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.
Similar content being viewed by others
References
Carter, D. C.; He, X. M. Science 1990, 249, 302.
Carter, D. C.; Ho, J. X. Adv. Protein Chem. 1994, 45, 153.
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.
Musa, M. A.; Cooperwood, J. S.; Khan, M. O. F. Curr. Med. Chem. 2008, 15, 2664.
Wagner, B. D. Molecules 2009, 14, 210.
Li, J.; Zhang, C. F.; Yang, S. H.; Yang, W. C.; Yang, G. F. Anal. Chem. 2014, 86, 3037.
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.
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.
Shi, Y. A.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2011, 21, 956.
Trenor, S. R.; Shultz, A. R.; Love, B. J.; Long, T. E. Chem. Rev. 2004, 104, 3059.
Żamojć, K.; Wiczk, W.; Zaborowski, B.; Jacewicz, D.; Chmurzyński, L. J. Fluoresc. 2014, 24, 713.
Yu, X.; Lu, S.; Yang,Y.; Li, X.; Yi, P. Spectrochim. Acta, Part A 2012, 91, 113.
Esenpınar, A. A.; Durmuş, M.; Bulut, M. Spectrochim. Acta, Part A 2011, 79, 608.
Purkey, R. M.; William, C. Biochemistry 1970, 9, 3569.
Saha Sardar, P.; Maity, S. S.; Ghosh, S.; Chatterjee, J.; Maiti, T. K.; Dasgupta, S. J. Phys. Chem. B 2006, 110, 21349.
Lakowicz, J. R. Principles of Fluorescence Spectroscopy; Springer: New York, 2006, 3rd ed.
Royer, C. A.; Gardner, J. A.; Beechem, J. M.; Brochon, J. C.; Matthews, K. S. Biophys. J. 1990, 58, 363.
Paul, S.; Sepay, N.; Sarkar, S.; Roy, P.; Dasgupta, S.; Sardar, P. S.; Majhi, A. New J. Chem. 2017, 41, 15392.
Krishnamoorthy, S.; Xie, F.; Brandon, M. C.; Su, L.; Barnhill, H. N.; Wang, Q. A. Org. Lett. 2004, 6, 4603.
Shi, Y. A.; Zhou, C. H. Bioorg. Med. Chem. Lett. 2011, 21, 956.
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.
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.
Shaikh, M. H.; Subhedar, D. D.; Kalam Khan, F. A.; Sangshetti, J. N.; Shingate, B. B. Chin. Chem. Lett. 2016, 27, 295.
López-Rojas, P.; Janeczko, M.; Kubiński, K.; Amesty, Á.; Masłyk, M.; Estévez-Braun, A. Molecules 2018, 23, 199.
Eftink, R.; Ghiron, C. A. Anal. Biochem. 1981, 114, 199.
Lakowicz, J. R.; Weber, G. Biochemistry 1973, 12, 4171.
Ge, Y. S.; Jin, C.; Song, Z.; Zhang, J. Q.; Jiang, F. L.; Liu, Y. Spectrochim. Acta, Part A 2014, 124, 265.
Hao, J.; Zhang, Y.; Wang, X.; Yan, H.; Liu, E.; Gao, X. PloS One 2015, 10(6), e0128919.
Zayane, M.; Rahmouni, A.; Daami-Remadi, M.; Ben Mansour, M.; Romdhane, A.; Ben Jannet, H. J. Enzyme Inhib. Med. Chem. 2016, 31, 1566.
Author information
Authors and Affiliations
Corresponding author
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
Electronic supplementary material
ESM 1
(PDF 618 kb)
Rights and permissions
About this article
Cite this article
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
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10593-019-02505-6