Biotechnological applications of cyclodextrins

Biotechnology Advances

Volumn 20, Issue 5-6, 2002, Pages 341-359

  Singh, Mamata ^a   Sharma, Rohit ^a   Banerjee, U C ^a  

^a NATIONAL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH NIPER   (India)

Author keywords

Cyclic glucans; Cyclodextrins; Enantiomers; Macrocyclic; Oligosaccharides

Indexed keywords

DRUG PRODUCTS; ENZYMES; ISOMERS; STARCH; TEXTILES;

ENZYMATIC DEGRADATIONS;

BIOTECHNOLOGY;

BIOTECHNOLOGY;

EID: 0036890313     PISSN: 07349750     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0734-9750(02)00020-4     Document Type: Article

References (121)

1. Anderson J.L., Ding J., McCulla R.D., Jenks W.S., Armstrong D.W. Separation of racemic sulfoxides and sulfonate esters on four derivatized cyclodextrin chiral stationary phases using capillary gas chromatography. J. Chromatogr. A. 946:2002;197-208.
2. Angell WF, France, PA. Detergent composition having granular cyclodextrin. PCT Int Appl WO 01 18,163, 2001.
3. Arima H., Kihara F., Hirayama F., Uekama K. Enhancement of gene expression by polyamidoamine dendrimer conjugates with alpha, beta and gamma-cyclodextrins. Bioconjug. Chem. 12:2001;476-484.
4. Arima H., Yunomae K., Miyake K., Irie T., Hirayama F., Uekama K. Comparative studies of the enhancing effects of cyclodextrins on the solubility and oral bioavailability of tacrolimus in rats. J. Pharm. Sci. 90:2001;690-701.
5. Atwood J.L. Inclusion Phenomenon and Molecular Recognition. 1990;Plenum, New York.
6. Bar R. Cyclodextrin aided bioconversions and fermentations. Trends Biotechnol. 7:1989;2-4.
7. Bar R. Cyclodextrin aided microbial transformation of aromatic aldehydes by S. cerevisiae. J. Appl. Microbiol. Biotechnol. 31:1990;25-28.
8. Bardi L., Mattei A., Steffan S., Marzona M. Hydrocarbon degradation by a soil microbial population with beta-cyclodextrin as surfactant to enhance bioavailability. Enzyme Microb. Technol. 27:2000;709-713.
9. Baudin C., Pean C., Perly B., Goselin P. Inclusion of organic pollutants in cyclodextrin and derivatives. Int. J. Environ. Anal. Chem. 77:2000;233-242.
10. Bekers O., Beijnen J.H., Tank M.J., Bult A., Underberg W.J. Effect of cyclodextrins on the chemical stability of mitomycins in alkaline solution. J. Pharm. Biomed. Anal. 9:1991;1055-1060.
11. Bhardwaj R., Dorr R.T., Blanchard J. Approaches to reducing toxicity of parenteral anticancer drug formulations using cyclodextrins. J. Pharm. Sci. Technol. 54:2000;233-239.
12. Bibby D.C., Davies N.M., Tucker I.G. Mechanism by which cyclodextrins modify drug release from polymeric drug delivery systems. Int. J. Pharm. 197:2000;1-11.
13. Bodor N., Drustrup J., Wu W. Effect of cyclodextrins on the solubility and stability of a novel soft corticosteroid, loteprednol etabonate. Pharmazie. 55:2000;206-209.
14. Boudad H., Legrand P., Lebas G., Cheron M., Duchene D., Ponchel G. Combined hydroxypropyl-beta-cyclodextrin and poly (alkylcyanoacrylate) nanoparticles intended for oral administration of saquinavir. Int. J. Pharm. 218:2001;113-124.
15. Bowser M.T., Kennedy R.T. In vivo monitoring of amine neurotransmitters using microdialysis with on-line capillary electrophoresis. Electrophoresis. 22:2001;3668-3676.
16. Breslow R., Dong S.D. Biomimectic reactions catalysed by cyclodextrin and their derivatives. Chem. Rev. 98:1998;1997-2011.
17. Buschmann H.J., Schollmeyer E. Applications of cyclodextrins in cosmetic products: a review. J. Cosmet. Sci. 53:2002;185-191.
18. Cavalli R., Peira E., Caputo O., Gasco M.R. Solid lipid nanoparticles as carriers of hydrocortisone and progesterone complexes with beta-cyclodextrins. Int. J. Pharm. 182:1999;59-69.
19. Cepeda A., Franco C.M., Fente C.A., Vazquez B.I., Rodriguez J.L., Prognon P.et al. Post column excitation of aflatoxins using cyclodextrins in liquid chromatography for food analysis. J. Chromatogr. A. 721:1996;69-74.
20. Chen W.H., Hayashi S., Tahara T., Nogami Y., Koga T., Yamaguchi M.et al. The dependence of catalytic activities of secondary functional beta-cyclodextrins on cavity structures. Chem. Pharm. Bull. 47:1999;588-589.
21. Cheng D., Tipton C.L. Activation of acyl-CoA cholesterol acyltransferase: redistribution in microsomal fragments of cholesterol and its facilitated movement by methyl-beta-cyclodextrin. Lipids. 34:1999;261-268.
22. Chiavaro E., Dallasta C., Galaverna G., Biancardi A., Gambarelli E., Dossena A.et al. New reversed-phase liquid chromatographic method to detect aflatoxins in food and feed with cyclodextrins as fluorescence enhancers added to the eluent. J. Chromatogr. A. 937:2001;31-40.
23. Croyle M.A., Cheng X., Wilson J.M. Development of formulations that enhance physical stability of viral vectors for gene therapy. Gene Ther. 8:2001;1281-1290.
24. Dass C.R., Jessup W. Apolipoprotiens A-I, Cyclodextrins and liposomes as potential drugs for the reversal of atherosclerosis. J. Pharm. Pharmacol. 52:2000;731-761.
25. de Beor T., de Zeeuw R.A., de Jong G.J., Ensing K. Recent innovations in the use of charged cyclodextrins in capillary electrophoresis for chiral separations in pharmaceutical analysis. Electrophoresis. 21:2000;3220-3239.
26. Duchene D., Ponchel G., Wouessidjewe D. Cyclodextrins in targeting. Application to nanoparticles. Adv. Drug Deliv. Rev. 36:1999;29-40.
27. Duchene D., Wouessidjewe D., Ponchel G. Cyclodextrins and carrier systems. J. Control. Release. 62:1999;263-268.
28. Dufosse L., Souchon I., Feron G., Latrasse A., Spinnler H.E. In situ detoxification of the fermentation medium during gamma-decalactone production with the yeast Sporidiobolus salmonicolor. Biotechnol. Prog. 15:1999;135-139.
29. Eastburn S.D., Tao B.Y. Applications of modified cyclodextrins. Biotechnol. Adv. 12:1994;325-339.
30. Ekberg B., Anderson L., Mosbach K. The synthesis of an active derivative of cyclomalto hexose for the hydrolysis of esters and the formation of amide bonds. Carbohydr. Res. 192:1989;111-117.
31. Fanali S. Enantioselective determination by capillary electrophoresis with cyclodextrin as chiral selectors. J. Chromatogr. 875:2000;89-122.
32. Fava F., Gioia D., Marchetti L. Cyclodextrin effects on the ex-situ bioremediation of a chronically polychlorobiphenyl-contaminated soil. Biotechnol. Bioeng. 58:1998;345-355.
33. Fekete F.K., Szabo E., Lenkey B. The formation of hyphae of Candida albicans induced by cyclodextrins. Mycoses. 40:1997;451-453.
34. Ferancova A., Labuda J. Cyclodextrin as electrode modifiers. Fresenius J. Anal. Chem. 370:2001;1-10.
35. 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.
36. Foulon C., Goossens J.F., Fourmaintraux E., Bonte J.P., Vaccher C. Chiral capillary electrophoretic determination of the enantiomeric purity of tetrahydronaphthalenic derivatives, melatoninergic ligands, using highly sulfated beta-cyclodextrins. Electrophoresis. 23:2002;1121-1128.
37. Fujishima N, Kusaka K, Umino T, Urushinata T, Terumi K. Flour based foods containing highly branched cyclodextrins. Japanese Patent JP 136,898, 2001.
38. Gao S., Wang L. Application of cyclodextrin in environmental science. Huanjing Kexue Jinzhan. 6:1998;80-86.
39. Ghosh M., Sanders T.C., Zhang R., Seto C.T. Inhibition of phosphatase activity by positively-charged cyclodextrins. Org. Lett. 1:1999;1945-1948.
40. Granados A.M., de Rossi R.H. Effect of cyclodextrin on the intramolecular catalysis of amide hydrolysis. J. Org. Chem. 66:2001;1548-1552.
41. Han S.M. Direct enantiomeric separations by high performance liquid chromatography using cyclodextrins. Biomed. Chromatogr. 11:1997;259-271.
42. Hayden B.M., Engel P.C. Construction, separation and properties of hybrid hexamers of glutamate dehydrogenase in which five of the six subunits are contributed by the catalytically inert D165S. Eur. J. Biochem. 268:2001;1173-1180.
43. Hedges R.A. Industrial applications of cyclodextrins. Chem. Rev. 98:1998;2035-2044.
44. 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.
45. Holland L, Rizzi, G, Malton P. Cosmetic compositions comprising cyclic oligosaccharides and fragrance. PCT Int Appl WO 67,716, 1999.
46. Irie T., Uekama K. Cyclodextrins in peptide and protein delivery. Adv. Drug Deliv. Rev. 36:1999;101-123.
47. Ishibashi M, Kashikura A, Ozaki S., Kawakubo H. Water absorbing sheet for packaging fresh product. Japanese Patent JP 11 285,368, 1999.
48. Iwata Y.T., Garcia A., Kanamori T., Inoue H., Kishi T., Lurie I.S. The use of a highly sulfated cyclodextrin for the simultaneous chiral separation of amphetamine-type stimulants by capillary electrophoresis. Electrophoresis. 23:2002;1328-1334.
49. Jarho P., Vander V.D., Stella V.J. Cyclodextrin-catalyzed deacetylation of spironolactone is pH and cyclodextrin dependent. J. Pharm. Sci. 89:2000;241-249.
50. Kamal A., Rabalingum T., Venugopalan N. Enantioselective hydrolysis of aryloxypopionic esters by bovine serum albumin: enhancement in selectivity by β-CD. Tetrahedron: Asymmetry. 2:1991;39.
51. Kamiya M., Kameyama K., Ishiwata S. Effects of cyclodextrins on photo degradation of organophosphorus pesticides in humic water. Chemosphere. 42:2001;251-255.
52. Koukiekolo R., Desseaux V., Moreau Y., Marchis M.G., Santimone M. Mechanism of porcine pancreatic alpha-amylase inhibition of amylose and maltopentaose hydrolysis by alpha-, beta- and gamma-cyclodextrins. Eur. J. Biochem. 268:2001;841-848.
53. Kumar R., Dahiya J.S., Singh D., Nigam P. Biotransformation of cholesterol using Lactobacillus bulgaricus in glucose controlled bioreactor. Bioresour. Technol. 28:2001;209-211.
54. Leventis R., Silvius J.R. Use of cyclodextrins to monitor transbilayer movement and differential lipid affinities of cholesterol. Biophys. J. 81:2001;2257-2267.
55. Lezcano M., Ai-Soufi W., Novo M., Rodriguez-Nunez E., Tato J.V. Complexation of several benzimidazole-type fungicides with alpha and beta-cyclodextrins. J. Agric. Food Chem. 50:2002;108-112.
56. Li J., Guo Y., Zografi G. The solid-state stability of amorphous quinapril in the presence of beta-cyclodextrins. J. Pharm. Sci. 91:2002;229-243.
57. Loftsson T., Brewster M.E. Pharmaceutical applications of cyclodextrins: 1. Drug solubilisation and stabilization. J. Pharm. Sci. 85:1996;1017-1025.
58. Loftssona T., Jarvinen T. Cyclodextrins in ophthalmic drug delivery. Adv. Drug Deliv. Rev. 36:1999;59-79.
59. Loftsson T., Leeves N., Bjornsdottir B., Duffy L., Masson M. Effect of cyclodextrins and polymers on triclosan availability and substantivity in toothpastes in vivo. J. Pharm. Sci. 88:1999;1254-1258.
60. Loung J.H., Nguyen A.L. Achiral selectivity in cyclodextrin modified capillary electrophoresis. J. Chromatogr. A. 792:1997;431-444.
61. Lu X., Chen Y. 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. 955:2002;133-140.
62. Luong J.H., Brown R.S., Male K.B., Cattaneo M.V., Zhao S. Enzyme reactions in the presence of cyclodextrins: biosensors and enzyme assays. Trends Biotechnol. 13:1995;457-463.
63. Ma H.M., Wang Z.H., Su M.H. New triazine spectroscopic reagent for the separation of DL-amino acids by micellar electrokinetic chromatography. J. Chromatogr. A. 955:2002;125-131.
64. Mabuchi N, Ngoa M. Controlled release powdered flavour preparations and confectioneries containing preparations. Japanese Patent JP 128,638, 2001.
65. Mahato S.B., Garai S. Advances in microbial steroid biotransformation. Steroids. 62:1997;332-345.
66. Mann C, Melzig M, Weigang U. Photochromatic plastic articles using cyclodextrins. European Patent 1,099,743, 1999.
67. Marchini A., Apolito M., Massari P., Atzeni M., Copass M., Olivieri R. Cyclodextrins for growth of Helicobacter pylori and production of vacuolating cytotoxin. Arch. Microbiol. 164:1995;290-293.
68. Matsuda H., Arima H. Cyclodextrins in transdermal and rectal delivery. Adv. Drug Deliv. Rev. 36:1999;81-99.
69. Merkus F.W., Verhoef J.C., Marttin E., Romeijn S.G., Van P.H., Hermens W.A., Schipper N.G. Cyclodextrins in nasal drug delivery. Adv. Drug Deliv. Rev. 36:1999;41-57.
70. Momose T., Mure M., Iida T., Goto J., Nambara T. Method for the separation of the unconjugates and conjugates of chenodeoxycholic acid and deoxycholic acid by two-dimensional reversed-phase thin layer chromatography with methyl beta-cyclodextrin. J. Chromatogr. A. 811:1998;171-180.
71. Monza S.A., Ponchel G., Puisieux F., Duchene D. Combined poly (isobutylcyanoacrylate) and cyclodextrins nanoparticles for enhancing the encapsulation of lipophilic drugs. Pharm. Res. 15:1998;1051-1055.
72. Morozumi T., Uetsuka H., Komiyama M., Pitha J. Selective synthesis using cyclodextrins as catalyst: Part 6. Cyclodextrin modification for para-selective hydroxymethylation and hydroxyetheylation of phenol. J. Mol. Catal. 70:1991;399-406.
73. Muñoz-Botella S., del Castillo B., Martín M.A. Cyclodetrin properties and applications of inclusion complex formation. Ars. Pharm. 36:1995;187-198.
74. Nicolazzi C., Abdou S., Collomb J., Marsura A., Finance C. Effect of the complexation with cyclodextrins on the in vitro antiviral activity of ganciclovir against human cytomegalovirus. Bioorg. Med. Chem. 9:2001;275-282.
75. Nie M.Y., Zhou L.M., Wang Q.H., Zhu D.Q. Enantiomer separation of mandelates and their analogs on cyclodextrin derivative chiral stationary phases by capillary GC. Anal. Sci. 17:2001;1183-1187.
76. Nunez-Delicado E., Sojo M.M., Sanchez-Ferrer A., Garcia-Carmona F. Hydroperoxidase activity of lipoxygenase in the presence of cyclodextrins. Arch. Biochem. Biophys. 367:1999;274-280.
77. Parrish MA. Cyclodextrins - A Review. Available from Sterling Organics. Newcastle-upon-Tyne NE3 3TT. England 1988.
78. Prabhu K.S., Ramadoss C.S. Penicillin acylase catalyzed synthesis of penicillin-G from substrates anchored in cyclodextrins. Indian J. Biochem. Biophys. 37:2000;6-12.
79. Prasad N, Strauss D, Reichart G. Cyclodextrins inclusion for food, cosmetics and pharmaceuticals. European Patent 1,084,625, 1999.
80. Pun S.H., Davis M.E. Development of a nonviral gene delivery vehicle for systemic application. Bioconjug. Chem. 13:2002;630-639.
81. Qin W., Wei H., Li S.F. Separation of ionic liquid cations and related imidazole derivatives by alpha-cyclodextrin modified capillary zone electrophoresis. Analyst. 127:2002;490-493.
82. Rao K.R., Bhanumathi N., Srinivasan T.N., Sattur P.B. A regioselective enzyme catalysed cycloaddition. Tetrahedron Lett. 31:1990;892-899.
83. Rao V.M., Haslam J.L., Stella V.J. Controlled and complete release of a model poorly water-soluble drug, prednisolone, from hydroxypropyl methylcellulose matrix tablets using (SBE)(7 m)-beta-cyclodextrin as a solubilizing agent. J. Pharm. Sci. 90:2001;807-816.
84. Redenti E., Pietra C., Gerloczy A., Szente L. Cyclodextrin in oligonucleotide delivery. Adv. Drug Deliv. Rev. 53:2001;235-244.
85. Reid BJ, Semple KT, Jhones KC. Soil test for determining bioavailability of pollutants. PCT Int Appl WO 99 54,727, 1999.
86. Roessler B.J., Bielinska A.U., Janczak K., Lee I., Baker J.R. Substituted beta-cyclodextrins interact with PAMAM dendrimer-DNA complexes and modify transfection efficiency. Biochem. Biophys. Res. Commun. 283:2001;124-129.
87. Roux M., Auzely-Velty R., Djedaini-Pilard F., Perly B. Cyclodextrin-induced lipid lateral separation in DMPC membranes: nuclear magnetic resonance study. Biophys. J. 82:2002;813-822.
88. Sawada H., Suzuki T., Akiyama S., Nakao Y. Stimulatory effect of cyclodextrins on the production of lankacidin-group antibiotics by Streptomyces species. Appl. Microbiol. Biotechnol. 26:1987;522-526.
89. Sawada H., Suzuki T., Akiyama S., Nakao Y. Mechanism of the stimulatory effect of cyclodextrins on lankacidin-producing Streptomyces species. Appl. Microbiol. Biotechnol. 32:1990;556-559.
90. Scalia S., Villani S., Casolari A. Inclusion complexation of the sunscreen agent 2-ethylhexyl-p-dimethylaminobenzoate with hydroxypropyl-beta-cyclodextrin: effect on photostability. J. Pharm. Pharmacol. 51:1999;1367-1374.
91. Schmid G. Cyclodextrin glucanotransferse production: yield enhancement by overexpression of cloned genes. Trends Biotechnol. 7:1989;244-248.
92. Schneiderman E., Stalcup A.M. Cyclodextrins: a versatile tool in separation science. J. Chromatogr. B. 745:2000;83-102.
93. Shitty H., Bar R. New approach for selective separation of dilute products from simulated Clostridial fermentation broths using cyclodextrins. Biotechnol. Bioeng. 39:1992;462-466.
94. Siefert B., Pleyer U., Muller M., Hartmann C., Keipert S. Influence of cyclodextrins on the in vitro corneal permeability and in vivo ocular distribution of thalidomide. Pharmacol. Ther. 15:1999;429-431.
95. Singer Y., Shitty H., Bar R. Microbial transformation in a cyclodextrin medium: part 2. Reduction of anrostenedione to testosterone by Saccharomyces cerevisiae. Appl. Microbiol. Biotechnol. 35:1991;731-737.
96. Sojo M.M., Nunez-Delicado E., Garcia-Carmona F., Sanchez-Ferrer A. Cyclodextrins as activator and inhibitor of latent banana pulp polyphenol oxidase. J. Agric. Food Chem. 47:1999;518-523.
97. Stalcup A.M., Gahm K.H., Gratz S.R., Sutton R.M. Application of classical gel electrophoresis to the chiral separation of milligram quantities of terbutaline. Anal. Chem. 1998;70144-70148.
98. Stella V.J., Rajewski R.A. Cyclodextrins: their future in drug formulation and delivery. Pharm. Res. 14:1997;556-567.
99. Subba R, Pillarisetti V, Kumble SP, Annadurai RS, Srinivasan M, Rao AS, Ramadoss CS. Insecticidal CD inclusion complexes of neem extract. PCT Int Appl WO 00 54,596, 2000.
100. Sumiyoshi H. Utilisation of inclusion complexes with plant components for foods. Nippon Shokuhin Shinsozai Kenkyukaishi. 2:1999;109-114.
101. Sung H. Composition for ginger preservation. Repub Korea KR 9,707,148, 1997.
102. Szetjli J. Downstream processing using cyclodextrins. TIBTECH. 7:1989;171-174.
103. Szetjli J. Introduction and general overview of cyclodextrin chemistry. Chem. Rev. 98:1998;1743-1753.
104. Takahashi K. Organic reactions mediated by cyclodextrins. Chem. Rev. 98:1998;2013-2031.
105. Takeshita K, Urata T. Antimicrobial food preservatives containing cyclodextrin inclusion complexes. Japanese Patent JP 29,054, 2001.
106. Tatsuya S. Stabilisation of fragrance in bathing preparations. Japanese Patent 11,209,787, 1999.
107. Toussaint B., Hubert P.H., Tjaden U.R., van der Greef J., Crommen J. Enantiomeric separation of clenbuterol by transient isotachophoresis-capillary zone electrophoresis-UV detection new optimization technique for transient isotachophoresis. J. Chromatogr. A. 871:2000;173-180.
108. Trinh J, Dodd TM, Bartolo R, Lucas JM. Cyclodextrin based compositions for reducing body odour. US Patent 5,897,855, 1999.
109. Uekama K., Hirayama F., Ikeda K., Inaba K. Utilization of cyclodextrin complexation for separation of E, A, and B prostaglandins by ion-exchange liquid chromatography. J. Pharm. Sci. 66:1977;706-710.
110. Uekama K., Adachi H., Irie T., Yano T., Saita M., Noda K. Improved transdermal delivery of prostaglandin E1 through hairless mouse skin: combined use of carboxymethyl ethyl beta-cyclodextrin and penetration enhancers. J. Pharm. Pharmacol. 44:1992;119-121.
111. Uekama K., Hrayama F., Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 98:1998;2045-2076.
112. Uekama K., Hirayama F., Irie T. Cyclodextrin drug carrier systems. Chem. Rev. 98:1998;2045-2076.
113. Uekama K., Hieda Y., Hirayama F., Arima H., Sudoh M., Yagi A.et al. Stabilizing and solubilizing effects of sulfobutyl ether beta-cyclodextrin on prostaglandin E1 analogue. Pharm. Res. 18:2001;1578-1585.
114. Vavia P.R., Adhage N.A. Inclusion complexation of nimesulide with beta-cyclodextrins. Drug Dev. Ind. Pharm. 25:1999;543-545.
115. Visconti P.E., Galantino-Homer H., Ning X., Moore G.D., Valenzuela J.P., Jorez C.J., Alvarez J.G., Kopf G.S. Cholesterol efflux-mediated signal transduction in mammalian sperm: beta-cyclodextrins initiate transmembrane signaling leading to an increase in protein tyrosine phosphorylation and capacitation. J. Biol. Chem. 274:1999;3235-3242.
116. 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.
117. Wu C., Fan J. Applications of cyclodextrin to water treatment. Shuichuli Jishu. 24:1998;67-70.
118. Ye H., Tong W., Dsouza V.T. Efficient catalysis of a redox reaction by an artificial enzyme. J. Am. Chem. Soc. 114:1992;5470-5472.
119. Zarzycki P.K., Kulhanek K.M., Smith R. Chromatographic behaviour of selected steroids and their inclusion complexes with beta-cyclodextrin on octadecylsilica stationary phases with different carbon loads. J. Chromatogr. A. 955:2002;125-131.
120. Zhang Y., Jiang X.G., Yao J. Nasal absorption enhancement of insulin by sodium deoxycholate in combination with cyclodextrins. Acta Pharmacol. Sin. 22:2001;1051-1156.
121. Zhao T., Temsamani J., Agarwal S. Use of cyclodextrin and its derivatives as carriers for oligonucleotide delivery. Antisense Res. 5:1995;185-192.