基于COF-JUZ2固定构象的左旋青霉胺分子印迹电化学传感器的制备和应用

引用本文: 张连明, 黎舒怀, 罗奎, 戴宇宁, 李建平. 基于COF-JUZ2固定构象的左旋青霉胺分子印迹电化学传感器的制备和应用[J]. 分析化学, 2022, 50(7): 995-1004. doi: 10.19756/j.issn.0253-3820.210894 shu

Citation: ZHANG Lian-Ming, LI Shu-Huai, LUO Kui, DAI Yu-Ning, LI Jian-Ping. Construction and Application of L-Penicillamine Molecular Imprinted Electrochemical Sensor Based on Covalent Organic Framework-JUZ2 Fixed Conformation[J]. Chinese Journal of Analytical Chemistry, 2022, 50(7): 995-1004. doi: 10.19756/j.issn.0253-3820.210894 shu

基于COF-JUZ2固定构象的左旋青霉胺分子印迹电化学传感器的制备和应用

张连明 ^{1,2,
,} ,
黎舒怀 ^{1,
,} ,
罗奎 ^2, ,
戴宇宁 ^2, ,
李建平 ^{2,
,}

1.
中国热带农业科学院分析测试中心, 海南省热带果蔬质量安全重点实验室, 海口 571101;
2.
桂林理工大学化学与生物工程学院, 食品安全检测新技术广西高校重点实验室, 桂林 541004

通讯作者: 张连明,E-mail:lianming226@126.com; 黎舒怀,E-mail:happylishuhuai@163.com; 李建平,E-mail:likianping@263.net

基金项目:
海南省热带果蔬质量安全重点实验室开放课题项目(No.KFKT2020001)、国家自然科学基金项目(No.21765006)、广西自然科学基金项目(No.2018GXNSFAA138145)、广西科技计划项目(No.桂科AD19110059)和桂林理工大学科研启动经费项目(No.GUTQDJJ2016024)资助。

摘要: 采用共价有机框架化合物COF-JUZ2选择性固定手性分子空间构象,以改善印迹孔穴结构并增加识别位点,基于此构建了一种对青霉胺对映体具有高效分辨识别能力的分子印迹手性识别体系。以左旋青霉胺(L-Pen)为模板分子,与COF-JUZ2相互作用形成复合物后,以壳聚糖作为载体,采用电沉积方法固定在金电极表面,以邻苯二胺为功能单体电聚合制备分子印迹聚合物膜,洗脱L-Pen后,制备得到对L-Pen具备高分辨识别能力的手性分子印迹传感器。利用电化学方法对传感器制备条件及检测条件进行了优化。结果表明,当沉积时间为300 s,以甲醇-乙酸-超纯水(8∶1∶1,V/V)混合溶液为洗脱剂洗脱5 min,重吸附时间为30 min时,传感器性能最优。传感器响应信号强度与L-Pen浓度的对数在1.0×10^-15~1.0×10^-9 mol/L范围内呈良好的线性关系,检出限(S/N=3)为7.91×10^-16 mol/L。本研究通过引入COF-JUZ2,制备的传感器对D-Pen和L-Pen的分离效果提高了13.4倍。传感器成功用于药物中L-Pen的测定,回收率在92.0%~102.0%之间。

关键词:

English

Construction and Application of L-Penicillamine Molecular Imprinted Electrochemical Sensor Based on Covalent Organic Framework-JUZ2 Fixed Conformation

ZHANG Lian-Ming ^{1,2,
,} ,
LI Shu-Huai ^{1,
,} ,
LUO Kui ^2, ,
DAI Yu-Ning ^2, ,
LI Jian-Ping ^{2,
,}

1.
Hainan Provincial Key Laboratory of Quality and Safety for Tropical Fruits and Vegetables, Analysis and Test Center of Chinese Academy of Tropical Agricultural Sciences, Haikou 571101, China;
2.
Key Laboratory of New Technology of Food Safety Testing of Guangxi University, College of Chemistry and Bioengineering, Guilin University of Technology, Guilin 541004, China

Corresponding author: ZHANG Lian-Ming, ; LI Shu-Huai, ; LI Jian-Ping,

Received Date: 06 December 2021
Revised Date: 15 February 2022
Fund Project:
Supported by the Open Fund of the Hainan Provincial Key Laboratory of Quality and Safety for Tropical Fruits and Vegetables (No.KFKT2020001), the National Natural Science Foundation of China (No.21765006), the Science and Technology Project of Guangxi (No.2018GXNSFAA138145, GuikeAD19110059) and the Guilin University of Technology (No.GUTQDJJ2016024).

Abstract: The improvement of sensor selection recognition ability is crucial to the performance of molecular imprinted sensors. Herein, a molecularly imprinted polymer-based sensor was developed for L-penicillamine (L-Pen) detection based on covalent organic framework compounds COF-JUZ2. The molecular imprint chiral recognition sensor with efficient separation and recognition ability was constructed via selectively fixing the conformation of chiral molecules by COF-JUZ2 to increase the recognition sites. The sensor showed the optimal detection performance for L-Pen when using the mixed solution of ultrapure water, acetic acid and methanol (1:1:8, V/V) as eluant and the COF-JUZ2-CS deposition time, electropolymerization cycle, eluent time and rebind time were 300 s, 15, 5 and 30 min, respectively. The sensor showed an excellent linear relationship with L-Pen concentration in the range of 1.0×10^-15 to 1.0×10^-9 mol/L, with a detection limit of 7.91×10^-16 mol/L. Due to introduction of COF-JUZ2, the separation and recognition performance of the sensor for D-Pen and L-Pen was increased by 13.4 folds. The sensor was applied to determination of L-Pen in real sample, with recoveries of 92.0%-102.0%.

Key words:

1. [1]
  YANG G, LIU Z, LAN T, DOU L, ZHANG K. Environ. Sci.:Water Res. Technol., 2021, 7:1220-1229.YANG G, LIU Z, LAN T, DOU L, ZHANG K. Environ. Sci.:Water Res. Technol., 2021, 7:1220-1229.
2. [2]
  ZHAO Y, ZHU X, JIANG W, LIU H, SUN B. Molecules, 2021, 26(4):1145-1176.ZHAO Y, ZHU X, JIANG W, LIU H, SUN B. Molecules, 2021, 26(4):1145-1176.
3. [3]
  CHEN Z, ZOU Y, WANG J, LI M, WEN Y. Sci. Total Environ., 2016, 548:139-147.CHEN Z, ZOU Y, WANG J, LI M, WEN Y. Sci. Total Environ., 2016, 548:139-147.
4. [4]
  GUO Y T, XIAO Y H, ZHANG J G, BIAN S D, ZHOU J Z, WU D Y, TIAN Z Q. Phys. Chem. Chem. Phys., 2021, 23(38):22119-22132.GUO Y T, XIAO Y H, ZHANG J G, BIAN S D, ZHOU J Z, WU D Y, TIAN Z Q. Phys. Chem. Chem. Phys., 2021, 23(38):22119-22132.
5. [5]
  ZHOU Xiao-Yan, LI Zai-Jun, WANG Guang-Li, GU Zhi-Guo. Chin. J. Anal. Lab., 2013, 32(9):1-5.周晓燕,李在均,王光丽,顾志国.分析试验室, 2013, 32(9):1-5.
6. [6]
  BUSKER E, GUNTHER K, MARTENS J. J. Chromatogr. A, 1985, 350(1):179-185.BUSKER E, GUNTHER K, MARTENS J. J. Chromatogr. A, 1985, 350(1):179-185.
7. [7]
  HE Min, ZHAO Shu-Lin, CHEN Jie. Chin. J. Anal. Chem., 2006, 34(5):655-658.何敏,赵书林,陈洁.分析化学, 2006, 34(5):655-658.
8. [8]
  BHUSHAN R, BRUCKNER H, KUMAR V. Biomed. Chromatogr., 2010, 21(10):1064-1068.BHUSHAN R, BRUCKNER H, KUMAR V. Biomed. Chromatogr., 2010, 21(10):1064-1068.
9. [9]
  HASSAN Y, ABOUL E. Anal. Lett., 1988, 21(12):2155-2163.HASSAN Y, ABOUL E. Anal. Lett., 1988, 21(12):2155-2163.
10. [10]
  WAND Y, HAN Q, ZHANG Q, HUANG Y, GUO L, FU Y. Anal. Methods, 2013, 5(20):5579-5583.WAND Y, HAN Q, ZHANG Q, HUANG Y, GUO L, FU Y. Anal. Methods, 2013, 5(20):5579-5583.
11. [11]
  ZHAO L, KUANG X, KUANG R, TONG L, WEI Q. ACS Appl. Mater. Interfaces, 2020, 12(1):1533-1538.ZHAO L, KUANG X, KUANG R, TONG L, WEI Q. ACS Appl. Mater. Interfaces, 2020, 12(1):1533-1538.
12. [12]
  ZHANG Y, WANG H Y, HE X W, LI W Y, ZHANG Y K. J. Hazard. Mater., 2021, 412:125249.ZHANG Y, WANG H Y, HE X W, LI W Y, ZHANG Y K. J. Hazard. Mater., 2021, 412:125249.
13. [13]
  DOLAI J, ALI H, JANA N R. ACS Appl. Polymer Mater., 2020, 2(2):691-698.DOLAI J, ALI H, JANA N R. ACS Appl. Polymer Mater., 2020, 2(2):691-698.
14. [14]
  LIU Y, LIU Y, LIU Z, ZHAO X, CAI Z. J. Hazard. Mater., 2020, 392:122251.LIU Y, LIU Y, LIU Z, ZHAO X, CAI Z. J. Hazard. Mater., 2020, 392:122251.
15. [15]
  ZHANG L, LUO K, LI D, ZHANG Y, LI J. Anal. Chim. Acta, 2020, 1136:82-90.ZHANG L, LUO K, LI D, ZHANG Y, LI J. Anal. Chim. Acta, 2020, 1136:82-90.
16. [16]
  COOPER A I. Crystengcomm, 2013, 15(8):1483.COOPER A I. Crystengcomm, 2013, 15(8):1483.
17. [17]
  YING Y, YANG Z, SHI D, PEH S B, ZHAO D. J. Membr. Sci., 2021, 632:119384.YING Y, YANG Z, SHI D, PEH S B, ZHAO D. J. Membr. Sci., 2021, 632:119384.
18. [18]
  SHI J L, HEN R C, HAO H, WANG C, LANG X. Angew. Chem., Int. Ed., 2020, 59(23):9088-9093.SHI J L, HEN R C, HAO H, WANG C, LANG X. Angew. Chem., Int. Ed., 2020, 59(23):9088-9093.
19. [19]
  LU Z, LU X, XIA L, ZHONG Y, HU Y. Talanta, 2021, 232:122428.LU Z, LU X, XIA L, ZHONG Y, HU Y. Talanta, 2021, 232:122428.
20. [20]
  ZHAO C, ZHANG L, WANG Q, ZHANG L, ZHANG Y. ACS Appl. Mater. Interfaces, 2021, 13(17):20397-20404.ZHAO C, ZHANG L, WANG Q, ZHANG L, ZHANG Y. ACS Appl. Mater. Interfaces, 2021, 13(17):20397-20404.
21. [21]
  CUI J, KAN L, LI Z, YANG L, ZHANG Z. Talanta, 2021, 228:122060.CUI J, KAN L, LI Z, YANG L, ZHANG Z. Talanta, 2021, 228:122060.
22. [22]
  ZHUO S Q, ZHANG X Y, LUO H, WANG X H, JI Y B. Macromol. Rapid Commun., 2020, 41(20):2004004.ZHUO S Q, ZHANG X Y, LUO H, WANG X H, JI Y B. Macromol. Rapid Commun., 2020, 41(20):2004004.
23. [23]
  BAI Ru-Yan, ZHANG Shuai, ZHANG Kun-Lei, LI De-Lei, ZHANG Qian, LIU Ting-Zhi, LIU Yi, HU Rong, YANG Yun-Hui. Phys. Test. Chem. Anal., Part B, 2017, 53(10):1129-1135.白茹燕,张帅,张坤蕾,李德蕾,张茜,刘婷知,刘仪,胡蓉,杨云慧.理化检验(化学分册), 2017, 53(10):1129-1135.
24. [24]
  SONG L J, GUO Z P, CHEN Y. Electrophoresis, 2012, 33(13):2056-2063.SONG L J, GUO Z P, CHEN Y. Electrophoresis, 2012, 33(13):2056-2063.

扫一扫看文章

计量

PDF下载量: 13
文章访问数: 616
HTML全文浏览量: 77

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

基于COF-JUZ2固定构象的左旋青霉胺分子印迹电化学传感器的制备和应用

通讯作者: 张连明,E-mail:lianming226@126.com; 黎舒怀,E-mail:happylishuhuai@163.com; 李建平,E-mail:likianping@263.net

English

Construction and Application of L-Penicillamine Molecular Imprinted Electrochemical Sensor Based on Covalent Organic Framework-JUZ2 Fixed Conformation

Corresponding author: ZHANG Lian-Ming, ; LI Shu-Huai, ; LI Jian-Ping,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

基于COF-JUZ2固定构象的左旋青霉胺分子印迹电化学传感器的制备和应用

通讯作者: 张连明,E-mail:lianming226@126.com; 黎舒怀,E-mail:happylishuhuai@163.com; 李建平,E-mail:likianping@263.net

English

Construction and Application of L-Penicillamine Molecular Imprinted Electrochemical Sensor Based on Covalent Organic Framework-JUZ2 Fixed Conformation

Corresponding author: ZHANG Lian-Ming, ; LI Shu-Huai, ; LI Jian-Ping,

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

计量

文章相关

通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

CCS Chemistry：颜徐州、鲍哲南：你的皮肤可能是一片SPMs