Skip to main content
Log in

Naphthyridine-based receptors for flurometric detection of urea and biotin

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

Abstract

Naphthyridine-based receptors 14 have been designed and synthesized for the recognition of urea in CHCl3 containing 1% CH3CN. Receptor 1 also binds biotin and its methyl ester with moderate binding constant values. In comparison, receptor 2 is less efficient in recognising biotin and its methyl ester analogue. Receptor 1 binds urea and biotin with binding constant values of 1.02 × 104 and 1.08 × 104 M−1, respectively, in CHCl3 containing 1% CH3CN and shows significant change in emission of naphthyridine upon complexation. Characterization and sensing properties of the receptors were evaluated by 1H NMR, UV–vis and fluorescence spectroscopic methods.

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.

Scheme 1
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Fig. 11
Fig. 12
Fig. 13
Fig. 14

Similar content being viewed by others

Notes

  1. Energy minimization was carried out using MMX (PC Model Serena Software (1993). Molecular modeling was performed using standard constants, and the dielectric constant was maintained at 1.5.

References

  1. Dugas, H.: Bio-organic Chemistry. Springer, New York (1996)

    Google Scholar 

  2. Lehn, J.M.: Supramolecular Chemistry. VCH, Weinheim (1995)

    Book  Google Scholar 

  3. Pedersen, C.J.: Crystalline complexes of macrocyclic polyethers with thiourea and related compounds. J. Org. Chem. 36, 1690 (1971)

    Article  CAS  Google Scholar 

  4. Goswami, S., Dey, S.: Directed molecular recognition: design and synthesis of neutral receptors for biotin to bind both its functional groups. J. Org. Chem. 71, 7280 (2006). and references cited therein

    Article  CAS  Google Scholar 

  5. Mazik, M., Kuschel, M., Sicking, W.: Crown ethers as building blocks for carbohydrate receptors. Org. Lett. 8, 855 (2006). and references cited therein

    Article  CAS  Google Scholar 

  6. Goswami, S., Ghosh, K., Dasgupta, S.: Troger’s base molecular scaffolds in dicarboxylic acid recognition. J. Org. Chem. 65, 1907 (2000)

    Article  CAS  Google Scholar 

  7. Wang, H., Chan, W.-H., Lee, A.W.M.: Cholic acid-based fluorescent probes for enantioselective recognition of trifunctional amino acids. Org. Biomol. Chem 6, 929 (2006)

    Article  Google Scholar 

  8. Cooke, I.J.: Toxic effect of urea on plants. Nature 194, 1262 (1962)

    Article  CAS  Google Scholar 

  9. Morris, J.G., Payne, E.: Ammonia and urea toxicoses in sheep and their relation to dietary nitrogen intake. J. Agric. Sci. 74, 259 (1970)

    Article  CAS  Google Scholar 

  10. Goswami, S., Mukherjee, R., Ray, J.: Design and synthesis of a neutral fluorescent macrocyclic receptor for the recognition of urea in chloroform. Org. Lett. 7, 1283 (2005)

    Article  CAS  Google Scholar 

  11. Chetia, B., Iyer, P.K.: 2, 6-Bis(2-benzimidazolyl)pyridine receptor for urea recognition. Tetrahedron Lett. 47, 8115 (2006)

    Article  CAS  Google Scholar 

  12. Ghosh, K., Masanta, G.: Anthracene-based open and macrocyclic receptors in flurometric detection of urea. New J. Chem. 33, 1965 (2009)

    Article  CAS  Google Scholar 

  13. van Staveren, C.J., Aarts, V.M.L.J., Grootenhuis, P.D.J., Droppers, W.J.H., van Eerden, J., Harkema, S., Reinhoudt, D.N.: Synthetic molecular receptors for urea macrocyclic ligands with intraannular acidic groups and the complexes with urea. J. Am. Chem. Soc. 110, 8134 (1988). and references cited therein

    Article  Google Scholar 

  14. van Staveren, C.J., van Eerden, J., Veggel, F.C.J.M., Herkema, S., Reinhoudt, D.N.: Cocomplexation of neutral guests and electrophilic metal cations in synthetic macrocyclic hosts. J. Am. Chem. Soc. 110, 4994 (1988)

    Article  Google Scholar 

  15. Bell, T.W., Liu, J.: Hexagonal lattice hosts for urea: a new series of designed heterocyclic receptors. J. Am. Chem. Soc. 110, 3673 (1988)

    Article  CAS  Google Scholar 

  16. Ghosh, K., Adhikari, S., Frohlich, R.: A pyridine-based macrocyclic host for urea and acetone. Tetrahedron Lett. 49, 5063 (2008)

    Article  CAS  Google Scholar 

  17. Goswami, S., Mukherjee, R.: Molecular Recognition: A simple dinaphthyridine receptor for urea. Tetrahedron Lett. 38, 1619 (1997)

    Article  CAS  Google Scholar 

  18. Nelson, D.L., Cox, M.M.: Lehninger Principles of Biochemistry, 3rd edn. Worth Publishers, New York (2000)

    Google Scholar 

  19. Traub, W.: Crystal structure of biotin. Nature (London) 178, 649 (1956)

    Article  CAS  Google Scholar 

  20. Adrian Jr, J.C., Wilcox, C.S.: Orderly Functional Group Dyads. Recognition of biotin and adenine derivatives by a new synthetic host. J. Am. Chem. Soc. 111, 8055 (1989)

    Article  CAS  Google Scholar 

  21. Herranz, F., Santa-María, M.D., Claramunt, R.M.: Molecular recognition: improved binding of biotin derivatives with synthetic receptors. J. Org. Chem. 71, 2944 (2006)

    Article  CAS  Google Scholar 

  22. Ghosh, K., Sen, T.: A benzthiazole-based simple receptor in fluorescence sensing of biotin ester and urea. Tetrahedron Lett. 50, 4096 (2009)

    Article  CAS  Google Scholar 

  23. Ghosh, K., Sarkar, A.R., Sen, T.: Naphthyridine-based symmetrical and unsymmetrical pyridinium amides in sensing of biotin salt. Supramol. Chem. doi: 10.1080/10610270903089738 (2009)

  24. Ghosh, K., Sen, T., Frohlich, R.: A naphthyridine-based receptor for sensing citric acid. Tetrahedron Lett. 48, 2935 (2007)

    Article  CAS  Google Scholar 

  25. Newkome, G.R., Garbis, S.J., Majestic, V.K., Fronczek, F.R., Chiari, G.: Chemistry of heterocyclic compounds. 61 Synthesis and conformational studies of macrocycles possessing 1,8- or 1,5-naphthyridino subunits connected by carbon-oxygen bridges. J.Org. Chem. 46, 833 (1981)

    Article  CAS  Google Scholar 

  26. de Silva, A.P., Gunaratne, H.Q.N., Gunnlaugsson, T., Huxley, A.J.M., McCoy, C.P., Rademacher, J.T., Rice, T.E.: Signaling recognition events with fluorescent sensors and switches. Chem. Rev. 97, 1515 (1997)

    Article  Google Scholar 

  27. Chou, P.T., Wu, G.R., Wei, C.Y., Cheng, C.C., Chang, C.P., Hung, F.T.: Excited-state amine-imine double proton transfer in 7-azaindoline. J. Phys. Chem. B 104, 7818 (2000)

    Article  CAS  Google Scholar 

  28. Kryachko, E., Nguyen, M.T., Zeegers-Huyskens, T.: Thiouracils: acidity, basicity, and interaction with water. J. Phys. Chem. A 105, 3379 (2001)

    Article  CAS  Google Scholar 

  29. Colquhoun, H.M., Goodings, E.P., Maud, J.M., Stoddart, J.F., Wolstenholme, J.B., Williams, D.J.: The complexation of the diquat dication by dibenzo-3n-crown-n-ethers. J. Chem. Soc., Perkin II. 607 (1985)

Download references

Acknowledgements

We thank DST, Government of India for providing facilities in the department under DST FIST program. TS thanks CSIR, Government of India for a fellowship.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Kumaresh Ghosh.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2186 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ghosh, K., Sen, T. Naphthyridine-based receptors for flurometric detection of urea and biotin. J Incl Phenom Macrocycl Chem 67, 271–280 (2010). https://doi.org/10.1007/s10847-009-9707-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10847-009-9707-6

Keywords

Navigation