Conventional study on Novel Dicationic Ionic Liquid Inclusion with β-Cyclodextrin

International Journal of Molecular Sciences

Volumn 12, Issue 9, 2011, Pages 6329-6345

  Mohamad, Sharifah ^a   Surikumaran, Hemavathy ^a   Raoov, Muggundha ^a,b   Marimuthu, Tilagam ^a   Chandrasekaram, Kumuthini ^a   Subramaniam, Puvaneswary ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

^b ADVANCED MEDICAL AND DENTAL INSTITUTE   (Malaysia)

Author keywords

Cyclodextrin; Dicationic ionic liquid; Inclusion complex

Indexed keywords

3,3' (1,4 PHENYLENEBIS[METHYLENE])BIS(1 METHYL 1H IMIDAZOL 3 IUM)DIBROMIDE; BETA CYCLODEXTRIN; BROMINE DERIVATIVE; UNCLASSIFIED DRUG; BETA CYCLODEXTRIN DERIVATIVE; DIVALENT CATION; IONIC LIQUID; MACROMOLECULE;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; HYDROPHOBICITY; INFRARED SPECTROSCOPY; LIGHT ABSORPTION; MOLECULAR INTERACTION; PHOTON CORRELATION SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; ROOM TEMPERATURE; SCANNING ELECTRON MICROSCOPY; STOICHIOMETRY; STRUCTURE ANALYSIS; TEMPERATURE MEASUREMENT; THERMOGRAVIMETRY; THERMOSTABILITY; X RAY DIFFRACTION; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; MACROMOLECULE; PROCEDURES; SPECTROPHOTOMETRY; SYNTHESIS;

BETA-CYCLODEXTRINS; CALORIMETRY, DIFFERENTIAL SCANNING; CATIONS, DIVALENT; CHEMISTRY TECHNIQUES, SYNTHETIC; IONIC LIQUIDS; KINETICS; MACROMOLECULAR SUBSTANCES; MICROSCOPY, ELECTRON, SCANNING; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PROTON MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; THERMOGRAVIMETRY; X-RAY DIFFRACTION;

EID: 80053211450     PISSN: None     EISSN: 14220067     Source Type: Journal    
DOI: 10.3390/ijms12096329     Document Type: Article

References (40)

1. Szejtli, J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 1998, 98, 1743-1753
2. Ashnagar, A.; Naseri, N.G.; Khanaki, B. Study of the β-cyclodextrin imipramine hydrochloride inclusion complex and determination of its stability constant (K) by UV-Visible spectroscopy. E-J. Chem. 2007, 4, 550-558
3. Letellier, S.; Maupas, B.; Gramond, J.P.; Guyon, F.; Gareil, P. Determination of the formation constant for the inclusion complex between rutin and methyl-β-cyclodextrin. Anal. Chim. Acta 1995, 315, 357-363
4. Schneiderman, E.; Stalcup, A.M. Cyclodextrins: A versatile tool in separation science. J. Chromatogr. B 2000, 745, 83-102
5. Bernini, A.; Spiga, O.; Ciutti, A.; Scarselli, M.; Bottoni, G.; Mascagni, P.; Niccolai, N. NMR studies of the inclusion complex between beta-cyclodextrin and paroxetine. Eur. J. Pharm. Sci. 2004, 22, 445-450
6. Bonenfant, D.; Niquette, P.; Mimeault, M.; Furtos-Matei, A.; Hauslera, R. UV-VIS and FTIR spectroscopic analyses of inclusion complexes of nonylphenol and nonylphenol ethoxylate with β-cyclodextrin. Water Res. 2009, 43, 3575-3581
7. Waleczek, K.J.; Marques, C.; Hempel, B.; Schmidt, P.C. Phase solubility study of pure (-)-α-bisabolol and camomile essential oil with β-cyclodextrin. Eur. J. Pharm. Biopharm. 2003, 55, 247-251
8. He, Y.; Shen, X. Interaction between β-cyclodextrin and ionic liquids in aqueous solutions investigated by a competitive method using a substituted 3H-indole probe. J. Photochem. Photobiol. Chem. 2008, 197, 253-259
9. Yáñez, C.; Salazar, R.; Núñez-Vergara, L.J.; Squella, J.A. Spectrophotometric and electrochemical study of the inclusion complex between β-cyclodextrin and furnidipine. J. Pharm. Biomed. Anal. 2004, 35, 51-56
10. Li, N.; Zhao, X.; Gao, Y.; Zheng, L.; Zhang, J.; Yu, L. Complex formation of ionic liquid surfactant and β-cyclodextrin. Colloids Surf. A 2007, 292, 196-201
11. Tavornvipas, S.; Hirayama, F.; Arima, H.; Uekama, K.; Ishiguro, T.; Oka, M.; Hamayasu, K.; Hashimoto, H. 6-O-a-(4-O-a-D-glucuronyl)-D-glucosyl-β-cyclodextrin solubilizing ability and some cellular effects. Int. J. Pharm. 2002, 249, 199-209
12. Padukka, I.; Bhandari, B.; Darcy, B. Evaluation of various extraction methods of encapsulated oil from β-cyclodextrin-lemon oil complex powder. J. Food Compos. Anal. 2000, 13, 59-70
13. Szente, L.; Szejtli, J. Cyclodextrins as food ingredients. Trends Food Sci. Technol. 2004, 15, 137-142
14. 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 2003, 1007, 165-177
15. Morillo, E.; Perez-Martinez, J.I.; Gines, J.M. Leaching of 2,4-D from a soil in the presence of β-cyclodextrin: Laboratory columns experiments. Chemosphere 2001, 44, 1065-1069
16. Jozefaciuk, G.; Muranyi, A.; Fenyvesi, E. Effect of randomly methylated β-cyclodextrin on physical properties of soils. Environ. Sci. Technol. 2003, 37, 3012-3017
17. McEwen, A.B.; Ngo, H.L.; LeCompte, K.; Goldman, J.L. Electrochemical properties of imidazolium salt electrolytes for electrochemical capacitor applications. J. Electrochem. Soc. 1999, 146, 1687-1695
18. Xue, H.; Shreeve, M.J. Ionic Liquids with Fluorine-Containing Cations. Eur. J. Inorg. Chem. 2005, 13, 2573-2580
19. Wilkes, J.S. Ionic Liquid in Synthesis; Wasserscheid, P., Welton, T., Eds.; Wiley-VCH: Hoboken, NJ, USA, 2002.
20. Anderson, J.L.; Ding, R.; Ellern, A.; Armstrong, D.W. Structure and properties of high stability geminal dicationic ionic liquids. J. Am. Chem. Soc. 2005, 127, 593-604
21. Qi, S.; Cui, S.; Chen, X.; Hu, Z. Rapid and sensitive determination of anthraquinones in Chinese herb using 1-butyl-3-methylimiazolium-based ionic liquid with β-cyclodextrin as modifier in capillary zone electrophoresis. J. Chromatogr. A 2004, 1059, 191-198
22. Yu, L.; Qin, W.; Li, S.F.Y. Ionic liquids as additives for separation of benzoic acid and chlorophenoxy acid herbicides by capillary electrophoresis. Anal. Chim. Acta 2006, 547, 165-171
23. Jing, B.; Chen, X.; Hao, J.C.; Qiu, H.Y.; Chai, Y.C.; Zhang, G.D. Supramolecular self-assembly of polypseudorotaxanes in ionic liquid. Colloids Surf. A 2007, 292, 51-55
24. Tian, K.; Wang, Y.S.; Chen, Y.L.; Chen, Y.G.; Hu, Z.D. Application of 1-alkyl-3-methylimidazolium-based ionic liquids as background electrolyte in capillary zone electrophoresis for the simultaneous determination of five anthraquinones in Rhubarb. Talanta 2007, 72, 587-593
25. Gao, Y.A.; Li, Z.H.; Du, J.M.; Han, B.X.; Li, G.Z.; Hou, W.G.; Shen, D.; Zheng, L.Q.; Zhang, G.Y. Preparation and characterization of inclusion complexes of β-cyclodextrin with ionic liquid. Chem. Eur. J. 2005, 11, 5875-5880
26. Gao, Y.; Zhao, X.; Dong, B.; Zheng, L.; Li, N.; Zhang, S. Inclusion complexes of β-cyclodextrin with ionic liquid surfactants. J. Phys. Chem. B 2006, 110, 8576-8581
27. Amajjahe, S.; Ritter, H. Anion complexation of vinylimidazolium salts and its influence on polymerization. Macromolecules 2008, 41, 716-718
28. He, Y.; Chen, Q.; Xu, C.; Zhang, J.; Shen, X. Interaction between ionic liquid and β-Cyclodextrin: A discussion of association pattern. J. Phys. Chem. B 2009, 113, 231-238
29. Li, H.G.; Zhang, Q.; Zhao, Q.; Liu, M.; Liu, J.; Sun, D.Z. Studies on interaction of ionic liquids with cyclodextrin aqueous solution. Indian J. Chem. 2010, 49A, 752-756
30. Puvaneswary, S.; Sharifah, M.; Alias, Y. Synthesis and characterization of the inclusion complex of dicationic ionic liquid and β-cyclodextrin. Int. J. Mol. Sci. 2010, 11, 3675-3685
31. Kilivelu, G.; Yatimah, A. Synthesis and characterization of novel dimeric ionic liquids by conventional approaches. Int. J. Mol. Sci. 2008, 9, 1207-1213
32. Cwiertnia, B.; Hladon, T.; Stobiecki, M. Stability of diclofenac sodium in the inclusion complex with β-cyclodextrin in the solid state. J. Pharm. Pharmacol. 1999, 51, 1213-1218
33. Li, J.; Ni, X.; Zhou, Z.; Leong, K.W. Preparation and characterization of polypseudorotaxanes based on block-selected inclusion complexation between poly(propylene oxide)-poly(ethylene oxide)-poly(propylene oxide) triblock copolymers and α-cyclodextrin. J. Am. Chem. Soc. 2003, 125, 1788-1795
34. Qian, L.; Guan, Y.; Xiao, H. Preparation and characterization of inclusion complexes of a cationic β-cyclodextrin polymer with butylparaben or triclosan. Int. J. Pharm. 2008, 357, 244-251
35. Nostro, P.L.; Santoni, I.; Bonini, M.; Baglioni, P. Inclusion compound from a semifluorinated alkane and β-cyclodextrin. Langmuir 2003, 19, 2313-2317
36. Dupont, J. On the solid, liquid and solution structural organization of imidazolium ionic liquids. J. Braz. Chem. Soc. 2004, 15, 341-350
37. Okumura, H.; Kawaguchi, Y.; Harada, A. Preparation and characterization of the inclusion complexes of poly(dimethylsilane)s with cyclodextrins. Macromolecules 2003, 36, 6422-6429
38. Liu, L.; Zhu, S. A study on the supramolecular structure of inclusion complex of β-cyclodextrin with prazosin hydrochloride. Carbohydr. Polym. 2007, 68, 472-476
39. Pralhad, T.; Rajendrakumar, K. Study of freeze-dried quercetin-cyclodextrin binary systems by DSC, FT-IR, X-ray diffraction and SEM analysis. J. Pharmaceut. Biomed. Anal. 2004, 34, 333-339
40. Wang, H.Y.; Han, J.; Feng, X.G. Spectroscopic study of orange G-β-cyclodextrin complex and its analytical application. Spectrochim. Acta Part A 2007, 66, 578-585.