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Synthesis of a novel coumarin derivative and its binding interaction with serum albumins

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Chemistry of Heterocyclic Compounds Aims and scope

A novel triazolylcoumarin derivative N-(4-methoxyphenyl)-6-(4-{[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]methyl}-1H-1,2,3-triazol-1-yl)hexanamide was synthesized and its interactions with the transport proteins bovine serum albumin and human serum albumin have been explored by the steady state absorption studies and fluorescence studies at 298 K. The fluorescence spectra show quenching of the tryptophan emission due to the complexation for both protein-ligand complexes. This study reveals appreciable binding of this compound to both proteins, and the values of binding constant are evaluated using different methods. The fluorescence study also helps to get an idea about the change in the microenvironment of the protein upon the ligand binding.

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References

  1. Carter, D. C.; He, X. M. Science 1990, 249, 302.

    Article  CAS  PubMed  Google Scholar 

  2. Carter, D. C.; Ho, J. X. Adv. Protein Chem. 1994, 45, 153.

    Article  CAS  PubMed  Google Scholar 

  3. Carter, D. C.; He, X. M.; Munson, S. H.; Twigg, P. D.; Gernert, K. M.; Broom, M. B.; Miller, T. Y. Science 1989, 244, 1195.

    Article  CAS  PubMed  Google Scholar 

  4. Musa, M. A.; Cooperwood, J. S.; Khan, M. O. F. Curr. Med. Chem. 2008, 15, 2664.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  5. Wagner, B. D. Molecules 2009, 14, 210.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. Li, J.; Zhang, C. F.; Yang, S. H.; Yang, W. C.; Yang, G. F. Anal. Chem. 2014, 86, 3037.

    Article  CAS  PubMed  Google Scholar 

  7. Stefani, H. A.; Gueogjan, K.; Manarin, F.; Farsky, S. H. P.; Zukerman-Schpector, J.; Caracelli, I.; Pizano Rodrigues, S. R.; Muscará, M. N.; Teixeira, S. A.; Santin, J. R.; Machado, I. D.; Bolonheis, S. M.; Curi, R.; Vinolo, M. A.. Eur. J. Med. Chem. 2012, 58, 117.

    Article  CAS  PubMed  Google Scholar 

  8. Zhang, W. J.; Li, Z.; Zhou, M.; Wu, F.; Hou, X. Y.; Luo, H.; Liu, H.; Han, X.; Yan, G. Y.; Ding, Z. Y.; Li. R. Bioorg. Med. Chem. Lett. 2014, 24, 799.

  9. Shi, Y. A.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2011, 21, 956.

    Article  CAS  PubMed  Google Scholar 

  10. Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. Chem. Rev. 2004, 104, 3059.

    Article  CAS  PubMed  Google Scholar 

  11. Żamojć, K.; Wiczk, W.; Zaborowski, B.; Jacewicz, D.; Chmurzyński, L. J. Fluoresc. 2014, 24, 713.

    Article  CAS  PubMed  Google Scholar 

  12. Yu, X.; Lu, S.; Yang,Y.; Li, X.; Yi, P. Spectrochim. Acta, Part A 2012, 91, 113.

  13. Esenpınar, A. A.; Durmuş, M.; Bulut, M. Spectrochim. Acta, Part A 2011, 79, 608.

    Article  CAS  Google Scholar 

  14. Purkey, R. M.; William, C. Biochemistry 1970, 9, 3569.

    Article  CAS  PubMed  Google Scholar 

  15. Saha Sardar, P.; Maity, S. S.; Ghosh, S.; Chatterjee, J.; Maiti, T. K.; Dasgupta, S. J. Phys. Chem. B 2006, 110, 21349.

    Article  CAS  Google Scholar 

  16. Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer: New York, 2006, 3rd ed.

    Book  Google Scholar 

  17. Royer, C. A.; Gardner, J. A.; Beechem, J. M.; Brochon, J. C.; Matthews, K. S. Biophys. J. 1990, 58, 363.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  18. Paul, S.; Sepay, N.; Sarkar, S.; Roy, P.; Dasgupta, S.; Sardar, P. S.; Majhi, A. New J. Chem. 2017, 41, 15392.

    Article  CAS  Google Scholar 

  19. Krishnamoorthy, S.; Xie, F.; Brandon, M. C.; Su, L.; Barnhill, H. N.; Wang, Q. A. Org. Lett. 2004, 6, 4603.

    Article  CAS  Google Scholar 

  20. Shi, Y. A.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2011, 21, 956.

    Article  CAS  PubMed  Google Scholar 

  21. Zhang, W. J.; Li, Z.; Zhou, M.; Wu, F.; Hou, X. Y.; Luo, H.; Liu, H.; Han, X.; Yan, G. Y.; Ding, Z. Y.; Li, R. Bioorg. Med. Chem. Lett. 2014, 24, 799.

    Article  CAS  PubMed  Google Scholar 

  22. Kraljević, T. G.; Harej, A.; Sedić, M.; Kraljević Pavelić, S.; Stepanić, V.; Drenjančević, D.; Talapko, J.; Raić-Malić, S. Eur. J. Med. Chem. 2016, 124, 794.

    Article  CAS  Google Scholar 

  23. Shaikh, M. H.; Subhedar, D. D.; Kalam Khan, F. A.; Sangshetti, J. N.; Shingate, B. B. Chin. Chem. Lett. 2016, 27, 295.

    Article  CAS  Google Scholar 

  24. López-Rojas, P.; Janeczko, M.; Kubiński, K.; Amesty, Á.; Masłyk, M.; Estévez-Braun, A. Molecules 2018, 23, 199.

    Article  CAS  PubMed Central  Google Scholar 

  25. Eftink, R.; Ghiron, C. A. Anal. Biochem. 1981, 114, 199.

    Google Scholar 

  26. Lakowicz, J. R.; Weber, G. Biochemistry 1973, 12, 4171.

    Article  CAS  PubMed  Google Scholar 

  27. Ge, Y. S.; Jin, C.; Song, Z.; Zhang, J. Q.; Jiang, F. L.; Liu, Y. Spectrochim. Acta, Part A 2014, 124, 265.

    Article  CAS  Google Scholar 

  28. Hao, J.; Zhang, Y.; Wang, X.; Yan, H.; Liu, E.; Gao, X. PloS One 2015, 10(6), e0128919.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  29. Zayane, M.; Rahmouni, A.; Daami-Remadi, M.; Ben Mansour, M.; Romdhane, A.; Ben Jannet, H. J. Enzyme Inhib. Med. Chem. 2016, 31, 1566.

    Article  CAS  PubMed  Google Scholar 

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Correspondence to Anjoy Majhi.

Additional information

Supplementary information file containing 1H NMR, 13C NMR, and ESI-MS spectra of compound 3 is available at the journal website at http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(7), 607–611

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Paul, S., Ghanti, R., Sardar, P.S. et al. Synthesis of a novel coumarin derivative and its binding interaction with serum albumins. Chem Heterocycl Comp 55, 607–611 (2019). https://doi.org/10.1007/s10593-019-02505-6

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  • DOI: https://doi.org/10.1007/s10593-019-02505-6

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