Cyclodextrins and their uses: a review

Villiers, 1891, Compt Rendu, 112, 536

Eastburn, 1994, Applications of modified cyclodextrins, Biotechnol. Adv., 12, 325, 10.1016/0734-9750(94)90015-9

Szetjli, 1998, Introduction and general overview of cyclodextrin chemistry, Chem. Rev., 98, 1743, 10.1021/cr970022c

Stella, 1997, Cyclodextrins: their future in drug formulation and delivery, Pharm. Res., 14, 556, 10.1023/A:1012136608249

Matsuda, 1999, Cyclodextrins in transdermal and rectal delivery, Adv. Drug Deliv. Rev., 36, 81, 10.1016/S0169-409X(98)00056-8

Mabuchi N, Ngoa M. Controlled release powdered flavour preparations and confectioneries containing preparations. Japanese Patent JP 128,638 (2001).

Buschmann HJ, Schollmeyer E. Applications of cyclodextrins in cosmetic products: a review. J Cosmet Sci 2002;53:575–92.

Hirose T, Yamamoto Y. Hinokitol containing cyclo-olefin polymer compositions and their molding with excellent antimicrobial and gas barrier properties. Japanese Patent JP 55480 (2001).

Hedges, 1998, Industrial applications of cyclodextrins, Chem. Rev., 98, 2035, 10.1021/cr970014w

Lu, 2002, Chiral separation of amino acids derivatized with fluoresceine-5-isothiocyanate by capillary electrophoresis and laser-induced fluorescence detection using mixed selectors of beta-cyclodextrin and sodium taurocholate, J. Chromatogr. A, 955, 133, 10.1016/S0021-9673(02)00186-3

Baudin, 2000, Inclusion of organic pollutants in cyclodextrin and derivatives, Int. J. Environ. Anal. Chem., 77, 233, 10.1080/03067310008032685

Kumar, 2001, Biotransformation of cholesterol using Lactobacillus bulgaricus in glucose controlledbioreactor, Bioresour Technol., 28, 209, 10.1016/S0960-8524(00)00174-7

Koukiekolo, 2001, Mechanism of porcine pancreatic alpha-amylase inhibition of amylose and maltopentaose hydrolysis by alpha-, beta- and gamma-cyclodextrins, Eur. J. Biochem., 268, 841, 10.1046/j.1432-1327.2001.01950.x

Szetjli, 1989, Downstream processing using cyclodextrins, TIBTRCH, 7, 171

Dass, 2000, Cyclodextrins and liposomes as potential drugs for the reversal of atherosclerosis, J. Pharm. Pharmacol., 52, 731, 10.1211/0022357001774606

Nash RA. Cyclodextrins. In: Wade A, Weller PJ, editors. Handbook of pharmaceutical excipients. London: Pharm. Press & Am. Pharm. Assoc.; 1994. p. 145–8.

Irie, 1997, Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation, J. Pharm. Sci., 86, 147, 10.1021/js960213f

Thompson, 1997, Cyclodextrins-enabling excipients: their present and future use in pharmaceuticals, Crit. Rev. Ther. Drug Carrier Syst., 14, 1, 10.1615/CritRevTherDrugCarrierSyst.v14.i1.10

Totterman, 1997, Intestinal safety of water-soluble β-cyclodextrins in paediatric oral solutions of spironolactone: effects on human intestinal epithelial Caco-2 cells, J. Pharm. Pharmacol., 49, 43, 10.1111/j.2042-7158.1997.tb06750.x

Szente, 1998, Spontaneous opalescence of aqueous γ-cyclodextrin solutions: complex formation or self-aggregation, J. Pharm. Sci., 87, 778, 10.1021/js9704341

Muñoz-Botella, 1995, Cyclodetrin properties and applications of inclusion complex formation, Ars. Pharm., 36, 187

Loftsson, 1996, Pharmaceutical applications of cyclodextrins: 1. Drug solubilisation and stabilization, J. Pharm. Sci., 85, 1017, 10.1021/js950534b

Schneiderman, 2000, Cyclodextrins: a versatile tool in separation science, J. Chromatogr. B, 745, 83, 10.1016/S0378-4347(00)00057-8

Schmid, 1989, Cyclodextrin glucanotransferse production: yield enhancement by overexpression of cloned genes, Trends Biotechnol., 7, 244, 10.1016/0167-7799(89)90015-2

Fujishima N, Kusaka K, Umino T, Urushinata T, Terumi K. Flour based foods containing highly branched cyclodextrins. Japanese Patent JP 136,898 (2001).

Bhardwaj, 2000, Approaches to reducing toxicity of parenteral anticancer drug formulations using cyclo-dextrins, J. Pharm. Sci. Technol., 54, 233

Holland L, Rizzi G, Malton P. Cosmetic compositions comprising cyclic oligosaccharides and fragrance. PCT Int Appl WO 67,716 (1999).

Lezcano, 2002, Complexation of several benzimidazole-type fungicides with alpha and beta-cyclodextrins, J. Agric. Food Chem., 50, 108, 10.1021/jf010927y

Dufosse, 1999, In situ detoxification of the fermentation medium during gamma-decalactone production with the yeast Sporidiobolus salmonicolor, Biotechnol. Prog., 15, 135, 10.1021/bp980113a

Hedges, 1998, Industrial applications of cyclodextrins, Chem. Rev., 98, 2035, 10.1021/cr970014w

Frömming KH, Szejtli J. Cyclodextrins in pharmacy. Topics in inclusion science. Dordrecht: Kluwer Academic Publishers; 1994.

Hirayama F, Uekama K. Methods of investigating and preparing inclusion compounds. In: Duchêne D, editor. Cyclodextrins and their industrial uses. Paris: Editions de Santé; 1987. p. 131–72.

Higuchi, 1965, Phase-solubility techniques, Adv. Anal. Chem. Instrum., 4, 117

Sigurdardottir, 1995, The effect of polyvinylpyrrolidone on cyclodextrin complexation of hydrocortisone and its diffusion through hairless mouse skin, Int. J. Pharm., 126, 73, 10.1016/0378-5173(95)04095-1

Hussain, 1993, Complexation of moricizine with nicotinamide and evaluation of the complexation constants by various methods, J. Pharm. Sci., 82, 77, 10.1002/jps.2600820117

Loftsson, 1995, Effects of cyclodextrins on chemical stability of drugs in aqueous solutions, Drug Stabil., 1, 22

Másson, 1998, Stabilisation of drugs through complexation with non-ionic and ionic cyclodextrins, Int. J. Pharm., 164, 45, 10.1016/S0378-5173(97)00387-6

Liu, 1992, Cyclodextrin/weak-electrolyte complexation: interpretation and estimation of association constants from phase solubility diagrams, Pharm. Res., 9, 1671, 10.1023/A:1015897332338

Suzuki, 1993, The freezing point depression method for the determination of binding parameters of drugs by polyvinylpyrrolidone and polyoxyethylene n-dodecylether, Chem. Pharm. Bull., 41, 1616, 10.1248/cpb.41.1616

Connors, 1997, The stability of cyclodextrin complexes in solution, Chem. Rev., 97, 1325, 10.1021/cr960371r

Connors, 1995, Population characteristics of cyclodextrin complex stabilities in aqueous solution, J. Pharm. Sci., 84, 843, 10.1002/jps.2600840712

Higuchi, 1965, Phase-solubility techniques, Adv. Anal. Chem. Instrum., 4, 117

Martin A. Physical pharmacy, 4th ed. Philadelphia: Lea & Fedbiger; 1993.

Bergeron RJ. Cycloamylose-substrate binding. Inclision Compounds. London: Academic Press; 1984.

Loftsson, 1996, Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization, J. Pharm. Sci., 85, 1017, 10.1021/js950534b

Loftsson, 1993, Cyclodextrin complexation of NSAIDS: physicochemical characteristics, Eur. J. Pharm. Sci., 1, 95, 10.1016/0928-0987(93)90023-4

Pitha, 1992, Effects of ethanol on formation of inclusion complexes of hydroxypropylcyclodextrins with testosterone or with methyl organe, Int. J. Pharm., 80, 243, 10.1016/0378-5173(92)90281-6

Loftsson, 1992, Interaction between preservatives and 2-hydroxypropyl-b-cyclodextrin, Drug Devel. Ind. Pharm., 18, 1477, 10.3109/03639049209040853

Furuta, 1993, Effects of water of inclusion complexes of d-limonene and cyclodextrins, Supramol. Chem., 1, 321, 10.1080/10610279308035175

Torres-Labandeira, 1990, Oversaturated solutions of drug in hydroxypropylcyclodextrins: parenteral preparation of pancratistatin, J. Pharm. Sci., 80, 384, 10.1002/jps.2600800421

Singh M, Sharma R, Banerjee UC. Biotechnological applications of cyclodextrins. Biotechnol Adv 2002;20:341–59.

Prasad N, Strauss D, Reichart G. Cyclodextrins inclusion for food, cosmetics and pharmaceuticals. European Patent 1,084,625 (1999).

Tatsuya S. Stabilisation of fragrance in bathing preparations. Japanese Patent 11,209,787 (1999).

Trinh J, Dodd TM, Bartolo R, Lucas JM. Cyclodextrin based compositions for reducing body odour. US Patent 5,897,855 (1999).

Woo RAM, Trinh T, Cobb DS, Schneiderman E, Wolff, AM, Rosenbalm EL, Ward TE, Chung AH, Reece S. Uncomplexed cyclodextrin compositions for odour control. US Patent 5,942,217 (1999).

Foley PR, Kaiser CE, Sadler JD, Burckhardt EE, Liu Z. Detergent composition with cyclodextrin perfume complexes to mask malodours. PCT Int Appl WO 01 23,516 (2000).

Angell WF, France, PA. Detergent composition having granular cyclodextrin. PCT Int Appl WO 01 18,163 (2001).

Loftsson, 1999, Effect of cyclodextrins and polymers on triclosan availability and substantivity in toothpastes in vivo, J. Pharm. Sci., 88, 1254, 10.1021/js9902466

Scalia, 1999, Inclusion complexation of the sunscreen agent 2-ethylhexyl-p-dimethylaminobenzoate with hydroxypropyl-beta-cyclodextrin: effect on photostability, J. Pharm. Pharmacol., 51, 1367, 10.1211/0022357991777182

Parrish MA. Cyclodextrins—a review. England: Sterling Organics; 1988 (Newcastle-upon-Tyne NE3 3TT).

Sojo, 1999, Cyclodextrins as activator and inhibitor of latent banana pulp polyphenol oxidase, J. Agric. Food Chem., 47, 518, 10.1021/jf9808978

Sung H. Composition for ginger preservation. Republic of Korea KR 9,707,148 (1997).

Sumiyoshi, 1999, Utilisation of inclusion complexes with plant components for foods, Nippon Shokuhin Shinsozai Kenkyukaishi, 2, 109

Takeshita K, Urata T. Antimicrobial food preservatives containing cyclodextrin inclusion complexes. Japanese Patent JP 29,054 (2001).

Frömming KH, Szejtli J. Cyclodextrins in pharmacy. Topics in inclusion science. Dordrecht: Kluwer Academic Publishers; 1994.

Rajewski, 1996, Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery, J. Pharm. Sci., 85, 1142, 10.1021/js960075u

Uekama, 1992, Improved transdermal delivery of prostaglandin E 1 through hairless mouse skin: combined use of carboxymethyl-ethyl-b-cyclodextrin and penetration enhancers, J. Pharm. Pharmacol., 44, 119, 10.1111/j.2042-7158.1992.tb03574.x

Kristmundsdóttir, 1996, Formulation and clinical evaluation of a hydrocortisone solution for treatment of oral disease, Int. J. Pharm., 139, 63, 10.1016/0378-5173(96)04565-6

Kublik, 1996, Nasal absorption of 17b-estradiol from different cyclodextrin inclusion formulations in sheep, Eur. J. Pharm. Biopharm., 42, 320

Loftsson, 1997, Effect of cyclodextrins on topical drug delivery to the eye, Drug Devel. Ind. Pharm., 23, 473, 10.3109/03639049709148496

van Dorne, 1993, Interaction between cyclodextrins and ophthalmic drugs, Eur. J. Pharm. Biopharm., 39, 133

Jarho, 1996, Increase in aqueous solubility, Int. J. Pharm., 137, 209, 10.1016/0378-5173(96)04522-X

Irie, 1999, Cyclodextrins in peptide and protein delivery, Adv. Drug Deliv. Rev., 36, 101, 10.1016/S0169-409X(98)00057-X

Zhao, 1995, Use of cyclodextrin and its derivatives as carriers for oligonucleotide delivery, Antisense Res., 5, 185, 10.1089/ard.1995.5.185

Ekberg, 1989, The synthesis of an active derivative of cyclomalto hexose for the hydrolysis of esters and the formation of amide bonds, Carbohydr. Res., 192, 111, 10.1016/0008-6215(89)85171-7

Morozumi, 1991, Selective synthesis using cyclodextrins as catalyst. 6. Cyclodextrin modification for para-selective hydroxymethylation and hydroxyetheylation of phenol, J. Mol. Catal., 70, 399, 10.1016/0304-5102(91)80135-P

Atwood JL. Inclusion phenomenon and molecular recognition. New York: Plenum; 1990.

Kamal, 1991, Enantioselective hydrolysis of aryloxypopionic esters by bovine serum albumin: enhancement in selectivity by β-CD, Tetrahedron: Asymmetry, 2, 39, 10.1016/S0957-4166(00)82154-0

Rao, 1990, A regioselective enzyme catalysed cycloaddition, Tetrahedron Letters, 31, 892, 10.1016/S0040-4039(00)94658-6

Gao, 1998, Application of cyclodextrin in environmental science, Huanjing Kexue Jinzhan, 6, 80

Wu, 1998, Applications of cyclodextrin to water treatment, Shuichuli Jishu, 24, 67

Reid BJ, Semple KT, Jhones KC. Soil test for determining bioavailability of pollutants. PCT Int Appl WO 99 54,727 (1999).

Bardi, 2000, Hydrocarbon degradation by a soil microbial population with beta-cyclodextrin as surfactant to enhance bioavailability, Enzyme Microb. Technol., 27, 709, 10.1016/S0141-0229(00)00275-1