Modified cyclodextrins with pendant cationic and anionic moieties as hosts for highly stable inclusion complexes and molecular recognition

Current Organic Chemistry

Volumn 15, Issue 6, 2011, Pages 802-814

  Kraus, Tomáš ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

Author keywords

Cyclodextrins; Host guest complexes; Inclusion complexes; Ionic interactions

Indexed keywords

EID: 80051819114     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527211794518907     Document Type: Review

References (104)

1. Szejtli, J. Historical backgroung. In: Cyclodextrins; Szejtli, J. and Osa, T., Eds.; Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., and Lehn, J.-M., Eds. Pergamon: Oxford, 1996, Vol. 3; 1-3.
2. Houk, K. N.; Leach, A. G.; Kim, S. P.; Zhang, X. Y. Binding affinities of host-guest, protein-ligand, and protein-transition-state complexes. Angew. Chem. Int. Ed., 2003, 42, 4872.
3. Uekama, K.; Hirayama, F.; Arima, H. Recent aspect of cyclodextrin-based drug delivery system. J. Inclusion Phenom. Macrocyclic Chem., 2006, 56, 3.
4. Davis, M. E.; Brewster, M. E. Cyclodextrin-based pharmaceutics: Past, present and future. Nat. Rev. Drug Discov., 2004, 3, 1023.
5. Connors, K. A. The stability of cyclodextrin complexes in solution. Chem. Rev., 1997, 97, 1325.
6. Liu, L.; Guo, Q. X. The driving forces in the inclusion complexation of cyclodextrins. J. Inclusion Phenom. Macrocyclic Chem., 2002, 42, 1.
7. Harries, D.; Rau, D. C.; Parsegian, V. A. Solutes probe hydration in specific association of cyclodextrin and adamantane. J. Am. Chem. Soc., 2005, 127, 2184.
8. Taulier, N.; Chalikian, T. V. Hydrophobic hydration in cyclodextrin complexation. J. Phys. Chem. B, 2006, 110, 12222.
9. Castro, E. A.; Barbiric, D. A. J. Molecular modeling and cyclodextrins: A relationship strengthened by complexes. Curr. Org. Chem., 2006, 10, 715.
10. Plyasunov, A. V.; Shock, E. L. Thermodynamic functions of hydration of hydrocarbons at 298.15 K and 0.1 MPa. Geochim. Cosmochim. Acta, 2000, 64, 439.
11. Plyasunov, A. V.; Shock, E. L. Group contribution values of the infinite dilution thermodynamic functions of hydration for aliphatic noncyclic hydrocarbons, alcohols, and ketones at 298.15 K and 0.1 MPa. J. Chem. Eng. Data, 2001, 46, 1016.
12. Cai, W.; Sun, T.; Shao, X.; Chipot, C. Can the anomalous aqueous solubility of beta-cyclodextrin be explained by its hydration free energy alone? Phys. Chem. Chem. Phys., 2008, 10, 3236.
13. Chen, W.; Chang, C. E.; Gilson, M. K. Calculation of cyclodextrin binding affinities: Energy, entropy, and implications for drug design. Biophys. J., 2004, 87, 3035.
14. Rudiger, V.; Eliseev, A.; Simova, S.; Schneider, H. J.; Blandamer, M. J.; Cullis, P. M.; Meyer, A. J. Conformational, calorimetric and NMR spectroscopic studies on inclusion complexes of cyclodextrins with substituted phenyl and adamantane derivatives. J. Chem. Soc. Perkin Trans. 2, 1996, 2119.
15. Eftink, M. R.; Andy, M. L.; Bystrom, K.; Perlmutter, H. D.; Kristol, D. S. Cyclodextrin inclusion complexes: studies of the variation in the size of alicyclic guests. J. Am. Chem. Soc., 1989, 111, 6765.
16. Liu, Y.; Chen, Y. Cooperative binding and multiple recognition by bridged bis(beta-cyclodextrin)s with functional linkers. Acc. Chem. Res., 2006, 39, 681.
17. Liu, Y.; Yang, Y. W.; Yang, E. C.; Guan, X. D. Molecular recognition thermodynamics and structural elucidation of interactions between steroids and bridged bis(beta-cyclodextrin)s. J. Org. Chem., 2004, 69, 6590.
18. Breslow, R.; Chung, S. Strong binding of ditopic substrates by a doubly linked occlusive C1 clamshell as distinguished from an aversive C2 loveseat cyclodextrin dimer. J. Am. Chem. Soc., 1990, 112, 9659.
19. Lecourt, T.; Mallet, J.-M.; Sinay, P. Eur. J. Org. Chem, 2003, 4553.
20. Bistri, O.; Lecourt, T.; Mallet, J. M.; Sollogoub, M.; Sinay, P. The first chemical synthesis of a cyclodextrin heteroduplex. Chem. Biodivers., 2004, 1, 129.
21. Bistri, O.; Mazeau, K.; uzely-Velty, R.; Sollogoub, M. A hydrophilic cyclodextrin duplex forming supramolecular assemblies by physical cross-linking of a biopolymer. Chem. Eur. J., 2007, 13, 8847.
22. Yuan, D. Q.; Koga, K.; Kouno, I.; Fujioka, T.; Fukudome, M.; Fujita, K. The first topologically controlled synthesis of doubly bridged beta-cyclodextrin dimers. Chem. Commun., 2007, 828.
23. Kumprecht, L.; Buděšínský, M.; Vondrášek, J.; Vymětal, J.; Černý, J.; Císařová, I.; Brynda, J.; Herzig, V.; Koutník, P.; Závada, J.; Kraus, T. Rigid Duplex α-Cyclodextrin Reversibly Connected With Disulfide Bonds. Synthesis and Inclusion Complexes. J. Org. Chem., 2009, 74, 1082.
24. Krejčí, L.; Buděšínský, M.; Císařová, I.; Kraus, T. Tubular duplex alphacyclodextrin triply bridged with disulfide bonds: synthesis, crystal structure and inclusion complexes. Chem. Commun., 2009, 3557.
25. Hembury, G.; Rekharsky, M.; Nakamura, A.; Inoue, Y. Direct correlation between complex conformation and chiral discrimination upon inclusion of amino acid derivatives by beta- and gamma-cyclodextrins. Org. Lett., 2000, 2, 3257.
26. Corradini, R.; Dossena, A.; Impellizzeri, G.; Maccarrone, G.; Marchelli, R.; Rizzarelli, E.; Sartor, G.; Vecchio, G. Chiral Recognition and Separation of Amino Acids by Means of a Copper(II) Complex of Histamine Monofunctionalized. beta.-Cyclodextrin. J. Am. Chem. Soc., 1994, 116, 10267.
27. Bellia, F.; La Mendola, D.; Pedone, C.; Rizzarelli, E.; Saviano, M.; Vecchio, G. Selectively functionalized cyclodextrins and their metal complexes. Chem. Soc. Rev., 2009, 38, 2756.
28. Lagona, J.; Mukhopadhyay, P.; Chakrabarti, S.; Isaacs, L. The cucurbit [n]uril family. Angew. Chem. Int. Ed., 2005, 44, 4844.
29. Rekharsky, M. V.; Mori, T.; Yang, C.; Ko, Y. H.; Selvapalam, N.; Kim, H.; Sobransingh, D.; Kaifer, A. E.; Liu, S. M.; Isaacs, L.; Chen, W.; Moghaddam, S.; Gilson, M. K.; Kim, K. M.; Inoue, Y. A synthetic host-guest system achieves avidin-biotin affinity by overcoming enthalpy-entropy compensation. Proc. Natl. Acad. Sci. U. S. A., 2007, 104, 20737.
30. Ashton, P. R.; Königer, R.; Stoddart, J. F. Amino acid derivatives of acyclodextrin. J. Org. Chem., 1996, 61, 903.
31. Gadelle, A.; Defaye, J. Selective Halogenation at Primary Positions of Cyclomaltooligosaccharides and a synthesis of Per-3,6-anhydro Cyclomaltooligosaccharides. Angew. Chem. Int. Ed., 1991, 30, 78.
32. Baer, H. H.; Berenguel, A. V.; Shu, Y. Y.; Defaye, J.; Gadelle, A.; Gonzales, F. S. Improved preparation of hexakis(6-deoxy)cyclomaltohexaose and heptakis(6-deoxy)cyclomaltoheptaose. Carbohydr. Res., 1992, 228, 307.
33. Boger, J.; Corcoran, R. J.; Lehn, J.-M. Selective Modification of all Primary Hydroxyl Groups of a- and b-Cyclodextrins. Helv. Chim. Acta, 1978, 61, 2190.
34. Kraus, T.; Buděšínský, M.; Závada, J. Novel amphiphilic cyclodextrins: Per [6-deoxy-6-(4,5-dicarboxy-1,2,3-triazol-1-yl)-2,3-di-O-methyl] derivatives. Coll. Czech. Chem. Commun., 1998, 63, 534.
35. Guillo, F.; Hamelin, B.; Jullien, L.; Canceill, J.; Lehn, J.-M.; De Robertis, L.; Driguez, H. Synthesis of symmetrical cyclodextrin derivatives bearing multiple charges. Bull. Soc. Chim. Fr., 1995, 132, 857.
36. Vizitiu, D.; Walkinshaw, C. S.; Gorin, B. I.; Thatcher, G. R. J. Synthesis of monofacially functionalized cyclodextrins bearing amino pendent groups. J. Org. Chem., 1997, 62, 8760.
37. Gomez-Garcia, M.; Benito, J. M.; Rodriguez-Lucena, D.; Yu, J. X.; Chmurski, K.; Ortiz Mellet, C.; Gutierrez Gallego, R.; Maestre, A.; Defaye, J.; Garcia Fernandez, J. M. Probing secondary carbohydrate-protein interactions with highly dense cyclodextrin-centered heteroglycoclusters: The Heterocluster Effect. J. Am. Chem. Soc., 2005, 127, 7970.
38. Steffen, A.; Thiele, C.; Tietze, S.; Strassnig, C.; Kamper, A.; Lengauer, T.; Wenz, G.; Apostolakis, J. Improved cyclodextrin-based receptors for camptothecin by inverse virtual screening. Chem. Eur. J., 2007, 13, 6801.
39. Wenz, G.; Strassnig, C.; Thiele, C.; Engelke, A.; Morgenstern, B.; Hegetschweiler, K. Recognition of ionic guests by ionic beta-cyclodextrin derivatives. Chem. Eur. J., 2008, 14, 7202.
40. Kraus, T.; Budesinsky, M.; Zavada, J. Synthesis of per-6-guanidinylated cyclodextrins. Tetrahedron Lett., 2006, 47, 679.
41. Yuan, D. Q.; Izuka, A.; Fukudome, M.; Rekharsky, M. V.; Inoue, Y.; Fujita, K. Heptakis(6-deoxy-6-guanidino)-beta-eyelodextrin: an artificial model for mitochondrial ADP/ATP carrier. Tetrahedron Lett., 2007, 48, 3479.
42. Mourtzis, N.; Eliadou, K.; Aggelidou, C.; Sophianopoulou, V.; Mavridis, I. M.; Yannakopoulou, K. Per(6-guanidino-6-deoxy)cyclodextrins: synthesis, characterisation and binding behaviour toward selected small molecules and DNA. Org. Biomol. Chem., 2007, 5, 125.
43. Brown, S. E.; Coates, J. H.; Coghlan, D. R.; Easton, C. J.; Vaneyk, S. J.; Janowski, W.; Lepore, A.; Lincoln, S. F.; Luo, Y.; May, B. L.; Schiesser, D. S.; Wang, P.; Williams, M. L. Synthesis and Properties of 6A-Amino-6ADeoxy- Alpha and 6A-Amino-6A-Deoxy-Beta-Cyclodextrin. Aust. J. Chem., 1993, 46, 953.
44. Tang, W.; Ng, S. C. Facile synthesis of mono-6-amino-6-deoxy-alpha-, beta-, gamma-cyclodextrin hydrochlorides for molecular recognition, chiral separation and drug delivery. Nat. Protoc., 2008, 3, 691.
45. Matsui, Y.; Okimoto, A. Binding and Catalytic Properties of A Positively Charged Cyclodextrin. Bull. Chem. Soc. Jpn., 1978, 51, 3030.
46. Yamamura, H.; Yamada, Y.; Miyagi, R.; Kano, K.; Araki, S.; Kawai, M. Preparation of beta-Cyclodextrin derivatives possessing two trimethylammonio groups on their primary hydroxy sides as chiral guest selectors. J. Inclusion Phenom. Macrocyclic Chem., 2003, 45, 211.
47. Tabushi, I.; Shimokawa, K.; Fujita, K. Specific Bifunctionalization on Cyclodextrin. Tetrahedron Lett., 1977, 1527.
48. Di Blasio, B.; Galdiero, S.; Saviano, M.; Pedone, C.; Benedetti, E.; Rizzarelli, E.; Pedotti, S.; Vecchio, G.; Gibbons, W. A. Synthesis and structural characterization of 6I,6II-diamino-6I,6II-dideoxy-cyclomaltoheptaose, a difunctionalized [beta]-Cyclodextrin. Carbohydr. Res., 1996, 282, 41.
49. Boger, J.; Brenner, D. G.; Knowles, J. R. Symmetrical Triamino-per-Omethyl- a-cyclodextrin: Preparation and Characterization of Primary Trisubstituted a-Cyclodextrins. J. Am. Chem. Soc., 1979, 101, 7630.
50. Kraus, T.; Buděšínský, M.; Závada, J. A simple synthesis of hexakis(6-Ocarboxymethyl-2,3-di-O-methyl)cyclomaltohexaose and heptakis(6-Ocarboxymethyl-2,3-di-O-methyl)cyclomaltoheptaose. Carbohydr. Res., 1997, 304, 81.
51. Kraus, T.; Buděšínský, M.; Závada, J. General approach to the synthesis of persubstituted hydrophilic and amphiphilic beta-Cyclodextrin derivatives. J. Org. Chem., 2001, 66, 4595.
52. Roehri-Stoeckel, C.; Dangles, O.; Brouillard, R. A Simple synthesis of a highly soluable symmetrical b-Cyclodextrin derivative. Tetrahedron Lett., 1997, 38, 1551.
53. Kraus, T.; Buděšínský, M.; Závada, J. Synthesis of per(5-carboxy-5- dehydroxymethyl)-alpha-cyclodextrin and beta-cyclodextrin - self-assembly of the per(2,3-di-O-methyl)-protected homologues into highly stable dimers, driven by multiple hydrogen bonds. Eur. J. Org. Chem., 2000, 3133.
54. Li, S. L.; Vigh, G. Single-isomer sulfated alpha-cyclodextrins for capillary electrophoresis: Hexakis(2,3-di-O-methyl-6-O-sulfo)-alpha-cyclodextrin, synthesis, analytical characterization, and initial screening tests. Electrophoresis, 2004, 25, 2657.
55. Vincent, J. B.; Sokolowski, A. D.; Nguyen, T. V.; Vigh, G. A family of single-isomer chiral resolving agents for capillary electrophoresis.1. Heptakis(2,3-diacetyl-6-sulfato)-beta-cyclodextrin. Anal. Chem., 1997, 69, 4226.
56. Vincent, J. B.; Kirby, D. M.; Nguyen, T. V.; Vigh, G. A family of singleisomer chiral resolving agents for capillary electrophoresis 2. Hepta-6- sulfato-beta-cyclodextrin. Anal. Chem., 1997, 69, 4419.
57. Cai, H.; Nguyen, T. V.; Vigh, G. A family of single-isomer chiral resolving agents for capillary electrophoresis. 3. Heptakis(2,3-dimethyl-6-sulfato)- beta-cyclodextrin. Anal. Chem., 1998, 70, 580.
58. Zhu, W. H.; Vigh, G. A family of single-isomer, sulfated gammacyclodextrin chiral resolving agents for capillary electrophoresis. 1. Octakis(2,3-diacetyl-6-sulfato)-gamma-cyclodextrin. Anal. Chem., 2000, 72, 310.
59. Zhu, W. H.; Vigh, G. A family of single-isomer, sulfated gammacyclodextrin chiral resolving agents for capillary electrophoresis: Octa(6-Osulfo)- gamma-cyclodextrin. Electrophoresis, 2003, 24, 130.
60. Li, S. L.; Vigh, G. Synthesis, analytical characterization and initial capillary electrophoretic use in acidic background electrolytes of a new, single-isomer chiral resolving agent: Hexakis(2,3-di-O-acetyl-6-O-sulfo)-alphacyclodextrin. Electrophoresis, 2003, 24, 2487.
61. Busby, M. B.; Lim, P.; Vigh, G. Synthesis, analytical characterization and use of octakis(2,3-di-O-methyl-6-O-sulfo)-gamma-cyclodextrin, a novel, single-isomer, chiral resolving agent in low-pH background electrolytes. Electrophoresis, 2003, 24, 351.
62. Li, S. L.; Vigh, G. Single-isomer sulfated alpha-cyclodextrins for capillary electrophoresis. Part 2. Hexakis(6-O-sulfo)-alpha-cyclodextrin: Synthesis, analytical characterization, and initial screening tests. Electrophoresis, 2004, 25, 1201.
63. Busby, M. B.; Vigh, G. Synthesis of heptakis(2-O-methyl-3-O-acetyl-6-Osulfo)- cyclomaltoheptaose, a single-isomer, sulfated beta-cyclodextrin carrying nonidentical substitutents at all the C2, C3, and C6 positions and its use for the capillary electrophoretic separation of enantiomers in acidic aqueous and methanolic background electrolytes. Electrophoresis, 2005, 26, 1978.
64. Busby, M. B.; Vigh, G. Synthesis of a single-isomer sulfated betacyclodextrin carrying nonidentical substituents at all of the C2, C3, and C6 positions and its use for the electrophoretic separation of enantiomers in acidic aqueous and methanolic background electrolytes, Part 2: Heptakis(2- O-methyl-6-O-sulfo) cyclomaltoheptaose. Electrophoresis, 2005, 26, 3849.
65. Maynard, D. K.; Vigh, G. Synthesis and analytical characterization of the sodium salt of heptakis(2-O-methyl-3,6-di-O-sulfo)cyclomalto-heptaose, a chiral resolving agent candidate for capillary electrophoresis. Carbohydr. Res., 2000, 328, 277.
66. Jindřich, J.; Tišlerová, I. Simple preparation of 3(I)-O-substituted betacyclodextrin derivatives using cinnamyl bromide. J. Org. Chem., 2005, 70, 9054.
67. Lopez, O.; Bols, M. Effective synthesis of negatively charged cyclodextrins. Selective access to phosphate cyclodextrins. Tetrahedron, 2008, 64, 7587.
68. Rousseau, C.; Ortega-Caballero, F.; Nordstrom, L. U.; Christensen, B.; Petersen, T. E.; Bols, M. Artificial glycosyl phosphorylases. Chem. Eur. J., 2005, 11, 5094.
69. Hanessian, S.; Hocquelet, C.; Jankowski, C. K. Synthesis of aminocyclodextrin carboxylic acids. Synlett, 2008, 715.
70. Kraus, T.; Buděšínský, M.; Císařová, I.; Závada, J. Per(6-amino-2-Ocarboxymethyl- 6-deoxy-3-O-methyl)-alpha-cyclodextrin: Helical selfassembly of a polyionic amino acid into nanotubes. Angew. Chem. Int. Ed., 2002, 41, 1715.
71. Kraus, T.; Buděšínský, M.; Císařová, I.; Závada, J. A homologous series of persubstituted cyclodextrin amino acids: The quest for tubular self-assembly. Eur. J. Org. Chem, 2004, 4060.
72. Matsui, Y.; Ogawa, K.; Mikami, S.; Yoshimoto, M.; Mochida, K. Binding and Catalytic Properties of Charged Beta-Cyclodextrins. Bull. Chem. Soc. Jpn., 1987, 60, 1219.
73. Boger, J.; Knowles, J. R. Symmetrical triamino-per-O-methyl-.alpha.- cyclodextrin: a host for phosphate esters exploiting both hydrophobic and electrostatic interactions in aqueous solution. J. Am. Chem. Soc., 1979, 101, 7631.
74. Eliseev, A. V.; Schneider, H. J. Molecular Recognition of Nucleotides, Nucleosides, and Sugars by Aminocyclodextrins. J. Am. Chem. Soc., 1994, 116, 6081.
75. Eliseev, A. V.; Schneider, H. J. Aminocyclodextrins as selective hosts with several binding-Sites for nucleotides. Angew. Chem. Int. Ed., 1993, 32, 1331.
76. Schwinte, P.; Darcy, R.; O'Keeffe, F. Ditopic binding of nucleotides by heptakis(6-hydroxyethylamino-6-deoxy)-beta-cyclodextrin. J. Chem. Soc. Perkin Trans. 2, 1998, 805.
77. Aggelidou, C.; Mavridis, I. M.; Yannakopoulou, K. Binding of Nucleotides and Nucleosides to Per(6-guanidino-6-deoxy)cyclodextrins in Solution. Eur. J. Org. Chem, 2009, 2299.
78. Cotner, E. S.; Smith, P. J. Phosphotyrosine binding by Ammonium- and guanidinium-modified cyclodextrins. J. Org. Chem., 1998, 63, 1737.
79. Vizitiu, D.; Thatcher, G. R. J. Binding of phosphates to aminocyclodextrin biomimetics. J. Org. Chem., 1999, 64, 6235.
80. Ghosh, M.; Zhang, R.; Lawler, R. G.; Seto, C. T. The effects of buffers on the thermodynamics and kinetics of binding between positively-charged cyclodextrins and phosphate ester guests. J. Org. Chem., 2000, 65, 735.
81. Breslow, R.; Schmuck, C. Goodness of fit in complexes between substrates and ribonuclease mimics: effects on binding, catalytic rate constants, and regiochemistry. J. Am. Chem. Soc., 1996, 118, 6601.
82. Kitae, T.; Nakayama, T.; Kano, K. Chiral recognition of alpha-amino acids by charged cyclodextrins through cooperative effects of Coulomb interaction and inclusion. J. Chem. Soc. Perkin Trans. 2, 1998, 207.
83. Kitae, T.; Takashima, H.; Kano, K. Chiral recognition of phenylacetic acid derivatives by aminated cyclodextrins. J. Inclusion Phenom. Macrocyclic Chem., 1999, 33, 345.
84. Liu, Y.; Zhang, Y. M.; Qi, A. D.; Chen, R. T.; Yamamoto, K.; Wada, T.; Inoue, Y. Molecular recognition study on a supramolecular system 10. Inclusion complexation of modified beta-cyclodextrins with amino acids: Enhanced enantioselectivity for L/D-leucine. J. Org. Chem., 1997, 62, 1826.
85. Liu, Y.; Bin, L.; Han, B. H.; Li, Y. M.; Chen, R. T. Enantioselective recognition of amino acids by beta-cyclodextrin 6-O-monophosphates. J. Chem. Soc. Perkin Trans. 2, 1997, 1275.
86. Rekharsky, M.; Yamamura, H.; Kawai, M.; Inoue, Y. Critical difference in chiral recognition of N-Cbz-D/L-aspartic and -glutamic acids by mono- and bis(trimethylammonio)-beta-cyclodextrins. J. Am. Chem. Soc., 2001, 123, 5360.
87. Yamamura, H.; Rekharsky, M. V.; Ishihara, Y.; Kawai, M.; Inoue, Y. Factors controlling the complex architecture of native and modified cyclodextrins with dipeptide (Z-Glu-Tyr) studied by microcalorimetry and NMR spectroscopy: Critical effects peripheral bis-tri methylamination and cavity size. J. Am. Chem. Soc., 2004, 126, 14224.
88. Brown, S. E.; Coates, J. H.; Duckworth, P. A.; Lincoln, S. F.; Easton, C. J.; May, B. L. Substituent Effects and Chiral Discrimination in the Complexation of Benzoic, 4-Methylbenzoic and (RS)-2-Phenylpropanoic Acids and Their Conjugate Bases by Beta-Cyclodextrin and 6(A)-Amino-6(A)-Deoxy- Beta-Cyclodextrin in Aqueous-Solution - Potentiometric Titration and H-1 Nuclear-Magnetic-Resonance Spectroscopic Study. J. Chem. Soc. Faraday Trans., 1993, 89, 1035.
89. Kano, K.; Kitae, T.; Shimofuri, Y.; Tanaka, N.; Mineta, Y. Complexation of polyvalent cyclodextrin ions with oppositely charged guests: Entropically favorable complexation due to dehydration. Chem. Eur. J., 2000, 6, 2705.
90. Kano, K.; Ishida, Y.; Kitagawa, K.; Yasuda, M.; Watanabe, M. Heat-capacity changes in host-guest complexation by coulomb interactions in aqueous solution. Chem. Asian J., 2007, 2, 1305.
91. Corbellini, F.; van Leeuwen, F. W. B.; Beijleveld, H.; Kooijman, H.; Spek, A. L.; Verboom, W.; Crego-Calama, M.; Reinhoudt, D. N. Multiple ionic interactions for noncovalent synthesis of molecular capsules in polar solvents. New J. Chem., 2005, 29, 243.
92. Berger, M.; Schmidtchen, F. P. The binding of sulfate anions by guanidinium receptors is entropy-driven. Angew. Chem. Int. Ed., 1998, 37, 2694.
93. Haj-Zaroubi, M.; Mitzel, N. W.; Schmidtchen, F. P. The rational design of anion host compounds: An exercise in subtle energetics. Angew. Chem. Int. Ed., 2002, 41, 104.
94. Jelesarov, I.; Bosshard, H. R. Isothermal titration calorimetry and differential scanning calorimetry as complementary tools to investigate the energetics of biomolecular recognition. J. Mol. Recognit., 1999, 12, 3.
95. Rekharsky, M. V.; Inoue, Y. Complexation and chiral recognition thermodynamics of 6-amino-6-deoxy-beta-cyclodextrin with anionic, cationic, and neutral chiral guests: Counterbalance between van der Waals and coulombic interactions. J. Am. Chem. Soc., 2002, 124, 813.
96. Gomez-Biagi, R. F.; Jagt, R. B. C.; Nitz, M. Remarkably stable inclusion complexes with heptakis-[6-deoxy-6-(2-aminoethylsulfanyl)]-beta-cyclodextrin. Org. Biomol. Chem., 2008, 6, 4622.
97. Liu, Y.; Yang, Y. W.; Cao, R.; Song, S. H.; Zhang, H. Y.; Wang, L. H. Thermodynamic origin of molecular selective binding of bile salts by aminated cyclodextrins. J. Phys. Chem. B, 2003, 107, 14130.
98. Borrajo, A. M. P.; Gorin, B. I.; Dostaler, S. M.; Riopelle, R. J.; Thatcher, G. R. J. Derivatized cyclodextrins as peptidomimetics: Influence on neurite growth. Bioorg. Med. Chem. Lett., 1997, 7, 1185.
99. Mourtzis, N.; Paravatou, M.; Mavridis, I. M.; Roberts, M. L.; Yannakopoulou, K. Synthesis, characterization, and remarkable biological properties of cyclodextrins bearing guanidinoalkylamino and aminoalkylamino groups on their primary side. Chem. Eur. J., 2008, 14, 4188.
100. Donati, F. Sugammadex: a cyclodextrin to reverse neuromuscular blockade in anaesthesia. Expert Opin. Pharmacother., 2008, 9, 1375.
101. Naguib, M. Sugammadex: Another milestone in clinical neuromuscular pharmacology. Anesth. Analg., 2007, 104, 575.
102. Nicholson, W. T.; Sprung, J.; Jankowski, C. J. Sugammadex: A novel agent for the reversal of neuromuscular blockade. Pharmacotherapy, 2007, 27, 1181.
103. Bom, A.; Bradley, M.; Cameron, K.; Clark, J. K.; van Egmond, J.; Feilden, H.; MacLean, E. J.; Muir, A. W.; Palin, R.; Rees, D. C.; Zhang, M. Q. A novel concept of reversing neuromuscular block: Chemical encapsulation of rocuronium bromide by a cyclodextrin-based synthetic host. Angew. Chem. Int. Ed., 2001, 41, 266.
104. Adam, J. M.; Bennett, D. J.; Bom, A.; Clark, J. K.; Feilden, H.; Hutchinson, E. J.; Palin, R.; Prosser, A.; Rees, D. C.; Rosair, G. M.; Stevenson, D.; Tarver, G. J.; Zhang, M. Q. Cyclodextrin-derived host molecules as reversal agents for the neuromuscular blocker rocuronium bromide: Synthesis and structure-activity relationships. J. Med. Chem., 2002, 45, 1806.