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Cyclodextrin Molecules, Polymers and Nanomaterials

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Abstract

Cyclodextrins (CDs) have been widely utilized for myriad applications due to their unique structural features such as hydrophobic cavity for inclusion complex formation and numerous hydroxyl groups for functionalization. In this review, we discuss various applications of CD-based molecules, polymers and nanomaterials. CD-based molecules have been developed for pharmaceutic applications and drug/gene carriers. CD-based polymers have been adopted for drug delivery, stimuli-responsive hydrogels and self-healing materials. CD hybrids with inorganic nanoparticles have been employed for stimuli-responsive carriers.

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References

  1. A. Villiers, Compt. Rend. Acad. Sci., 112, 435 (1891).

    Google Scholar 

  2. A. Villiers, Compt. Rend. Acad. Sci., 112, 536 (1891).

    Google Scholar 

  3. S. D. Esastburn and B. Y. Tao, Biotechnol. Adv., 12, 325 (1994).

    Article  Google Scholar 

  4. E. M. M. Del Valle, Process Biochem., 39, 1033 (2004).

    Article  CAS  Google Scholar 

  5. G. Becket, L. J. Schep, and M. Y. Tan, Int. J. Pharm., 179, 65 (1999).

    Article  CAS  PubMed  Google Scholar 

  6. M. E. Davis and M. E. Brewster, Nat. Rev. Drug Discov., 3, 1023 (2004).

    Article  CAS  PubMed  Google Scholar 

  7. J. Wankar, N. G. Kotla, S. Gera, S. Rasala, A. Pandit, and Y. A. Rochev, Adv. Funct. Mater., 30, 1909049 (2020).

    Article  CAS  Google Scholar 

  8. G. Varan, C. Varan, N. Erdoğar, A. A. Hincal, and E. Bilensoy, Int. J. Pharm., 531, 457 (2017).

    Article  CAS  PubMed  Google Scholar 

  9. R. P. Singh, T. Hidalgo, P.-A. Cazade, R. Darcy, M. F. Cronin, I. Dorin, C. M. O’Driscoll, and D. Thompson, Mol. Pharm., 16, 1358 (2019).

    Article  CAS  PubMed  Google Scholar 

  10. G. Rivero-Barbarroja, J. M. Benito, C. Ortiz Mellet, and J. M. García Fernández, Nanomaterials, 10, 2517 (2020).

    Article  CAS  PubMed Central  Google Scholar 

  11. Z. Ye, Q. Zhang, S. Wang, P. Bharate, S. Varela-Aramburu, M. Lu, P. H. Seeberger, and J. Yin, Chem. Eur. J., 22, 15216 (2016).

    Article  CAS  PubMed  Google Scholar 

  12. M. A. Przybyla, G. Yilmaz, and C. R. Becer, Polym. Chem., 11, 7582 (2020).

    Article  CAS  Google Scholar 

  13. X. Yao, P. Huang, and Z. Nie, Prog. Polym. Sci., 93, 1 (2019).

    Article  CAS  Google Scholar 

  14. G. Sinawang, M. Osaki, Y. Takashima, H. Yamaguchi, and A. Harada, Chem. Commun., 56, 4381 (2020).

    Article  CAS  Google Scholar 

  15. B. Tian and J. Liu, New J. Chem., 44, 9137 (2020).

    Article  CAS  Google Scholar 

  16. C. Park, I. H. Lee, S. Lee, Y. Song, M. Rhue, and C. Kim, Proc. Natl. Acad. Sci. U.S.A., 103, 1199 (2006).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. C. Park, M. S. Im, S. Lee, J. Lim, and C. Kim, Angew. Chem. Int. Ed., 47, 9922 (2008).

    Article  CAS  Google Scholar 

  18. C. Park, J. Lee, and C. Kim, Chem. Commun., 47, 12042 (2011).

    Article  CAS  Google Scholar 

  19. J. Lee, S. Park, C. R. Lohani, K.-H. Lee, and C. Kim, Chem. Eur. J., 18, 7351 (2012).

    Article  CAS  PubMed  Google Scholar 

  20. C. Park, H. Youn, H. Kim, T. Noh, Y. H. Kook, E. T. Oh, H. J. Park, and C. Kim, J. Mater. Chem., 19, 2310 (2009).

    Article  CAS  Google Scholar 

  21. C. Park, K. Oh, S. C. Lee, and C. Kim, Angew. Chem. Int. Ed., 46, 1455 (2007).

    Article  CAS  Google Scholar 

  22. C. Park, K. Lee, and C. Kim, Angew. Chem. Int. Ed., 48, 1275 (2009).

    Article  CAS  Google Scholar 

  23. C. Park, H. Kim, S. Kim, and C. Kim, J. Am. Chem. Soc., 131, 16614 (2009).

    Article  CAS  PubMed  Google Scholar 

  24. H. Kim, S. Kim, C. Park, H. Lee, H. J. Park, and C. Kim, Adv. Mater., 22, 4280 (2010).

    Article  CAS  PubMed  Google Scholar 

  25. J. Lee, E.-T. Oh, H. Yoon, C. W. Kim, Y. Han, J. Song, H. Jang, H. J. Park, and C. Kim, Nanoscale, 9, 6901 (2017).

    Article  CAS  PubMed  Google Scholar 

  26. J. Szejtli and T. Osa, Comprehensive Supramolecular Chemistry Vol. 3: Cyclodextrins, Pergamon, New York, 1996.

    Google Scholar 

  27. F. van de Manakker, T. Vermonden, C. F. van Nostrum, and W. E. Hennink, Biomacromolecules, 10, 3157 (2009).

    Article  CAS  PubMed  Google Scholar 

  28. P. Saokham, C. Muankaew, P. Jansook, and T. Loftsson, Molecules, 23, 1161 (2018).

    Article  PubMed Central  Google Scholar 

  29. J. Szejtli, Chem. Rev., 98, 1743 (1998).

    Article  CAS  PubMed  Google Scholar 

  30. Z. H. Qi and C. T. Sikorski, ACS Symp. Ser., 728, 113 (1999).

    Article  CAS  Google Scholar 

  31. A. S. Braegelman and M. J. Webber, Theranostics, 9, 3017 (2019).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. A. R. Khan, P. Forgo, K. J. Stine, and V. T. D’Souza, Chem. Rev., 98, 1977 (1998).

    Article  CAS  PubMed  Google Scholar 

  33. T. Irie and K. Uekama, J. Pharm. Sci., 86, 147 (1997).

    Article  CAS  PubMed  Google Scholar 

  34. D. O. Thompson, Crit. Rev. Ther. Drug Carrier Syst., 14, 1 (1997).

    Article  CAS  PubMed  Google Scholar 

  35. A. Gerlóczy, A. Fónagy, P. Keresztes, L. Perlaky, and J. Szejtli, Arzneim.-Forsch, 35, 1042 (1985).

    Google Scholar 

  36. J. H. Perrin, F. P. Field, D. A. Hansen, R. A. Mufson, and G. Torosian, Res. Commun. Chem. Pathol. Pharmacol., 19, 373 (1978).

    CAS  PubMed  Google Scholar 

  37. D. Duchene, A. Bochot, and T. Loftsson, S.T.P. Pharma Prat., 19, 15 (2009).

    CAS  Google Scholar 

  38. S. Gould and R. C. Scott, Food Chem. Toxicol., 43, 1451 (2005).

    Article  CAS  PubMed  Google Scholar 

  39. V. J. Stella and Q. He, Toxicol Pathol., 36, 30 (2008).

    Article  CAS  PubMed  Google Scholar 

  40. L. M. Tasić, M. D. Jovanović, and Z. R. Djurić, J. Pharm. Pharmacol., 44, 52 (1992).

    Article  PubMed  Google Scholar 

  41. R. A. Prentis, Y. Lis, and S. R. Walker, Br. J. Clin. Pharmacol., 25, 387 (1988).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. T. Loftsson, J. Incl. Phenom. Macrocycl. Chem., 44, 63 (2002).

    Article  CAS  Google Scholar 

  43. R. G. Strickley, Pharm. Res., 21, 201 (2004).

    Article  CAS  PubMed  Google Scholar 

  44. J. Dressman, J. Butler, J. Hempenstall and C. Reppas, Pharm. Technol., 25, 68 (2001).

    CAS  Google Scholar 

  45. R. Challa, A. Ahuja, J. Ali, and R. K. Khar, AAPS PharmSciTech, 6, E329 (2005).

    Article  PubMed  PubMed Central  Google Scholar 

  46. R. Arun, Sci. Pharm., 76, 567 (2008).

    Article  Google Scholar 

  47. T. Higuchi and K. A. Connors, Adv. Anal. Chem. Instr., 4, 117 (1965).

    CAS  Google Scholar 

  48. T. Loftsson and E. Stefánsson, Drug Dev. Ind. Pharm., 23, 473 (1997).

    Article  CAS  Google Scholar 

  49. H. van Doorne, Eur. J. Pharm. Biopharm., 39, 133 (1993).

    CAS  Google Scholar 

  50. K. Uekama and M. Otagiri, Crit. Rev. Ther. Drug Carrier Syst., 3, 1 (1987).

    CAS  PubMed  Google Scholar 

  51. T. Loftsson, M. E. Brewster, and M. Másson, Am. J. Drug Deliv., 2, 261 (2004).

    Article  CAS  Google Scholar 

  52. M. Tsuboshima, K. Matsumoto, Y. Aral, H. Wakatsuka, and A. Kawasaki, Yakugaku Zasshi., 112, 447 (1992).

    Article  CAS  PubMed  Google Scholar 

  53. K. Inaba, Denpun Kagaku, 31, 107 (1984).

    CAS  Google Scholar 

  54. F. Giordano and R. Bettini, Chiesi Farmaceutici S.p.A., US Patent 7935685 (2003).

  55. F. Carli and P. Chiesi, Chiesi Farmaceutici S.p.A., US Patent 5164380 (1991).

  56. A. Capocchi, Chiesi Farmaceutici S.p.A, US Patent 7700579 (2003).

  57. E. Redenti, T. Peveri, M. Zanol, P. Ventura, G. Gnappi, and A. Montenero, Int. J. Pharm., 129, 289 (1996).

    Article  CAS  Google Scholar 

  58. L. Szente, Adv. Drug Del. Rev., 36, 17 (1999).

    Article  CAS  Google Scholar 

  59. U. Mester, C. Lohmann, U. Pleyer, G. Steinkamp, E. Völcker, H. Kruger, and P. S. Raj, Drugs R. D., 3, 143 (2002).

    Article  CAS  PubMed  Google Scholar 

  60. J. Peeters, P. Neeskens, J. P. Tollenaere, P. Van Remoortere, and M. E. Brewster, J. Pharm. Sci., 91, 1414 (2002).

    Article  CAS  PubMed  Google Scholar 

  61. K. De Beule and J. Van Gestel, Drugs, 61, 27 (2001).

    Article  CAS  PubMed  Google Scholar 

  62. D. Slain, P. D. Rogers, J. D. Cleary, and S. W. Chapman, Ann. Pharmacother., 35, 720 (2001).

    Article  CAS  PubMed  Google Scholar 

  63. L. Willems, R. van der Geest, and K. de Beule, J. Clin. Phar. Ther., 26, 159 (2001).

    Article  CAS  Google Scholar 

  64. H. Ueda, D. Ou, T. Endo, H. Nagase, K. Tomono, and T. Nagai, Drug Dev. Ind. Pharm., 24, 863 (1998).

    Article  CAS  PubMed  Google Scholar 

  65. V. D. Harding, Pfizer Inc, US Patent 6632803 (1998).

  66. E. Bilensoy and A. A. Hincal, Expert Opin. Drug Deliv., 6, 1161 (2009).

    Article  CAS  PubMed  Google Scholar 

  67. C. Conte, A. Scala, G. Siracusano, N. Leone, S. Patanè, F. Ungaro, A. Miro, M. T. Sciortino, F. Quaglia, and A. Mazzaglia, RSC Adv., 4, 43903 (2014).

    Article  CAS  Google Scholar 

  68. A. Méndez-Ardoy, A. Díaz-Moscoso, C. O. Mellet, C. D. Giorgio, P. Vierling, J. M. Benito, and J. M. G. Fernández, RSC Adv., 5, 76464 (2015).

    Article  Google Scholar 

  69. C. Park, M. S. Im, J. Lee, Y. S. Ko, and C. Kim, Bull. Kor. Chem. Soc., 30, 2759 (2009).

    Article  CAS  Google Scholar 

  70. M. Yun, C. Park, J. Lee, and C. Kim, J. Polym. Sci., Part A: Polym. Chem., 48, 730 (2010).

    Article  CAS  Google Scholar 

  71. J. Lee, J. Hwang, and C. Kim, Macromol. Res., 23, 496 (2015).

    Article  CAS  Google Scholar 

  72. J. Lee, C. R. Lohani, E. K. Choi, K.-H. Lee, and C. Kim, New J. Chem., 37, 3598 (2013).

    Article  CAS  Google Scholar 

  73. J. Lee, D. Min, E.-T. Oh, H. Yoon, H. J. Park, and C. Kim, ChemPlusChem, 81, 229 (2016).

    Article  CAS  PubMed  Google Scholar 

  74. Y. Yang, X. Jia, Y.-M. Zhang, N. Li, and Y. Liu, Chem. Commun., 54, 8713 (2018).

    Article  CAS  Google Scholar 

  75. M. E. Davis, J. E. Zuckerman, C. H. J. Choi, D. Seligson, A. Tolcher, C. A. Alabi, Y. Yen, J. D. Heidel, and A. Ribas, Nature, 464, 1067 (2010).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  76. J. E. Zuckerman, I. Gritli, A. Tolcher, J. D. Heidel, D. Lim, R. Morgan, B. Chmielowski, A. Ribas, M. E. Davis, and Y. Yen, Proc. Natl. Acad. Sci. U.S.A., 111, 11449 (2014).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  77. A. S. Piotrowski-Daspit, A. C. Kauffman, L. G. Bracaglia, and W. M. Saltzman, Adv. Drug Deliv. Rev., 156, 119 (2020).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  78. J. Cheng, K. T. Khin, G. S. Jensen, A. Liu, and M. E. Davis, Bioconjug. Chem., 14, 1007 (2003).

    Article  CAS  PubMed  Google Scholar 

  79. J. Cheng, K. T. Khin, and M. E. Davis, Mol. Pharm., 1, 183 (2004).

    Article  CAS  PubMed  Google Scholar 

  80. B.-W. Liu, H. Zhou, S.-T. Zhou, H.-J. Zhang, A.-C. Feng, C.-M. Jian, J. Hu, W.-P. Gao, and J.-Y. Yuan, Macromolecules, 47, 2938 (2014).

    Article  CAS  Google Scholar 

  81. R. Namgung, Y. Mi Lee, J. Kim, Y. Jang, B.-H. Lee, I.-S. Kim, P. Sokkar, Y. M. Rhee, A. S. Hoffman, and W. J. Kim, Nat. Commun., 5, 3702 (2014).

    Article  CAS  PubMed  Google Scholar 

  82. Y. Zhang, D. Yang, H. Chen, W. Q. Lim, F. S. Z. Phua, G. An, P. Yang, and Y. Zhao, Biomaterials, 163, 14 (2018).

    Article  CAS  PubMed  Google Scholar 

  83. Q. Yu, B. Zhang, Y.-M. Zhang, Y.-H. Liu, and Y. Liu, ACS Appl. Mater. Interfaces, 12, 13709 (2020).

    Article  CAS  PubMed  Google Scholar 

  84. D. J. Newman and G. M. Cragg, J. Nat. Prod., 67, 1216 (2004).

    Article  CAS  PubMed  Google Scholar 

  85. J. R. Stehn, N. K. Haass, T. Bonello, M. Desouza, G. Kottyan, H. Treutlein, J. Zeng, P. R. B. B. Nascimento, V. B. Sequeira, T. L. Butler, M. Allanson, T. Fath, T. A. Hill, A. McCluskey, G. Schevzov, S. J. Palmer, E. C. Hardeman, D. Winlaw, V. E. Reeve, I. Dixon, W. Weninger, T. P. Cripe, and P. W. Gunning, Cancer Res., 73, 5169 (2013).

    Article  CAS  PubMed  Google Scholar 

  86. A. Hashidzume, H. Yamaguchi, and A. Harada, Eur. J. Org. Chem., 2019, 3344 (2019).

    Article  CAS  Google Scholar 

  87. Y. Arisaka and N. Yui, J. Mater. Chem. B, 7, 2123 (2019).

    Article  CAS  PubMed  Google Scholar 

  88. M. Arunachalam and H. W. Gibson, Prog. Polym. Sci., 39, 1043 (2014).

    Article  CAS  Google Scholar 

  89. A. Yamashita, D. Kanda, R. Katoono, N. Yui, T. Ooya, A. Maruyama, H. Akita, K. Kogure, and H. Harashima, J. Control. Release, 131, 137 (2008).

    Article  CAS  PubMed  Google Scholar 

  90. T. Ooya, H. S. Choi, A. Yamashita, N. Yui, Y. Sugaya, A. Kano, A. Maruyama, H. Akita, R. Ito, K. Kogure, and H. Harashima, J. Am. Chem. Soc., 128, 3852 (2006).

    Article  CAS  PubMed  Google Scholar 

  91. A. Harada, R. Kobayashi, Y. Takashima, A. Hashidzume, and H. Yamaguchi, Nat. Chem., 3, 34 (2011).

    Article  CAS  PubMed  Google Scholar 

  92. G. Sinawang, M. Osaki, Y. Takashima, H. Yamaguchi, and A. Harada, Polym. J., 52, 839 (2020).

    Article  CAS  Google Scholar 

  93. H. Yamaguchi, Y. Kobayashi, R. Kobayashi, Y. Takashima, A. Hashidzume, and A. Harada, Nat. Commun., 3, 603 (2012).

    Article  PubMed  Google Scholar 

  94. H. Wang, C. N. Zhu, H. Zeng, X. Ji, T. Xie, X. Yan, Z. L. Wu, and F. Huang, Adv. Mater., 31, 1807328 (2019).

    Article  Google Scholar 

  95. M. Nakahata, Y. Takashima, and A. Harada, Angew. Chem. Int. Ed., 53, 3617 (2014).

    Article  CAS  Google Scholar 

  96. M. Nakahata, Y. Takashima, H. Yamaguchi, and A. Harada, Nat. Commun., 2, 511 (2011).

    Article  PubMed  Google Scholar 

  97. T. Kakuta, Y. Takashima, M. Nakahata, M. Otsubo, H. Yamaguchi, and A. Harada, Adv. Mater., 25, 2849 (2013).

    Article  CAS  PubMed  Google Scholar 

  98. M. Nakahata, Y. Takashima, and A. Harada, Macromol. Rapid Commun., 37, 86 (2016).

    Article  CAS  PubMed  Google Scholar 

  99. S.-Y. Jeong, S.-J. Park, S. M. Yoon, J. Jung, H. N. Woo, S. L. Yi, S. Y. Song, H. J. Park, C. Kim, J. S. Lee, J. S. Lee, and E. K. Choi, J. Control. Release, 139, 239 (2009).

    Article  CAS  PubMed  Google Scholar 

  100. H. Wang, Y. Chen, X.-Y. Li, and Y. Liu, Mol. Pharm., 4, 189 (2007).

    Article  CAS  PubMed  Google Scholar 

  101. M. Koo, K. T. Oh, G. Noh, and E. S. Lee, ACS Appl. Mater. Interfaces, 10, 24450 (2018).

    Article  CAS  PubMed  Google Scholar 

  102. K. Hayashi, K. Ono, H. Suzuki, M. Sawada, M. Moriya, W. Sakamoto, and T. Yogo, ACS Appl. Mater. Interfaces, 2, 1903 (2010).

    Article  CAS  PubMed  Google Scholar 

  103. L. Du, S. Liao, H. A. Khatib, J. F. Stoddart, and J. I. Zink, J. Am. Chem. Soc., 131, 15136 (2009).

    Article  CAS  PubMed  Google Scholar 

  104. Q.-L. Li, D. Wang, Y. Cui, Z. Fan, L. Ren, D. Li, and J. Yu, ACS Appl. Mater. Interfaces, 10, 12155 (2018).

    Article  CAS  PubMed  Google Scholar 

  105. D. P. Ferris, Y. L. Zhao, N. M. Khashab, H. A. Khatib, J. F. Stoddart, and J. I. Zink, J. Am. Chem. Soc., 131, 1686 (2009).

    Article  CAS  PubMed  Google Scholar 

  106. K. Patel, S. Angelos, W. R. Dichtel, A. Coskun, Y.-W. Yang, J. I. Zink, and J. F. Stoddart, J. Am. Chem. Soc., 130, 2382 (2008).

    Article  CAS  PubMed  Google Scholar 

  107. J.-W. Lee, J.-H. Lee, S.-H. Kim, C.-J. Kim, S.-Y. Lee, B.-C. Min, Y.-T. Shin, and C.-H. Kim, Bull. Korean Chem. Soc., 32, 1357 (2011).

    Article  CAS  Google Scholar 

  108. N. M. Khashab, A. Trabolsi, Y. A. Lau, M. W. Ambrogio, D. C. Friedman, H. A. Khatib, J. I. Zink, and J. F. Stoddart, Eur. J. Org. Chem., 1669 (2009).

  109. S. Kizaka-Kondoh, M. Inoue, H. Harada, and M. Hiraoka, Cancer Sci., 94, 1021 (2003).

    Article  CAS  PubMed  Google Scholar 

  110. D. Siegel, W. A. Franklin, and D. Ross, Clin. Cancer Res., 4, 2065 (1998).

    CAS  PubMed  Google Scholar 

  111. S. Rockwell, I. T. Dobrucki, E. Y. Kim, S. T. Marrison, and V. T. Vu, Curr. Mol. Med., 9, 442 (2009).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

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  1. Department of Polymer Science and Engineering, Inha University, Incheon, 22212, Korea

    Jeonghun Lee & Chulhee Kim

  2. Program in Environmental and Polymer Engineering, Inha University, Incheon, 22212, Korea

    Chulhee Kim

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  1. Jeonghun Lee
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Footnote: The image from this article is used as the cover image of the Volume 29, Issue 11.

Acknowledgment: This work was supported by the National Research Foundation of Korea (NRF) (NRF-2020R1A2C1013219, NRF-2021R1C1C2011651). C. K. also thanks Inha University for support.

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Lee, J., Kim, C. Cyclodextrin Molecules, Polymers and Nanomaterials. Macromol. Res. 29, 745–760 (2021). https://doi.org/10.1007/s13233-021-9090-8

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