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

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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.

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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).

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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
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  2. Fang-Fang Tian
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Correspondence to Yi Liu or Feng-Lei Jiang.

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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

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

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