Cyclodextrin based rotaxanes, polyrotaxanes and polypseudorotaxanes and their biomedical applications

Current Topics in Medicinal Chemistry

Volumn 14, Issue 4, 2014, Pages 478-493

  García Río, Luis ^a   Otero Espinar, Francisco J ^b   Luzardo Alvarez, Asteria ^b   Blanco Méndez, José ^b  

^a Universidad de Santiago de Compostela ^*  (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Cyclodextrin; Drug delivery; Gene delivery; Polypseudorotaxane; Polyrotaxane; Pseudorotaxane; Rotaxane; Tissue engineering

Indexed keywords

CHITOSAN; CICLOPIROXOLAMINE; CYCLODEXTRIN; GLYCOSAMINOGLYCAN; HYDROXYAPATITE; MACROCYCLIC COMPOUND; METAL COMPLEX; PHENYLALANINE; POLYETHYLENEIMINE; POLYPSEUDOROTAXANE; POLYROTAXANE; ROTAXANE; TAXANE DERIVATIVE; TRIAMCINOLONE ACETONIDE; UNCLASSIFIED DRUG;

CELL ADHESION; CELL MIGRATION; CELL PROLIFERATION; CELL SURVIVAL; CHEMICAL STRUCTURE; COVALENT BOND; CYTOTOXICITY; DNA BINDING; ENCAPSULATION; ENDOCYTOSIS; GENE EXPRESSION; GENE TARGETING; GENETIC TRANSFECTION; HUMAN; MOLECULAR WEIGHT; NERVE DEGENERATION; NIEMANN PICK DISEASE; NONHUMAN; OSSIFICATION; POLYMERIZATION; REVIEW; TISSUE ENGINEERING; TISSUE REGENERATION; X RAY CRYSTALLOGRAPHY;

CYCLODEXTRINS; DRUG DELIVERY SYSTEMS; HUMANS; MODELS, MOLECULAR; ROTAXANES; TISSUE ENGINEERING;

EID: 84894079615     PISSN: 15680266     EISSN: 18734294     Source Type: Journal    
DOI: 10.2174/1568026613666131219123910     Document Type: Review

References (175)

1. Credi, A, Artificial Molecular Motors Powered by Light. Aus. J. Chem., 2006, 59 (3), 157-169.
2. Tian, H.; Wang, Q.-C. Recent progress on switchable rotaxanes. Chem. Soc. Rev., 2006, 35 (4), 361-374.
3. Sauvage, J.P. Transition metal-complexed catenanes and rotaxanes as molecular machine prototypes. Chem. Commun., 2005, 28 (12), 1507-10.
4. Kay, E.; Leigh, D. Hydrogen Bond-Assembled Synthetic Molecular Motors and Machines. In Molecular Machines, Kelly, T.R. Ed. Springer Berlin Heidelberg: 2005; Vol. 262, pp 133-177.
5. Kay, E.R.; Leigh, D.A. Photochemistry: Lighting up nanomachines. Nature, 2006, 440 (7082), 286-287.
6. Harada, A. Cyclodextrin-Based Molecular Machines. Acc. Chem. Res., 2001, 34 (6), 456-464.
7. Balzani, V.; Credi, A.; Raymo, F.M.; Stoddart, J.F. Artificial Molecular Machines. Ang. Chemie Int. Ed., 2000, 39 (19), 3348-3391.
8. Nepal, D.; Samal, S.; Geckeler, K.E. The First Fullerene-Terminated Soluble Poly(azomethine) Rotaxane. Macromolecules, 2003, 36 (11), 3800-3802.
9. Born, M.; Ritter, H. Pseudo-polymer analogous reactions: Methylation of alcohol groups of non-covalently anchored 2,6-dimethyl--cyclodextrin components located in branched side chains of a poly(tandem-rotaxane). Ad. Materials, 1996, 8 (2), 149-151.
10. Chatterjee, M.N.; Kay, E.R.; Leigh, D.A. Beyond Switches: Ratcheting a Particle Energetically Uphill with a Compartmentalized Molecular Machine. J. Am. Chem. Soc., 2006, 128 (12), 4058-4073.
11. Qu, D.-H.; Wang, Q.-C.; Ma, X.; Tian, H. A [3]Rotaxane with Three Stable States That Responds to Multiple-Inputs and Displays Dual Fluorescence Addresses. Chem. Eur. J., 2005, 11 (20), 5929-5937.
12. Wang, Q.-C.; Qu, D.-H.; Ren, J.; Chen, K.; Tian, H. A Lockable Light-Driven Molecular Shuttle with a Fluorescent Signal. Ang. Chem. Int. Ed., 2004, 43 (20), 2661-2665.
13. Feringa, B.L. In Control of Motion: From Molecular Switches to Molecular Motors. Acc. Chem. Res., 2001, 34 (6), 504-513.
14. Asakawa, M.; Higuchi, M.; Mattersteig, G.; Nakamura, T.; Pease, A.R.; Raymo, F.M.; Shimizu, T.; Stoddart, J. F. Current/Voltage Characteristics of Monolayers of Redox-Switchable [2]Catenanes on Gold. Adv. Materials, 2000, 12 (15), 1099-1102.
15. Qu, D.-H.; Wang, Q.-C.; Tian, H. A Half Adder Based on a Photochemically Driven [2]Rotaxane. Ang. Chem. Int. Ed., 2005, 44 (33), 5296-5299.
16. Qu, D.H.; Ji, F.Y.; Wang, Q.C.; Tian, H. A Double INHIBIT Logic Gate Employing Configuration and Fluorescence Changes. Adv. Materials, 2006, 18 (15), 2035-2038.
17. Collier, C.P.; Wong, E.W.; Belohradsk, M.; Raymo, F.M.; Stoddart, J.F.; Kuekes, P.J.; Williams, R.S.; Heath, J.R. Electronically Configurable Molecular-Based Logic Gates. Science, 1999, 285 (5426), 391-394.
18. Wong, E.W.; Collier, C.P.; B hloradsk, M.; Raymo, F.M.; Stoddart, J.F.; Heath, J.R. Fabrication and Transport Properties of Single-Molecule-Thick Electrochemical Junctions. J. Am. Chem. Soc., 2000, 122(24), 5831-5840.
19. Leigh, D.A.; Morales, M.Á. F.; Pérez, E.M.; Wong, J.K.Y.; Saiz, C.G.; Slawin, A.M.Z.; Carmichael, A.J.; Haddleton, D.M.; Brouwer, A.M.; Buma, W.J.; Wurpel, G.W.H.; León, S.; Zerbetto, F. Patterning through Controlled Submolecular Motion: Rotaxane-Based Switches and Logic Gates that Function in Solution and Polymer Films. Ang. Chem. Int. Ed., 2005, 44 (20), 3062-3067.
20. Cacialli, F.; Wilson, J.S.; Michels, J.J.; Daniel, C.; Silva, C.; Friend, R.H.; Severin, N.; Samori, P.; Rabe, J.P.; O'Connell, M.J.; Taylor, P.N.; Anderson, H.L. Cyclodextrin-threaded conjugated polyrotaxanes as insulated molecular wires with reduced interstrand interactions. Nat. Mater., 2002, 1 (3), 160-164.
21. Taylor, P.N.; Hagan, A.J.; Anderson, H.L. Hindered fluorescence quenching in an insulated molecular wire. Org. Biomol. Chem., 2003, 1 (21), 3851-3856.
22. Taylor, P.N.; O'Connell, M.J.; McNeill, L.A.; Hall, M.J.; Aplin, R.T.; Anderson, H.L. Insulated Molecular Wires: Synthesis of Conjugated Polyrotaxanes by Suzuki Coupling in Water. Ang. Chem. Int. Ed., 2000, 39 (19), 3456-3460.
23. Willner, I.; Pardo-Yissar, V.; Katz, E.; Ranjit, K.T. A photoactivated 'molecular train' for optoelectronic applications: light-stimulated translocation of a -cyclodextrin receptor within a stoppered azobenzene-alkyl chain supramolecular monolayer assembly on a Au-electrode. J. Electroanaly. Chem., 2001, 497 (1-2), 172-177.
24. Li, J. Cyclodextrin-based self-assembled supramolecular hydrogels and cationic polyrotaxanes for drug and gene delivery applications. J. Drug Delivery Sci. Tech., 2010, 20 (6), 399-405.
25. Li, J.; Zhao, F.; Li, J. Polyrotaxanes for applications in life science and biotechnology. App. Microbiol. Biotech., 2011, 90 (2), 427-443.
26. Schalley, C.A.; Vögtle, F.; Dötz, K.H. Templates in Chemistry I. Springer: Berlin Heidelberg, 2004; Vol. 248.
27. Balzani, V.; Credi, A.; Venturi, M. Light powered molecular machines. Chem. Soc. Rev., 2009, 38 (6), 1542-1550.
28. Balzani, V.; Credi, A.; Silvi, S.; Venturi, M. Artificial nanomachines based on interlocked molecular species: recent advances. Chem. Soc. Rev.,2006, 35 (11), 1135-1149.
29. Schliwa, M. Molecular Motors. Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2004; pp 79-109.
30. Cavallini, M.; Biscarini, F.; Léon, S.; Zerbetto, F.; Bottari, G.; Leigh, D.A. Information Storage Using Supramolecular Surface Patterns. Science, 2003, 299 (5606), 531.
31. Altieri, A.; Bottari, G.; Dehez, F.; Leigh, D.A.; Wong, J.K.Y.; Zerbetto, F. Remarkable Positional Discrimination in Bistable Light-and Heat-Switchable Hydrogen-Bonded Molecular Shuttles. Ang. Chem. Int. Ed., 2003, 42 (20), 2296-2300.
32. Wurpel, G.W.H.; Brouwer, A.M.; van Stokkum, I.H.M.; Farran, A.; Leigh, D.A. Enhanced Hydrogen Bonding Induced by Optical Excitation: Unexpected Subnanosecond Photoinduced Dynamics in a Peptide-Based [2]Rotaxane. J. Am. Chem. Soc., 2001, 123 (45), 11327-11328.
33. Brouwer, A.M.; Frochot, C.; Gatti, F.G.; Leigh, D.A.; Mottier, L.C.; Paolucci, F.; Roffia, S.; Wurpel, G.W.H. Photoinduction of Fast, Reversible Translational Motion in a Hydrogen-Bonded Molecular Shuttle. Science, 2001, 291 (5511), 2124-2128.
34. Balzani, V.; Credi, A.; Marchioni, F.; Stoddart, J.F. Artificial molecular-level machines. Dethreading-rethreading of a pseudorotaxane powered exclusively by light energy. Chem. Commu., 2001, 18, 1860-1861.
35. Jeppesen, J.O.; Nielsen, K.A.; Perkins, J.; Vignon, S.A.; Di Fabio, A.; Ballardini, R.; Gandolfi, M.T.; Venturi, M.; Balzani, V.; Becher, J.; Stoddart, J.F. Amphiphilic Bistable Rotaxanes. Chem. Eur. J., 2003, 9 (13), 2982-3007.
36. Bottari, G.; Dehez, F.; Leigh, D.A.; Nash, P.J.; Pérez, E.M.; Wong, J.K.Y.; Zerbetto, F. Entropy-Driven Translational Isomerism: A Tristable Molecular Shuttle. Ang. Chem. Int. Ed., 2003, 42 (47), 5886-5889.
37. Ma, X.; Cao, J.; Wang, Q.; Tian, H. Photocontrolled reversible room temperature phosphorescence (RTP) encoding[small beta]-cyclodextrin pseudorotaxane. Chem. Commu., 2011, 47 (12), 3559-3561.
38. Cheetham, A.G.; Hutchings, M.G.; Claridge, T.D.W.; Anderson, H.L. Enzymatic Synthesis and Photoswitchable Enzymatic Cleavage of a Peptide-Linked Rotaxane. Ang. Chem. Int. Ed., 2006, 45 (10), 1596-1599.
39. Dawson, R.E.; Maniam, S.; Lincoln, S.F.; Easton, C.J. Synthesis of [small alpha]-cyclodextrin [2]-rotaxanes using chlorotriazine capping reagents. Org. Biomol. Chem., 2008, 6 (10), 1814-1821.
40. Anelli, P.L.; Ashton, P.R.; Spencer, N.; Slawin, A.M.Z.; Stoddart, J.F.; Williams, D.J. Self-Assembling[2]Pseudorotaxanes. Ang. Chem. Int. Ed.,1991, 30 (8), 1036-1039.
41. Flood, A.H.; Ramirez, R.J.A.; Deng, W.-Q.; Muller, R.P.; Goddard III W.A.; Stoddart, J.F. Meccano on the Nanoscale; Blueprint for Making Some of the World Tiniest Machines. Aus. J. Chem., 2004, 57 (4), 301-322.
42. Dietrich-Buchecker, C.; Jimenez-Molero, M.C.; Sartor, V.; Sauvage, J.P. Rotaxanes and catenanes as prototypes of molecular machines and motors. Pure Appl. Chem., 2003, 75 (10), 10.
43. Kern, J.-M.; Sauvage, J.-P.; Bidan, G.; Divisia-Blohorn, B. Transition-metal-templated synthesis of rotaxanes and catenanes: From small molecules to polymers. J. Polym. Sci. A: Polym. Chem., 2003, 41 (22), 3470-3477.
44. Chambron, J.C.; Heitz, V.; Sauvage, J.P. Transition metal templated formation of [2]-and [3]-rotaxanes with porphyrins as stoppers. J. Am. Chem. Soc., 1993, 115 (26), 12378-12384.
45. Gibson, H.W.; Bheda, M.C.; Engen, P.T. Rotaxanes, catenanes, polyrotaxanes, polycatenanes and related materials. Prog. Polym. Sci., 1994, 19 (5), 843-945.
46. Kim, K. Mechanically interlocked molecules incorporating cucurbituril and their supramolecular assemblies. Chem. Soc. Rev., 2002, 31 (2), 96-107.
47. Johnston, A.G.; Leigh, D.A.; Murphy, A.; Smart, J.P.; Deegan, M.D. The Synthesis and Solubilization of Amide Macrocycles via Rotaxane Formation. J. Am. Chem. Soc.,1996, 118 (43), 10662-10663.
48. Lukin, O.; Vögtle, F. Knotting and Threading of Molecules: Chemistry and Chirality of Molecular Knots and Their Assemblies. Ang. Chem. Int. Ed.,2005, 44 (10), 1456-1477.
49. Vögtle, F.; Dünnwald, T.; Schmidt, T. Catenanes and Rotaxanes of the Amide Type. Acc.Chem.Res., 1996, 29 (9), 451-460.
50. Wenz, G. Cyclodextrins as Building Blocks for Supramolecular Structures and Functional Units. Ang. Chem. Int. Ed. English,1994, 33 (8), 803-822.
51. Preece, J.A.; Stoddart, J.F. Concept transfer from biology to materials. Nanobiology, 1994, 3, 7.
52. Gómez-López, M.; Preece, J.A.; Stoddart, J.F. The art and science of self-assembling molecular machines Nanotechnology, 1996, 7 (3), 9.
53. Amabilino, D.B.; Stoddart, J.F. Interlocked and Intertwined Structures and Superstructures. Chem. Rev., 1995, 95 (8), 2725-2828.
54. Philp, D.; Stoddart, J.F. Self-Assembly in Natural and Unnatural Systems. Ang. Chem. Int. Ed. English, 1996, 35(11), 1154-1196.
55. Fyfe, M.C.T.; Stoddart, J.F. Synthetic Supramolecular Chem. Acc. Chem. Res., 1997, 30 (10), 393-401.
56. Stoddart, J.F. Cyclodextrins, Off-the-Shelf Components for the Construction of Mechanically Interlocked Molecular Systems. Ang. Chem. Int. Ed. English, 1992, 31 (7), 846-848.
57. Nepogodiev, S.A.; Stoddart, J.F. Cyclodextrin-Based Catenanes and Rotaxanes. Chem. Rev.,1998, 98 (5), 1959-1976.
58. Wenz, G.; Han, B.-H.; Müller, A. Cyclodextrin Rotaxanes and Polyrotaxanes. Chem. Rev., 2006, 106 (3), 782-817.
59. Harada, A.; Hashidzume, A.; Yamaguchi, H.; Takashima, Y. Polymeric Rotaxanes. Chem. Rev., 2009, 109 (11), 5974-6023.
60. Chen, Y.; Zhang, Y.-M.; Liu, Y. Multidimensional nanoarchitectures based on cyclodextrins. Chem. Commu., 2010, 46 (31), 5622-5633.
61. Hanni, K.D.; Leigh, D.A. The application of CuAAC 'click' chemistry to catenane and rotaxane synthesis. Chem. Soc. Rev., 2010, 39 (4), 1240-1251.
62. Ashton, P.R.; Chrystal, E.J.T.; Glink, P.T.; Menzer, S.; Schiavo, C.; Spencer, N.; Stoddart, J.F.; Tasker, P.A.; White, A.J.P.; Williams, D.J. Pseudorotaxanes Formed Between Secondary Dialkylammonium Salts and Crown Ethers. Chem. Eur. J., 1996, 2 (6), 709-728.
63. Ashton, P.R.; Goodnow, T.T.; Kaifer, A.E.; Reddington, M.V.; Slawin, A.M.Z.; Spencer, N.; Stoddart, J.F.; Vicent, C.; Williams, D.J. A [2] Catenane Made to Order. Ang. Chem. Int. Ed. English, 1989, 28 (10), 1396-1399.
64. Crowley, J.D.; Goldup, S.M.; Lee, A.-L.; Leigh, D.A.; McBurney, R.T. Active metal template synthesis of rotaxanes, catenanes and molecular shuttles. Chem. Soc. Rev., 2009, 38 (6), 1530-1541.
65. Beves, J.E.; Blight, B.A.; Campbell, C.J.; Leigh, D.A.; McBurney, R.T. Strategies and Tactics for the Metal-Directed Synthesis of Rotaxanes, Knots, Catenanes, and Higher Order Links. Ang. Chem. Int. Ed., 2011, 50 (40), 9260-9327.
66. Schill, G.; Beckmann, W.; Schweickert, N.; Fritz, H. Untersuchungen zur statistischen Synthese von Rotaxanen. Chem. Berichte, 1986, 119 (8), 2647-2655.
67. Connors, K.A. The Stability of Cyclodextrin Complexes in Solution. Chem. Rev., 1997, 97 (5), 1325-1358.
68. Rekharsky, M.V.; Inoue, Y. Complexation Thermodynamics of Cyclodextrins. Chem. Rev.,1998, 98 (5), 1875-1918.
69. Schneider, H.-J.; Hacket, F.; Rüdiger, V.; Ikeda, H. NMR Studies of Cyclodextrins and Cyclodextrin Complexes. Chem. Rev.,1998, 98 (5), 1755-1786.
70. Giastas, P.; Mourtzis, N.; Yannakopoulou, K.; Mavridis, I. Pseudorotaxanes of -Cyclodextrin with Diamino End-functionalized Oligo-phenyl and -benzyl Compounds in Solution and in the Solid State. J. Inc. Phenomena Macrocyc. Chem., 2002, 44 (1/4), 247-250.
71. Eliadou, K.; Yannakopoulou, K.; Rontoyianni, A.; Mavridis, I.M. NMR Detection of Simultaneous Formation of [2]-and[3]Pseudorotaxanes in Aqueous Solution between -Cyclodextrin and Linear Aliphatic, -Amino acids, an, Diamine and an -Diacid of Similar Length, and Comparison with the Solid-State Structures. J. Org. Chem., 1999, 64 (17), 6217-6226.
72. Avram, L.; Cohen, Y. Complexation in Pseudorotaxanes Based on -Cyclodextrin and Different -Diaminoalkanes by NMR Diffusion Measurements. J. Org. Chem., 2002, 67 (8), 2639-2644.
73. Ashton, P.R.; Baxter, I.; Fyfe, M.C.T.; Raymo, F.M.; Spencer, N.; Stoddart, J.F.; White, A.J.P.; Williams, D.J. Rotaxane or Pseudorotaxane? That Is the Question. J. Am. Chem. Soc., 1998, 120 (10), 2297-2307.
74. Tsortos, A.; Yannakopoulou, K.; Eliadou, K.; Mavridis, I.M.; Nounesis, G. Partial Thermal Dethreading of[3]pseudorotaxanes of -Cyclodextrin with Linear Aliphatic, -Amino Acids in Aqueous Solution. J. Physic. Chem. B, 2001, 105 (13), 2664-2671.
75. Saito, H.; Yonemura, H.; Nakamura, H.; Matsuo, T. Stability and Exchange Properties of Through-ring Cyclodextrin Complexes. Effects of Chain Length in Polymethylene Bis[1-pyridinium] as Guest Molecules. Chem. Lett., 1990, 19 (4), 535-538.
76. Yonemura, H.; Saito, H.; Matsushima, S.; Nakamura, H.; Matsuo, T. Anomalously stable cyclodextrin complexes of phenothiazineviologen linked compounds with a long spacer chain. Tetrahedron Lett., 1989, 30 (24), 3143-3146.
77. Yonemura, H.; Kasahara, M.; Saito, H.; Nakamura, H.; Matsuo, T. Spectroscopic studies on exchange properties in through-ring cyclodextrin complexes of carbazole-viologen linked compounds: effects of spacer chain length. J. Physic. Chem.,1992, 96 (14), 5765-5770.
78. Toki, A.; Yonemura, H.; Matsuo, T. Thermodynamic Parameters for Formation of Through-Ring -Cyclodextrin Complexes of Donor-Acceptor Linked Compounds: Comparison between D2O and H2O Solutions of Anthracene-Viologen Systems with Intramolecular Charge-Transfer Absorption Spectra. Bull. Chem. Soc. Japan, 1993, 66 (11), 3382-3386.
79. Watanabe, M.; Nakamura, H.; Matsuo, T. Formation of Through-Ring alpha-Cyclodextrin Complexes with alpha,omega-Alkane-dicarboxylate Anion. Effects of the Aliphatic Chain Length and Electrostatic Factors on the Complexation Behavior. Bull. Chem. Soc. Japan,1992, 65 (1), 164-169.
80. Mirzoian, A.; Kaifer, A.E. Reactive Pseudorotaxanes: Inclusion Complexation of Reduced Viologens by the Hosts -Cyclodextrin and Heptakis(2,6-di-o-Methyl)--Cyclodextrin. Chem. Eur. J.,1997, 3 (7), 1052-1058.
81. Macartney, D.H. The self-assembly of a[2]pseudorotaxane of[small alpha]-cyclodextrin by the slippage mechanism. J.Chem. Soc. Perkin Transact. 2, 1996, 12, 2775-2778.
82. Ogino, H. Relatively high-yield syntheses of rotaxanes. Syntheses and properties of compounds consisting of cyclodextrins threaded by alpha, omega-diaminoalkanes coordinated to cobalt(III) complexes. J. Am. Chem. Soc.,1981, 103 (5), 1303-1304.
83. Wylie, R.S.; Macartney, D.H. Self-assembling metal rotaxane complexes of alpha-cyclodextrin. J. Am. Chem. Soc.,1992, 114 (8), 3136-3138.
84. Wylie, R.S.; Macartney, D.H. The self-assembly of -cyclodextrin rotaxanes of μ-(1,1 -(, -alkanediyl)bis-(4,4 -bipyridinium))bis[pentacyanoferrate-(II)] complexes. Supramol. Chem., 1993, 3 (1), 29-35.
85. Macartney, D.H.; Waddling, C.A. Kinetic and Spectroscopic Studies on Pentacyano(N-heterocycle)ferrate(II) Rotaxanes of alpha-Cyclodextrin with Symmetric and Asymmetric Threads. Inorg. Chem., 1994, 33 (25), 5912-5919.
86. Lyon, A.P.; Macartney, D.H. Kinetic and Spectroscopic Studies on -Cyclodextrin Rotaxanes with Pentacyano(cyanopyridinium) ferrate(II) Stoppers. Inorg. Chem.,1997, 36 (4), 729-736.
87. Hannak, R.B.; Färber, G.; Konrat, R.; Kräutler, B. An Organometallic B12-Rotaxane and a B12-Dimer, Relaxed and Loaded Forms of a Molecular Spring. J. Am. Chem. Soc.,1997, 119 (9), 2313-2314.
88. Harada, A.; Li, J.; Kamachi, M. Non-ionic[2]rotaxanes containing methylated[small alpha]-cyclodextrins. Chem.Comm.,1997, (15), 1413-1414.
89. Kawaguchi, Y.; Harada, A. A Cyclodextrin-Based Molecular Shuttle Containing Energetically Favored and Disfavored Portions in Its Dumbbell Component. Org. Lett., 2000, 2 (10), 1353-1356.
90. Onagi, H.; Carrozzini, B.; Cascarano, G.L.; Easton, C.J.; Edwards, A.J.; Lincoln, S.F.; Rae, A.D. Separated and Aligned Molecular Fibres in Solid State Self-Assemblies of Cyclodextrin[2]Rotaxanes. Chem. Eur. J., 2003, 9 (24), 5971-5977.
91. J. Easton; F. Lincoln; G. Meyer; Onagi, H. Synthesis and conformational analysis of an[small alpha]-cyclodextrin[2]-rotaxane. J. Chem. Soc, Perkin Transact. 1, 1999, 17, 2501-2506.
92. Craig, M.R.; Hutchings, M.G.; Claridge, T.D.W.; Anderson, H.L. Rotaxane-Encapsulation Enhances the Stability of an Azo Dye, in Solution and when Bonded to Cellulose. Ang. Chem. Int. Ed., 2001, 40 (6), 1071-1074.
93. Craig, M.R.; Claridge, T.D.W.; Anderson, H.L.; Hutchings, M.G. Synthesis of a cyclodextrin azo dye[3]rotaxane as a single isomer. Chem.Comm.,1999, 16, 1537-1538.
94. Haque, S.A.; Park, J.S.; Srinivasarao, M.; Durrant, J.R. Molecular-level insulation: An approach to controlling interfacial charge transfer. Adv. Materials, 2004, 16 (14), 1177.
95. Stanier, C.A.; O'Connell, M.J.; Clegg, W.; Anderson, H.L. Synthesis of fluorescent stilbene and tolan rotaxanes by Suzuki coupling. Chem.Comm., 2001, 5, 493-494.
96. Michels, J.J.; O'Connell, M.J.; Taylor, P.N.; Wilson, J.S.; Cacialli, F.; Anderson, H.L. Synthesis of Conjugated Polyrotaxanes. Chem. Eur. J., 2003, 9 (24), 6167-6176.
97. Terao, J.; Tang, A.; Michels, J.J.; Krivokapic, A.; Anderson, H.L. Synthesis of poly(para-phenylenevinylene) rotaxanes by aqueous Suzuki coupling. Chem.Comm.,2004, 1, 56-57.
98. Wang, Q.-C.; Ma, X.; Qu, D.-H.; Tian, H. Unidirectional Threading Synthesis of Isomer-Free[2]Rotaxanes. Chem. Eur. J., 2006, 12 (4), 1088-1096.
99. Ma, X.; Qu, D.; Ji, F.; Wang, Q.; Zhu, L.; Xu, Y.; Tian, H. A light-driven[1]rotaxane via self-complementary and Suzuki-coupling capping. Chem.Comm., 2007, 14, 1409-1411.
100. Zalewski, L.; Wykes, M.; Brovelli, S.; Bonini, M.; Breiner, T.; Kastler, M.; Dötz, F.; Beljonne, D.; Anderson, H. L.; Cacialli, F.; Samorì, P. A Conjugated Thiophene-Based Rotaxane: Synthesis, Spectroscopy, and Modeling. Chem. Eur. J., 2010, 16 (13), 3933-3941.
101. Liu, Y.; Song, S.-H.; Chen, Y.; Zhao, Y.-L.; Yang, Y.-W. The construction of a supramolecular polymeric rotaxane from bipyridine-ruthenium and cyclodextrin. Chem. Comm., 2005, 13, 1702-1704.
102. Liu, Y.; Zhao, Y.-L.; Zhang, H.-Y.; Song, H.-B. Polymeric Rotaxane Constructed from the Inclusion Complex of -Cyclodextrin and 4,4 -Dipyridine by Coordination with Nickel(II) Ions. Ang. Chem. Int. Ed., 2003, 42 (28), 3260-3263.
103. Liu, Y.; Zhao, Y.-L.; Zhang, H.-Y.; Yang, E.-C.; Guan, X.-D. Binding Ability and Assembly Behavior of -Cyclodextrin Complexes with 2,2'-Dipyridine and 4,4'-Dipyridine. J. Org. Chem., 2004, 69 (10), 3383-3390.
104. Zhao, Y.-L.; Zhang, H.-Y.; Guo, D.-S.; Liu, Y. Nanoarchitectures constructed from resulting polypseudorotaxanes of the beta-cyclodextrin/4,4 '-dipyridine inclusion complex with Co2+ and Zn2+ coordination centers. Chem. Mat., 2006, 18 (18), 4423-4429.
105. Yang, Y.W.; Chen, Y.; Liu, Y. Linear polypseudorotaxanes possessing many metal centers constructed from inclusion complexes of alpha-, beta-, and gamma-cyclodextrins with 4,4 '-dipyridine. Inorg. Chem., 2006, 45 (7), 3014-3022.
106. Iijima, T.; Uemura, T.; Tsuzuku, S.; Komiyama, J. Diffusion of cyclodextrins in aqueous polymer solutions. J. Polym. Sci: Polym. Phy. Ed., 1978, 16 (5), 793-802.
107. Kitano, H.; Okubo, T. Esterolysis in cyclodextrin-polyelectrolyte systems. J. Chem. Soc. Perkin Transact. 2, 1977, 4, 432-435.
108. Harada, A.; Kamachi, M. Complex formation between poly(ethylene glycol) and -cyclodextrin. Macromolecules, 1990, 23 (10), 2821-2823.
109. Harada, A.; Kamachi, M. Complex formation between cyclodextrin and poly(propylene glycol). Journal of the Chemical Society, Chem. Comm., 1990, 19, 1322-1323.
110. Wenz, G.; Keller, B. Threading Cyclodextrin Rings on Polymer Chains. Ang. Chem. Int. Ed. English, 1992, 31 (2), 197-199.
111. Harada, A.; Li, J.; Kamachi, M. Preparation and properties of inclusion complexes of polyethylene glycol withalpha-cyclodextrin. Macromolecules, 1993, 26 (21), 5698-5703.
112. Harada, A. Preparation and structures of supramolecules between cyclodextrins and polymers. Coord. Chem. Rev., 1996, 148 (0), 115-133.
113. Harada, A.; Li, J.; Kamachi, M. Formation of Inclusion Complexes of Monodisperse Oligo(ethylene glycol)s with alpha Cyclodextrin. Macromolecules, 1994, 27 (16), 4538-4543.
114. Harada, A. Construction of supramolecular structures from cyclodextrins, polymers. Carbohyd. Polymers, 1997, 34 (3), 183-188.
115. Harada, A.; Li, J.; Kamachi, M.; Kitagawa, Y.; Katsube, Y. Structures of polyrotaxane models. Carbohyd. Res., 1997, 305 (2), 127-129.
116. Harada, A.; Okada, M.; Li, J.; Kamachi, M. Preparation and Characterization of Inclusion Complexes of Poly(propylene glycol) with Cyclodextrins. Macromolecules, 1995, 28 (24), 8406-8411.
117. Harada, A.; Okada, M.; Kamachi, M. Preparation and Characterization of Inclusion Complexes of Poly(alkyl vinyl ether) with Cyclodextrins. Bull. Chem. Soc. Jpn., 1998, 71, 7.
118. Harada, A.; Li, J.; Kamachi, M. Complex Formation between Poly(methyl vinyl ether) and -Cyclodextrin. Chem. Lett., 1993, 237-240.
119. Harada, A.; Li, J.; Kamachi, M. Double-stranded inclusion complexes of cyclodextrin threaded on poly(ethylene glycol). Nature, 1994, 370 (6485), 126-128.
120. Udachin, K.A.; Wilson, L.D.; Ripmeester, J.A. Solid Polyrotaxanes of Polyethylene Glycol and Cyclodextrins: The Single Crystal X-ray Structure of PEG -cyclodextrin. J. Am. Chem. Soc., 2000, 122 (49), 12375-12376.
121. Shirakawa, H.; Louis, E.J.; MacDiarmid, A.G.; Chiang, C.K.; Heeger, A.J. Synthesis of electrically conducting organic polymers: halogen derivatives of polyacetylene, (CH). J. Chem. Soc. Chem. Commun., 1977, 16, 578-580.
122. Cardin, D.J. Encapsulated Conducting Polym.s. Adv. Materials, 2002, 14 (8), 553-563.
123. Yoshida, K.-i.; Shimomura, T.; Ito, K.; Hayakawa, R. Inclusion Complex Formation of Cyclodextrin and Polyaniline. Langmuir, 1999, 15 (4), 910-913.
124. Hbaieb, S.; Amdouni, N.; Parrot-Lopez, H.; Kalfat, R.; Chevalier, Y. Insulated molecular wires of polyaniline pseudopolyrotaxane. New J. Chem., 2011, 35 (1), 36-40.
125. Choi, H.S.; Ooya, T.; Lee, S.C.; Sasaki, S.; Kurisawa, M.; Uyama, H.; Yui, N. Dependence of polypseudorotaxane formation between cationic linear polyethylenimine and cyclodextrins. Macromolecules, 2004, 37 (18), 6705-6710.
126. Huh, K.M.; Ooya, T.; Sasaki, S.; Yui, N. Polymer Inclusion Complex Consisting of Poly(-lysine) and -Cyclodextrin. Macromolecules, 2001, 34 (8), 2402-2404.
127. Huh, K.M.; Tomita, H.; Ooya, T.; Lee, W.K.; Sasaki, S.; Yui, N. pH Dependence of Inclusion Complexation between Cationic Poly(-lysine) and -Cyclodextrin. Macromolecules, 2002, 35 (9), 3775-3777.
128. Choi, H.S.; Ooya, T.; Sasaki, S.; Yui, N.; Kurisawa, M.; Uyama, H.; Kobayashi, S. Spontaneous change of physical state from hydrogels to crystalline precipitates during poly-pseudorotaxane formation. Chem. Phys. Chem., 2004, 5 (9), 1431-1434.
129. Lee, S.C.; Choi, H.S.; Ooya, T.; Yui, N. Block-Selective Polypseudorotaxane Formation in PEI-b-PEG-b-PEI Copolymers via pH Variation. Macromolecules, 2004, 37 (20), 7464-7468.
130. Choi, H.S.; Lee, S.C.; Yamamoto, K.; Yui, N. Block-Selective Movement of -Cyclodextrins in Polyrotaxanes of PEI-b-PEG-b-PEI Copolymer. Macromolecules, 2005, 38 (23), 9878-9881.
131. Choi, H.S.; Hirasawa, A.; Ooya, T.; Kajihara, D.; Hohsaka, T.; Yui, N. pH-Sensitive Locomotion of Cyclodextrins in a Block-Selective Mobile Polyrotaxane. Chem. Phys. Chem., 2006, 7 (8), 1671-1673.
132. Al-Dosari, M.; Gao, X. Nonviral Gene Delivery: Principle, Limitations, and Recent Progress. AAPS J., 2009, 11 (4), 671-681.
133. Morille, M.; Passirani, C.; Vonarbourg, A.; Clavreul, A.; Benoit, J.-P. Progress in developing cationic vectors for non-viral systemic gene therapy against cancer. Biomaterials, 2008, 29 (24/25), 3477-3496.
134. Arima, H.; Motoyama, K.; Higashi, T. Cyclodextrin/dendrimer conjugates as DNA and olignucleotide carriers. Cur.Topics Med. Chem., 2014, 14 (4), 465-477.
135. Gonzalez, H.; Hwang, S.J.; Davis, M.E. New Class of Polymers for the Delivery of Macromolecular Therapeutics. Bioconjug. Chem.,1999, 10 (6), 1068-1074.
136. Li, J.; Loh, X.J. Cyclodextrin-based supramolecular architectures: Syntheses, structures, and applications for drug and gene delivery. Ad. Drug Delivery Rev., 2008, 60 (9), 1000-1017.
137. Li, J.J.; Zhao, F.; Li, J. Polyrotaxanes for applications in life science and biotechnology. App. Microbiol. Biotech., 2011, 90 (2), 427-443.
138. Shuai, X.T.; Merdan, T.; Unger, F.; Kissel, T. Supramolecular gene delivery vectors showing enhanced transgene expression and good biocompatibility. Bioconjug. Chem., 2005, 16 (2), 322-329.
139. Yamashita, A.; Choi, H.S.; Ooya, T.; Yui, N.; Akita, H.; Kogure, K.; Harashima, H. Improved cell viability of linear polyethylenimine through gamma-cyclodextrin inclusion for effective gene delivery. Chem. Bio.chem., 2006, 7 (2), 297-302.
140. Motoyama, K.; Hayashida, K.; Higashi, T.; Arima, H. Polypseudorotaxanes of pegylated alpha-cyclodextrin/ polyamidoamine dendrimer conjugate with cyclodextrins as a sustained release system for DNA. Bioorg. Med. Chem., 2012, 20 (4), 1425-1433.
141. Li, Z.; Yin, H.; Zhang, Z.; Liu, K. L.; Li, J. Supramolecular Anchoring of DNA Polyplexes in Cyclodextrin-Based Polypseudorotaxane Hydrogels for Sustained Gene Delivery. Biomacromolecules, 2012, 13, 3162-3172.
142. Yang, C.; Wang, X.; Li, H.; Tan, E.; Lim, C.T.; Li, J. Cationic Polyrotaxanes as Gene Carriers: Physicochemical Properties and Real-Time Observation of DNA Complexation, and Gene Transfection in Cancer Cells. J. Physic. Chem. B, 2009, 113 (22), 7903-7911.
143. Yang, C.; Wang, X.; Li, H.; Ding, J.L.; Wang, D.Y.; Li, J. A supramolecular gene carrier composed of multiple cationic alpha-cyclodextrins threaded on a PPO-PEO-PPO triblock polymer. Polymer, 2009, 50 (6), 1378-1388.
144. Nogueiras-Nieto, L.; Alvarez-Lorenzo, C.; Sandez-Macho, I.; Concheiro, A.; Otero-Espinar, F.J. Hydrosoluble Cyclodextrin/Poloxamer Polypseudorotaxanes at the Air/Water Interface, in Bulk Solution, and in the Gel State. J. Physic. Chem. B, 2009, 113 (9), 2773-2782.
145. Dandekar, P.; Jain, R.; Keil, M.; Loretz, B.; Muijs, L.; Schneider, M.; Auerbach, D.; Jung, G.; Lehr, C.-M.; Wenz, G. Cellular delivery of polynucleotides by cationic cyclodextrin polyrotaxanes. J. Controll.Rel: off. J. Controll.Rel Soc., 2012, 164 (3), 387-93.
146. Zhou, Y.; Wang, H.; Wang, C.; Li, Y.; Lu, W.; Chen, S.; Luo, J.; Jiang, Y.; Chen, J. Receptor-Mediated, Tumor-Targeted Gene Delivery Using Folate-Terminated Polyrotaxanes. Mol. Pharmaceutics, 2012, 9, 1067-1076.
147. Ooya, T.; Choi, H.S.; Yamashita, A.; Yui, N.; Sugaya, Y.; Kano, A.; Maruyama, A.; Akita, H.; Ito, R.; Kogure, K.; Harashima, H. Biocleavable Polyrotaxane-Plasmid DNA Polyplex for Enhanced Gene Delivery. J. Am. Chem. Soc., 2006, 128, 3852-3853.
148. Yamashita, A.; Yui, N.; Ooya, T.; Kano, A.; Maruyama, A.; Akita, H.; Kogure, K.; Harashima, H. Synthesis of a biocleavable polyrotaxane-plasmid DNA (pDNA) polyplex and its use for the rapid nonviral delivery of pDNA to cell nuclei. Nat. Protoc., 2006, 1, 2861-2869.
149. Yamashita, A.; Kanda, D.; Katoono, R.; Yui, N.; Ooya, T.; Maruyama, A.; Akita, H.; Kogure, K.; Harashima, H. Supramolecular control of polyplex dissociation and cell transfection: Efficacy of amino groups and threading cyclodextrins in biocleavable polyrotaxanes. J. Controll. Rel., 2008, 131 (2), 137-144.
150. Yamada, Y.; Nomura, T.; Harashima, H.; Yamashita, A.; Yui, N. Post-nuclear gene delivery events for transgene expression by biocleavable polyrotaxanes. Biomaterials, 2012, 33, 3952-3958.
151. Kulkarni, A.; DeFrees, K.; Schuldt, R.A.; Hyun, S.-H.; Wright, K.J.; Yerneni, C.K.; VerHeul, R.; Thompson, D.H. Cationic -Cyclodextrin:Poly(ethylene glycol) Polyrotaxanes for siRNA Delivery. Mol. Pharma., 2013, 10 (4), 1299-1305.
152. Kulkarni, A.; DeFrees, K.; Schuldt, R.A.; Vlahu, A.; VerHeul, R.; Hyun, S.-H.; Deng, W.; Thompson, D.H. Multi-armed cationic cyclodextrin:poly(ethylene glycol) polyrotaxanes as efficient gene silencing vectors. Integ. Biol., 2013, 5 (1), 115-121.
153. Watanabe, J.; Ooya, T.; Nitta, K.-H.; Park, K.D.; Kim, Y.H.; Yui, N. Fibroblast adhesion and proliferation on poly(ethylene glycol) hydrogels crosslinked by hydrolyzable polyrotaxane. Biomaterials, 2002, 23 (20), 4041-4048.
154. Watanabe, J.; Ooya, T.; Park, K.D.; Kim, Y.H.; Yui, N. Preparation and characterization of poly(ethylene glycol) hydrogels cross-linked by hydrolyzable polyrotaxane. J. Biomat. Sci, Polym. Ed., 2000, 11 (12), 1333-1345.
155. Watanabe, J.; Ooya, T.; Yui, N. Effect of acetylation of biodegradable polyrotaxanes on its supramolecular dissociation via terminal ester hydrolysis. J. Biomat. Sci, Polym. Ed., 1999, 10 (12), 1275-1288.
156. Liu, X.M.; Wiswall, A.T.; Rutledge, J.E.; Akhter, M.R.; Cullen, D.M.; Reinhardt, R.A.; Wang, D. Osteotropic beta-cyclodextrin for local bone regeneration. Biomaterials, 2008, 29 (11), 1686-1692.
157. Ichi, T.; Watanabe, J.; Ooya, T.; Yui, N. Controllable Erosion Time and Profile in Poly(ethylene glycol) Hydrogels by Supramolecular Structure of Hydrolyzable Polyrotaxane. Biomacromolecules, 2001, 2 (1), 204-210.
158. Tachaboonyakiat, W.; Furubayashi, T.; Katoh, M.; Ooya, T.; Yui, N. Novel biodegradable cholesterol-modified polyrotaxane hydrogels for cartilage regeneration. J. Biomat. Sci, Polym. Ed., 2004, 15 (11), 1389-1404.
159. Karageorgiou, V.; Kaplan, D. Porosity of 3D biomaterial scaffolds and osteogenesis. Biomaterials, 2005, 26 (27), 5474-5491.
160. Ooya, T.; Ichi, T.; Furubayashi, T.; Katoh, M.; Yui, N. Cationic hydrogels of PEG crosslinked by a hydrolyzable polyrotaxane for cartilage regeneration. React. Funct. Polymers, 2007, 67 (11), 1408-1417.
161. Teixeira, S.; Rodriguez, M.A.; Pena, P.; De Aza, A.H.; De Aza, S.; Ferraz, M.P.; Monteiro, F.J. Physical characterization of hydroxyapatite porous scaffolds for tissue engineering. Mat. Sci. Eng: C, 2009, 29 (5), 1510-1514.
162. Motoyama, K.; Hayashida, K.; Higashi, T.; Arima, H. Polypseudorotaxanes of pegylated -cyclodextrin/polyamidoamine dendrimer conjugate with cyclodextrins as a sustained release system for DNA. Bioorg. Med. Chem., 2012, 20, 1425-1433.
163. Simoes, S.M.N.; Veiga, F.; Torres-Labandeira, J.J.; Ribeiro, A.C.F.; Sandez-Macho, M.I.; Concheiro, A.; Alvarez-Lorenzo, C. Syringeable Pluronic-alpha-cyclodextrin supramolecular gels for sustained delivery of vancomycin. Eur. J. Pharm. Biopharm., 2012, 80 (1), 103-112.
164. He, Z.-X.; Wang, Z.-H.; Zhang, H.-H.; Pan, X.; Su, W.-R.; Liang, D.; Wu, C. Doxycycline and hydroxypropyl--cyclodextrin complex in poloxamer thermal sensitive hydrogel for ophthalmic delivery. Acta Pharmac. Sinica B, 2011, 1 (4), 254-260.
165. Qi, H.; Li, L.; Huang, C.; Li, W.; Wu, C. Optimization and Physicochemical Characterization of Thermosensitive Poloxamer Gel Containing Puerarin for Ophthalmic Use. Chem. Pharma. Bull., 2006, 54 (11), 1500-1507.
166. Lee, B.-J.; Lee, T.-S.; Cha, B.-J.; Kim, S.-H.; Kim, W.-B. Percutaneous absorption and histopathology of a poloxamer-based formulation of capsaicin analog. Int. J. Pharm., 1997, 159 (1), 105-114.
167. Nogueiras-Nieto, L.; Begona, D.-C. M.; Otero-Espinar, F.J. Thermogelling hydrogels of cyclodextrin/poloxamer polypseudorotaxanes as aqueous-based nail lacquers: application to the delivery of triamcinolone acetonide and ciclopirox olamine. Eur. J. Pharm. Biopharm., 2013, 83 (3), 370-7.
168. Nogueiras-Nieto, L.; Sobarzo-Sanchez, E.; Gomez-Amoza, J.L.; Otero-Espinar, F.J. Competitive displacement of drugs from cyclodextrin inclusion complex by polypseudorotaxane formation with poloxamer: implications in drug solubilization and delivery. Eur. J. Pharm. Biopharm., 2012, 80 (3), 585-95.
169. Bilensoy, E.; Rouf, M.A.; Vural, I.; Hincal, A.A. Thermosensitive vaginal gel formulation for the controlled release of clotrimazole via complexation to beta-cyclodextrin. J. Controll. Rel., 2006, 116 (2), e107-e109.
170. Bilensoy, E.; Abdur Rouf, M.; Vural, I.; en, M.; Atilla Hincal, A. Mucoadhesive, thermosensitive, prolonged-release vaginal gel for clotrimazole: -cyclodextrin complex. AAPS Pharm.Sci.Tech., 2006, 7 (2), E54-E60.
171. Singh, R.P.; Kumar, A.; Pathak, K. Thermally Triggered Mucoadhesive In Situ Gel of Loratadine: -Cyclodextrin Complex for Nasal Delivery. AAPS Pharm.Sci.Tech., 2013, 14 (1), 412-424.
172. Cho, H.-J.; Balakrishnan, P.; Park, E.-K.; Song, K.-W.; Hong, S.-S.; Jang, T.-Y.; Kim, K.-S.; Chung, S.-J.; Shim, C.-K.; Kim, D.-D. Poloxamer/cyclodextrin/chitosan-based thermoreversible gel for intranasal delivery of fexofenadine hydrochloride. J. Pharm. Sci., 2011, 100 (2), 681-691.
173. Abd EL-Gawad, H.A.E.-G.; Soliman, O.A.; Barker, S.A.; Girgis, G.N.S. Formulation and Physical Characterization of a Novel Sustained-Release Ophthalmic Delivery System for Sparfloxacin: the Effect of the Biological Environment. Ophthal. Res: Int J., 2013, 1 (1), 22.
174. Collins, C.J.; McCauliff, L.A.; Hyun, S.-H.; Zhang, Z.; Paul, L.N.; Kulkarni, A.; Zick, K.; Wirth, M.; Storch, J.; Thompson, D.H. Synthesis, Characterization, and Evaluation of Pluronic-Based -Cyclodextrin Polyrotaxanes for Mobilization of Accumulated Cholesterol from Niemann-Pick Type C Fibroblasts. Biochemistry, 2013, 52 (19), 3242-3253.
175. Otero-Espinar, F.J.; Luzardo-Alvarez, A.; Blanco-Mendez, J. Cyclodextrins: More than Pharmaceutical Excipients. Mini. Rev. Med. Chem., 2010, 10 (8), 715-725