Synthesis of caffeic acid derivatives and their targeting on brain

张静; 李标; 刘戟; 王欣; 王毓杰; 李钰婷; 张艺; 罗维早

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Synthesis of caffeic acid derivatives and their targeting on brain

更新时间：2026-01-09

- Synthesis of caffeic acid derivatives and their targeting on brain
- Journal of Army Medical University Vol. 32, Issue 3, Pages: 233-237(2010)
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  CLC： R282.71;R914.5;R961
- Published：2010
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张静,李标,刘戟,王欣,王毓杰,李钰婷,张艺,罗维早.咖啡酸衍生物的合成及其脑靶向性的研究[J].陆军军医大学学报(原第三军医大学学报),2010,32(03):233-237.

　Zhang Jing,Li Biao,Liu Ji,Wang Xin,Wang Yujie,Li Yuting,Zhang Yi,Luo Weizao.Synthesis of caffeic acid derivatives and their targeting on brain[J].J Amry Med Univ (J Third Mil Med Univ),2010,32(03):233-237.
张静,李标,刘戟,王欣,王毓杰,李钰婷,张艺,罗维早.咖啡酸衍生物的合成及其脑靶向性的研究[J].陆军军医大学学报(原第三军医大学学报),2010,32(03):233-237. DOI：

　Zhang Jing,Li Biao,Liu Ji,Wang Xin,Wang Yujie,Li Yuting,Zhang Yi,Luo Weizao.Synthesis of caffeic acid derivatives and their targeting on brain[J].J Amry Med Univ (J Third Mil Med Univ),2010,32(03):233-237. DOI：

摘要

目的咖啡酸衍生物的合成及其脑靶向性评价。方法以浓硫酸为催化剂，咖啡酸与甲醇和乙醇直接反应合成咖啡酸甲酯和乙酯，咖啡酸在磷酸催化下与醋酐酰化得3

4-二乙酰基咖啡酸；并测定了咖啡酸及其衍生物在正辛醇-磷酸盐缓冲溶液（pH 7.4）系统中的分配系数；采用原代脑微血管内皮细胞（brain microvascular endothelial cell

BMVEC）和星形胶质细胞(astrocytes

AC)共培养建立的体外血脑屏障模型来评价其脑靶向性。结果得到3个咖啡酸衍生物的油水分配系数均较咖啡酸高，亲脂性增强；其中咖啡酸甲酯和3

4-二乙酰基咖啡酸透过体外血脑屏障的能力较咖啡酸强。结论所合成的3个化合物经MS、HNMR、IR和UV证实其结构；咖啡酸甲酯和3

4-二乙酰基咖啡酸能突破血脑屏障具有脑靶向性特点。

Abstract

Objective To evaluate the synthesis of caffeic acid derivatives and their targeting on brain. Methods Methyl and ethyl esters of caffeic acid were synthesized by direct reaction of caffeic acid to methanol and ethanol with sulfate acid used as a catalyst. 3

4-diacetyl caffeic acid was synthesized by acetyla-ting caffeic acid with phosphate acid used as a catalyst. Their partition coefficient (P) in 1-octanol-phosphate buffer system (pH 7.4) was detected. An in vitro blood brain barrier (BBB) model was established by co-culturing brain capillary endothelial cells (BMVEC) and astrocytes (AC) for the evaluation of their targeting on brain. Results The partition coefficients (P) of the three derivatives were much higher th

an that of caffeic acid

and their lipophilicity was stronger than that of caffeic acid. The potency of methyl ester of caffeic acid and 3

4-diacetyl-caffeic acid across the in vitro BBB was better than that of caffeic acid. Conclusion The structure of three synthesized caffeic acid derivatives can be conformed by MS

HNMR

and UV spectra. Methyl ester of caffeic acid and 3

4-diacetyl-caffeic acid can cross the BBB and can thus be used as brain targets.

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