氨基酸功能化的果胶/姜黄素胶体粒子的合成与性质

doi:10.7503/cjcu20150591

高等学校化学学报 ›› 2016, Vol. 37 ›› Issue (2): 381.doi: 10.7503/cjcu20150591

氨基酸功能化的果胶/姜黄素胶体粒子的合成与性质

杨泽川^1,², 李帆², 黄庆荣³, 张国¹(), 石彤非²()

1. 吉林大学材料科学与工程学院, 长春 130012
2. 中国科学院长春应用化学研究所, 高分子物理与化学国家重点实验室, 长春 130022
3. Department of Food Science, Rutgers University, New Jersey 08901, USA

收稿日期:2015-07-27 出版日期:2016-02-10 发布日期:2016-01-06
作者简介:联系人简介: 张国, 男, 博士, 教授, 主要从事遇水膨胀及半导高分子智能材料研究. E-mail:guozhang@jlu.edu.cn;石彤非, 男, 博士, 研究员, 主要从事合成高分子与生物大分子相行为及相转变研究. E-mail:tfshi@ciac.jl.cn
基金资助:
国家自然科学基金(批准号: 21174146)资助

Synthesis and Properties of the Amino Acid Functionalized Curcumin/His-Pectin Colloidal Particles^†

YANG Zechuan^1,², LI Fan², HUANG Qingrong³, ZHANG Guo^1,^*(), SHI Tongfei^2,^*()

1. Institute of Materials Science and Engineering, Jilin University, Changchun 130012, China
2. State Key Laboratory of Polymer Physics and Chemistry, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, China
3. Department of Food Science, Rutgers University, New Jersey 08901, USA

Received:2015-07-27 Online:2016-02-10 Published:2016-01-06
Contact: ZHANG Guo,SHI Tongfei E-mail:guozhang@jlu.edu.cn;tfshi@ciac.jl.cn
Supported by:
† Supported by the National Natural Science Foundation of China(No.21174146)

摘要/Abstract

摘要：

通过酯化反应合成了新型的氨基酸功能化的果胶衍生物, 通过红外光谱(FTIR)和元素分析确认了果胶衍生物的化学组成及结构, 用动态光散射(DLS)和透射电子显微镜(TEM)表征了果胶衍生物胶体的形貌和尺寸. 结果表明, 果胶衍生物胶体呈现不规则的球状结构, 粒度分布较均一, 平均粒径200 nm. 用紫外-可见(UV-Vis)光谱测试了果胶衍生物胶体对姜黄素的包裹和控制释放, 结果表明, 姜黄素能够有效被果胶衍生物胶束包裹. 体外细胞毒理实验结果表明, 果胶衍生物胶体载体能显著提高姜黄素对HepG2细胞生长的抑制作用.

关键词: pH响应, 胶体粒子, 药物输运, 肿瘤抑制, 氨基酸功能化, 果胶衍生物, 姜黄素

Abstract:

New pH-responsive pectin derivatives were designed and synthesized by esterification. The architectures of the polymers were confirmed by Fourier transform infrared(FTIR) spectrophoto meter and Elemental analyses(EA). The prepared micelles properties were determined by UV-Vis spectra and transmission electron microscope(TEM). The cytotoxicity of Curcumin/His-Pectin colloidal particles was assessed using the cell counting kit-8 assay. The His-Pectin colloidal particles exhibited an irregular spherical shape from TEM photographs. Moreover, curcumin can be efficiently encapsulated in His-Pectin colloidal particles. The mean diameter of the curcumin colloidal particles was about 200 nm with narrow size distribution. The cytotoxic assays of Curcumin/His-Pectin colloidal particles demonstrated high inhibitory effect on HepG2 cell growth compared to the free curcumin. It was concluded that His-Pectin colloidal particles can efficiently encapsulate curcumin in vitro and promote the inhibition of HepG2 cell growth in vitro.

Key words: pH-Responsive, Colloidal particles, Drug delivery, Growth inhibition of tumor cells, Amino acid functionalized, Pectin derivatives, Curcumin

中图分类号:

O636.1⁺3

TrendMD:

杨泽川, 李帆, 黄庆荣, 张国, 石彤非. 氨基酸功能化的果胶/姜黄素胶体粒子的合成与性质. 高等学校化学学报, 2016, 37(2): 381.

YANG Zechuan, LI Fan, HUANG Qingrong, ZHANG Guo, SHI Tongfei. Synthesis and Properties of the Amino Acid Functionalized Curcumin/His-Pectin Colloidal Particles^†. Chem. J. Chinese Universities, 2016, 37(2): 381.

图/表 11

Scheme 1 Synthetic routes of His-Pectin colloidal particles

Fig.1 FTIR spectra of Pectin(a) and His-Pectin(b)

Table 1 Characterization of Pectin and His-Pectin by elemental analyses

Sample	N(mass fraction, %)	n(Glucose unit):n(Boc-Histidine)	DS(%)
Pectin	0.20
His_0.5-Pectin	2.58	1:0.5	13.3
His-Pectin	5.00	1:1	30.6

Fig.2 Effect of pH on the solubility of Pectin(a) and His-Pectin colloidal particles(b) in water(3 mg/mL)

Fig.3 UV-Vis spectra of His-Pectin(a), Curcumin(b) and mixture of His-Pectin and Curcumin(c)

Fig.4 TEM images of His-Pectin(A) and Curcumin/His-Pectin colloidal particles(B—D) m(Curcumin):m(His-Pectin): (B) 1:20; (C) 1:10; (D) 1:5.

Table 2 Characterization of the size and distribution of the colloidal particles at 37 ℃(n=3)

Polymer	Size/nm	PDI
His_0.5-Pectin	285	0.21
His-Pectin	131	0.17
m(Curcumin):m(His_0.5-Pectin)=1:20	218	0.12
m(Curcumin):m(His-Pectin)=1:20	115	0.14
m(Curcumin):m(His-Pectin)=1:10	157	0.11
m(Curcumin):m(His-Pectin)=1:5	233	0.13

Table 3 LE and LC of Curcumin/His-Pectin colloidal particles

Sample	LE(%)	LC(%)
m(Curcumin):m(His_0.5-Pectin)=1:20	86.9	4.2
m(Curcumin):m(His-Pectin)=1:20	86.2	4.2
m(Curcumin):m(His-Pectin)=1:10	78.3	7.3
m(Curcumin):m(His-Pectin)=1:5	69.6	12.2

Fig.5 The in vitro Curcumin release profiles for Curcumin/His-Pectin [m(Curcumin):m(His-Pectin)=1:20] colloidal particles with different pH value

Fig.6 Cytotoxicity of His-Pectin colloidal particles in HepG2 cells Mean±standard derivation(n=4).

Fig.7 Effect of Curcumin/His-Pectin colloidal particles(a), Curcumin(b) and His-Pectin(c) on growth inhibition in HepG2 cell

参考文献 17

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氨基酸功能化的果胶/姜黄素胶体粒子的合成与性质

Synthesis and Properties of the Amino Acid Functionalized Curcumin/His-Pectin Colloidal Particles^†

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氨基酸功能化的果胶/姜黄素胶体粒子的合成与性质

Synthesis and Properties of the Amino Acid Functionalized Curcumin/His-Pectin Colloidal Particles†

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Synthesis and Properties of the Amino Acid Functionalized Curcumin/His-Pectin Colloidal Particles^†