Skip to main content
SpringerLink
Log in

Interactions of cucurbit[7]uril and β-cyclodextrin with some nucleobases

  • Original Article
  • Published:
Journal of Inclusion Phenomena and Macrocyclic Chemistry Aims and scope Submit manuscript

Abstract

The binding affinity of both macrocyclic receptors, cucurbit[7]uril (CB[7]) and β-cyclodextrin (β-CD), respectively, towards guanine and cytosine was investigated in solution by means of UV spectroscopy and fluorescence spectroscopy. The association constants and the stoichiometry of host–guest complexes were determined. Thus by the Job’s method of continuous variations, the stoichiometry of CB[7]-cytosine and β-cyclodextrin-guanine was found to be 1:1 for both complexes under study. The UV absorption and fluorescence intensity of guanine increased in the presence of β-cyclodextrin highlighting the formation of the complex between guanine and β-cyclodextrin. Correlating the results obtained by UV absorption spectroscopy with the findings from fluorescence measurements leads to concluding that formation of an inclusion complex of β-cyclodextrin with guanine at pH 3.0 is possible.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Chart 1

Similar content being viewed by others

References

  1. Lehn, J.-M.: Supramolecular Chemistry: Concepts and Perspective. Wiley-VCH, Weinheim (1995)

    Book  Google Scholar 

  2. Assaf, K.I., Nau, W.M.: Cucurbiturils: from synthesis to high-affinity binding and catalysis. Chem. Soc. Rev. 44, 394–418 (2015)

    Article  CAS  Google Scholar 

  3. Chui, J.K.W., Fyles, T.M.: Cyclodextrin ion channels. Org. Biomol. Chem. 12, 3622–3634 (2014)

    Article  CAS  Google Scholar 

  4. Lee, T.-C., Kalenius, E., Lazar, A.I., Assaf, K.I., Kuhnert, N., Grün, C.H., Jänis, J., Scherman, O.A., Nau, W.M.: Chemistry inside molecular containers in the gas phase. Nat. Chem. 5, 376–382 (2013)

    Article  CAS  Google Scholar 

  5. Mutihac, R.-C., Riegler, H.: Phase transition broadening due to interfacial premelting: a new quantitative access to intermolecular interactions within submonolayer films at solid/vapor interfaces. Langmuir 26, 6394–6399 (2010)

    Article  CAS  Google Scholar 

  6. Mutihac, L., Lee, J.H., Kim, J.S., Vicens, J.: Recognition of amino acids by functionalized calixarenes. Chem. Soc. Rev. 40, 2777–2796 (2011)

    Article  CAS  Google Scholar 

  7. Kim, K., Selvapalam, N., Ko, Y.H., Park, K.M., Kim, D., Kim, J.: Functionalized cucurbiturils and their applications. Chem. Soc. Rev. 36, 267–279 (2007)

    Article  CAS  Google Scholar 

  8. Buschmann, H.-J., Mutihac, R.-C., Schollmeyer, E.: Interactions between crown ethers and water, methanol, acetone, and acetonitrile in halogenated solvents. J. Solut. Chem. 39, 291–299 (2010)

    Article  CAS  Google Scholar 

  9. Popeney, C.S., Setaro, A., Mutihac, R.-C., Blummel, P., Trappman, B., Vonnem, J., Reich, S., Haag, R.: Polyglycerol-derived amphiphiles for the solubilization of single-walled carbon nanotubes in water: a structure-property study. ChemPhysChem 13, 203–211 (2012)

    Article  CAS  Google Scholar 

  10. Buschmann, H.-J., Mutihac, L., Mutihac, R.: Physicochemical parameters of the transport of amines and amino acids through liquid membranes by macrocyclic ligands. Sep. Sci. Technol. 34, 331–341 (1999)

    Article  CAS  Google Scholar 

  11. Mutihac, L., Mutihac, R., Buschmann, H.-J.: Liquid membrane transport of supramolecular complexes of some amines and amino acids with macrocyclic ligands. J. Incl. Phenom. Macrocycl. Chem. 23, 167–174 (1995)

    Article  CAS  Google Scholar 

  12. Schneider, H.-J.: Binding mechanisms in supramolecular complexes. Angew. Chem. Int. Ed. 48, 3924–3977 (2009)

    Article  CAS  Google Scholar 

  13. Ghale, G., Nau, W.M.: Dynamically analyte-responsive macrocyclic host- fluorophore systems. Acc. Chem. Res. 47, 2150–2159 (2014)

    Article  CAS  Google Scholar 

  14. Lagona, J., Mukhopadhyay, P., Chakrabarti, S., Isaacs, L.: The cucurbit[n]uril family. Angew. Chem. Int. Ed. 44, 4844–4870 (2005)

    Article  CAS  Google Scholar 

  15. Florea, M., Nau, W.M.: Strong binding of hydrocarbons to cucurbituril probed by fluorescent dye displacement: A supramolecular gas-sensing ensemble. Angew. Chem. Int. Ed. 50, 9338–9342 (2011)

    Article  CAS  Google Scholar 

  16. Behrend, R., Meyer, E., Rusche, F.: Ueber Condensatiosprodukte aus Glycoluril und Formaldehyd. Liebigs Ann. Chem. 339, 1–37 (1905)

    Article  Google Scholar 

  17. Freeman, W.A., Mock, W.L., Shih, N.-Y.: Cucurbituril. J. Am. Chem. Soc. 103, 7367–7368 (1981)

    Article  CAS  Google Scholar 

  18. Day, A., Arnold, A.P., Blanch, R.J., Snushall, B.: Controlling factors in the synthesis of cucurbituril and its homologues. J. Org. Chem. 66, 8094–8100 (2001)

    Article  CAS  Google Scholar 

  19. Lee, J.W., Samal, S., Selvapapm, N., Kim, H.-J., Kim, K.: Cucurbituril homologues and derivatives: new opportunities in supramolecular chemistry. Acc. Chem. Res. 36, 621–630 (2002)

    Article  Google Scholar 

  20. Kim, C., Agasti, S.S., Zhu, Z., Isaacs, L., Rotello, V.: Host-guest chemistry inside the cell: recognition-mediated activation of therapeutic gold nanoparticles. Nat. Chem. 2, 962–966 (2010)

    Article  CAS  Google Scholar 

  21. Buschmann, H.-J., Mutihac, L., Schollmeyer, E.: Complex formation of crown ethers with the cucurbit[6]uril-spermidine- and cucurbit[6]uril-spermine-complex in aqueous solution. J. Incl. Phenom. Macrocycl. Chem. 53, 85–88 (2005)

    Article  CAS  Google Scholar 

  22. Cao, L., Isaacs, L.: Absolute and relative binding affinity of cucurbit[7]uril towards a series of cationic guests. Supramol. Chem. 26, 251–258 (2014)

    Article  CAS  Google Scholar 

  23. Yang, H., Yuan, B., Scherman, O.A.: Supramolecular chemistry at interfaces: host-guest interactions for fabricating multifunctional biointerfaces. Acc. Chem. Res. 47, 2106–2115 (2014)

    Article  CAS  Google Scholar 

  24. Urbach, A.R., Ramalingam, V.: Molecular recognition of amino acids, peptides, and proteins by cucurbit[n]uril receptors. Isr. J. Chem. 51, 664–678 (2011)

    Article  CAS  Google Scholar 

  25. Buschmann, H.-J., Cleve, E., Mutihac, L., Schollmeyer, E.: A novel experimental method for the study of complex formation between alpha-, beta-, and gamma- cyclodextrin and nearly insoluble cucurbituril-[2]rotaxanes in aqueous solution. Microchem. J. 64, 99–103 (2000)

    Article  CAS  Google Scholar 

  26. Lu, X., Masson, E.: Formation and stabilization of silver nanoparticles with cucurbit[n]urils (n = 5–8) and cucurbituril-based pseudorotaxanes in aqueous medium. Langmuir 27, 3051–3058 (2011)

    Article  CAS  Google Scholar 

  27. Buschmann, H.-J., Schollmeyer, E., Mutihac, L.: The formation of amino acid and peptide complexes with α-cyclodextrin and cucurbit[6]uril in aqueous solutions studied by titration calorimetry. Thermochim. Acta 399, 203–208 (2003)

    Article  CAS  Google Scholar 

  28. Buschmann, H.-J., Mutihac, L., Mutihac, R.-C., Schollmeyer, E.: Complexation behavior of cucurbit[6]uril with short polypeptides. Thermochim. Acta 430, 79–82 (2005)

    Article  CAS  Google Scholar 

  29. Stancu, A.-D., Hillebrand, M., Tablet, C.: Mutihac, L.:β-cyclodextrin derivative as chiral carrier in membrane transport of some aromatic amino acids. J. Incl. Phenom. Macrocycl. Chem. 78, 71–76 (2014)

    Article  CAS  Google Scholar 

  30. Chen, Y., Zhang, Y.-M., Liu, Y.: Molecular selective binding and nanofabrication of cucurbituril/cyclodextrin pairs. Isr. J. Chem. 51, 515–524 (2011)

    Article  CAS  Google Scholar 

  31. Buschmann, H.-J., Mutihac, L., Schollmeyer, E.: 11-Aminoundecanoic acid, cyclodextrins (α, β) and cucurbit[n]urils (n = 6, 7) as building blocks for supramolecular assemblies. A thermodynamic study. J. Incl. Phenom. Macrocycl. Chem. 56, 363–368 (2006)

    Article  CAS  Google Scholar 

  32. Marquez, C., Hudgins, R.R., Nau, W.M.: Mechanism of host–guest complexation by cucurbituril. J. Am. Chem. Soc. 126, 5806–5816 (2004)

    Article  CAS  Google Scholar 

  33. Buschmann, H.-J., Mutihac, L., Schollmeyer, E.: The formation of homogeneous and heterogeneous 2:1 complexes between dialkyl- and diarylammonium ions and alpha-cyclodextrin and cucurbit[6]uril in aqueous formic acid. Thermochim. Acta 495, 28–32 (2009)

    Article  CAS  Google Scholar 

  34. Valluru, G., Georghiou, P.E., Sleem, H.F., Perret, F., Montaser, I., Grandvoinnet, A., Brolles, L., Coleman, A.W.: Molecular recognition of nucleobases and amino acids by sulphonato-calixnaphthalene-capped silver nanoparticles. Supramol. Chem. 26, 561–568 (2014)

    Article  CAS  Google Scholar 

  35. Shimojo, K., Oshima, T., Goto, M.: Calix[6]arene acetic acid extraction behavior and specificity with respect to nucleobases. Anal. Chim. Acta 521, 163–171 (2004)

    Article  CAS  Google Scholar 

  36. Hao, X., Liang, C., Jian-Bin, C.: Preparation and spectroscopic studies of an inclusion complex of adenine with β-cyclodextrin in solution and in the solid state. Analyst 127, 834–837 (2002)

    Article  Google Scholar 

  37. Huang, Y., Xue, S.-F., Zhu, Q.-J., Zhu, T.: Inclusion interactions of cucurbit[7]uril with adenine and its derivatives. Supramol. Chem. 20, 279–287 (2008)

    Article  CAS  Google Scholar 

  38. Marquez, C., Huang, F., Nau, W.M.: Cucurbiturils: molecular nanocapsules for time-resolved fluorescence-based assays. IEEE Trans. Nanobiosci. 3, 39–45 (2004)

    Article  Google Scholar 

  39. Billinghurst, B.E., Oladepo, S.A., Loppnow, G.R.: pH-dependent UV resonance raman spectra of cytosine and uracil. J. Phys. Chem. B 113, 7392–7397 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Elena Iulia Cucolea is grateful for financial support to strategic grant POSDRU 159/1.5/S/133652, Project “Support for Doctoral students and Postdoctoral researchers” cofinanced by the European Social Found within the Sectorial Operational Program Human Resources Development 2007–2013.

Author information

Authors and Affiliations

  1. Department of Analytical Chemistry, University of Bucharest, 4-12 Blvd. Regina Elisabeta, 030018, Bucharest, Romania

    Elena Iulia Cucolea & Lucia Mutihac

  2. Faculty of Pharmacy, Titu Maiorescu University, Gh. Şincai Bd. 16, Bucharest, Romania

    Cristina Tablet

  3. Department of Physical Chemistry, University of Bucharest, 4-12 Blvd. Regina Elisabeta, 030018, Bucharest, Romania

    Cristina Tablet

  4. University Duisburg-Essen, NETZ/DTNW gGmbH, Carl-Benz-Strase 199, 47057, Duisburg, Germany

    Hans-Jürgen Buschmann

Authors
  1. Elena Iulia Cucolea
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Cristina Tablet
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hans-Jürgen Buschmann
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Lucia Mutihac
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Lucia Mutihac.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Cucolea, E.I., Tablet, C., Buschmann, HJ. et al. Interactions of cucurbit[7]uril and β-cyclodextrin with some nucleobases. J Incl Phenom Macrocycl Chem 83, 103–110 (2015). https://doi.org/10.1007/s10847-015-0544-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-015-0544-5

Keywords

Search

Navigation