Skip to main content
SpringerLink
Log in

Dimeric (Oligomeric) Derivatives of Cyclodextrins as a New Class of Supramolecular Systems: Their Synthesis and Inclusion Complexes

  • MINI-REVIEW
  • Published:
Russian Journal of Bioorganic Chemistry Aims and scope Submit manuscript

Abstract

We have summarized the works on the synthesis and application of dimeric (oligomeric) cyclodextrin derivatives. Due to the presence of two or more internal cyclodextrin cavities and their spatial proximity and other properties of these derivatives, they have an increased so-called cooperative effect with respect to the inclusion of numerous guests. It allows us to define these compounds as a new class of supramolecular structures. We have briefly analyzed the opportunities for their application in different fields of organic, analytical, and medicinal chemistry.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1.

Similar content being viewed by others

REFERENCES

  1. Len, Zh.-M., Supramolekulyarnaya khimiya: kontseptsii i perspektivy (Supramolecular Chemistry: Concepts and Prospects), Novosibirsk: Nauka, Sib. Predpr. Ross. Akad. Nauk, 1998.

  2. Steed, J.W. and Atwood, J.L., Supramolecular Chemistry, Chichester: Wiley, 2000.

    Google Scholar 

  3. Dodziuk, H., Cyclodextrins and Their Complexes. Chemistry, Analytical Methods, Application, Wiley-VCH, Weinheim, 2006.

    Book  Google Scholar 

  4. Chem. Rev. (special issue), 1998, vol. 98, no. 5.

  5. Beilstein J. Org. Chem. (special issue), 2012, vol. 8.

  6. Beilstein J. Org. Chem. (special issue), 2014, vol. 10.

  7. Khan, A.R., Forgo, P., Stine, K.J., and D’Souza, V.T., Chem. Rev., 1998, vol. 98, no. 5, pp. 1977–1996.

    Article  CAS  PubMed  Google Scholar 

  8. Szejtli, J., Chem. Rev., 1998, vol. 98, no. 5, pp. 1743–1753.

    Article  CAS  PubMed  Google Scholar 

  9. Saenger, W., Jacob, J., Gessler, K., Steiner, T., Hoffman, D., Sanbe, H., Kozumi, K., Smith, S.M., and Tanaka, T., Chem. Rev., 1998, vol. 98, no. 5, pp. 1787–1802.

    Article  CAS  PubMed  Google Scholar 

  10. Croft, A.P. and Bartsch, R.A., Tetrahedron, 1983, vol. 39, no. 9, pp. 1417–1474.

    Article  CAS  Google Scholar 

  11. Clazyrin, A.E., Kurochkina, G.I., Crachev, M.K., and Nifant’ev, E.E., Mendeleev Commun., 2001, no. 6, pp. 218–219.

  12. Grachev, M.K., Glazyrin, A.E., Kurochkina, G.I., and Nifant’ev, E.E., Russ. J. Gen. Chem., 2004, vol. 74, pp. 808–809.

    Article  CAS  Google Scholar 

  13. Glazyrin, A.E., Syrtsev, A.N., Kurochkina, G.I., Kononov, L.O., Crachev, M.K., and Nifant’ev, E.E., Russ. Chem. Bull., 2003, vol. 52, pp. 237–243.

    Article  CAS  Google Scholar 

  14. Crachev, M.K., Russ. Chem. Rev., 2013, vol. 82, pp. 1034–1046.

    Article  CAS  Google Scholar 

  15. de Miranda, J.C., Martins, T.E.A., Veiga, F., and Ferraz, H.G., Braz. J. Pharm. Sci., 2011, vol. 47, no. 4, pp. 665–681.

    Article  Google Scholar 

  16. Harada, A., Furue, M., and Nozakura, S.I., Macromolecules, 1977, vol. 10, pp. 676–679.

    Article  CAS  Google Scholar 

  17. Tabushi, I., Kuroda, Y., and Shimokawa, K., J. Am. Chem. Soc., 1979, vol. 101, pp. 1614–1615.

    Article  CAS  Google Scholar 

  18. Harada, A., Furue, M., and Nozakura, S.I., Polymers, 1981, vol. 13, pp. 777–781.

    CAS  Google Scholar 

  19. Fujita, K., Ejima, S., and Imoto, T., Chem. Soc.,Chem. Commun., 1984, pp. 1277–1278.

  20. Breslow, R., Greenspoon, N., Guo, T., and Zarzycki, R., J. Am. Chem. Soc., 1989, vol. 111, pp. 8296–8297.

    Article  CAS  Google Scholar 

  21. Cho, E. and Jung, S., Molecules, 2015, vol. 20, pp. 19620–19646.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Liu, Y. and Chen, Y., Acc. Chem. Res., 2006, vol. 39, pp. 681–691.

    Article  CAS  PubMed  Google Scholar 

  23. Tilloy, S., Binkowski-Machut, C., Menuel, S., Bricout, H., and Monflier, E., Molecules, 2012, vol. 17, pp. 13062–13072.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  24. Blaszkiewicz, C., Bricout, H., Leonard, E., Len, C., Landy, D., Cezard, C., Djedaϊni-Pilard, F., Monflier, E., and Tilloy, S., Chem. Commun., 2013, vol. 49, pp. 6989–6991.

    Article  CAS  Google Scholar 

  25. Breslow, R., Belvedere, S., Gershell, L., and Leung, D., Pure Appl. Chem., 2000, vol. 72, no. 3, pp. 333–342.

    Article  CAS  Google Scholar 

  26. Beilstein J. Org. Chem. (special issue), 2015, vol. 11.

  27. Breslow, R. and Chung, S., J. Am. Chem. Soc., 1990, vol. 112, pp. 9659–9660.

    Article  CAS  Google Scholar 

  28. Zhang, B. and Breslow, R., J. Am. Chem. Soc., 1993, vol. 115, pp. 9353–9354.

    Article  CAS  Google Scholar 

  29. Zhang, B. and Breslow, R., J. Am. Chem. Soc., 1997, vol. 119, pp. 1676–1681.

    Article  CAS  Google Scholar 

  30. Yan, J. and Breslow, R., Tetrahedron Lett., 2000, vol. 41, pp. 2059–2062.

    Article  CAS  Google Scholar 

  31. Breslow, R., Yang, Z., Ching, R., Trojandt, G., and Odobel, F., J. Am. Chem. Soc., 1998, vol. 120, pp. 3536–3537.

    Article  CAS  Google Scholar 

  32. Zutschi, R., Brickner, M., and Chmielewski, J., Curr. Opin. Chem. Biol., 1998, vol. 2, pp. 62–66.

    Article  Google Scholar 

  33. Chmielewski, J., Biopolymers, 1998, vol. 47, pp. 277–283.

    Article  PubMed  Google Scholar 

  34. Zutshi, R., Shultz, M.D., Ulysse, L., Lutgring, R., Bishop, P., Schweitzer, B., Vogel, K., Franciskovich, J., Wilson, M., and Chmielewski, J., Synlett, 1998, vol. 10, pp. 1040–1044.

    Article  Google Scholar 

  35. Zutshi, R., Franciskovich, M., Shultz, M., Schweitzer, B., Bishop, M., Wilson, M., and Chmielewski, J., J. Am. Chem. Soc., 1997, vol. 119, pp. 4841–4845.

    Article  CAS  Google Scholar 

  36. Daugherty, D.L. and Gellman, S.H., J. Am. Chem. Soc., 1999, vol. 121, pp. 4325–4333.

    Article  CAS  Google Scholar 

  37. Park, H.S., Lin, Q., and Hamilton, A.D., J. Am. Chem. Soc., 1999, vol. 121, pp. 8–13.

    Article  CAS  Google Scholar 

  38. Lin, Q., Park, H.S., Humaro, Y., Lee, C.S., and Hamilton, A.D., Biopolymers, 1998, vol. 47, pp. 285–297.

    Article  CAS  PubMed  Google Scholar 

  39. Clackson, T., Ultsch, M.H., Wells, J.A., and de Vos, A.M., J. Mol. Biol., 1998, vol. 277, pp. 1111–1128.

    Article  CAS  PubMed  Google Scholar 

  40. Ruebner, A., Yang, Z., Leung, D., and Breslow, R., Proc. Natl. Acad. Sci. U. S. A., 1999, vol. 96, pp. 14692–14693.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  41. Liy, Y., Chen, G.-S., Li, L., Zhang, H.-Y., Cao, D.-X., and Yuan, Y.-J., J. Med. Chem., 2003, vol. 46, pp. 4634–4637.

    Article  CAS  Google Scholar 

  42. Aykaҫ, A., Martos-Maldonado, M.C., Casas-Solvas, J.M., Garsiá-Fuentes, L., and Vargas-Berenguel, A., J. Drug Del. Sci. Tech., 2012, vol. 22, pp. 270–272.

    Article  Google Scholar 

  43. Kritskiy, I., Kumeev, R., Volkova, T., Shipilov, D., Kutysheva, N., Grachev, M., and Terekhova, I., New J. Chem., 2018, vol. 42, pp. 14559–14567.

    Article  CAS  Google Scholar 

  44. Grachev, M.K., Malenkovskaya, M.A., and Vasyanina, L.K., J. Incl. Phenom. Macrocycl. Chem., 2015, vol. 83, nos. 3–4, pp. 209–214.

    Article  CAS  Google Scholar 

  45. Malenkovskaya, M.A., Vasyanina, L.K., and Grachev, M.K., Russ. J. Gen. Chem., 2015, vol. 85, pp. 1161–1165.

    Article  CAS  Google Scholar 

  46. Breslow, R., Zhang, X., and Huang, Y., J. Am. Chem. Soc., 1997, vol. 119, pp. 4535–4536.

    Article  CAS  Google Scholar 

  47. Breslow, R., Gabriele, B., and Yang, J., Tetrahedron Lett., 1998, vol. 39, pp. 2887–2890.

    Article  CAS  Google Scholar 

  48. Breslow, R. and Zhang, B., J. Am. Chem. Soc., 1996, vol. 118, no. 35, pp. 8495–8496.

    Article  CAS  Google Scholar 

  49. Leung, D.K., Atkins, J.H., and Breslow, R., Tetrahedron Lett., 2001, vol. 42, no. 36, pp. 6255–6258.

    Article  CAS  Google Scholar 

  50. Bistri, O., Lecourt, T., Mallet, J.-M., Sollogoub, M., and Sinaӱ, P., Chem. Biodiversity, 2004, vol. 1, no. 1, pp. 129–137.

    Article  CAS  Google Scholar 

  51. Lecourt, T., Mallet, J.-M., and Sinaӱ, P., Tetrahedron Lett., 2002, vol. 43, pp. 5533–5536.

    Article  CAS  Google Scholar 

  52. Chen, Y., Li, L., and Liu, Y., Chem. J. Chin. Univ., 2002, vol. 23, no. 6, pp. 1091–1093.

    CAS  Google Scholar 

  53. Zheng, X.Q., Wang, Y.H., Guo, Q.X., Yang, L., and Liu, Y.C., Chin. Chem. Lett., 2003, vol. 14, no. 8, pp. 848–851.

    CAS  Google Scholar 

  54. Song, L.X., Chin. Chem. Lett., 2002, vol. 13, no. 10, pp. 1005–1006.

    CAS  Google Scholar 

  55. Zhao, Y., Liu, X.Q., Wang, L.-Q., Zhu, H.-Y., Huang, R., Wang, Y.-F., and Yang, Z.-M., J. Phys. Org. Chem., 2008, vol. 21, no. 6, pp. 440–448.

    Article  CAS  Google Scholar 

  56. Pham, D.-T., Ngo, H.T., Lincoln, S.F., May, B.L., and Easton, C.J., Tetrahedron, 2010, vol. 66, pp. 2895–2898.

    Article  CAS  Google Scholar 

  57. Takashima, Y., Yuting, Y., Otsubo, M., Yamaguchi, H., and Harada, A., Beilstein J. Org. Chem., 2012, vol. 8, pp. 1594–1600.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  58. Malenkovskya, M.A., Levina, I.I., and Grachev, M.K., J. Org. Chem., 2014, vol. 50, pp. 1211–1215.

    Google Scholar 

  59. Shipilov, D.A., Kurochkina, G.I., Akhlebinin, A.K., Kutyasheva, N.V., and Grachev, M.K., Macroheterocycles, 2019, vol. 12, no. 1, pp. 94–97.

    Article  CAS  Google Scholar 

  60. Tripodo, G., Wischke, C., Neffe, A.T., and Lendlein, A., Carbohydr. Res., 2013, vol. 381, pp. 59–63.

    Article  CAS  PubMed  Google Scholar 

  61. Kurlemann, M. and Kavoo, B.J., Beilstein J. Org. Chem., 2014, vol. 10, pp. 2428–2440.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  62. Hamon, F., Blaszkiewicz, C., Monflier, E., and Djedaim-Pilard, F., Beilstein J. Org. Chem., 2014, vol. 10, pp. 2874–2885.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  63. Kuad, P., Miyawaki, A., Takashima, Y., Yamaguchi, H., and Harada, A., J. Am. Chem. Soc., 2007, vol. 129, no. 42, pp. 12630–12631.

    Article  CAS  PubMed  Google Scholar 

  64. Ohga, K., Takashima, Y., Takashima, Y., Kawaguchi, Y., Yamaguchi, H., and Harada, A., Macromolecules, 2005, vol. 38, no. 14, pp. 5897–5904.

    Article  CAS  Google Scholar 

  65. Städe, L.W., Nielsen, T.T., Duroux, L., Wimmer, R., Shimizu, K., and Larsen, K.L., Beilstein J. Org. Chem., 2015, vol. 11, pp. 514–523.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  66. Trotta, F., Zanetti, M., and Cavelli, R., Beilstein J. Org. Chem., 2012, vol. 8, pp. 2091–2099.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  67. Maurer, M., Hapiot, F., Monflier, E., and Menuel, S., Tetrahedron, 2008, vol. 64, pp. 7159–7163.

    Article  CAS  Google Scholar 

  68. Manuel, S., Azaroul, N., Landy, D., Six, N., Hapiot, F., and Monflier, E., Chem.-Eur. J., 2011, vol. 17, pp. 3949–3955.

    Article  CAS  Google Scholar 

  69. Voskuhl, J., Schaepc, K., and Ravoo, B.J., Int. J. Mol. Sci., 2011, vol. 12, pp. 4637–4646.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  70. Terao, J., Konoshima, Y., Matono, A., Masai, H., Fujihara, T., and Tsuji, Y., Beilstein J. Org. Chem., 2014, vol. 10, pp. 2800–2808.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  71. Edwards, W.B., Reichert, D.E., d’Avignon, D.A., and Welch, M.J., Chem. Commun., 2001, pp. 1312–1313.

  72. Casas-Solvas, J.M., Quesad-Soriano, I., Carreno-Gazquez, D., Gimenez-Martinez, J.J., Garcia-Fuentes, L., and Vargas-Berenguel, Langmuir, 2011, vol. 27, pp. 9729–9737.

    Article  CAS  PubMed  Google Scholar 

  73. Venema, F., Baselier, C.M., van Dienst, E., Ruel, B.H.M., Feiters, M.C., Endersen, J.F.J., Reinhoudt, D.N., and Nolte, R.J.M., Tetrahedron Lett., 1994, vol. 35, no. 11, pp. 1773–1776.

    Article  CAS  Google Scholar 

  74. Yan, J. and Breslow, R., Tetrahedron Lett., 2000, vol. 41, no. 13, pp. 2059–2062.

    Article  CAS  Google Scholar 

  75. von Piekartz, I., Grote, GanseyM.H.B., Venema, F., Feiters, M.C., Nolte, R.J.M., Engbersen, J.F.J., and Reinhoudt, D.N., Org. Chem., 1995, vol. 60, pp. 6537–6545.

    Article  Google Scholar 

  76. Jiang, T., Sukumaran, D.K., Soni, S.-D., and Lawrence, D.S., Org. Chem., 1994, vol. 59, no. 18, pp. 5149–5155.

    Article  CAS  Google Scholar 

  77. Chiu, S.-H., Myles, D.C., Garrell, R.L., and Stoddart, J.F., Org. Chem., 2000, vol. 65, no. 9, pp. 2792–2796.

    Article  CAS  Google Scholar 

  78. De Jong, M.R., Engbersen, J.F.J., Huskens, J., and Reinhoudt, D.N., Chem.-Eur. J., 2000, vol. 6, pp. 4034–4040.

    Article  CAS  PubMed  Google Scholar 

  79. Jia, S.-Y., Hao, Y.-Q., Li, L.-N., Chen, K., Wu, Y., Liu, J., Wu, L., and Ding, Y.-H., Chem. Lett., 2005, vol. 34, no. 9, pp. 1248–1249.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Moscow State University of Education, Institute of Biology and Chemistry, 129164, Moscow, Russia

    M. K. Grachev, D. A. Shipilov, N. V. Kutyasheva & E. Y. Emelianova

  2. G.A. Krestov Institute of Solution Chemistry, Russian Academy of Sciences, 153045, Ivanovo, Russia

    I. V. Terekhova

Authors
  1. M. K. Grachev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. I. V. Terekhova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. D. A. Shipilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. N. V. Kutyasheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. E. Y. Emelianova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. K. Grachev.

Ethics declarations

COMPLIANCE WITH ETHICAL STANDARDS

This article does not contain studies that use humans and animals as objects of research.

Conflict of Interests

The authors state that there is no conflict of interest.

Additional information

Translated by A. Levina

Corresponding author: phone: +7 (495) 682-02-45; e-mail: mkgrachev@yandex.ru.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Grachev, M.K., Terekhova, I.V., Shipilov, D.A. et al. Dimeric (Oligomeric) Derivatives of Cyclodextrins as a New Class of Supramolecular Systems: Their Synthesis and Inclusion Complexes. Russ J Bioorg Chem 46, 14–31 (2020). https://doi.org/10.1134/S1068162020010021

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1068162020010021

Keywords:

Search

Navigation