Interaction of naproxen with β-cyclodextrin and its derivatives/polymer: Experimental and molecular modeling studies

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 72, Issue 3-4, 2012, Pages 449-458

  Banik, Abhijit ^a   Gogoi, Paramartha ^b   Saikia, Monali Dutta ^a  

^a ARYA VIDYAPEETH COLLEGE   (India)

^b INDIAN INSTITUTE OF TECHNOLOGY GUWAHATI   (India)

Author keywords

Cyclodextrin; Formation constant; Inclusion complex; Naproxen; Stabilization energy

Indexed keywords

EID: 84862115682     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-011-0014-7     Document Type: Article

References (57)

1. Connors, K.A.: The stability of cyclodextrin complexes in solution. Chem. Rev. 97, 1325-1357 (1997) (Pubitemid 127659601)
2. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743-1753 (1998) (Pubitemid 128633435)
3. Inoue, Y., Hakushi, T., Liu, Y., Tong, L.H., Shen, B.J., Jin, D.S.: Thermodynamics of molecular recognition by cyclodextrins. 1. Calorimetric titration of inclusion complexation of naphthalenesulfonates with alpha-, beta-, and gamma-cyclodextrins: enthalpy-entropy compensation. J. Am. Chem. Soc. 115, 475-481 (1993)
4. Inoue, Y., Liu, Y., Tong, L.H., Shen, B.J., Jin, D.S.: Calorimetric titration of inclusion complexation with modified beta-cyclodextrins. Enthalpy-entropy compensation in host-guest complexation: from ionophore to cyclodextrin and cyclophane. J. Am. Chem. Soc. 115, 10637-10644 (1993)
5. Tavornvipas, S., Hirayama, F., Arima, H., Uekama, K., Ishiguro, T., Oka, M., Hamayasu, K., Hashimoto, H.: 6-O-a-(4-O-a-Dglucuronyl)-D-glucosyl-β- cyclodextrin:solubilizing ability and some cellular effects. Int. J. Pharm. 249, 199-209 (2002) (Pubitemid 35333446)
6. Padukka, I., Bhandari, B.D., Arcy, B.: Evaluation of various extraction methods of encapsulated oil from β-cyclodextrin-lemon oil complex powder. J. Food Compos. Anal. 13, 59-70 (2000)
7. Szente, L., Szejtli, J.: Cyclodextrins as food ingredients. Trends Food Sci. Technol. 15, 137-142 (2004) (Pubitemid 38300185)
8. Schneiderman, E., Stalcup, A.M.: Cyclodextrins: a versatile tool in separation science. J. Chromatogr. B 745, 83-102 (2000) (Pubitemid 30497221)
9. Perrin, C., Fabre, H., Maftouh, M., Massart, D.L., Heyden, Y.V.: Robustness testing of chiral separations by capillary electrophoresis using highly-sulfated cyclodextrins. J. Chromatogr. A 1007, 165-177 (2003) (Pubitemid 38352612)
10. Morillo, E., Pérez-Martínez, J.I., Ginés, J.M.: Leaching of 2,4-D from a soil in the presence of β-cyclodextrin: laboratory columns experiments. Chemosphere 44, 1065-1069 (2001) (Pubitemid 32728984)
11. Jozefaciuk, G., Muranyi, A., Fenyvesi, E.: Effect of randomly methylated β-cyclodextrin on physical properties of soils. Environ. Sci. Technol. 37, 3012-3017 (2003) (Pubitemid 36799096)
12. Szejtli, J.: Cyclodextrins and their inclusion complexes. Akademiai Kiado, Budapest (1982)
13. Pharr, D.Y., Fu, Z.F., Smith, T.K., Hinze, W.L.: Solubilization of cyclodextrins for analytical applications. Anal. Chem. 61, 275 (1989)
14. Nasongkla, N., Wiedmann, A.F., Bruening, A., Beman, M., Ray, D., Bornmann, W.G., Boothman, D.A., Gao, J.: Enhancement of solubility and bioavailability of beta-lapachone using cyclodextrin inclusion complexes. M. Pharm. Res. 20, 1626-1633 (2003) (Pubitemid 37268279)
15. Uzqueda, M., Martín, C., Zornoza, A., Sánchez, M., Martínez-Ohárriz, M.C., Vélaz, I.: Characterization of complexes between naftifine and cyclodextrin in solution and in the solid state. Pharm. Res. 23, 980-988 (2006) (Pubitemid 43781406)
16. Szente, L., Szejtli, J.: Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development. Adv. Drug Deliv. Rev. 36, 17-28 (1999) (Pubitemid 29074474)
17. Wenz, G.: Cyclodextrins as synthons for supramolecular structures and functional units. Angew. Chem. Int. Ed. Engl. 33, 803-822 (1994) (Pubitemid 24986848)
18. Liu, Y., You, C.-C.: Molecular recognition studies on modified cyclodextrins. Chin. J. Chem. 19, 533-544 (2001)
19. Lipkowitz, K.B.: Applications of computational chemistry to the study of cyclodextrins. Chem. Rev. 98, 1829-1874 (1998)
20. Bonnet, P., Jaime, C., Morin-Allory, L.: Alpha-, beta-, and gamma-Cyclodextrin dimmers: molecular modelling studies by molecular mechanics and molecular dynamics simulations. J. Org. Chem. 66, 689-692 (2001) (Pubitemid 32163061)
21. Oana, M., Tintaru, A., Gavriliu, D., Maior, O., Hillebrand, M.: Spectral study and molecular modeling of inclusion complexes of β-cyclodextrin with some phenoxathiine derivatives. J. Phys. Chem. B 106, 257-263 (2002) (Pubitemid 35281714)
22. Varady, J., Wu, X., Wang, S.: Competitive and reversible binding of a guest molecule to its host in aqueous solution through molecular dynamics simulation. J. Phys. Chem. B 106, 4863-4872 (2002) (Pubitemid 35281999)
23. Liu, L., Guo, Q.-X.: Use of quantum chemical methods to study cyclodextrin chemistry. J. Incl. Phenom. Macrocycl. Chem. 50, 95-103 (2004) (Pubitemid 40137324)
24. Junco, S., Teresa, C., Nuno, R., Da Manuel, P., Helena, C.M.: A Comparative study of naproxen-beta cyclodextrin complexes prepared by conventional methods and using supercritical carbon dioxide. J. Incl. Phenom. Macrocycl. Chem. 44, 117-121 (2002) (Pubitemid 38075675)
25. Bettinetti, G., Gazzaniga, A., Mura, P., Giordano, F., Setti, M.: Thermal behaviour and dissolution properties of naproxen in combinations with chemically modified β-cyclodextrins. Drug Dev. Ind. Pharm. 18, 39-53 (1992)
26. Frijlink, H.W., Eissens, A.C., Schoonen, A.J.M., Lerk, C.F.: The effects of cyclodextrins on drug absorption II. In vivo observations. Int. J. Pharm. 64, 195-205 (1990)
27. Otero-Espinar, F.J., Anguiano-Igea, S., Garcia-Gonzalez, N., Vila-Jato, J.L., Blanco-Mendez, J.: Interaction of naproxen with β-cyclodextrin in solution and in the solid state. Int. J. Pharm. 79, 149-157 (1992)
28. Sosnowska-Sadlej, N., Kozerski, L., Bednarek, E., Sitkowski, J.: Fluorometric and NMR studies of the naproxen-cyclodextrin inclusion complexes in aqueous solutions. J. Incl. Phenom. Macrocycl. Chem. 37, 383-394 (2000)
29. Ganza-Gonzalez, A., Vila-Jato, J.L., Anguiano-Igea, S., Otero-Espinar, F.J., Blanco-Mendez, J.: A proton nuclear magnetic resonance study of the inclusion complex of naproxen with bcyclodextrin. Int. J. Pharm. 106, 179-185 (1994) (Pubitemid 24133694)
30. Valsami, G.N., Macheras, P.E., Koupparis, M.A.: Binding studies of ions with cyclodextrins using ion-selective electrodes. J. Pharm. Sci. 79(12), 1087-1094 (1990)
31. Saikia, M.D.: Studies on adsorption of amino acids on β-cyclodextrin bonded to silica particles. Colloids Surf. A 329, 177-183 (2008)
32. Feng, Y.Q., Xie, M.J., Da, S.L.: Preparation and characterization of an L-tyrosine-derivatized β-cyclodextrin-bonded silica stationary phase for liquid chromatography. Anal. Chim. Acta 403, 187-195 (2000)
33. Hu, Y., Zheng, Y., Li, G.: Solid phase microextraction of phenol compounds using a fused-silica fiber coated with β-cyclodextrin bonded silica particles. Anal. Sci. 20, 667-671 (2004)
34. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E. Robb, M.A., Cheeseman, J.R., Scalmani, G., Barons, V., Mennucci, B., Peterson, G.A., Nakatsuji, H., Carcicato, M., Li, Y., Hratchian, H.P., Izmaylov, A., Bloino, J., Zheng, G., Sonnenberg, J.L, Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery, J.A., Peratta, Jr.J.E, Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, N., Staroveroy, V.N., Keith, T., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millan, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jarmillo, J., Gomperts, R., Stratmann, R.E., Yazev, O., Austin, A.J., Cammi, R., Pommeli, C., Ochierski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Ciolowski, J., Fox D.J.: Gaussian 09, Revision B.01. Gaussian, Inc., Wallingford CT (2010)
35. Piel, G., Dive, G., Evrard, B., Van Hees, T., Hassonville de, S.H., Delattre, L.: Molecular modelling study of beta-and gammacyclodextrin complexes with miconazole. Eur. J. Pharm. Sci. 13, 271-279 (2001) (Pubitemid 32522579)
36. Moore, D.E., Chappuis, P.P.: A comparative study of the photochemistry of the non-steroidal anti-inflammatory drugs naproxen, benoxaprofen and indomethacin. Photochem. Photobiol. 65, 828-832 (1988)
37. Sobczuk, D., Craig, R., Nogueroles, M., Radisi, S., Shen, B., Simon, S.: The study of the interactions between naproxen and n-acetyl-L-tyrosine ethyl ester. Zesz. Nauk. Chemica Spozywcza I Biotechnologia. Z 70, 23-35 (2006)
38. Singh, R., Bharti, N., Madan, J., Hiremath, S.N.: Characterization of cyclodextrin inclusion complexes-a review. J. Pharm. Sci. Tech. 2(3), 171-183 (2010)
39. Wernersson, E., Heyda, J., Kubickova, A., Coufal, P., Jungwirth, P.: Effect of association with sulfate on the electrophoretic mobility of polyarginine and polylysine. J. Phys. Chem. B 114(36), 11934-11941 (2010)
40. Kano, K., Hasegawa, H.: Chiral recognition of helical metal complexes by modified cyclodextrins. J. Am. Chem. Soc. 123, 10616-10627 (2001) (Pubitemid 33015707)
41. Benesi, H.A., Hildebrand, J.H.: Spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J. Am. Chem. Soc. 71, 2703-2707 (1949)
42. Song, L.X., Wang, H.M., Xu, P., Zhang, Z.Q., Liu, Q.Q.: Formation, structure, and stability of α-and β-cyclodextrin Inclusion complexes of phenol and benzoic acid derivatives in vacuo and in water. Bull. Chem. Soc. Jpn. 80, 2313-2322 (2007)
43. 1H NMR titration and quantum calculation for the inclusion complexes of styrene and a α-methyl styrene with a, b and γ-cyclodextrins. J. Mol. Struct. 660, 73-80 (2003)
44. St. Pierre, L.A., Sentell, K.B.: Cyclodextrins as enantioselective mobile-phase modifiers for chiral capillary electrophoresis. Effects of pH and cyclodextrin concentration. J. Chromatogr. B Biomed. Appl. 657(2), 291-300 (1994) (Pubitemid 24253449)
45. Chao, J., Li, J., Meng, D., Huang, S.: Preparation and study on the solid inclusion inclusion complex of sparfloxacin with HP-bcyclodextrin. Spectrochim Acta Part A 59, 705-711 (2003)
46. Blanco, J., Vila-Jato, J.L., Otero, F., Anguiano, S.: Influence of method of preparation on inclusion complexes of naproxen with different cyclodextrins. Drug Dev. Ind. Pharm. 17, 943-957 (1991)
47. Bettinetti, G.P., Mura, P., Liguori, A., Bramanti, G., Giordano, F.: Solubilization and interaction of naproxen with cyclodextrins in aqueous solution and in the solid state. IL Farmaco 44, 195-213 (1989) (Pubitemid 19121872)
48. Lin, S.Y., Kao, Y.H.: Solid particulates of drug-β-cyclodextrin inclusion complexes directly prepared by a spray-drying technique. Int. J. Pharm. 56(3), 249-259 (1989)
49. Schneider, H.J., Hacket, F., Rudigger, V.: NMR studies of cyclodextrins and cyclodextrin complexes. Chem. Rev. 98, 1755-1785 (1998) (Pubitemid 128633436)
50. Caterina, M.F., Rui, A.C., Saul, Pereira, D.C., Francisco, J.B.: Multimodal molecular encapsulation of nicardipine hydrochloride by * * *β-cyclodextrin, hydroxypropyl-β-cyclodextrin and triacetyl-β-cyclodextrin in solution. Structural studies by 1H NMR and ROSEY experiments. Eur. J. Pharm. Sci. 18, 285-296 (2003)
51. Ho, Y.S., McKay, G.: Pseudo-second order model for sorption processes. Process Biochem. 34(5), 451-465 (1999) (Pubitemid 29347292)
52. Ho, Y.S.: Review of second-order models for adsorption systems. J. Hazard. Mater. B 136(3), 681-689 (2006)
53. Mestre, A.S., Pires, J., Nogueira, J.M.F., Carvalho, A.P.: Activated carbons for the adsorption of ibuprofen. Carbon 45(10), 1979-1988 (2007) (Pubitemid 47238067)
54. Onal, Y., Akmil-Başar, C., Sarici-Ozdemir, C.: Elucidation of the naproxen sodium adsorption onto activated carbon prepared from waste apricot: kinetic, equilibrium and thermodynamic characterization. J. Hazard. Mater. 148(3), 727-734 (2007) (Pubitemid 47320935)
55. Rubin, A.J., Mercer, D.L.: Adsorption of Inorganics at Solidliquid Interfaces. Ann Arbor Science, Ann Arbor, MI. Chapter 8 (1981)
56. Romo, A., Penas, F.J., Isasi, J.R.: Sorption of dibenzofuran derivatives from aqueous solutions by β-cyclodextrin polymers: an isosteric heat approach. J. Colloid Interface Sci. 279, 55-60 (2004) (Pubitemid 39221839)
57. Chen, W., Chang, C.-E., Gilson, M.K.: Calculation of cyclodextrin binding affinities: energy, entropy, and implication for drug design. Biophys. J. 87, 3035-3049 (2004) (Pubitemid 40468563)