Self-assembly of cyclodextrins: Formation of cyclodextrin polymer based nanoparticles

Journal of Drug Delivery Science and Technology

Volumn 22, Issue 3, 2012, Pages 215-221

  Fulop Z ^a   Kurkov, S V ^a   Nielsen, T T ^b   Larsen, K L ^b   Loftsson, T ^a  

^a UNIVERSITY OF ICELAND   (Iceland)

^b AALBORG UNIVERSITY   (Denmark)

Author keywords

Aggregation; Cyclodextrin polymers; Cyclodextrins; Nanoparticles; Self assembly; Stabilization

Indexed keywords

ALPHA CYCLODEXTRIN; BETA CYCLODEXTRIN; CYCLODEXTRIN; DEXTRAN; DRUG CARRIER; GAMMA CYCLODEXTRIN; MONOMER; NANOPARTICLE;

ATOMIC FORCE MICROSCOPY; BINDING SITE; CHEMICAL STRUCTURE; CLICK CHEMISTRY; ELECTRON MICROSCOPY; LIPOPHILICITY; MATHEMATICAL ANALYSIS; MEMBRANE PERMEABILITY; NANOMEDICINE; NANOTECHNOLOGY; NEUTRON SCATTERING; NUCLEAR MAGNETIC RESONANCE IMAGING; OSMOLALITY; PROTEIN AGGREGATION; RAMAN SPECTROMETRY; REVIEW; SCANNING ELECTRON MICROSCOPY; SOLUBILITY; TRANSMISSION ELECTRON MICROSCOPY;

EID: 84862850770     PISSN: 17732247     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1773-2247(12)50032-8     Document Type: Review

References (70)

1. Boulaiz H., Alvarez P.J., Ramirez A., Marchal J.A., Prados J., Rodriguez-Serrano F., Perán M., Melguizo C., Aranega A. Nanomedicine: application areas and development prospects - International Journal of Molecular Sciences, 12, 3303-3321, 2011.
2. Feynman R. - There's plenty of room at the bottom. - Eng. Sc., 23, 22-36, 1960.
3. Yu B., Meyyappan M. - Nanotechnology: role in emerging nanoelectronics - Solid-State Electronics, 50, 536-544, 2006.
4. Sahoo S.K., Parveen S., Panda J.J. - The present and future of nanotechnology in human health care. - Nanomedicine: Nanotechnology Biology and Medicine, 3, 20-31, 2007. (Pubitemid 46428187)
5. De Jong W.H., Borm P.J.A. - Drug delivery and nanoparticles: applications and hazards. - International Journal of Nanomedicine, 3 (2), 133-149, 2008. (Pubitemid 352042401)
6. Sanvicens N., Marco M.P. - Multifunctional nanoparticles-properties and prospects for their use in human medicine. - Trends in Biotechnology, 26 (8), 425-433, 2008.
7. Loftsson T., Duchêne D. - Cyclodextrins and their pharmaceutical applications. - International Journal of Pharmaceutics, 329, 1-11, 2007.
8. Messner M., Kurkov S.V., Jansook P., Loftsson T. - Self-assembled cyclodextrin aggregates and nanoparticles. - International Journal of Pharmaceutics, 387, 199-208, 2010.
9. Villiers A. - Sur la fermentation de la fécule par l'action du ferment butyrique. - Compt. Rend. Acad. Sci., 112, 536-538, 1891.
10. Larsen K.L. - Large cyclodextrins. - Journal of Inclusion Phenomena and Macrocyclic Chemistry, 43, 1-13, 2002.
11. Davis M.E., Brewster M.E. - Cyclodextrin-based pharmaceutics: past present and future. - Nature Reviews Drug Discovery, 3, 1023-1035, 2004. (Pubitemid 39642365)
12. Frömming K., Szejtli J. (Eds.) - Cyclodextrins in Pharmacy. - Kluwer Academic Publishers, Dordrecht-Boston, 1994.
13. Sabadini E., Cosgrove T., Egidio F.d.C. - Solubility of cyclomaltooligosaccharides (cyclodextrins) in H2O and D2O: a comparative study. - Carbohydrate Research, 341, 270-274, 2006. (Pubitemid 43042611)
14. Loftsson T., Brewster M.E. - Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. - Journal of Pharmaceutical Sciences, 85 (10), 1017-1025, 1996. (Pubitemid 26338912)
15. Higuchi T.C., Connors K.A. - Phase-solubility techniques. - Adv. Anal. Chem. Instrum., 4, 117-212, 1965.
16. Nielsen A.L., Steffensen K., Larsen K.L. - Self-assembling microparticles with controllable disruption properties based on cyclodextrin interactions. - Colloids and Surfaces B Biointerfaces, 73 (2), 267-275, 2009.
17. Miyajima K., Mukai T., Nakagaki M., Otagiri M., Uekama K. - Activity coefficients of dimethyl-β-cyclodextrin in aqueous solutions. - Bulletin of the Chemical Society of Japan, 59 (2), 643-644, 1986.
18. Miyajima K., Sawada M., Nakagaki M. - Viscosity B-coefficients apparent molar volumes and activity coefficients for α- and β-cyclodextrins in aqueous solutions. - Bulletin of the Chemical Society of Japan, 56 (12), 3556-3560, 1983. (Pubitemid 14546889)
19. Miyajima K., Sawada M., Nakagaki M. - Studies on aqueous solutions of saccharides. II. Viscosity B-coefficients apparent molar volumes and activity coefficients of D-glucose maltose and maltotriose in aqueous solutions. - Bulletin of the Chemical Society of Japan, 56 (7), 1954-1957, 1983. (Pubitemid 13602520)
20. Coleman A.W., Nicolis I., Keller N., Dalbiez J.P. - Aggregation of cyclodextrins: an explanation of the abnormal solubility of β-cyclodextrin. - Journal of Inclusion Phenomena and Molecular Recognition in Chemistry, 13 (2), 139-143, 1992.
21. Szente L., Szejtli J., Kis G.L. - Spontaneous opalescence of aqueous γ-cyclodextrin solutions: complex formation or self-aggregation? - Journal of Pharmaceutical Sciences, 87 (6), 778-781, 1998. (Pubitemid 28268581)
22. González-Gaitano G., Rodriguez P., Isasi J.R., Fuentes M., Tardajos G., Sánchez M. - The aggregation of cyclodextrins as studied by photon correlation spectroscopy - J. Incl. Phenom. Macrocycl. Chem., 44, 101-105, 2002. (Pubitemid 38075672)
23. Wu A., Shen X., He Y. - Investigation on γ-cyclodextrin nanotube induced by NN′NN′-diphenylbenzidine molecule. - Journal of Colloid and Interface Science, 297 (2), 525-533, 2006.
24. Loftsson T., Másson M., Brewster M.E. - Self-association of cyclodextrins and cyclodextrin complexes. - Journal of Pharmaceutical Sciences, 93, 1091-1099, 2004.
25. Loftsson T., Másson M., Sigurdsson H.H. - Cyclodextrins and drug permeability through semi-permeable cellophane membranes. - International Journal of Pharmaceutics, 232, 35-43, 2002. (Pubitemid 34076752)
26. Messner M., Kurkov S.V., Brewster M.E., Jansook P., Loftsson T. - Self-assembly of cyclodextrin complexes: aggregation of hydrocortisone/ cyclodextrin complexes. - International Journal of Pharmaceutics, 407, 174-183, 2011.
27. Messner M., Kurkov S.V., Flavià-Piera R., Brewster M.E., Loftsson T. - Self-assembly of cyclodextrins: the effect of the guest molecule. - International Journal of Pharmaceutics, 408, 235-247, 2011.
28. Messner M., Kurkov S.V., Palazon M.M., Fernandez B.Á., Brewster M.E., Loftsson T. - Self-assembly of cyclodextrin complexes: effect of temperature agitation and media composition on aggregation. - International Journal of Pharmaceutics, 419, 322-328, 2011.
29. Chatziefthimiou S.D., Yannakopoulou K., Mavridis I.M. - β-Cyclodextrin trimers enclosing an unusual organization of guest: the inclusion complex β-cyclodextrin/4-pyridinealdazine. - CrystEngComm, 9 (11), 976-976, 2007.
30. Makedonopoulou S., Mavridis I.M., Yannakopoulou K., Papaioannou J. - Organisation of long aliphatic monocarboxylic acids in β-cyclodextrin channels: crystal structures of the inclusion complexes of tridecanoic acid and (Z)-tetradec-7-enoic acid in β-cyclodextrin. - Chemical Communications, (19), 2133-2134, 1998.
31. Mourtzis N., Cordoyiannis G., Nounesis G., Yannakopoulou K. - Single and double threading of congo red into γ-cyclodextrin. solution structures and thermodynamic parameters of 1:1 and 2:2 adducts as obtained from NMR spectroscopy and microcalorimetry. - Supramolecular Chemistry, 15 (7-8), 639-649, 2003. (Pubitemid 37373967)
32. Paulidou A., Maffeo D., Yannakopoulou K., Mavridis I.M. - Similar modes of inclusion in complexes of β-cyclodextrin with sulfonylurea hypoglycemic drugs. - CrystEngComm, 12 (2), 517-517, 2010.
33. nd ed., Wiley & Sons, Chichester, 2002.
34. Layre A.-M., Wintgens V., Gosselet N.-M., Dalmas F., Amiel C. - Tuning the interactions in cyclodextrin polymer nanoassem-blies. - European Polymer Journal, 45, 3016-3026, 2009.
35. van de Manakker F., Vermonden T., van Nostrum C.F., Hennink W.E. - Cyclodextrin-based polymeric materials: synthesis properties and pharmaceutical/biomedical applications. - Biomacromolecules, 10 (12), 3157-3175, 2009.
36. Wintgens V., Amiel C. - Water-soluble γ-cyclodextrin polymers with high molecular weight and their complex forming properties. - European Polymer Journal, 46, 1915-1922, 2010.
37. Kolb H.C., Finn M.G., Sharpless K.B. - Click chemistry: diverse chemical function from a few good reactions. - Angewandte Chemie International Edition, 40 (11), 2004-2021, 2001.
38. Nielsen T.T., Wintgens V., Amiel C., Wimmer R., Larsen K.L. - Facile synthesis of beta-cyclodextrin-dextran polymers by "click" chemistry. - Biomacromolecules, 11 (7), 1710-1715, 2010.
39. Cavalli R., Trotta F., Tumiatti W. - Cyclodextrin-based nanosponges for drug delivery. - Journal of Inclusion Phenomena and Macrocyclic Chemistry, 56 (1-2), 209-213, 2006.
40. Swaminathan S., Pastero L., Serpe L., Trotta F., Vavia P., Aquilano D., Trotta M., Zara G., Cavalli R. - Cyclodextrin-based nanosponges encapsulating camptothecin: physicochemical characterization stability and cytotoxicity. - European Journal of Pharmaceutics and Biopharmaceutics, 74 (2), 193-201, 2010.
41. Duchêne D., Gref R. - Cyclodextrins and polymer nanoparticles. - In: Cyclodextrins in Pharmaceutics Cosmetics and Biomedicine, Current and Future Industrial Applications, E. Bilensoy Ed., Wiley & Sons, New Jersey, 2011, p. 371-391.
42. Jiang L., Yan Y., Huang J. - Versatility of cyclodextrins in self-assembly systems of amphiphiles. - Advances in Colloid and Interface Science, 169, 13-25, 2011.
43. Layre A.-M., Volet G., Wintgens V., Amiel C. - Associative network based on cyclodextrin polymer: a model system for drug delivery. - Biomacromolecules, 10 (12), 3283-3289, 2009.
44. Amiel C., Layre A.-M., Wintgens V., Dalmas F., Gosselet N.-M. - pH sensitive polymer nanoassemblies based on cyclodextrin polymer. - Journal of Inclusion Phenomena and Macrocyclic Chemistry, 69, 487-490, 2010.
45. Wintgens V., Nielsen T.T., Larsen K.L., Amiel C. - Size-controlled nanoassemblies based on cyclodextrin-modified dextrans. - Macromolecular Bioscience, 11, 1254-1263, 2011.
46. Davis M.E. - The first targeted delivery of siRNA in humans via a self-assembling cyclodextrin polymer-based nanoparticle: from concept to clinic. - Molecular Pharmaceutics, 6, 659-668, 2009.
47. Li Y., Ji L., Wang G., Song L., He B., Li L., Nie Y., Wu Y., Gu Z. - Study on the α-cyclodextrin/poly(ethylene glycol) self-assembly supramolecular nanoparticles for drug delivery. - Science China Chemistry, 53, 495-501, 2010.
48. Liu Y., Zhao D., Ma R., Xiong D.a., An Y., Shi L. - Chaperone-like α-cyclodextrins assisted self-assembly of double hydrophilic block copolymers in aqueous medium. - Polymer, 50, 855-859, 2009.
49. Zhang J., Ma P.X. - Host-guest interactions mediated nanoassemblies using cyclodextrin-containing hydrophilic polymers and their biomedical applications. - Nano Today, 5, 337-350, 2010.
50. El Fagui A., Dalmas F., Lorthioir C., Wintgens V., Volet G., Amiel C. - Well-defined core-shell nanoparticles containing cyclodextrin in the shell: a comprehensive study. - Polymer, 52, 3752-3761, 2011.
51. Zhang J., Shen X., Wu A., Zhang C., Chen Q., Gao H. - Formation of nanotubes and secondary assemblies of cyclodextrins induced by BBOT - Science China Chemistry, 53, 2019-2025, 2010.
52. Azaroual-Bellanger N., Perly B. - Investigation of the dynamics of cyclodextrins and their inclusion complexes in water by deuterium NMR. - Magnetic Resonance in Chemistry, 32 (1), 8-11, 1994.
53. Dagade D.H., Kolhapurkar R.R., Patil K.J. - Studies of osmotic coefficients and volumetric behaviour on aqueous solutions of β-cyclodextrin at 298.15 K. - Indian Journal of Chemistry Section A, 43, 2073-2080, 2004.
54. Moya-Ortega M.D., Alvarez-Lorenzo C., Sigurdsson H.H., Concheiro A., Loftsson T. - Cross-linked hydroxypropyl-β-cyclodextrin and γ-cyclodextrin nanogels for drug delivery: Physicochemical and loading/release properties - Carbohydrate Polymers 87(3), 2344-2351, 2012.
55. Moya-Ortega M.D., Alvarez-Lorenzo C., Sigurdsson H.H., Concheiro A., Loftsson T. - Cross-linked hydroxypropyl-βcyclodextrin and γ-cyclodextrin nanogels for drug delivery: physicochemical and loading/release properties. - Carbohydrate Polymers, 2011.
56. Nielsen T.T., Wintgens V., Larsen K.L., Amiel C. - Synthesis and characterization of poly(ethylene glycol) based β-cyclodextrin polymers. - Journal of Inclusion Phenomena and Macrocyclic Chemistry, 65, 341-348, 2009.
57. Choi S., Munteanu M., Ritter H. - Monoacrylated cyclodextrin via "click" reaction and copolymerization with N-isopropylacrylamide: guest controlled solution properties. - Journal of Polymer Research, 16 (4), 389-394, 2008.
58. Tanida F., Tojima T., Han S.-M., Nishi N., Tokura S., Sakairi N., Seino H., Hamada K. - Novel synthesis of a water-soluble cyclodextrin-polymer having a chitosan skeleton. - Polymer, 39, 5261-5263, 1998. (Pubitemid 128369414)
59. Daoud-Mahammed S., Couvreur P., Gref R. - Novel self-assembling nanogels: stability and lyophilisation studies. - International Journal of Pharmaceutics, 332, 185-191, 2007. (Pubitemid 46227769)
60. Daoud-Mahammed S., Ringard-Lefebvre C., Razzouq N., Rosilio V., Gillet B., Couvreur P., Amiel C., Gref R. - Spontaneous association of hydrophobized dextran and poly-β-cyclodextrin into nanoassemblies.Formation and interaction with a hydrophobic drug. - Journal of Colloid and Interface Science, 307, 83-93, 2007. (Pubitemid 46275703)
61. Gref R., Amiel C., Molinard K., Daoud-Mahammed S., Sébille B., Gillet B., Beloeil J.-C., Ringard C., Rosilio V., Poupaert J., Couvreur P. - New self-assembled nanogels based on host-guest interactions: characterization and drug loading. - Journal of Controlled Release, 111, 316-324, 2006.
62. Othman M., Bouchemal K., Couvreur P., Desmaële D., Morvan E., Pouget T., Gref R. - A comprehensive study of the spontaneous formation of nanoassemblies in water by a "lock-and-key" interaction between two associative polymers. - Journal of Colloid and Interface Science, 354, 517-527, 2011.
63. Mahmoud A.A., El-Feky G.S., Kamel R., Awad G.E.A. - Chitosan/ sulfobutylether-β-cyclodextrin nanoparticles as a potential approach for ocular drug delivery. - International Journal of Pharmaceutics, 413, 229-236, 2011.
64. Teijeiro-Osorio D., Remuñán-López C., Alonso M.J. - Chitosan/cyclodextrin nanoparticles can efficiently transfect the airway epithelium in vitro. - European Journal of Pharmaceutics and Biopharmaceutics, 71, 257-263, 2009.
65. Lopedota A., Trapani A., Cutrignelli A., Chiarantini L., Pantucci E., Curci R., Manuali E., Trapani G. - The use of Eudragit RS 100/cyclodextrin nanoparticles for the transmucosal administration of glutathione. - European Journal of Pharmaceutics and Biopharmaceutics, 72, 509-520, 2009.
66. Shu S., Zhang X., Wu Z., Wang Z., Li C. - Gradient cross-linked biodegradable polyelectrolyte nanocapsules for intracellular protein drug delivery. - Biomaterials, 31, 6039-6049, 2010.
67. Bilensoy E., Gürkaynak O., Dogan A.L., Hincal A.A. - Safety and efficacy of amphiphilic β-cyclodextrin nanoparticles for paclitaxel delivery. - International Journal of Pharmaceutics, 347(1-2), 163-170, 2008. (Pubitemid 350180328)
68. Cirpanli Y., Bilensoy E., Dogan A.L., Calis S. - Development of polymeric and cyclodextrin nanoparticles for camptothecin delivery. - Journal of Controlled Release, 148, e21-e23-e21-e23, 2010.
69. Chung J.W., Guo Y., Priestley R.D., Kwak S.-Y. - Colloidal gold nanoparticle formation derived from self-assembled supramolecular structure of cyclodextrin/Au salt complex. - Nanoscale, 3, 1766-1766, 2011.
70. Li R.X., Liu S.M., Zhao J.Q., Otsuka H., Takahara A. - Preparation and characterization of cross-linked β-cyclodextrin polymer/Fe304 composite nanoparticles with core-shell structures. - Chinese Chemical Letters, 22 (2), 217-220, 2011.