奎宁功能化聚乙烯咪唑修饰硅胶亲水相互作用色谱固定相的制备及应用

doi:10.3724/SP.J.1123.2019.06008

色谱 ›› 2020, Vol. 38 ›› Issue (4): 438-444.DOI: 10.3724/SP.J.1123.2019.06008

奎宁功能化聚乙烯咪唑修饰硅胶亲水相互作用色谱固定相的制备及应用

周行¹^,², 陈佳¹^,², 张樱山³, 赵亮¹, 邱洪灯¹^,^*()

1. 中国科学院兰州化学物理研究所,中国科学院西北特色植物资源化学重点实验室, 甘肃省天然药物重点实验室,甘肃兰州 730000
2. 中国科学院大学,北京 100049
3. 甘肃省中药现代制药工程研究院有限公司,甘肃兰州730000

收稿日期:2019-06-14 出版日期:2020-04-08 发布日期:2020-12-10
通讯作者: 邱洪灯
基金资助:
国家自然科学基金(21822407)

Preparation and application of quinine-functionalized poly(1-vinylimidazole)-modified silica stationary phase in hydrophilic interaction chromatography

ZHOU Hang¹^,², CHEN Jia¹^,², ZHANG Yingshan³, ZHAO Liang¹, QIU Hongdeng¹^,^*()

1. CAS Key Laboratory of Chemistry of Northwestern Plant Resources, Key Laboratory for Natural Medicine of Gansu Province, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, China
2. University of Chinese Academy of Sciences, Beijing 100049, China
3. Gansu Province Traditional Chinese Medicine Modern Pharmaceutical Engineering Research Institute, Lanzhou 730000, China

Received:2019-06-14 Online:2020-04-08 Published:2020-12-10
Contact: QIU Hongdeng
Supported by:
National Natural Science Foundation of China(21822407)

摘要/Abstract

摘要：

通过表面自由基链转移聚合和亲核取代反应制备了一种新型奎宁功能化聚乙烯咪唑修饰硅胶亲水色谱固定相(Sil-PIm-Qn)。通过元素分析和红外光谱对该固定相进行表征,并在亲水相互作用色谱(HILIC)模式下对其进行了色谱性能评价。结果表明,该固定相对5种氨基酸、9种磺胺以及10种碱基核苷有较好的分离选择性。实验考察了流动相中有机相乙腈体积分数和水相中乙酸铵浓度对待分离物质保留行为的影响,并进一步对固定相分离的重复性进行了考察,其保留时间的相对标准偏差(RSD)为0.08%~2.30%(n=10)。该亲水色谱固定相制备方法简单,并且表现出了优异的亲水色谱分离性能,有望在磺胺类药物及生物样品中碱基核苷等亲水性物质的分离分析中有一定应用。

关键词: 亲水相互作用色谱, 色谱固定相, 制备, 奎宁, 聚乙烯咪唑, 亲水性物质

Abstract:

A quinine-functionalized poly(1-vinylimidazole)-modified hydrophilic silica stationary phase (Sil-PIm-Qn) was prepared by surface radical chain transfer and nucleophilic substitution reactions. Sil-PIm-Qn was characterized by elemental analysis and FT-IR. The chromatographic characteristics of the stationary phase were investigated in the hydrophilic interaction chromatographic (HILIC) mode. The results showed that five amino acids, nine sulfonamides, and ten nucleosides/nucleobases could be successfully separated on this stationary phase, respectively. The retention behavior of the compounds on the column was evaluated under different chromatographic conditions, i. e., for different salt concentrations and acetonitrile contents in the mobile phases. The stability of this column was also investigated, and the relative standard deviation (RSD, n=10) of the retention time of Sil-PIm-Qn was 0.08%-2.30%. Given its simple and green preparation as well as its unique selectivity and high separation efficiency, Sil-PIm-Qn is expected to find widespread application in the separation of hydrophilic compounds, including sulfonamides and nucleosides/nucleobases, in real samples.

Key words: hydrophilic interaction chromatography (HILIC), chromatographic stationary phase, preparation, quinine, poly(1-vinylimidazole), hydrophilic compounds

中图分类号:

O658

周行, 陈佳, 张樱山, 赵亮, 邱洪灯. 奎宁功能化聚乙烯咪唑修饰硅胶亲水相互作用色谱固定相的制备及应用[J]. 色谱, 2020, 38(4): 438-444.

ZHOU Hang, CHEN Jia, ZHANG Yingshan, ZHAO Liang, QIU Hongdeng. Preparation and application of quinine-functionalized poly(1-vinylimidazole)-modified silica stationary phase in hydrophilic interaction chromatography[J]. Chinese Journal of Chromatography, 2020, 38(4): 438-444.

图/表 9

图1 Sil-PIm-Qn的制备示意图

Fig. 1 Schematic diagram for the preparation of Sil-PIm-Qn Sil-PIm-Qn: quinine-functionalized poly(1-vinylimidazole)-modified hydrophilic silica stationary phase; Sil-MPS: γ-mercaptopropyltriethoxysilane-modified silica; DES: deep eutectic solvents.

表1 裸硅胶、Sil-MPS、Sil-PIm和Sil-PIm-Qn的元素分析结果

Table 1 Elemental analysis results of bare silica, Sil-MPS, Sil-PIm and Sil-PIm-Qn

Analyte	Elemental contents/%
Analyte	N	C	H
Bare silica	0	0.94	0.44
Sil-MPS	0	4.01	0.71
Sil-PIm	2.62	8.70	1.09
Sil-PIm-Qn	3.20	11.18	1.44

图2 Sil-MPS、Sil-PIm和Sil-PIm-Qn的红外光谱图

Fig. 2 FT-IR spectra of the Sil-MPS, Sil-PIm and Sil-PIm-Qn

图3 Ci-Qn的核磁共振氢谱图

Fig. 3 1H NMR of 2-chloroethyl isocyanate-modified quinine (Ci-Qn)

图4 5种氨基酸在Sil-PIm-Qn柱上的色谱图

Fig. 4 Chromatogram of the five amino acids on the Sil-PIm-Qn column

图5 9种磺胺类药物在(a)Sil-PIm-Qn柱和(b) Sil-PIm柱上的色谱图

Fig. 5 Chromatograms of the nine sulfonamides on the (a) Sil-PIm-Qn and (b) Sil-PIm columns

图6 10种碱基核苷在Sil-PIm-Qn柱上的色谱图

Fig. 6 Chromatogram of the ten nucleosides and nucleobases on the Sil-PIm-Qn column

图7 8种碱基核苷在Sil-PIm-Qn上的lg k值与流动相中乙腈体积分数的关系图

Fig. 7 Plots of lg k vs. volume fractions of acetonitrile in the mobile phase for the eight nucleosides and nucleobases on the Sil-PIm-Qn column k: retention factor.

图8 8种碱基和核苷在Sil-PIm-Qn上的lg k值与流动相水相中乙酸铵浓度的关系图

Fig. 8 Plots of lg k vs. concentrations of ammonium acetate in the mobile phases for the eight nucleosides and nucleobases on the Sil-PIm-Qn column

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奎宁功能化聚乙烯咪唑修饰硅胶亲水相互作用色谱固定相的制备及应用

Preparation and application of quinine-functionalized poly(1-vinylimidazole)-modified silica stationary phase in hydrophilic interaction chromatography

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