Synthesis of Two Cinnamic Oxime Ester Derivatives and Their Interaction Mechanism with Human Serum Albumin

LU Dong-wei; WU Xiao-yu; XIE Xian; YU Kai-li; LIN Cui-wu

doi:10.3788/fgxb20173803.0402

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Synthesis of Two Cinnamic Oxime Ester Derivatives and Their Interaction Mechanism with Human Serum Albumin

更新时间：2020-08-12

- Synthesis of Two Cinnamic Oxime Ester Derivatives and Their Interaction Mechanism with Human Serum Albumin
- Chinese Journal of Luminescence Vol. 38, Issue 3, Pages: 402-412(2017)
- 作者机构：
  
  1. 广西大学化学化工学院,广西南宁,530004
  2. 广西高校应用化学技术与资源开发重点实验室, 广西南宁 530004
- 作者简介：
- 基金信息：
  
  Supported by National Natural Science Foundation of China(21362001);Guangxi Colleg
- DOI：10.3788/fgxb20173803.0402
  CLC： O625.5
- Received：31 August 2016，
  
  Revised：21 September 2016，
  
  Published：05 March 2017
- 稿件说明：
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逯东伟, 吴啸宇, 谢宪等. 两种肉桂酸肟酯衍生物的合成及其与人血清白蛋白的结合[J]. 发光学报, 2017,38(3): 402-412

LU Dong-wei, WU Xiao-yu, XIE Xian etc. Synthesis of Two Cinnamic Oxime Ester Derivatives and Their Interaction Mechanism with Human Serum Albumin[J]. Chinese Journal of Luminescence, 2017,38(3): 402-412
逯东伟, 吴啸宇, 谢宪等. 两种肉桂酸肟酯衍生物的合成及其与人血清白蛋白的结合[J]. 发光学报, 2017,38(3): 402-412 DOI： 10.3788/fgxb20173803.0402.

LU Dong-wei, WU Xiao-yu, XIE Xian etc. Synthesis of Two Cinnamic Oxime Ester Derivatives and Their Interaction Mechanism with Human Serum Albumin[J]. Chinese Journal of Luminescence, 2017,38(3): 402-412 DOI： 10.3788/fgxb20173803.0402.

摘要

以间甲氧基肉桂酸、对位取代的苯甲醛为原料，设计合成了2种未见报道的肉桂酸肟酯类衍生物，并用MS、IR、

H NMR、

C NMR进行结构表征。采用分子对接技术和荧光光谱法、紫外-可见光谱法、位点竞争法研究了2种衍生物分别和人血清白蛋白（HSA）相结合的机理。通过Stern-Volmer方程等处理荧光猝灭相关数据得到了衍生物与HSA相互作用的结合常数和热力学参数。结合紫外-可见光谱对两种衍生物与HSA的相互作用进行了进一步的分析，结果表明在体外生理条件下，衍生物都可以与HSA结合，对HSA内源荧光产生静态猝灭并对其构象产生影响，其主要的结合力为氢键和范德华力。位点竞争实验表明衍生物与HSA相互作用都发生在Sudlow site 1（亚域Ⅱ A）处。以上实验结果均验证了分子模拟对实验的预测。

Abstract

Two novel cinnamic acid oxime ester derivatives were designed and synthesized with

-methoxy cinnamic acid and

-substituted benzaldehyde. Their structures were characterized by mass spectrometry

infrared spectroscopy

and nuclear magnetic resonance. The interaction mechanism of derivatives and human serum albumin (HSA) were explored by molecular docking

fluorescence spectroscopy

UV-visible absorption spectroscopy and site marker competitive experiments.The binding constants and corresponding thermodynamic parameters of the derivative-HSA systems were calculated by Stern-Volmer equation. Combined with UV-Vis absorption spectra

the results indicate that the derivatives can get complexes with HSA respectively and strongly quench the intrinsic fluorescence of HSA

and hydrogen bonds and van der Waals forces are main acting forces. Site marker competitive experiments indicate that the binding of the derivatives to HSA primarily take place in sub-domain ⅡA. The above results verify the prediction of molecular simulation experiment.

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references

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