Spectrofluorometric, thermal, and molecular mechanics studies of the inclusion complexation of selected imidazoline-derived drugs with β-cyclodextrin in aqueous media

Journal of Inclusion Phenomena and Macrocyclic Chemistry

Volumn 60, Issue 3-4, 2008, Pages 293-301

  Dawoud, Abdulilah A ^a,b   Al Rawashdeh, Nathir ^c  

^a TAIBAH UNIVERSITY   (Saudi Arabia)

^b VIRGINIA BIOINFORMATICS INSTITUTE   (United States)

^c JORDAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Jordan)

Author keywords

B cyclodextrin; Differential scanning calorimetry; Fluorescence; Imidazoline derived drugs; Inclusion complex; Molecular mechanics

Indexed keywords

EID: 41549105002     PISSN: 09230750     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10847-007-9377-1     Document Type: Article

References (52)

1. Szejtli, J.: Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98, 1743 (1998)
2. Dodziuk, H. (ed.): Cyclodextrins, their complexes: chemistry, analytical methods, applications. Wiley-VCH, Weinheim (2006)
3. Kuwabara, T., Shiba, K., Nakajima, H., Ozawa, M., Miyajima, N., Hosoda, M., Kuramoto, N., Suzuki, Y.: Host-guest complexation affected by pH and length of spacer for hydroxyazobenzene-modified cyclodextrins. J. Phys. Chem. A 110, 13521 (2006)
4. Liu, Y., Han, B., Zhang, H.: Spectroscopic studies on molecular recognition of modified cyclodextrins. Curr. Org. Chem. 81, 35 (2004)
5. Galia, A., Navarre, E.C., Scialdone, O., Ferreira, M., Filardo, G., Tilloy, S., Monflier, E.: Complexation of phosphine ligands with peracetylated β-cyclodextrin in supercritical carbon dioxide: spectroscopic determination of equilibrium constants. J. Phys. Chem. B 111, 2573 (2007)
6. Cravotto, G., Binello, A., Baranelli, E., Carraro, P., Trotta, F.: Cyclodextrins as food additives and in food processing. Curr. Nutr. Food Sci. 2, 343 (2006)
7. Loftsson, T., Brewster, M.E., Masson, M.: Role of cyclodextrins in improving oral drug delivery. Am. J. Drug Deliv. 2, 261 (2004)
8. Loftsson, T., Duchêne, D.: Cyclodextrins and their pharmaceutical applications. Int. J. Pharm. 329, 1 (2007)
9. Kirschner, D.L., Jaramillo, M., Green, T.K.: Enantio separation and stacking of cyanobenz[f]isoindole-amino acids by reverse polarity capillary electrophoresis and sulfated β-cyclodextrin. Anal. Chem. 79, 736 (2007)
10. Yang, G.S., Chen, D.M., Yang, Y., Tang, B., Gao, J.J., Aboul-Enein, H.Y., Koppenhoefer, B.: Enantioseparation of some clinically used drugs by capillary electrophoresis using sulfated β-cyclodextrin as a chiral selector. Chromatographia 62, 441 (2005)
11. Henley, W.H., Wilburn, R.T., Crouch, A.M., Jorgenson, J.W.: Flow counterbalanced capillary electrophoresis using packed capillary columns: Resolution of enantiomers and isotopomers. Anal. Chem. 77, 7024 (2005)
12. Wistuba, D., Kang, J., Schurig, V.: Chiral separation by capillary electrochromatography using cyclodextrin phases. Meth. Mol. Biol. 243, 401 (2004)
13. Pino, V., Lantz, A.W., Anderson, J.L., Berthod, A., Armstrong, D.W.: Theory and use of the pseudophase model in gas-liquid chromatographic enantiomeric separations. Anal. Chem. 78, 113 (2006)
14. Zhong, Q., He, L., Beesley, T.E., Trahanovsky, W.S., Sun, P., Wang, C., Armstrong, D.W.: Development of dinitrophenylated cyclodextrin derivatives for enhanced enantiomeric separations by high-performance liquid chromatography. J. Chromatogr. A 1115, 19 (2006)
15. Singh, M., Sharma, R., Banerjee, U.C.: Biotechnological applications of cyclodextrins. Biotech. Adv. 20, 341 (2002)
16. Qi, Q., Zimmermann, W.: Cyclodextrin glucanotransferase: from gene to applications. Appl. Microbiol. Biotechnol. 66, 475 (2005)
17. Kim, C.K., Park, J.S.: Solubility enhancers for oral drug delivery: can chemical structure manipulation be avoided? Am. J. Drug Deliv. 2, 113 (2004)
18. Figueiras, A., Sarraguca, J.M.G., Carvalho, R.A., Pais, A.A.C.C., Veiga, F.J.B.: Interaction of omeprazole with a methylated derivative of β-cyclodextrin: phase solubility, NMR spectroscopy and molecular simulation. Pharmaceut. Res. 24, 377 (2007)
19. Cirri, M., Maestrelli, F., Corti, G., Furlanetto, S., Mura, P.: Simultaneous effect of cyclodextrin complexation, pH, and hydrophilic polymers on naproxen solubilization. J. Pharm. Biomed. Anal. 42, 126 (2006)
20. Bortolus, P., Marconi, G., Monti, S., Mayer, B.: Chiral discrimination of camphorquinone enantiomers by cyclodextrins: a spectroscopic and Photophysical Study. J. Phys. Chem. A 106, 1686 (2002)
21. Krois, D., Brinker, U.H.: Induced circular dichroism and UV-Vis absorption spectroscopy of cyclodextrin inclusion complexes: structural elucidation of supramolecular Azi-adamantane (Spiro[adamantane-2,3'-diazirine]). J. Am. Chem. Soc. 120, 11627 (1998)
22. de Marino, A., Rubio, L., Mendicuti, F.: Fluorescence and molecular mechanics of 1-methyl naphthalenecarboxylate/cyclodextrin complexes in aqueous medium. J. Incl. Phenom. Macrocyclic Chem. 58, 103 (2007)
23. Pastor, I., Di Marino, A., Mendicuti, F.: Thermodynamics and molecular mechanics studies on a- and b-cyclodextrins complexation and diethyl 2,6-naphthalenedicarboxylate guest in aqueous medium. J. Phys. Chem. B 106, 1995 (2002)
24. Tommasini, S., Calabrò, M.L., Stancanelli, R., Donato, P., Costa, C., Catania, S., Villari, V., Ficarra, P., Ficarra, R.: The inclusion complexes of hesperetin and its 7-rhamnoglucoside with (2-hydroxypropyl)-β- cyclodextrin. J. Pharm. Biomed. Anal. 39, 572 (2005)
25. Guzzo, M.R., Uemi, M., Donate, P.M., Nikolaou, S., Machado, A.E.H., Okano, L.T.: Study of the complexation of fisetin with cyclodextrins. J. Phys. Chem. A 110, 10545 (2006)
26. Zhang, H., Chen, G., Wang, L., Ding, L., Tian, Y., Jin, W., Zhang, H.: Study on the inclusion complexes of cyclodextrin and sulphonated azo dyes by electrospray ionization mass spectrometry. Int. J. Mass Spectrom. 252, 1 (2006)
27. Bollo, S., Yáñez, C., Sturm, N., Squella, J.A.: Cyclic Voltammetric and Scanning Electrochemical Microscopic Study of thiolated β-cyclodextrin adsorbed on a gold electrode. Langmuir 19, 3365 (2003)
28. Choi, S., Choi, B., Park, S.: Electrochemical sensor for electrochemically inactive β-D(+)-Glucose Using α-cyclodextrin template molecules. Anal. Chem. 74, 1998 (2002)
29. Jullian, C., Miranda, S., Zapata-Torres, G., Mendizabal, F., Olea-Azar, C.: Studies of inclusion complexes of natural and modified cyclodextrin with (+)catechin by NMR and molecular modeling. Bioorg. Med. Chem. 15, 3217 (2007)
30. Jiang, H., Sun, H., Zhang, S., Hua, R., Xu, Y., Jin, S., Gong, H., Li, L.: NMR investigations of inclusion complexes between β-cyclodextrin and naphthalene/anthraquinone derivatives. J. Incl. Phenom. Macrocyclic Chem. 58, 133 (2007)
31. Xu, J., Tan, T., Janson, J.C., Kenne, L., Sandstroem, C.: NMR Studies on the interaction between (-)-epigallocatechin gallate and cyclodextrins, free and bonded to silica gels. Carbohydr. Res. 342, 843 (2007)
32. Marques, H.M.C., Hadgraft, J., Kellaway, I.W.: Studies of cyclodextrin inclusion complexes. I. The salbutamol-cyclodextrin complex as studied by phase solubility and DSC. Int. J. Pharm. 63, 259 (1990)
33. Yang, G.-F., Wang, H.-B., Yang, W.-C., Gao, D., Zhan, C.-G.: Bioactive permethrin/β-cyclodextrin inclusion complex. J. Phys. Chem. B 110, 7044 (2006)
34. Giordano, F., Novak, C., Moyano, J.R.: Thermal analysis of cyclodextrins and their inclusion compounds. Thermochim. Acta 380, 123 (2001)
35. Crupi, V., Ficarra, R., Guardo, M., Majolino, D., Stancanelli, R., Venuti, V.: UV-vis and FTIR-ATR spectroscopic techniques to study the inclusion complexes of genistein with β-cyclodextrins. J. Pharm. Biomed. Anal. 44, 110 (2007)
36. Vandelli, M.A., Ruozi, B., Forni, F., Mucci, A., Salvioli, G., Galli, E.: A solution and solid state study on 2-hydroxypropyl-β-cyclodextrin complexation with hyodeoxycholic acid. J. Incl. Phenom. Macrocyclic Chem. 37, 237 (2000)
37. Lipkowit, K.B.: Applications of computational chemistry to the Study of Cyclodextrins. Chem. Rev. 98, 1829 (1998)
38. Castro, E.A., Barbiric, D.A.: Molecular modeling and cyclodextrins: a relationship strengthened by complexes. J. Curr. Org. Chem. 10, 715 (2006)
39. Thompson, D., Larsson, J.A.: Modeling competitive guest binding to β-cyclodextrin molecular print-boards. J. Phys. Chem. B 110, 16640 (2006)
40. Petrusewicz, J., Kaliszan, R.: Human blood platelet alpha adrenoceptor in view of the effects of various imidazol(in)e drugs on aggregation. Gen. Pharm. 22, 819 (1991)
41. Kaliszan, W., Petrusewicz, J., Kaliszan, R.: Imidazoline receptors in relaxation of acetylcholine-constricted isolated rat jejunum. Pharm. Rep. 58, 700 (2006)
42. Parini, A., Moudanos, C.G., Pizzinat, N., Lanier, S.M.: The elusive family of imidazoline binding sites. Trends Pharmacol. Sci. 17, 13 (1996)
43. Souri, E., Amanlou, M., Farsam, H., Afshari, A.: A rapid derivative spectrophotometric method for simultaneous determination of naphazoline and antazoline in eye drops. Chem. Pharm. Bull. 54, 119 (2006)
44. Ghoreishi, S.M., Behpour, M., Nabi, M.: A novel naphazoline -selective membrane sensor and its pharmaceutical applications. Sens. Actuators B 113, 963 (2006)
45. Casado-Terrones, S., Fernandez-Sanchez, J.F., Diaz, B., Carretero, A.C., Fernandez-Gutierrez, A.: A fluorescence optosensor for analyzing naphazoline in pharmaceutical preparations. J. Pharm. Biomed. Anal. 38, 785 (2005)
46. Milojevic, Z., Agbaba, D., Eric, S., Boberic-Borojevic, D., Ristic, P., Solujic, M.: High-performance liquid chromatographic method for the assay of dexamethasone and xylometazoline in nasal drops containing methyl p-hydroxybenzoate. J. Chromatogr. A 949, 79 (2002)
47. Marchesini, A.F., Williner, M.R., Mantovani, V.E., Robles, J.C., Goicoechea, H.C.: Simultaneous determination of naphazoline, diphenhydramine, and phenylephrine in nasal solutions by capillary electrophoresis. J. Pharm. Biomed. Anal. 31, 39 (2003)
48. Harata, K.: The structure of the cyclodextrin complexes. XIII. Crystal structure of β-cyclodextrin-1,4- diazabicyclo[1.2.2] octane complex tridecahydrate. Bull. Chem. Soc. Japan 55, 2315 (1982)
49. Liu, L., Guo, Q.-X.: The driving forces in the inclusion complexation of cyclodextrins. J. Incl. Phenom. 42, 1 (2002)
50. Valero, M., Costa, S.M.B., Ascenso, J.R., Velazquez, M., RodrIguez, L.J.: Complexation of the non-steroidal anti-inflamCatory drug nabumetone with modified and unmodified cyclodextrins. J. Incl. Phenom. 35, 663 (1999)
51. Faucci, M.T., Melani, F., Mura, P.: Computer-aided molecular modeling techniques for predicting the stability of drug-cyclodextrin inclusion complexes in aqueous solutions. Chem. Phys. Lett. 358, 383 (2002)
52. Madrid, J.M., Mendicuti, F., Mattice, W.L.: Cyclic Voltammetric and Scanning Electrochemical Microscopic Study of thiolated β-cyclodextrin adsorbed on a gold electrode. J. Phys. Chem. B 102, 2037 (1998)