Synthesis of Three Cinnamamide Derivatives and Their Interaction Mechanism with Human Serum Albumin

DU Chuan-rong; LU Dong-wei; SHI Kang; CHEN Dan-dan; LIN Cui-wu

doi:10.3788/fgxb20153611.1342

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Synthesis of Three Cinnamamide Derivatives and Their Interaction Mechanism with Human Serum Albumin

更新时间：2020-08-12

- Synthesis of Three Cinnamamide Derivatives and Their Interaction Mechanism with Human Serum Albumin
- Chinese Journal of Luminescence Vol. 36, Issue 11, Pages: 1342-1352(2015)
- 作者机构：
  
  1. 广西大学化学化工学院, 广西南宁 530004
  2. 广西桂林电子科技大学信息与通信学院,广西桂林,541000
  3. 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：
- DOI：10.3788/fgxb20153611.1342
  CLC： O625.5
- Received：11 August 2015，
  
  Revised：21 September 2015，
  
  Published：10 November 2015
- 稿件说明：
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杜传荣, 逯东伟, 石康等. 三种肉桂酰胺衍生物的制备及其与人血清白蛋白的结合[J]. 发光学报, 2015,36(11): 1342-1352

DU Chuan-rong, LU Dong-wei, SHI Kang etc. Synthesis of Three Cinnamamide Derivatives and Their Interaction Mechanism with Human Serum Albumin[J]. Chinese Journal of Luminescence, 2015,36(11): 1342-1352
杜传荣, 逯东伟, 石康等. 三种肉桂酰胺衍生物的制备及其与人血清白蛋白的结合[J]. 发光学报, 2015,36(11): 1342-1352 DOI： 10.3788/fgxb20153611.1342.

DU Chuan-rong, LU Dong-wei, SHI Kang etc. Synthesis of Three Cinnamamide Derivatives and Their Interaction Mechanism with Human Serum Albumin[J]. Chinese Journal of Luminescence, 2015,36(11): 1342-1352 DOI： 10.3788/fgxb20153611.1342.

摘要

基于临床上肉桂酰胺类药物的广泛应用及优异性能

以间羟基肉桂酸为母体

分别与不同氨基酸反应

设计合成了3种未见报道的肉桂酰胺类衍生物

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、同步荧光光谱法、紫外-可见光谱法共同研究了3种衍生物分别和人血清白蛋白(HSA)相结合的机理.AutoDock对接显示

这3种衍生物结合在HSA亚结构域ⅡA(即site Ⅰ)的疏水腔内

维系衍生物与HSA的主要作用力为氢键和范德华力

同时还存在着疏水作用.光谱实验结果表明

在体外生理条件下

衍生物都与HSA形成复合物

对HSA内源荧光产生静态猝灭

且对其构象产生影响.根据不同温度下的热力学函数

确定主要作用力均是氢键和范德华力.分子对接与实验获得了一致的结果.

Abstract

Because of the excellent properties and wide applications of cinnamamide medicines in clinic

three

-hydroxycinnamic acid derivatives were designed and synthetised by the reaction of

-hydroxybenzoic acid with different amino acids

respectively. Their structures were characterized by mass spectrometry

infrared spectroscopy

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

fluorescence spectroscopy and UV-visible absorption spectroscopy. The results of molecular docking represent that derivatives exist in the hydrophobic pocket of subdomainⅡA(site Ⅰ) of HSA. Hydrogen bonds and van der Waals' forces are main acting forces and hydrophobic force is just the secondary consideration. The spectra experiment results indicate that the derivatives can form complexes with HSA respectively and strongly quench the intrinsic fluorescence of HSA through static quenching at different temperatures. Meanwhile

the secondary structure of HSA is influenced. The change in enthalpy (

) and entropy (

) suggest that hydrogen bonds and van der Waals forces are main acting forces. The molecular docking data are consistent with experimental results.

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references

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Related Institution

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