Skip to main content
Log in

Recognition and Sensing of Guanidine-containing Biomolecules in Aqueous Medium

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

A dicarboxylate-based fluorescent receptor has been synthesized for the recognition of the guanidinium ion and guanidine-containing biomolecules in aqueous medium to address the issue of biomolecular interaction. The acyclic receptor binds to guests in a 1: 2 mode due to the flexibility of its binding motifs. The host-guest binding behavior was studied by means of UV and fluorescence titration. The binding of the host with the guanidinium ion was found to be stronger than with the other guanidine-containing guests.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. (a) Fujisawa, K., Humbert-Droz, M., Letrun, R., Vauthey, E., Wesolowski, T.A., Sakai, N., and Matile, S., J. Am. Chem. Soc., 2015, vol. 137, p. 11047. (b) Wang, X., Sarycheva, O.V., Koivisto, B.D., McKie, A.H. and Hof, F., Org. Lett., 2008, vol. 10, p. 297.

    Article  CAS  PubMed  Google Scholar 

  2. (a) Balakrishnan, S., Scheuermann, M. J., and Zondlo, N.J., ChemBioChem, 2012, vol. 13, p. 259. (b) Chen, H., Gu, L., Yin, Y., Koh, K., and Lee, J., Int. J. Mol. Sci., 2011, vol. 12, p. 2315.

    Article  CAS  PubMed  Google Scholar 

  3. Guinovart, T., Hernandez-Alonso, D., Adriaenssens, L., Blondeau, P., Martinez-Belmonte, M., Rius, F.X., Andrade, F. J., and Ballester, P., Angew. Chem. Int. Ed., 2016, vol. 55, p. 2435.

    Article  CAS  Google Scholar 

  4. Bell, T.W., Khasanov, A.B., and Drew, M.G.B., J. Am. Chem. Soc., 2002, vol. 124, p. 14092.

    Article  CAS  PubMed  Google Scholar 

  5. Fokkens, M., Schrader, T., and Klarner, F.-G., J. Am. Chem. Soc., 2005, vol. 127, p. 14415.

    Article  CAS  PubMed  Google Scholar 

  6. Potocky, T.B., Silvius, J., Menon, A.K., and Gellman, S.H., ChemBioChem, 2007, vol. 8, p. 917.

    Article  CAS  PubMed  Google Scholar 

  7. Schug, K.A. and Lindner, W., Chem. Rev., 2005, vol. 105, p. 67.

    Article  CAS  PubMed  Google Scholar 

  8. Wender, P.A., Galliher, W.C., Goun, E.A., Jones, L.R., and Pillow, T.H., Adv. Drug Delivery Rev., 2008, vol. 60, p. 452.

    Article  CAS  Google Scholar 

  9. Mueller, N., Pasternak, A.O., Klaver, B., Cornelissen, M., Berkhout, B., and Das, A.T., J. Virol., 2018, vol. 92, p. e01855–17.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. Hammond, J.A., Zhou, L., Lamichhane, R., Chu, H.-Y., Millar, D.P., Gerace, L., and Williamson, J.R., J. Mol. Biol., 2018, vol. 430, p. 537.

    Article  CAS  PubMed  Google Scholar 

  11. Lee, S.D., Yu, K.L., Park, S.H., Jung, Y.M., Kim, M.J., and You, J.C., BMB Rep., 2018, vol. 51, p. 388.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  12. (a) Best, M.D., Tobey, S.L., and Anslyn, E.V., Coord. Chem. Rev., 2003, vol. 240, p. 3. (b) Leow, D., and Tan, C.H., Chem. Asian J., 2009, vol. 4, p. 488. (c) Blondeau, P., Segura, M., Prez-Fernndez, R., and de Mendoza, J., Chem. Soc. Rev., 2007, vol. 36, p. 198. (d)Schmuck, C., Coord. Chem. Rev., 2006, vol. 250, p. 3053.

    Article  CAS  Google Scholar 

  13. Gokel, G.W., Leevy, M., and Weber, M.E., Chem. Rev., 2004, vol. 104, p. 2723.

    Article  CAS  PubMed  Google Scholar 

  14. (a) James, L.I., Beaver, J.E., Rice, N.W. and Waters, M.L., J. Am. Chem. Soc., 2013, vol. 135, p. 6450. (b) Zhou, X., Jin, X., Li, D., and Wu, X. Chem. Commun., 2011, vol. 47, p. 3921.

    Article  CAS  Google Scholar 

  15. Barrow, S.J., Kasera, S., Rowland, M.J., del Barrio, J., and Scherman, O.A., Chem. Rev., 2015, vol. 115, p. 12320.

    Article  CAS  PubMed  Google Scholar 

  16. Chen, H., Gu, L., Yin, Y., Koh, K., and Lee, J., Int. J. Mol. Sci., 2011, vol. 12, p. 2315.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. Späth, A., and König, B., Beilstein J. Org. Chem., 2010, vol. 6, no. 32. doi 10.3762/bjoc.6.32; (b) Gersthagen, T., Schmuck, C., and Schrader, T. Supramol. Chem., 2010, vol. 22, p. 853.

    Google Scholar 

  18. (a) Oshovsky, G.V., Reinhoudt, D.N., and Verboom, W., Angew. Chem. Int. Ed., 2007, vol. 46, p. 2366. (b) Zhao, Y., Chem. Eur. J., 2018, vol. 24, p. 14001.

    Article  CAS  Google Scholar 

  19. So, S.M., Moozeh, K., Lough, A.J., and Chin, J., Angew. Chem. Int. Ed., 2014, vol. 53, p. 829.

    Article  CAS  Google Scholar 

  20. (a) Marcotte, N., Fery-Forgues, S., and Lavabre, D., J. Phys. Chem. A, 1999, vol. 103, p. 3163. (b) Marcotte, N., and Fery-Forgues, S., J. Chem. Soc., Perkin Trans. 2, 2000, p. 1711.

    Article  Google Scholar 

  21. The minimization of energy was carried out by MMX (PC MODEL by Serena Software)

  22. (a) Connors K.A., Binding Constant: The Measurement of Molecular Complex Stability, New York: John Wiley & Sons, 1987. (b) Benesi, H. and Hildebrand, J.H., J. Am. Chem. Soc., 1949, vol. 71, p. 2703.

    Google Scholar 

  23. (a) Hargrove, A.E., Zhong, Z., Sessler, J.L., Anslyn, E.V., New J. Chem., 2010, vol. 34, p. 348. (b) Thordarson, P., Chem. Soc. Rev., 2011, vol. 40, p. 1305.

    Article  CAS  PubMed  Google Scholar 

  24. Gel’man, N.E., Terent’eva, E.A., Shanina, T.M., Kipa-renko, L.M., and Rezl, V., Metody kolichestvennogo orga-nicheskogo elementnogo mikroanaliza (The Methods of Quantitative Organic Elemental Microanalysis), Moscow: Khimiya, 1987.

    Google Scholar 

Download references

Acknowledgments

Subrata Jana thanks to MPCST, Govt. of Madhya Pradesh, India for financial support. Kishor Kumar Suryavanshi thanks to Indira Gandhi National Tribal University (Central University), Amarkantak, M.P., India for research fellowship.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Subrata Jana.

Additional information

Russian Text © The Author(s), 2019, published in Zhurnal Organicheskoi Khimii, 2019, Vol. 55, No. 5, pp. 818.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jana, S., Suryavanshi, K.K. Recognition and Sensing of Guanidine-containing Biomolecules in Aqueous Medium. Russ J Org Chem 55, 707–715 (2019). https://doi.org/10.1134/S1070428019050208

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019050208

Key words

Navigation