Skip to main content
SpringerLink
Log in

Thermodynamic Properties of the Site-selective Binding of a Bromo-hydrazone and Its Unsubstituted Analogue to Human Serum Albumin

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

A bromine-substituted hydrazone derivative, named N′-(4-bromobenzylidene)-2-hydroxybenzohydrazide (BBH), and its unsubstituted analogue, named N′-benzylidene-2-hydroxybenzohydrazide (BH), have been synthesized by a simple and effective one-pot synthesis method. Their interactions with human serum albumin (HSA) were comprehensively studied employing spectroscopy, electrochemistry, and molecular docking. Our attention was largely on the thermodynamic properties of their binding to HSA, in order to evaluate the impact of a bromine atom in BBH to its biological activity comparing to BH. BBH is a stronger ligand with a binding constant of 105 L·mol−1 and formed a more stable complex with HSA compared with BH. The binding processes of both BBH and BH are mainly an enthalpy driven process occurring in site I, mainly bound by hydrogen bonding and the van der Waals force.

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Tian, F.-F., Jiang, F.-L., Han, X.-L., Xiang, C., Ge, Y.-S., Li, J.-H., Zhang, Y., Li, R., Ding, X.-L., Liu, Y.: Synthesis of a novel hydrazone derivative and biophysical studies of its interactions with bovine serum albumin by spectroscopic, electrochemical, and molecular docking methods. J. Phys. Chem. B 114, 14842–14853 (2010)

    Article  CAS  Google Scholar 

  2. Rollas, S., Küçükgüzel, Ş.: Biological activities of hydrazone derivatives. Molecules 12, 1910–1939 (2007)

    Article  CAS  Google Scholar 

  3. Lovejoy, D., Richardson, D.: Novel “hybrid” iron chelators derived from aroylhydrazones and thiosemicarbazones demonstrate selective antiproliferative activity against tumor cells. Blood 100, 666–676 (2002)

    Article  CAS  Google Scholar 

  4. Kalinowski, D., Sharpe, P., Bernhardt, P., Richardson, D.: Design, synthesis, and characterization of new iron chelators with anti-proliferative activity: structure–activity relationships of novel thiohydrazone analogues. J. Med. Chem. 50, 6212–6225 (2007)

    Article  CAS  Google Scholar 

  5. Kucukguzel, S., Oruc, E., Rollas, S., Sahin, F., Ozbek, A.: Synthesis, characterization and biological activity of novel 4-thiazolidinones, 1,3,4-oxadiazoles and some related compounds. Eur. J. Med. Chem. 37, 197–206 (2002)

    Article  CAS  Google Scholar 

  6. Himmel, D., Sarafianos, S., Dharmasena, S., Hossain, M., McCoy-Simandle, K., Ilina, T., Clark, A., Knight, J., Julias, J., Clark, P., Krogh-Jespersen, K., Levy, R., Hughes, S., Parniak, M., Arnold, E.: HIV-1 reverse transcriptase structure with RNase H inhibitor DHBNH bound at a novel site. ACS Chem. Biol. 1, 702–712 (2006)

    Article  CAS  Google Scholar 

  7. Dimmock, J., Vashishtha, S., Stables, J.: Anticonvulsant properties of various acetyl hydrazones, oxamoyl hydrazones and semicarbazones derived from aromatic and unsaturated carbonyl compounds. Eur. J. Med. Chem. 35, 241–248 (2000)

    Article  CAS  Google Scholar 

  8. Bukowski, L., Janowiec, M., Zwolska-Kwiek, Z., Andrzejczyk, Z.: Synthesis and some reactions of 2-acetylimidazo[4,5-b]pyridine. Antituberculotic activity of the obtained compounds. Pharmazie 54, 651–654 (1999)

    CAS  Google Scholar 

  9. Emsley, J.: Nature’s building blocks: an A–Z guide to the elements. Oxford University Press, New York (2001)

    Google Scholar 

  10. Gribble, G.: The diversity of naturally occurring organobromine compounds. Chem. Soc. Rev. 28, 335–346 (1999)

    Article  CAS  Google Scholar 

  11. Gribble, G.: Naturally occurring organohalogen compounds. Acc. Chem. Res. 31, 141–152 (1998)

    Article  CAS  Google Scholar 

  12. Cuenca, R., Pories, W., Bray, J.: Bromine levels in human serum, urine, hair. Biol. Trace Elem. Res. 16, 151–154 (1988)

    Article  CAS  Google Scholar 

  13. Flury, M., Papritz, A.: Bromide in the natural environment: occurrence and toxicity. J. Environ. Qual. 22, 747–758 (1993)

    Article  CAS  Google Scholar 

  14. Fisher, D., Burton, D., Yonkos, L., Turley, S., Ziegle, G.: The relative acute toxicity of continuous and intermittent exposures of chlorine and bromine to aquatic organisms in the presence and absence of ammonia. Water Res. 33, 760–768 (1999)

    Article  CAS  Google Scholar 

  15. Tian, F.-F., Li, J.-H., Jiang, F.-L., Han, X.-L., Xiang, C., Ge, Y.-S., Li, L.-L., Liu, Y.: The adsorption of an anticancer hydrazone by protein: an unusual static quenching mechanism. RSC Adv. 2, 501–513 (2012)

    Article  CAS  Google Scholar 

  16. Han, X.-L., Mei, P., Liu, Y., Xiao, Q., Jiang, F.-L., Li, R.: Binding interaction of quinclorac with bovine serum albumin: a biophysical study. Spectrochim. Acta A 74, 781–787 (2009)

    Article  Google Scholar 

  17. Hu, Y.-J., Liu, Y., Wang, J., Xiao, X.-H., Qu, S.-S.: Study of the interaction between monoammonium glycyrrhizinate and bovine serum albumin. J. Pharm. Biomed. Anal. 36, 915–919 (2004)

    Article  CAS  Google Scholar 

  18. Li, R., Jiang, F.-L., Xiao, Q., Li, J.-H., Yu, Q., Liu, Y., Zeng, C.: Microcalorimetric, spectroscopic and microscopic investigation on the toxic effects of CdTe quantum dots on Halobacterium halobium R1. Nanotechnology 21, 475102 (2010)

    Article  Google Scholar 

  19. Valeur, B.: Molecular fluorescence: principles and applications. Wiley-VCH, Weinheim (2001)

    Book  Google Scholar 

  20. Sahoo, B.-K., Ghosh, K.-S., Dasgupta, S.: Molecular interactions of isoxazolcurcumin with human serum albumin: spectroscopic and molecular modeling studies. Biopolymers 91, 108–119 (2008)

    Article  Google Scholar 

  21. Chen, J., Jiang, X.-Y., Chen, X.-Q., Chen, Y.: Effect of temperature on the metronidazole–BSA interaction: multi-spectroscopic method. J. Mol. Struct. 876, 121–126 (2008)

    Article  CAS  Google Scholar 

  22. Xiao, Q., Huang, S., Liu, Y., Tian, F.-F., Zhu, J.-C.: Thermodynamics, conformation and active sites of the binding of Zn–Nd hetero-bimetallic Schiff base to bovine serum albumin. J. Fluoresc. 19, 317–326 (2009)

    Article  CAS  Google Scholar 

  23. Hu, Y.-J., Ou-Yang, Y., Bai, A.-M., Zhao, R.-M., Liu, Y.: A series of novel rare earth molybdotungstosilicate heteropolyoxometalates binding to bovine serum albumin: spectroscopic approach. Biol. Trace Elem. Res. 136, 8–17 (2009)

    Article  Google Scholar 

  24. Zhang, Y.-Z., Xiang, X., Mei, P., Dai, J., Zhang, L.-L., Liu, Y.: Spectroscopic studies on the interaction of Congo Red with bovine serum albumin. Spectrochim. Acta A 72, 907–914 (2009)

    Article  Google Scholar 

  25. Hu, Y., Ou-Yang, Y., Dai, C.-M., Liu, Y., Xiao, X.-H.: Site-selective binding of human serum albumin by palmatine: spectroscopic approach. Biomacromolecules 11, 106–112 (2010)

    Article  CAS  Google Scholar 

  26. Zhang, Y.-Z., Dai, J., Zhang, X.-P., Yang, X., Liu, Y.: Studies of interaction between Sudan I and bovine serum albumin by spectroscopic methods. J. Mol. Struct. 888, 152–159 (2008)

    Article  CAS  Google Scholar 

  27. Zhang, Y.-Z., Zhang, X.-P., Hou, H.-N., Dai, J., Liu, Y.: Study on the interaction between Cu(phen) 2+3 and bovine serum albumin by spectroscopic methods. Biol. Trace Elem. Res. 121, 276–287 (2008)

    Article  CAS  Google Scholar 

  28. Zhou, B., Zhang, Z., Zhang, Y., Li, R., Xiao, Q., Liu, Y., Li, Z.-Y.: Binding of cationic porphyrin to human serum albumin studied using comprehensive spectroscopic methods. J. Pharm. Sci. 98, 105–113 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors gratefully acknowledge financial support of the National Natural Science Foundation of China (Grant No. 21173026, 20921062), Program for Changjiang Scholars and Innovative Research Team in University (IRT1030).

Author information

Authors and Affiliations

  1. College of Chemical and Environmental Engineering, Yangtze University, Jinzhou, 434023, People’s Republic of China

    Jin-Qiang Tong & Yi Liu

  2. State Key Laboratory of Virology and Key Laboratory of Analytical Chemistry for Biology and Medicine (MOE), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, People’s Republic of China

    Fang-Fang Tian, Yi Liu & Feng-Lei Jiang

Authors
  1. Jin-Qiang Tong
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Fang-Fang Tian
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yi Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Feng-Lei Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Yi Liu or Feng-Lei Jiang.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Tong, JQ., Tian, FF., Liu, Y. et al. Thermodynamic Properties of the Site-selective Binding of a Bromo-hydrazone and Its Unsubstituted Analogue to Human Serum Albumin. J Solution Chem 44, 193–205 (2015). https://doi.org/10.1007/s10953-015-0303-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-015-0303-7

Keywords

Search

Navigation