Cyclodextrins and Their Inclusion Complexes

Cyclodextrins in Pharmaceutics, Cosmetics, and Biomedicine: Current and Future Industrial Applications

Volumn , Issue , 2011, Pages 1-18

  Duchêne, Dominique ^a  

^a UNIV PARIS SUD   (France)

Author keywords

Cyclodextrin size influence on inclusion complex structure; Cyclodextrins (CDs) and their inclusion complexes main natural CDs and their characteristics; Inclusion complexes and preparation methods

Indexed keywords

EID: 84886536214     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9780470926819.ch1     Document Type: Chapter

References (88)

1. Loftsson, T., Duchecirc;ne, D. (2007). Cyclodextrins and their pharmaceutical applications: historical perspectives. Int. J. Pharm., 329, 1-11.
2. Sicard, P.J., Saniez, M.-H. (1987). Biosynthesis of cycloglycosyl transferase and obtention of its enzymatic reaction products. In: Duchêne, D., Ed., Cyclodextrins and Their Industrial Uses. Editions de Santé, Paris, pp. 75-103.
3. Le Bas, G., Rysanek, N. (1987). Structural aspects of cyclodextrins. In: Duchecirc;ne, D. Ed., Cyclodextrins and Their Industrial Uses. Editions de Santé, Paris, pp. 105-130.
4. Loftsson, T., Brewster, M.E. (1996). Pharmaceutical applications of cyclodextrins: 1. Drug solubilisation and stabilization. J. Pharm. Sci., 85, 1017-1025.
5. Zia, V., Rajewski, R.A., Stella, V.J. (2001). Effect of cyclodextrin charge on complexation of neutral and charged substrates: comparison of (SBE)7M-b-CD to HP-b-CD. Pharm. Res., 18, 667-673.
6. Gabelica, V., Galic, N., De Pauw, E. (2002). On the specificity of cyclodextrin complexes detected by electrospray mass spectroscopy. J. Am. Soc. Mass Spectrom., 13, 946-953.
7. Bikádi, Z., Iványi, R., Szente, L., Hazai, E. (2007). Cyclodextrin complexes: chiral recognition and complexation behavior. Curr. Drug Discov. Technol., 4, 282-294.
8. Loftsson, T., Matthíasson, K., Másson, M. (2003). The effects of organic salts on the cyclodextrin solubilization of drugs. Int. J. Pharm., 262, 101-107.
9. Zhao, D.G., Liao, K.I., Ma, X.Y.,Yan, X.H. (2002). Study of the supramolecular inclusion of b-cyclodextrin with andrographolide. J. Inclusion Phenom. Macrocyclic Chem., 43, 259-264.
10. Loftsson, T., Magnúsdóttir, A., Másson, M., Sigurjónsdóttir, J.F. (2002). Self-association and cyclodextrin solubilization of drugs. J. Pharm. Sci., 91, 2307-2316.
11. Loftsson, T., Másson, M., Sigurdsson, H.H. (2002). Cyclodextrins and drug permeability through semi-permeable cellophane membranes. Int. J. Pharm., 232, 35-43.
12. Bikádi, Z., Kurdi, R., Balogh, S., Szemán, J., Hazai, E. (2006). Aggregation of cyclodextrins as an important factor to determine their complexation behavior. Chem. Biodiversity, 3, 1266-1278.
13. Brochsztain, S., Politi, M.J. (1999). Solubilization of 1,4,5,8-naphthalenediimides and 1, 8-naphthalimides through the formation of novel host-guest complexes with a-cyclodextrin. Langmuir, 15, 4486-4494.
14. Fernandes, C.M., Carvalho, R.A., Pereira da Costa, S., Veiga, F.J.B. (2003). Multimodal molecular encapsulation of nicardipine hydrochloride by b-cyclodextrin, hydroxylpropylb-cyclodextrin and triacetyl-b-cyclodextrin in solution: structural studies by 1H NMR and ROESY experiments. Eur. J. Pharm. Sci., 18, 285-296.
15. Másson, M., Loftsson, T., Jónsdottir, S., Fridriksdóttir, H., Petersen, D.S. (1998). Stabilisation of ionic drugs through complexation with non-ionic and ionic cyclodextrins. Int. J. Pharm., 164, 45-55.
16. Loftsson, T.,Másson, M., Sigurjónsdóttir, J.F. (1999). Methods to enhance the complexation efficiency of cylodextrins. STP Pharma Sci., 9, 237-242.
17. Pitha, J., Hoshino, T. (1992). Effects of ethanol on the formation of inclusion complexes of hydroxypropylcyclodextrins with testosterone or with methyl orange. Int. J. Pharm., 80, 243-251.
18. Kim, Y., Oksanen, D.A., Massefski, W., Blake, J.F., Duffy, E. M., Chrunyk, B. (1998). Inclusion of ziprasidone mesylate with b-cyclodextrin sulfobutyl ether. J. Pharm. Sci., 87, 1560-1567.
19. Selva, A., Redenti, E.,Ventura, P., Zanol,M., Casetta, B. (1998). Study of b-cyclodextrin-ketokonazole-tartaric acid multicomponent non-covalent association by positive and negative ionspray mass spectrometry. J. Mass Spectrom., 33, 729-734.
20. Csabai, K., Vikmon, M., Szejtli, J., Redenti, E., Poli, G., Ventura, P. (1998). Complexation of manidipine with cyclodextrins and their derivatives. J. Inclusion Phenom. Mol. Recognit. Chem., 31, 169-178.
21. Loftsson, T. (1998). Increasing the cyclodextrin complexation of drugs and drug bioavailability through addition of watersoluble polymers. Pharmazie, 53, 733-740.
22. Al-Marzouqi, A.H., Jobe, B., Dowaidar, A., Maestrelli, F., Mura, P. (2007). Evaluation of supercritical fluid technology as preparative technique of benzocaine-cyclodextrin complexes; comparison with conventional methods. J. Pharm. Biomed. Anal., 43, 566-574.
23. Jambhekar, S., Casella, R., Maher, T. (2004). The physicochemical characteristics and bioavailability of indomethacin from b-cyclodextrin, hydroxyethyl-b-cyclodextrin, and hydroxypropyl-b-cyclodextrin complexes. Int. J. Pharm., 270, 149-166.
24. Ribeiro, A., Figueiras, A., Santos, D., Veiga, F. (2008). Preparation and solid state characterization on inclusion complexes formed between miconazole and methyl-b-cyclodextrin. AAPS PharmSciTech, 9, 1102-1109.
25. Ribeiro, L.S.S., Ferreira, D.C., Veiga, F.J.B. (2003). Physicochemical investigation of the effects of water-soluble polymers on vinpocetine complexation with b-cyclodextrin and its sulfobutyl ether derivative in solution and solid state. Eur. J. Pharm. Sci., 20, 253-266.
26. Al-Marzouqi, A.H., Elwy, H.M., Shehadi, I., Adem, A. (2009). Physicochemical properties of antifungal drug-cyclodextrin complexes prepared by supercritical carbon dioxide and by conventional techniques. J. Pharm. Biomed. Anal., 49, 227-233.
27. Figueiras, A., Carvalho, R.A., Ribeiro, L., Torres-Labandeira, J.J., Veiga, F.J.B. (2007). Solid-state characterization and dissolution profiles of the inclusion complexes of omeprazole with native and chemically modified b-cyclodextrin. Eur. J. Pharm. Biopharm., 67, 531-539.
28. Salústio, P.J., Feio, G., Figueirinhas, J.L., Pinto, J.F., Cabral Marques, H.M. (2009). The influence of the preparation methods on the inclusion of model drugs in a b-cyclodextrin cavity. Eur. J. Pharm. Biopharm., 71, 377-386.
29. Badr-Eldin, S.M., Elkheshen, S.A., Ghorab, M.M. (2008). Inclusion complexes of tadalafil with natural and chemically modified b-cyclodextrins: I. Preparation and in-vitro evaluation. Eur. J. Pharm. Biopharm., 70, 819-827.
30. Cirri, M., Maestrelli, F., Mennini, N., Mura, P. (2009). Influence of the preparation method on the physical-chemical properties of ketoprofen-cyclodextrin-phosphatidylcholine ternary systems. J. Pharm. Biomed. Anal., 50, 690-694.
31. Van Hees, T., Piel, G., Evrard, B., Otte, X., Thunus, L., Delattre, L. (1999). Application of supercritical carbon dioxide for the preparation of a piroxicam-b-cyclodextrin inclusion compound. Pharm. Res., 16, 1864-1870.
32. York, P. (1999). Strategies for particle design using supercritical fluid technologies. Pharm. Sci. Technol. Today, 2, 430-440.
33. Toropainen, T., Velaga, S., Heikkilä, T., Matilainen, L., Jarho, P., Carlfors, J., Lehto, V.P., Jeuroärvinen, T., Järvinen, K. (2006). Preparation of budesonide/c-cyclodextrin complexes in supercritical fluids with a novel SEDS method. J. Pharm. Sci., 95, 2235-2245.
34. Bandi, N.,Wei,W., Roberts, C.B., Kotra, L.P., Kompella, U.B. (2004). Preparation of budesonide-and indomethacin-hydroxypropyl-b-cyclodextrin (HPBCD) complexes using a single-step, organic-solvent-free supercritical fluid porcess. Eur. J. Pharm. Sci., 23, 159-168.
35. Hassan H.A., Al-Marzouqi, A.H., Jobe, B., Hamza, A.A., Ramadan, G.A. (2007). Enhancement of dissolution amount and in vivo bioavailability of itraconazole by complexation with b-cyclodextrin using supercritical carbon dioxide. J. Pharm. Biomed. Anal., 45, 243-250.
36. Charoenchaitrakool, M., Dehghani, F., Foster, N.R. (2002). Utilization of supercritical carbon dioxide for complex formation of ibuprofen and methyl-b-cyclodextrin. Int. J. Pharm., 239, 103-112.
37. Wen, X.H., Tan, F., Jing, Z.J., Liu, Z.Y. (2004). Preparation and study the 1: 2 inclusion of carvedilol with b-cyclodextrin. J. Pharm. Biomed. Anal., 34, 517-523.
38. Nacsa, Á., Ambrus, R., Berkesi, O., Szabó-Révész, P., Aigner, Z. (2008).Water-soluble loratadine inclusion complex: analytical control of the preparation by microwave irradiation. J. Pharm. Biomed. Anal., 48, 1020-1023.
39. Cirri, M., Maestrelli, F., Mennini, N., Mura, P. (2009). Physical-chemical characterization of binary and ternary systems of ketoprofen with cyclodextins and phospholipids. J. Pharm. Biomed. Anal., 50, 683-689.
40. Mura, P., Fauci, M.T., Parrini, P.L., Furlanetto, S., Pinzauti, S. (1999). Influence of the preparation method on the physicochemical properties of ketoprofen-cyclodextrin binary systems. Int. J. Pharm., 179, 117-128.
41. Loftsson, T., Fridriksdóttir, H., Sigurdardóttir, A.M., Ueda, H. (1994). The effect of water-soluble polymers on drug-cyclodextrin complexation. Int. J. Pharm., 110, 169-177.
42. Faucci, M.T., Mura, P. (2001). Effect of water-soluble polymers on naproxen complexation with natural and chemically modified b-cyclodextrins. Drug Dev. Ind. Pharm., 27, 909-917.
43. Alexanian, C., Papademou, H., Vertzoni, M., Archontaki, H., Valsami, G. (2008). Effect of pH and water-soluble polymers on the aqueous solubility of nimesulide in the absence and presence of b-cyclodextrin derivatives. J. Pharm. Pharmacol., 60, 1433-1439.
44. Valero, M., Tejedor, J., Rodríguez, L.J. (2007). Encapsulation of nabumetone by means of drug:(b-cyclodextrin)2:polyvinylpyrrolidone ternary complex formation. J. Luminesc., 126, 297-302.
45. Selvam, A.P., Geetha, D. (2008). Ultrasonic studies on lamivudine:b-cyclodextrin and polymer inclusion compexes. Pak. J. Biol. Sci., 11, 656-659.
46. Loftsson, T., Gudmundsdóttir, T.K., Fridriksdóttir, H. (1996). The influence of water-soluble polymers and pH on hydro-xypropyl-b-cyclodextrin complexation of drugs. Drug Dev. Ind. Pharm., 22, 401-405.
47. Valero, M., Esteban, B., Pelaez, R., Rodríguez, L. (2004). Naproxen:hydroxypropyl-b-cyclodextr:polyvinylpyrrolidone ternary complex formation. J. Inclusion Phenom. Macrocyclic Chem., 48, 157-163.
48. Ribeiro, L., Carvalho, R.A., Ferreira, D.C., Veiga, F.J.B. (2005). Multicomponent complex formation between vinpocetine, cyclodextrins, tartaric acid and water-soluble polymers monitored by NMR and solubility studies. Eur. J. Pharm. Sci., 24, 1-13.
49. Cirri, M., Maestrelli, F., Corti, G., Furlanetto, S., Mura, P. (2006). Simultaneous effect of cyclodextrin complexation, pH, and hydrophilic polymers on naproxen solubilization. J. Pharm. Biomed. Anal., 42, 126-131.
50. Loftsson, T., Sigurdsson, H.H., Másson, M., Schipper, N. (2004). Preparation of solid drug/cyclodextrin complexes of acidic and basic drugs. Pharmazie, 59, 25-29.
51. Ribeiro, L.S.S., Falcão, A.C., Patrício, J.A.B., Ferreira, D.C., Veiga, F.J.B. (2007). Cyclodextrin multicomponent complexation and controlled release delivery strategies to optimize the oral bioavailability of vinpocetine. J. Pharm. Sci., 96, 2018-2028.
52. Barillaro, V., Dive, G., Bertholet, P., Evrard, B., Delattre, L., Ziémons, E., Piel, G. (2007). Theoretical and experimental investigations on miconazole/cyclodextrin/acid complexes: molecular modeling studies. Int. J. Pharm., 342, 152-160.
53. Sinha, V.R., Anitha, R., Ghosh, S., Nanda, A., Kumria, R. (2005). Complexation of celecoxib with b-cyclodextrin: characterization of the interaction in solution and in solid state. J. Pharm. Sci., 94, 676-687.
54. Lemesle-Lamache, V., Wouessidjewe, D., Chéron, M., Duchecirc;ne, D. (1996). Study of b-cyclodextrin and ethylated b-cyclodextrin salbutamol complexes, in vitro evaluation of sustained-release behavior of salbutamol. Int. J. Pharm., 141, 117-124.
55. Ventura, C.A., Giannone, I., Musumeci, T., Pignatello, R., Ragni, L., Landolfi, C., Milanese, C., Paolino, D., Puglisi, G. (2006). Physico-chemical characterization of disoxaril-dimethyl-b-cyclodextrin inclusion complex and in vitro permeation studies. Eur. J. Med. Chem., 41, 233-240.
56. Dotsikas, Y., Loukas, Y.L. (2002). Kinetic degradation study of insulin complexed with methyl-beta cyclodextrin: confirmation of complexation with electrospray mass spectrometry and 1H NMR. J. Pharm. Biomed. Anal., 29, 487-494.
57. Guernelli, S., Lagana, M.F., Mezzina, E., Ferroni, F., Siani, G. (2003). Supramolecular complex formation: a study of the interactions between b-cyclodextrin and some different classes of organic compounds by ESI-MS, surface tension measurements, and UV/Vis and 1H NMR spectroscopy. Eur. J. Org. Chem., 24, 4765-4776.
58. Béni, S., Szakács, Z., Csernák, O.,Barcza, L.,Noszál, B. (2007). Cyclodextrin/imatinib complexation: binding mode and charge dependent stabilities. Eur. J. Pharm. Sci., 30, 167-174.
59. Djedaïni, F., Perly, B. (1991). Nuclear magnetic resonance of cyclodextrins, derivatives and inclusion compounds. In: Duchêne, D., Ed., New Trends in Cyclodextrins and Derivatives. Editions de Santé, Paris, pp. 215-246.
60. Loftsson, T., Másson, M., Brewster, M.E. (2004). Self-association of cyclodextrins and cyclodextrin complexes. J. Pharm. Sci., 93, 1091-1099.
61. Higuchi, T., Connors, K.A. (1965). Phase-solubility techniques. Adv. Anal. Chem. Instrum., 4, 117-212.
62. Brewster, M.E., Loftsson, T. (2007). Cyclodextrins as pharmaceutical solubilizers. Adv. Drug Deliv. Rev., 59, 645-666.
63. Hirayama, F., Uekama, K. (1987). Methods of investigating and preparing inclusion compounds. In: Duchêne, D. Ed., Cyclodextrins and Their Industrial Uses. Editions de Santé, Paris, pp. 131-172.
64. Ono, N., Hirayama, F., Arima, H., Uekama, K. (1999). Determination of stability constant of b-cyclodextrin complexes using the membrane permeation technique and the permeation behaviour of drug-competing agent-b-cyclodextrin ternary systems. Eur. J. Pharm. Sci., 8, 133-139.
65. Cirri, M., Maestrelli, F., Orlandini S., Furlanetto, S., Pinzauti, S., Mura, P. (2005). Determination of stability constant values of flurbiprofen-cyclodextrin complexes using different techniques. J. Pharm. Biomed. Anal., 37, 995-1002.
66. Hildebrand, J.A., Benesi, H.A. (1949). A graphical method for the determination of binding constants. J. Am. Chem. Soc., 71, 2703-2710.
67. Djedaïni, F., Lin, S.Z., Perly, B., Wouessidjewe, D. (1990). High-field nuclear magnetic resonance techniques for the investigation of a b-cyclodextrin:indomethacin inclusion complex. J. Pharm. Sci., 79, 643-646.
68. Jullian, C., Miranda, S., Zapata-Torres, G., Mendizábal, F., Olea-Azar, C. (2007). Studies on inclusion complexes of natural and modified cyclodextrin with ({thorn})catechin by NMR and molecular modeling. Bioorg. Med. Chem., 15, 3217-3224.
69. Tapia, M.J., Burrows, H.D., García, J.M., Pais, A.A.C.C. (2004). Lanthanide ion interaction with a crown ether methacrylic polymer, poly(1,4,7,10-tetraoxacyclododecan-2-methyl methacrylate), as seen by spectroscopic, calorimetric, and theoretical studies. Macromolecules, 37, 856-862.
70. Job, P. (1928). Recherches sur la formation de complexes minéraux en solution et sur leur stabilité. Ann. Chim., 9, 113-125.
71. Veiga, F.J.B., Fernandes, C.M., Carvalho, R.A., Geraldes, C.F. G.C. (2001). Molecular modelling and 1H-NMR: ultimate tools for the investigation of tolbutamide:b-cyclodextrin and tolbutamide: hydroxypropyl-b-cyclodextrin complexes. Chem. Pharm. Bull., 49, 1251-1256.
72. Figueiras, A., Sarraguça, J.M.G., Carvalho, R.A., Pais, A.A.C. C., Veiga, J.B. (2007). Interaction of omeprazole with a methylated derivative of b-cyclodextrin: phase solubility, NMR spectroscopy and molecular simulation. Pharm. Res., 24, 377-389.
73. Grillo, R., de Melo, N.F.S., Moraes, C.M., de Lima, R., Menezes, C.M.S., Ferreira, E.I., Rosa, A.H., Fraceto, L.F. (2008). Study of the interaction between hydroxymethylnitrofurazone and 2-hydroxypropyl-b-cyclodextrin. J. Pharm. Biomed. Anal., 47, 295-302.
74. Whang, H.S., Vendeix, F.A.P., Gracz, H.S., Gadsby, J., Tonelli, A. (2007). NMR studies of the inclusion complex of cloprostenol sodium salt with b-cyclodextrin in aqueous solution. Pharm. Res., 25, 1142-1149.
75. Paulidou, A., Maffeo, D., Yannakopoulou, K., Mavridis, I.M. (2008). Crystal structure of the inclusion complex of the antibacterial agent triclosan with cyclomaltoheptaose and NMR study of its molecular encapsulation in positively and negatively charged cyclomaltoheptaose derivatives. Carbohydr. Res., 343, 2634-2640.
76. Gibaud, S., Ben Zizar, S., Mutzenhardt, P., Fries, I., Astier, A. (2005). Melarsoprol-cyclodextrins inclusion complexes. Int. J. Pharm., 306, 107-121.
77. Ziémons, E., Dive, G., Debrus, B., Barillaro, V., Frederich, M., Lejeune, R., Angenot, L., Delattre, L., Thunus, L., Hubert, Ph. (2007). Study of the physicochemical properties in aqueous medium and molecular modeling of tagitinin C/cyclodextrin complexes. J. Pharm. Biomed. Anal., 43, 910-919.
78. Salvatierra, D., Diez, C., Jaime, C. (1997). Host/guest interactions and NMR spectroscopy: a computer program for association constant determination. J. Inclusion Phenom. Mol. Recognit., 27, 215-231.
79. Yang, C., Liu, L., Mu, T.W., Guo, Q.X. (2000). The performance of the Benesi-Hildebrand method in measuring the binding constants of the cyclodextrin complexation. Anal. Sci., 16, 537-539.
80. Song, L.S., Wang, H.M., Xu, P., Yang, Y., Zhang, Z.Q. (2008). Experimental and theoretical studies on the inclusion complexation of syringic acid with a-, b-, c-and heptakis(2, 6-di-O-methyl)-b-cyclodextrin. Chem.Pharm.Bull., 56, 468-474.
81. Lemesle-Lamache, V., Taverna, M., Wouessidjewe, D., Duchêne, D., Ferrier, D. (1996). Determination of the binding constant of salbutamol to unmodified and ethylated cyclodextrins by affinity capillary electrophoresis. J. Chromatogr. A, 735, 321-331.
82. Castronuovo, G., Niccoli, M. (2006). Thermodynamics of inclusion complexes of natural and modified cyclodextrins with propranolol in aqueous solution at 298 K. Bioorg. Med. Chem., 14, 3883-3887.
83. Salim, N.N., Feig, A.L. (2009). Isothermal titration calorimetry of RNA. Methods, 47, 198-205.
84. Illapakurthy, A.C., Wyandt, C.M., Stodghill, S.P. (2005). Isothermal titration calorimetry method for determination of cyclodextrin complexation thermodynamic between artemisinin and naproxen under varying environmental conditions. Eur. J. Pharm. Biopharm., 59, 325-332.
85. Segura-Sanchez, F., Bouchemal, K., Le Bas, G., Vauthier, C., Santos-Magalhaes, N.S., Ponchel, G. (2009). Elucidation of the complexation mechanism between (+)-usnic acid and cyclodextrins studied by isothermal titration calorimetry and phasesolubility diagram experiments. J. Mol. Recognit., 22, 232-241.
86. Metha, S.K., Bhasin, K.K., Dham, S. (2008). Energetically favorable interactions between diclofenac sodium and cyclodextrin molecules in aqueous media. J. Colloid Interface Sci., 326, 374-381.
87. Faucci, M.T., Melani, F., Mura, P. (2002). Computer-aided molecular modeling techniques for predicting the stability of drug-cyclodextrin inclusion complexes in aqueous solutions. Chem. Phys. Lett., 358, 383-390.
88. Melani, F., Mura, P., Adamo, M., Maestrelli, F., Gratteri, P., Bonaccini, C. (2003). New docking CFF91 parameters specific for cyclodextrin inclusion complexes. Chem. Phys. Lett., 370, 280-292.