Guardo M., De Luca L., Barreca M.L., Pagano B., Rotondo A., Bruno G., Russo E., De Sarro G., and Chimirri A. Bioorg. Med. Chem. 15 (2007) 5417-5423
21. Gitto, R.; Pagano, B.; Citraro, R.; Scicchitano, F.; De Sarro, G.; Chimirri, A. Eur. J. Med. Chem., in press. doi:10.1016/j.ejmech.2008.02.025.
22. Rizzo M., Ventrice D., Casale F., De Sarro G., Gitto R., and Chimirri A. J. Chromat. B Anal. Technol. Biomed. Life Sci. 850 (2007) 161-167
23. Higuchi T., and Connors K.A. Adv. Anal. Chem. Instr. 4 (1965) 117-212
24. Crupi V., Ficarra R., Guardo M., Majolino D., Stancanelli R., and Venuti V. J. Pharm. Biomed. Anal. 44 (2007) 110-117
25. Stancanelli R., Ficarra R., Cannavà C., Guardo M., Calabrò M.L., Ficarra P., Ottanà R., Maccari R., Crupi V., Majolino D., and Venuti V. J. Pharm. Biomed. Anal. 47 (2008) 704-708
26. Cannavà, C.; Crupi, V.; Ficarra, P.; Guardo, M.; Majolino, D.; Stancanelli, R.; Venuti V. Vib. Spectrosc., in press. doi:10.1016/j.vibspec.2007.12.013.
27. Crupi V., Longo F., Majolino D., and Venuti V. J. Chem. Phys. 123 (2005) 154702
28. Hahn B.D., Neubert R.H.N., Wartewig S., Christ A., and Hentzsch C. J. Pharm. Sci. 89 (2000) 1106-1113
29. Armenta S., Garrigures G., de la Guardia M., and Rondeau P. Anal. Chim. Acta 289 (2005) 99-106
30. Carolei L., and Gutz I.G.R. Talanta 66 (2005) 118-124
31. Ilario R., Iñón F.A., Garrigues S., and de la guardia M. Talanta 69 (2006) 469-480
32. Wartewig S., and Neubert R.H.H. Adv. Drug Del. Rev. 57 (2005) 1144-1170
33. de Sousa F.B., Oliveira M.F., Lula I.S., Sansiviero M.T.C., Cortés M.E., and Sinisterra R.D. Vib. Spectrosc. 46 (2008) 57-62
34. Stancanelli R., Mazzaglia A., Tommasini S., Calabrò M.L., Villari V., Guardo M., Ficarra P., and Ficarra R. J. Pharm. Biomed. Anal. 44 (2007) 980-984
35. Loftsson T., Hreinsdóttir D., and Másson M. Evaluation of cyclodextrin solubilization of drugs. Int. J. Pharm. 302 (2005) 18-28
36. Gavira J.M., Hernanz A., and Bratu I. Vib. Spectrosc. 32 (2003) 137-146
37. Bratu I., Veiga F., Fernandes C., Hernanz A., and Gavira J.M. Spectroscopy 18 (2004) 459-467
38. Montassier P., Duchêne D., and Poelmann M.C. Int. J. Pharm. 153 (1997) 199-209
39. Bratu I., Hernanz A., Gavira J.M., and Bora G.H. Rom. J. Phys. 50 (2005) 1063-1069
40. Mura P., Bettinetti G.P., Manderioli A., Faucci M.T., Bramanti G., and Sorrenti M. Int. J. Pharm. 166 (1998) 189
41. Connors K.A. In: Szejtli J., and Osa T. (Eds). Cyclodextrins Comprehensive Supramolecular Chemistry Vol. 3 (1996), Pergamon, Oxford, UK 205-241
42. Maestro; version 8.0; Schrödinger LLC: New York, 2007.
43. Macromodel; version 9.5; Schrödinger LLC: New York, 2007.
44. Jorgensen W.L., Maxwell D.S., and Tirado-Rives J. J. Am. Chem. Soc. 118 (1996) 11225-11236
45. Clark Still W., Tempczyk A., Hawley R.C., and Hendrickson T. J. Am. Chem. Soc. 112 (1990) 6127-6129
46. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shaw D.E., Shelley M., Perry J.K., Sander L.C., and Shenkin P.S. J. Med. Chem. 47 (2004) 1739-1749
47. Kalè L.S., Bhandarkar R., Brunner M., Gursoy R., Krawetz A., Phillips N., Shinozaki J., Varadarajan A., and Schulten K. J. Comput. Phys. 151 (1999) 283-312
48. Pedretti A., Villa L., and Vistoli G. J. Mol. Graph. Model. 21 (2002) 47-49