Synthesis of Vanillylamide Derivatives and Their Hemostatic Activity in Vitro by Kinetics Methods

DU Chuan-rong; LIN Fa-quan; LU Dong-wei; CHEN Dan-dan; FAN Xi-wang; LIN Cui-wu

doi:10.3788/fgxb20163704.0487

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Synthesis of Vanillylamide Derivatives and Their Hemostatic Activity in Vitro by Kinetics Methods

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- Synthesis of Vanillylamide Derivatives and Their Hemostatic Activity in Vitro by Kinetics Methods
- Chinese Journal of Luminescence Vol. 37, Issue 4, Pages: 487-497(2016)
- 作者机构：
  
  1. 广西大学化学化工学院,广西南宁,530004
  2. 广西医科大学第一附属医院,广西南宁,530021
  3. 南宁市化工研究设计院,广西南宁,530022
  4. 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/fgxb20163704.0487
  CLC： O625.5
- Received：26 November 2015，
  
  Revised：12 January 2016，
  
  Published：05 April 2016
- 稿件说明：
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杜传荣, 林发全, 逯东伟等. 香草酸酰胺衍生物的制备及其止血活性的动力学法研究[J]. 发光学报, 2016,37(4): 487-497

DU Chuan-rong, LIN Fa-quan, LU Dong-wei etc. Synthesis of Vanillylamide Derivatives and Their Hemostatic Activity in Vitro by Kinetics Methods[J]. Chinese Journal of Luminescence, 2016,37(4): 487-497
杜传荣, 林发全, 逯东伟等. 香草酸酰胺衍生物的制备及其止血活性的动力学法研究[J]. 发光学报, 2016,37(4): 487-497 DOI： 10.3788/fgxb20163704.0487.

DU Chuan-rong, LIN Fa-quan, LU Dong-wei etc. Synthesis of Vanillylamide Derivatives and Their Hemostatic Activity in Vitro by Kinetics Methods[J]. Chinese Journal of Luminescence, 2016,37(4): 487-497 DOI： 10.3788/fgxb20163704.0487.

摘要

以香草酸为母体

分别与6-氨基己酸(EACA)、止血芳酸(AMBA)和止血环酸(AMCA)反应

合成3种未见文献报道的香草酸酰胺衍生物

并采用IR、ESI-MS、

H NMR和

C NMR进行结构鉴定。以传统方法、荧光动力学法和紫外动力学法测定其对血浆复钙时间(PRT)的影响。为了研究衍生物在血液中的稳定性

在模拟生理条件下

运用荧光光谱、紫外光谱及分子对接技术研究了它分别与人血清白蛋白(HSA)的结合。结果表明

3种衍生物在一定浓度范围内都可以有效缩短PRT

具有显著的止血活性。新的动力学测定方法

不仅有效避免了传统方法引入的人为误差

重现性良好

而且判断标准更加科学

并可以获得更多血浆凝结过程中的信息。3种衍生物均主要通过氢键和范德华力与HSA结合形成稳定的复合物

表明它可通过HSA在血液中传递并运输到相应部位而发生药理作用。

Abstract

Three novel amide derivatives were designed and prepared by the reaction of vanillic acid with 6-aminocaproic acid (EACA)

p-aminomethylbeozoic acid (AMBA) or tranexamic acid (AMCA)

respectively. The structures were identified by IR

ESI-MS

H NMR and

C NMR. In order to study their hemostatic activity

in vitro

the plasma recalcification time (PRT) was determined by traditional method

fluorescence kinetics method and UV kinetics method

respectively. In order to study the stability of derivatives in blood

the interaction between derivatives and human serum albumin (HSA) was investigated under imitated physiological condition by fluorescence spectroscopy

UV-visible absorption spectroscopy and molecular docking

respectively. The results stated clearly that derivatives could reduce PRT significantly and exhibit obvious procoagulant effect

in vitro.

Moreover

in some concentrations

the hemostatic activity of derivative Ⅱ was better than AMBA. The results obtained by three different methods were in correspondence. New kinetics methods not only avoided artificial error effectually but also had good repeatability. In addition

more reasonable and credible information could be obtained in the process of serum agglutination. On the other hand

the spectra experiments showed that three derivatives could all form stable complexes with HSA respectively. The binding types between derivatives and HSA were all van der Waals force and hydrogen bonds. The results were accordant with molecular docking. It indicates that all the derivatives can be transferred and delivered by HSA to play pharmacological effects at corresponding site. Consequently

there is a strong possibility that the three vanillylamide derivatives can be applied to practice.

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