Comparison of the complexation between methylprednisolone and different cyclodextrins in solution by1H-NMR and molecular modeling studies

Journal of Pharmaceutical Sciences

Volumn 99, Issue 9, 2010, Pages 3863-3873

  Thi, Thao Do ^a   Nauwelaerts, Koen ^b   Froeyen, Matheus ^b   Baudemprez, Luc ^b   Van Speybroeck, Michiel ^a   Augustijns, Patrick ^a   Annaert, Pieter ^a   Martens, Johan ^c   Van Humbeeck, Jan ^c   Van Den Mooter, Guy ^a  

^a DEPARTMENT OF PHARMACEUTICAL AND PHARMACOLOGICAL SCIENCES   (Belgium)

^b REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

^c UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

Cyclodextrins; Inclusion complexes; Methylprednisolone; Molecular modeling; ROESY

Indexed keywords

2 HYDROXYPROPYL B CYCLODEXTRIN; 2 HYDROXYPROPYL GAMMA CYCLODEXTRIN; CYCLODEXTRIN; GAMMA CYCLODEXTRIN; METHYLPREDNISOLONE; PROTON; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; HYDROPHOBICITY; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE;

EID: 77956385166     PISSN: 00223549     EISSN: 15206017     Source Type: Journal    
DOI: 10.1002/jps.22227     Document Type: Article

References (45)

1. Brewster M, Loftsson T. 2007. Cyclodextrins as pharmaceutical solubilizers. Adv Drug Deliv Rev 59:645-666.
2. Szejtli J. 1998. Introduction and general overview of cyclodextrin chemistry. Chem Rev 98:1743-1753.
3. Uekema K, Hirayama F, Irie T. 1998. Cyclodextrin drug carrier system. Chem Rev 98:2045-2076.
4. Loftsson T, Duchêne D. 2007. Cyclodextrins and their pharmaceutical applications. Int J Pharm 329:1-11.
5. Szejtli J. 1994. Cyclodextrin inclusion complexes. In: Frömming K, Szejtli J, editors. Cyclodextrins in pharmacy. Dordrecht: Kluwer. pp. 45-82.
6. Djedäine F, Lin SZ, Perly B, Wouessidjewe D. 1990. High-field nuclear magnetic resonance techniques for the investigation of a β-cyclodextrin:indomethacin inclusion complex. J Pharm Sci 79:643-646.
7. Salvatierra D, Jaime C, Virgili A, Sánchez-Ferrando F. 1996. Determination of the inclusion geometry for the β-cyclodextrin / benzoic acid complex by NMR and molecular modeling. J Org Chem 61:9578-9581. (Pubitemid 127562827)
8. Redenti E, Fronza G, Spisni A. 1992. Nuclear Overhauser effect, a powerful tool for the investigation of the geometry in solution of different inclusion complexes with β-cyclodextrin. Proceedings of the 6th International Symposium on Cyclodextrins. Editions de Santé, pp 220-225.
9. Schneider H, Hacket F, Rüdiger V. 1998. NMR studies of cyclodextrins and cyclodextrin complexes. Chem Rev 98:1755-1785.
10. Djedäine F, Perly B. 1991. Nuclear magnetic resonance of cyclodextrins, derivatives and inclusion compounds. In: Duchêne D, editor. New trends in cyclodextrins and derivatives. Paris: Editions de Santé. pp. 215-246.
11. Neuhaus P, Williamso MP. 2000. The nuclear Overhauser effect in structural and conformational analysis, 2nd edition. USA: J. Wiley and Sons. pp. 282-293.
12. Chankvetadze B, Burjanadze N, Breitkreutz J, Bergander K, Bergenthal D, Kataeva O, Frohlich R, Luftmann H, Blaschke G. 2002. Mechanistic study on the opposite migration order of the enantiomers of ketamine with alpha- and beta-cyclodextrin in capillary electrophoresis. J Sep Sci 25:1155-1166.
13. Chankvetadze B, Lomsadze K, Bergenthal D, Breitkreutz J, Bergander K, Blaschke G. 2001. Mechanistic study on the opposite migration order of clenbuterol enantiomers in capillary electrophoresis with beta-cyclodextrin and single-isomer heptakis(2,3-diacetyl-6-sulfo)-beta- cyclodextrin. Electrophoresis 22:3178-3184.
14. Waibel B, Scheiber J, Meier C, Hammitzsch M, Baumann K, Scriba GKE, Holzgrabe U. 2007. Comparison of cyclodextrindipeptide inclusion complexes in the absence and presence of urea by means of capillary electrophoresis, nuclear magnetic resonance and molecular modeling. Eur J Org Chem 18:2921-2930.
15. Kahle C, Deubner R, Schollmayer C, Scheiber J, Baumann K, Holzgrabe U. 2005. NMR spectroscopic and molecular modelling studies on cyclodextrin- dipeptide inclusion complexes. Eur J Org Chem 15:1578-1589. (Pubitemid 40622378)
16. Albert E, Muller BW. 1992. Complexation of steroid-hormones with cyclodextrin derivatives - Substutient effects of the guest molecule on solubility and stability in aqueous solution. J Pharm Sci 81:756-761.
17. Filipa M, Sanchos MI, Gasull E. 2008. Encapsulation of methyl and ethyl salicylates by b-cyclodextrin: HOLC, UV-Vis and molecular modeling studies. J Pharm Biol Anal 48:969-973.
18. Higuchi T, Connors KA. 1965. Phase solubility technique. Adv Anal Chem Inst 4:212-217.
19. Keller R. 2004. The computer aided resonance assignment tutorial. 1st edition. PL Goldau, Switzerland: PN CANTINA Verlag. ISBN 3-85600-112-3.
20. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE. 2000. The Protein Data Bank. Nucl Acid Res 28:235-242.
21. Uitdehaag JC, Kalk KH, van Der Veen BA, Dijkhuizen L, Dijkstra BW. 1999. The cyclization mechanism of cyclodextrin glycosyltransferase (CGTase) as revealed by a gamma-cyclodextrin-CGTase complex at 1. 8-A resolution J Biol Chem 274:34868-34876.
22. Schuettelkopf AW, van Aalten DMF. 2004. PRODRG - A tool for high-throughput crystallography of protein-ligand complexes. Acta Crystallogr D60:1355-1363.
23. Schmidt M, Baldridge K, Boatz J, Elbert S, Gordon M, Jensen J, Koseki S, Matsunaga N, Nguyen K, Su S, Windus T, Dupuis M, Montgomery J. 1993. General atomic and molecular electronic structure system. J Comput Chem 14:1347-1363.
24. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ. 1998. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 19:1639-1662.
25. Case DA, Cheatham TE III, Darden T, Gohlke H, Luo R, Merz KM, Jr., Onufriev A, Simmerling C, Wang B, Woods R. 2005. The Amber biomolecular simulation programs. J Comput Chem 26:1668-1688.
26. Wang J, Wolf RM, Caldwell JW, Kollman PA, Case DA. 2004. Development and testing of a general amber force field. J Comput Chem 25:1157-1174.
27. Jakalian A, Bush BL, Jack DB, Bayly CI. 2000. Fast, efficient generation of high-quality atomic charges. AM1-BCC model: I. Method. J Comput Chem 21:132.
28. Kirschner KN, Yongye AB, Tschampel SM, González-Outeiriño J, Daniels CR, Foley BL, Woods RJ. 2008. GLYCAM06: A generalizable biomolecular force field. Carbohydrates. J Comput Chem 29:622-655. (Pubitemid 351238844)
29. Loftsson T, Brewster M. 1996. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci 85:1017-1025.
30. Yoshida A, Yamamoto M, Irie T, Uekama K. 1989. Some pharmaceutical properties of 3-hydroxypropyl- and 2,3-hydroxypropyl-β-cyclodextrins and their solubilizing and stabilizing abilities. Chem Pharm Bull 37:1059-1063. (Pubitemid 19144147)
31. Ribeiro L, Veiga F. 2002. Complexation of vinpocetine with cyclodextrins in the presence or absence of polymers: Binary and ternary complexes preparation and characterization. J Incl Phenom Macrocycl Chem 44:251-256.
32. 1H NMR and ROESY experiments. Eur J Pharm Sci 18:285-296.
33. Ganza-Gonzalez A, Vila-Jato JL, Anguiano-Igea S, Otero-Espinar FJ, Blanco-Méndez J. 1994. A proton nuclear magnetic resonance study of the inclusion complex of naproxen with b-cyclodextrin. Int J Pharm 106:179-185.
34. Amato ME, Lipkowitz KB, Lombardo GM, Pappalardo GC. 1998. High-field NMR spectroscopic techniques combined with molecular dynamics simulations for the study of the inclusion complexes of α- and β-cyclodextrins with the cognition activator 3-phenoxypyridine sulphate (CI-844). Magn Reson Chem 36:693-705.
35. 2O. In: Duchêne D, editors. Proceedings of the 5th International Symposium on Cyclodextrins. Editions de Santé. pp. 146-149.
36. Másson M, Loftsson T, Jónsdóttir S, Fridriksdóttir H, Peterson DS. 1998. Stabilisation of ionic drugs through complexation with non-ionic and ionic cyclodextrins. Int J Pharm 164:45-55. (Pubitemid 28160097)
37. Larsen KL, Acchmann FL, Wimmer R, Stella VJ, Kjølner UM. 2005. Phase dolubility and structure of the inclusion complexes of prednisolone and 6á-methylprednisolone with various cyclodextrin. J Pharm Sci 94:507-515.
38. Chankvetadze B, Lomsadze K, Burjanadze N, Breitkeutz J, Pinto G, Chesse M, Berganthal K, Blaschke G. 2003. Comparative enantioseparations with native beta-cyclodextrin, randomly acetylated beta-cyclodextrin and heptakis-(2,3-di-O-acetyl)-beta-cyclodextrin in capillary electrophoresis. Electrophoresis 24:1083-1091.
39. Chankvetadze B, Fillet M, Burjanadze N, Bergenthal D, Bergander C, Luftmann H, Crommen J, Blaschke G. 2000. Enantioseparation of aminoglutethimide with cyclodextrins in capillary electrophoresis and studies of selector-selectand interactions using NMR spectroscopy and electrospray ionization mass spectrometry. Enantiomer 5:313-322.
40. Kahle C, Deubner R, Schollmayer C, Scheiber J, Baumann K, Holzgrabe U. 2005. NMR spectroscopic and molecular modelling studies on cyclodextrin- dipeptide inclusion complexes. Eur J Org Chem 1578-1589. (Pubitemid 40622378)
41. Waibel B, Scheiber J, Meier C, Hammitzsch M, Baumann K, Scriba GKE, Holzgrabe U. 2007. Comparison of cyclodextrindipeptide inclusion complexes in the absence and presence of urea by means of capillary electrophoresis, nuclear magnetic resonance and molecular modeling. Eur J Org Chem 2921-2930.
42. Jorgensen WL. 1982. Revised TIPS for simulations of liquid water and aqueous solutions. J Chem Phys 77:4156-4163.
43. Jorgensen WL, Chandrasekhar J, Madura JD, Impey RW, Klein ML. 1983. Comparison of simple potential functions for simulating liquid water. J Chem Phys 79:926-935.
44. Darden T, York D, Pedersen L. 1993. Particle mesh Ewald: An NLog(N) method for Ewald sums in large systems. J Chem Phys 98:10089-10092.
45. Miyamoto S, Kollman PA. 1992. SETTLE: An analytical version of the SHAKE and RATTLE algorithm for rigid water models. J Comput Chem 13:952-962.