Crystal and molecular structure of β-cyclodextrins functionalized with the anti-inflammatory drug etodolac

Biopolymers - Peptide Science Section

Volumn 91, Issue 12, 2009, Pages 1227-1235

  Puglisi, Antonino ^a   Rizzarelli, Enrico ^a,b   Vecchio, Graziella ^a   Iacovino, Rosa ^c   Benedetti, Ettore ^b,d   Pedone, Carlo ^b,d   Saviano, Michele ^b,d  

^a UNIVERSITY OF CATANIA   (Italy)

^b CNR   (Italy)

^c SECOND UNIVERSITY OF NAPLES   (Italy)

^d UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

cyclodestrin conjugates; Anti inflammatory drug; Conformation; Etodolac; X ray diffraction

Indexed keywords

ANTI-INFLAMMATORY DRUGS; AQUEOUS SOLUTIONS; COVALENTLY BONDED; CRYSTAL AND MOLECULAR STRUCTURE; ETHYL GROUPS; ETODOLAC; FOLDED CONFORMATION; FUNCTIONALIZED; HYDROPHOBIC CAVITIES; HYDROXYL GROUPS; INTERMOLECULAR HYDROGEN BOND NETWORK; MACROCYCLES; METHYL GROUP; NEIGHBORING MOLECULES; NMR SPECTROSCOPY; VAN DER WAALS INTERACTIONS; WATER MOLECULE; X-RAY STRUCTURE; ONLINE VERSIONS;

CONFORMATIONS; CRYSTAL STRUCTURE; CYCLODEXTRINS; DATA STORAGE EQUIPMENT; DIFFRACTION; FLUORINE CONTAINING POLYMERS; GLUCOSE; HYDROCARBONS; HYDROGEN BONDS; HYDROPHOBICITY; MOLECULES; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; VAN DER WAALS FORCES; X RAY DIFFRACTION;

X RAY DIFFRACTION ANALYSIS;

BETA CYCLODEXTRIN; ETODOLAC; ANTIINFLAMMATORY AGENT; BETA CYCLODEXTRIN DERIVATIVE; GLUCOSE; HYDROGEN; HYDROXYL GROUP; METHYL GROUP; WATER;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; CONJUGATE; CONTROLLED STUDY; COVALENT BOND; CRYSTAL STRUCTURE; DRUG STRUCTURE; ENANTIOMER; HYDROGEN BOND; HYDROPHOBICITY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN FOLDING; X RAY DIFFRACTION; CHEMICAL INTERACTION; DRUG CONFORMATION; DRUG CONJUGATION; DRUG SOLUBILITY; PROTON NUCLEAR MAGNETIC RESONANCE;

ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BETA-CYCLODEXTRINS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; ETODOLAC; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN BINDING; PROTEIN CONFORMATION; SOLUTIONS; STEREOISOMERISM;

CLUPEIDAE;

EID: 71749090051     PISSN: 00063525     EISSN: 10970282     Source Type: Journal    
DOI: 10.1002/bip.21202     Document Type: Article

References (50)

1. Hart, F. D.; Huskisson, E. C. Drugs 1984, 27, 232-255.
2. Schwartz, K. A. Adv Clin Chem 2006, 42, 81-110.
3. Jachak, S. M. Curr Med Chem 2006, 13, 659-678.
4. Martelletti, P.; Farinelli, I.; Coloprisco, G.; Patacchioli, F. R. Drug Dev Res 2007, 68, 276-281.
5. Hochberg, M. C. Curr Top Med Chem 2005, 5, 443-448.
6. Sharma, S.; Prasad, A.; Anand, K. S. Am J Ther 1999, 6, 3-11.
7. Everts, B.; Wahrborg, P.; Hedner, T. Clin Rheumatol 2000, 19, 331-343.
8. Verburg, K. M.; Maziasz, T. J.; Weiner, E.; Loose, L.; Geis, G. S.; Isakson, P. C. Am J Therap 2001, 8, 49-64.
9. Bennett, A.; Tavares, I. A. Exp Opin Pharmacother 2001, 2, 1859-1876.
10. McGeer, P. L.; McGeer, E. G. Neurobiol Aging 2007, 28, 639-647.
11. Giovannini, M. G.; Scali, C.; Prosperi, C.; Bellucci, A.; Pepeu, G.; Casamenti, F. Int J Immunopathol Pharmacol 2003, 16, 31-40.
12. Voutsadakis, I. A. J. Cell Mol Med 2007, 11, 252-285.
13. Sarkar, F. H.; Adsule, S.; Li, Y.; Padhye, S. Mini-Rev Med Chem 2007, 7, 599-608.
14. Kamijo, T.; Sato, T.; Nagatomi, Y.; Kitamura, T. Int J Urol 2001, 8, S35-S39.
15. Markarian, B. M.; Cohen, G. L. European Patent Application EP88-300119 (1988).
16. Rozou, S.; Michaleas, S.; Antoniadou-Vyza, E. J Chromatogr A 2005, 1087, 86-94.
17. Fronza, G.; Mele, A.; Redenti, E.; Ventura, P. J Org Chem 1996, 61, 909-914.
18. Caira, M. R.; Griffith, V.; Nassimbeni, L. R.; van Oudtshoorn, B. J Chem Soc, Chem Commun 1994, 9, 1061-1062.
19. Otero-Espinar, F. J.; Anguiano-Igea, S.; Garcia-Gonzalez, N.; Vila-Jato, J. L.; Blanco-Mendez, J. Int J Pharmacol 1991, 75, 37-44.
20. Singla, A. K.; Chawla, M.; Singh, A. J Pharm Pharmacol 2000, 52, 467-486.
21. Milic-Askrabic, J.; Rajic, D. S.; Tasic, L. J.; Djuric, S.; Kasa, P.; Pintye-Hodi, K. Drug Dev Ind Pharm 1997, 23, 1123-1129.
22. Bannwarth, B.; Bertin, P.; Pehourcq, F.; Schaeverbeke, T.; Gillet, P.; Lefrancois, G.; Treves, R.; Dehais, J.; Netter, P.; Gaucher, A. Int J Clin Pharmacol Ther 2001, 39, 33-36.
23. Hirayama, F.; Uekama, K. Adv Drug Deliv Rev 1999, 36, 125-141.
24. Zhao, M.; Hao, A.; Li, J.; Wei, Y.; Guo, P. Carbohydr Res 2005, 340, 1563-1565.
25. Reuter, B. K.; Mauleon, D.; Wallace, J. L. J. Gastroen Hepatol 1998, 13, S266-S269.
26. Demerson, C. A.; Humber, L. G.; Abraham, N. A.; Schilling, G.; Martel, R. R.; Pace-Asciak, C. J Med Chem 1983, 26, 1778-1780.
27. Humber L. G.; Demerson, C. A.; Swaminathan, P.; Bird, P. H. J Med Chem 1986, 29, 871-874.
28. Jensen, M.; Engert, A.; Weissinger, F.; Knauf, W.; Kimby, E.; Poynton, C.; Oliff, I. A.; Rummel, M. J. Oesterborg A Invest N Drug 2008, 26, 139-149.
29. Behari, J.; Zeng, G.; Otruba, W.; Thompson, M. D.; Muller, P.; Micsenyi, A.; Sekhon, S. S.; Leoni, L.; Monga, S. P. S. J Hepatol 2007, 46, 849-857.
30. Brenna, E.; Fuganti, C.; Fuganti, D.; Grasselli, P.; Malpezzi, L.; Pedrocchi-Fantoni, G. Tetrahedron 1997, 53, 17769-17780.
31. Chou, S.; Tseng, C.; Chang, L. J Chinese Chem Soc 2001, 48, 229-234.
32. De Ferra, L.; Ullucci, E. US Patent Application 014953, 2005.
33. Mizuguchi, E.; Itanami, M.; Achiwa, K. Heterocycles 1997, 46, 149-152.
34. Wang, N.; Wu, Q.; Xiao, Y.; Chen, C.; Lin, X. Bioinorg Med Chem 2005, 13, 3667-3671.
35. Rizzarelli, E.; Vecchio, G.; Puglisi, A., La Mendola, D. European Patent Application EP 1860110 (2007).
36. Yano, H.; Hirayama, F.; Arima, H.; Uekama, K.; Yano, H. J Pharm Sci 2001, 90, 493-503.
37. Hirayama, F.; Arima, H.; Uekama, K.; Yano, H. J Pharm Sci 2001, 90, 2103-2112.
38. Hirayama, F.; Kamada, M.; Arima, H.; Uekama, K. J Control Rel 2002, 79, 103-112.
39. Bonomo, R. P.; Cucinotta, V.; D'Alessandro, F; Impellizzeri, G; Maccarrone, G; Rizzarelli, E.; Vecchio, G.; Carima, L.; Corradini, R.; Sartor, G.; Marchelli, R. Chirality 1997, 9, 341-349.
40. Campagna, T.; Marchelli, R.; Rizzarelli, E.; Vecchio, G. J. Supramol Chem 2001, 1, 117-124.
41. Cremer, D.; Pople, J. A. J Am Chem Soc 1975, 97, 1354-1358.
42. Betzel, C.; Saenger, W.; Hingerty, B. E.; Brown, G. M. J Am Chem Soc 1984, 106, 7545-7557.
43. Lindner, K.; Saenger, W. Carbohydr Res 1982, 99, 103-108.
44. Zabel, V.; Saenger, W.; Mason, S. A. J Am Chem Soc 1986, 108, 3663-3673.
45. Di Blasio, B.; Pavone, V.; Nastri, F.; Isernia, C.; Saviano, M.; Pedone, C.; Cucinotta, V.; Impellizzeri, G.; Rizzarelli, E.; Vecchio, G. Proc Natl Acad Sci USA 1992, 89, 7218-7221.
46. Di Blasio, B.; Galdiero, S.; Saviano, M.; De Simone, G.; Benedetti, E.; Pedone, C.; Gibbons, W. A.; Deschenaux, R.; Rizzarelli, E.; Vecchio, G. Supramol Chem 1996, 7, 47-54.
47. Harata, K.; Uekama, K.; Otagiri, M.; Hirayama, F.; Ohtani, Y. Bull Chem Soc Jpn 1985, 58, 1234-1238.
48. Burla, M. C.; Camalli, M.; Carrozzini, B.; Cascarano, G. L.; Giacovazzo, C.; Polidori, G.; Spagna, R. J Appl Crystallogr 2003, 36, 1103.
49. Sheldrick, G. M. SHELXL 97, Program for crystal structure refinement; University of Göttingen, 1997.
50. Cromer, D. T.; Waber, J. T. International Tables for X-Ray Crystallography, Vol.4; Kynoch: Birmingham, UK, 1974. Table II.2.B.