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Cyclodextrin Inclusion Polymers Forming Hydrogels

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Inclusion Polymers

Part of the book series: Advances in Polymer Science ((POLYMER,volume 222))

Abstract

This chapter reviews the advances in the developments of supramolecular hydrogels based on the polypseudorotaxanes and polyrotaxanes formed by inclusion complexes of cyclodextrins threading onto polymer chains. Both physical and chemical supramolecular hydrogels of many different types are discussed with respect to their preparation, structure, property, and gelation mechanism. A large number of physical supramolecular hydrogels were formed induced by self-assembly of densely packed cyclodextrin rings threaded on polymer or copolymer chains acting as physical crosslinking points. The thermo-reversible and thixotropic properties of these physical supramolecular hydrogels have inspired their applications as injectable drug delivery systems. Chemical supramolecular hydrogels synthesized from polypseudorotaxanes and polyrotaxanes were based on the chemical crosslinking of either the cyclodextrin molecules or the included polymer chains. The chemical supramolecular hydrogels were often made biodegradable through incorporation of hydrolyzable threading polymers, end caps, or crosslinkers, for their potential applications as biomaterials.

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References

  1. Peppas NA (1987) Hydrogels in medicine and pharmacy, vol. 1. CRC, Florida

    Google Scholar 

  2. Park K, Shalaby WSW, Park H (1993) Biodegradable hydrogels for drug delivery. Technomic, Lancaster

    Google Scholar 

  3. Kishida A, Ikada Y (2002) Hydrogels for biomedical and pharmaceutical applications. In: Dumitriu S (ed) Polymeric biomaterials. Marcel Dekker, New York

    Google Scholar 

  4. Li J (2004) Polymeric hydrogels. In: Teoh SH (ed) Biomaterials engineering and processing series, vol. 1. Engineering materials for biomedical applications. World Scientific, New Jersey

    Google Scholar 

  5. Park H, Park K (1996) Pharm Res 13:1770–1776

    Article  CAS  Google Scholar 

  6. Kim S, Bae Y, Okano T (1992) Pharm Res 9:283–290

    Article  CAS  Google Scholar 

  7. Heller J (1993) Adv Drug Deliv Rev 10:163–204

    Article  CAS  Google Scholar 

  8. Kamath KR, Park K (1993) Adv Drug Deliv Rev 11:59–84

    Article  CAS  Google Scholar 

  9. Graham NB (1987) Poly(ethylene oxide) and related hydrogels. In: Peppas NA (ed) Hydrogels in medicine and pharmacy, vol. 2. CRC, Boca Raton

    Google Scholar 

  10. Harris JM (1992) Poly(ethylene glycol) chemistry: biotechnical and biomedical applications. Plenum, New York

    Google Scholar 

  11. Apicella A, Capello B, Del Nobile MA, La Rotonda MI, Mensitieri GL, Nicolais S, Seccia S (1994) Poly(ethylene oxide)-based delivery systems. In: Ottenbrite M (ed) Polymeric drugs and drug administration. American Chemical Society, Washington DC

    Google Scholar 

  12. Dimitrov I, Trzebicka B, Muller AHE, Dworak A, Tsvetanov CB (2007) Prog Polym Sci 32:1275–1343

    Article  CAS  Google Scholar 

  13. Bender ML, Komiyama M (1978) Cyclodextrin chemistry. Springer, Berlin Heidelberg New York

    Book  Google Scholar 

  14. Szejtli J (1982) Cyclodextrins and their inclusion complexes. Akademiai Kiado, Budapest

    Google Scholar 

  15. Szejtli J (1998) Chem Rev 98:1743–1753

    Article  CAS  Google Scholar 

  16. Harada A, Kamachi M (1990) Macromolecules 23:2821–2823

    Article  CAS  Google Scholar 

  17. Harada A, Li J, Kamachi M (1992) Nature 356:325–327

    Article  CAS  Google Scholar 

  18. Wenz G, Keller B (1992) Angew Chem Int Ed Engl 31:197–199

    Article  Google Scholar 

  19. Wenz G (1994) Angew Chem Int Ed Engl 33:803–822

    Article  Google Scholar 

  20. Wenz G, Han BH, Muller A (2006) Chem Rev 106:782–817

    Article  CAS  Google Scholar 

  21. Harada A, Li J, Kamachi M (1993) Macromolecules 26:5698–5703

    Article  CAS  Google Scholar 

  22. Harada A, Li J, Kamachi M (1994) Nature 370:126–128

    Article  CAS  Google Scholar 

  23. Li J, Harada A, Kamachi M (1994) Bull Chem Soc Jpn 67:2808–2818

    Article  CAS  Google Scholar 

  24. Li J, Uzawa J, Doi Y (1998) Bull Chem Soc Jpn 71:1953–1957

    Article  CAS  Google Scholar 

  25. Fujita H, Ooya T, Yui N (1999) Macromolecules 32:2534–2541

    Article  CAS  Google Scholar 

  26. Li J, Li X, Toh KC, Ni XP, Zhou ZH, Leong KW (2001) Macromolecules 34:8829–8831

    Article  CAS  Google Scholar 

  27. Li J, Toh KC (2002) J Chem Soc Perkin Trans 2:35–40

    CAS  Google Scholar 

  28. Jiao H, Goh SH, Valiyaveettil S (2002) Macromolecules 35:1980–1983

    Article  CAS  Google Scholar 

  29. Li J, Ni XP, Leong K (2003) Angew Chem Int Ed 42:69–72

    Article  Google Scholar 

  30. Li X, Li J, Leong KW (2003) Macromolecules 36:1209–1214

    Article  CAS  Google Scholar 

  31. Li J, Ni XP, Zhou ZH, Leong KW (2003) J Am Chem Soc 125:1788–1795

    Article  CAS  Google Scholar 

  32. Jiao H, Goh SH, Valiyaveettil S, Zheng JW (2003) Macromolecules 36:4241–4243

    Article  CAS  Google Scholar 

  33. Shuai XT, Porbeni FE, Wei M, Shin ID, Tonelli AE (2001) Macromolecules 34:7355–7361

    Article  CAS  Google Scholar 

  34. Lu J, Mirau PA, Shin ID, Nojima S, Tonelli AE (2002) Macromol Chem Phys 203:71–79

    Article  CAS  Google Scholar 

  35. Zhao TJ, Beckham HW (2003) Macromolecules 36:9859–9865

    Article  CAS  Google Scholar 

  36. Li J, Chen B, Wang X, Goh SH (2004) Polymer 45:1777–1785

    Article  CAS  Google Scholar 

  37. Li X, Li J, Leong KW (2004) Polymer 45:6845–6851

    Article  CAS  Google Scholar 

  38. Girardeau TE, Zhao TJ, Leisen J, Beckham HW, Bucknall DG (2005) Macromolecules 38:2261–2270

    Article  CAS  Google Scholar 

  39. Liu Y, Liang P, Chen Y, Zhang YM, Zheng JY, Yue H (2005) Macromolecules 38:9095–9099

    Article  CAS  Google Scholar 

  40. Liu Y, Yang YW, Chen Y, Zou HX (2005) Macromolecules 38:5838–5840

    Article  CAS  Google Scholar 

  41. Huang JC, Li X, Lin TT, He CB, Mya KY, Xiao Y, Li J (2004) J Polym Sci B Polym Phys 42:1173–1180

    Article  CAS  Google Scholar 

  42. Huang FH, Gibson HW (2005) Prog Polym Sci 30:982–1018

    Article  CAS  Google Scholar 

  43. Choi HS, Yui N (2006) Prog Polym Sci 31:121–144

    Article  CAS  Google Scholar 

  44. Nepogodiev SA, Stoddart JF (1998) Chem Rev 98:1959–1976

    Article  CAS  Google Scholar 

  45. Raymo FM, Stoddart JF (1999) Chem Rev 99:1643–1663

    Article  CAS  Google Scholar 

  46. Rusa CC, Tonelli AE (2000) Macromolecules 33:1813–1818

    Article  CAS  Google Scholar 

  47. Rusa CC, Rusa M, Gomez M, Shin ID, Fox JD, Tonelli AE (2004) Macromolecules 37:7992–7999

    Article  CAS  Google Scholar 

  48. Hernandez R, Rusa M, Rusa CC, Lopez D, Mijangos C, Tonelli AE (2004) Macromolecules 37:9620–9625

    Article  CAS  Google Scholar 

  49. Liu KL, Goh SH, Li J (2008) Macromolecules 41:6027–6034

    Article  CAS  Google Scholar 

  50. Li J, Loh XJ (2008) Adv Drug Deliv Rev 60:1000–1017

    Article  CAS  Google Scholar 

  51. Yui N, Ooya T (2006) Chem Eur J 12:6730–6737

    Article  CAS  Google Scholar 

  52. Yui N, Ooya T, Kumeno T (1998) Bioconjugate Chem 9:118–125

    Article  CAS  Google Scholar 

  53. Ooya T, Yui N (1999) J Control Release 58:251–269

    Article  CAS  Google Scholar 

  54. Li J, Yang C, Li HZ, Wang X, Goh SH, Ding JL, Wang DY, Leong KW (2006) Adv Mater 18:2969–2974

    Article  CAS  Google Scholar 

  55. Yang C, Wang X, Li HZ, Goh SH, Li J (2007) Biomacromolecules 8:3365–3374

    Article  CAS  Google Scholar 

  56. Yang C, Li H, Wang X, Li J (2009) J Biomed Mater Res A: DOI: 10.1002/jbm.a.31976

    Google Scholar 

  57. Shuai XT, Merdan T, Unger F, Wittmar M, Kissel T (2003) Macromolecules 36:5751–5759

    Article  CAS  Google Scholar 

  58. Loethen S, Kim JM, Thompson DH (2007) Polym Rev 47:383–418

    Article  CAS  Google Scholar 

  59. Li J, Harada A, Kamachi M (1994) Polym J 26:1019–1026

    Article  CAS  Google Scholar 

  60. Deng W, Yamaguchi H, Takashima Y, Harada A (2007) Angew Chem Int Ed 46:5144–5147

    Article  CAS  Google Scholar 

  61. Amiel C, Sebille B (1999) Adv Colloid Interf Sci 79:105–122

    Article  CAS  Google Scholar 

  62. Weickenmeier M, Wenz G, Huff J (1997) Macromol Rapid Commun 18:1117–1123

    Article  CAS  Google Scholar 

  63. Wenz G, Weickenmeier M, Huff J (2000) ACS Symp Ser 765:271

    Article  CAS  Google Scholar 

  64. Guo XH, Abdala AA, May BL, Lincoln SF, Khan SA, Prud'homme RK (2005) Macromolecules 38:3037–3040

    Article  CAS  Google Scholar 

  65. Kretschmann O, Choi SW, Miyauchi M, Tomatsu I, Harada A, Ritter H (2006) Angew Chem Int Ed 45:4361–4365

    Article  Google Scholar 

  66. Zhang ZX, Liu X, Xu FJ, Loh XJ, Kang ET, Neoh KG, Li J (2008) Macromolecules 41:5967–5970

    Article  CAS  Google Scholar 

  67. Li J, Ni XP, Leong KW (2003) J Biomed Mater Res A 65A:196–202

    Article  CAS  Google Scholar 

  68. Li J, Li X, Zhou ZH, Ni XP, Leong KW (2001) Macromolecules 34:7236–7237

    Article  CAS  Google Scholar 

  69. Li J, Li X, Ni XP, Wang X, Li HZ, Zhou ZH (2005) Key Eng Mater 288289:117120

    Article  Google Scholar 

  70. Ni X, Cheng A, Li J (2009) J Biomed Mater Res A: DOI: 10.1002/jbm.a.31906

    Google Scholar 

  71. Li J, Li X, Ni XP, Wang X, Li HZ, Leong KW (2006) Biomaterials 27:4132–4140

    Article  CAS  Google Scholar 

  72. Li X, Li J (2008) J Biomed Mater Res A 86A:1055–1061

    Article  CAS  Google Scholar 

  73. Li J, Li X, Ni XP, Leong KW (2003) Macromolecules 36:2661–2667

    Article  CAS  Google Scholar 

  74. Li J, Ni XP, Li X, Tan NK, Lim CT, Ramakrishna S, Leong KW (2005) Langmuir 21:8681–8685

    Article  CAS  Google Scholar 

  75. Li X, Mya KY, Ni XP, He CB, Leong KW, Li J (2006) J Phys Chem B 110:5920–5926

    Article  CAS  Google Scholar 

  76. Jongpaiboonkit L, Zhou ZH, Ni XP, Wang YZ, Li J (2006) J Biomater Sci Polym Ed 17:747–763

    Article  CAS  Google Scholar 

  77. Huh KM, Ooya T, Lee WK, Sasaki S, Kwon IC, Jeong SY, Yui N (2001) Macromolecules 34:8657–8662

    Article  CAS  Google Scholar 

  78. Huh KM, Cho YW, Chung H, Kwon IC, Jeong SY, Ooya T, Lee WK, Sasaki S, Yui N (2004) Macromol Biosci 4:92–99

    Article  CAS  Google Scholar 

  79. He LH, Huang J, Chen YM, Xu XJ, Liu LP (2005) Macromolecules 38:3845–3851

    Article  CAS  Google Scholar 

  80. Wang ZM, Chen YM (2007) Macromolecules 40:3402–3407

    Article  CAS  Google Scholar 

  81. Choi HS, Ooya T, Sasaki S, Yui N, Kurisawa M, Uyama H, Kobayashi S (2004) ChemPhysChem 5:1431–1434

    Article  CAS  Google Scholar 

  82. Choi HS, Yamamoto K, Ooya T, Yui N (2005) ChemPhysChem 6:1081–1086

    Article  CAS  Google Scholar 

  83. Choi HS, Kontani K, Huh KM, Sasaki S, Ooya T, Lee WK, Yui N (2002) Macromol Biosci 2:298–303

    Article  CAS  Google Scholar 

  84. Joung YK, Ooya T, Yamaguchi M, Yui N (2007) Adv Mater 19:396

    Article  CAS  Google Scholar 

  85. Jeong B, Bae YH, Lee DS, Kim SW (1997) Nature 388:860–862

    Article  CAS  Google Scholar 

  86. Jeong B, Bae YH, Kim SW (2000) J Control Release 63:155–163

    Article  CAS  Google Scholar 

  87. Kataoka T, Kidowaki M, Zhao CM, Minamikawa H, Shimizu T, Ito K (2006) J Phys Chem B 110:24377–24383

    Article  CAS  Google Scholar 

  88. Fleury G, Schlatter G, Brochon C, Hadziioannou G (2005) Polymer 46:8494–8501

    Article  CAS  Google Scholar 

  89. Okumura Y, Ito K (2001) Adv Mater 13:485–487

    Article  CAS  Google Scholar 

  90. Takata T (2006) Polym J 38:1–20

    Article  CAS  Google Scholar 

  91. Ito K (2007) Polym J 39:489–499

    Article  CAS  Google Scholar 

  92. Watanabe J, Ooya T, Park KD, Kim YH, Yui N (2000) J Biomater Sci Polym Ed 11:1333–1345

    Article  CAS  Google Scholar 

  93. Ichi T, Watanabe J, Ooya T, Yui N (2001) Biomacromolecules 2:204–210

    Article  CAS  Google Scholar 

  94. Watanabe J, Ooya T, Nitta KH, Park KD, Kim YH, Yui N (2002) Biomaterials 23:4041–4048

    Article  CAS  Google Scholar 

  95. Ichi T, Ooya T, Yui N (2003) Macromol Biosci 3:373–380

    Article  CAS  Google Scholar 

  96. Feng ZG, Zhao SP (2003) Polymer 44:5177–5186

    Article  CAS  Google Scholar 

  97. Wei HL, He JY, Sun LG, Zhu KQ, Feng ZG (2005) Eur Polym J 41:948–957

    Article  CAS  Google Scholar 

  98. Wei HL, Zhang AY, Qian LJ, Yu HQ, Hou DD, Qiu RX, Feng ZG (2005) J Polym Sci Pol Chem 43:2941–2949

    Article  CAS  Google Scholar 

  99. Wei HL, Yu HQ, Zhang AY, Sun LG, Hou DD, Feng ZG (2005) Macromolecules 38:8833–8839

    Article  CAS  Google Scholar 

  100. Zhao SP, Zhang LM, Ma D, Yang C, Yan L (2006) J Phys Chem B 110:16503–16507

    Article  CAS  Google Scholar 

  101. Yu HQ, Feng ZG, Zhang AY, Sun LG, Qian LJ (2006) Soft Matter 2:343–349

    Article  CAS  Google Scholar 

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Acknowledgement

The author acknowledges the financial support from the Academic Research Fund, Ministry of Education, Singapore (Grant codes: R-397-000-031-112 and R-397-000-019-112) and the Institute of Materials Research and Engineering, A*STAR, Singapore.

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Authors and Affiliations

  1. Division of Bioengineering Faculty of Engineering, National University of Singapore, 7 Engineering Drive 1, 117574, Singapore

    Jun Li

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  1. Jun Li
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Correspondence to Jun Li .

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  1. Inst. Organische Makromolekulare Chemie, Universität des Saarlandes, Saarbrücken, 66123, Germany

    Gerhard Wenz

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© 2009 Springer-Verlag London

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Li, J. (2009). Cyclodextrin Inclusion Polymers Forming Hydrogels. In: Wenz, G. (eds) Inclusion Polymers. Advances in Polymer Science, vol 222. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_2008_9

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