Citation: SONG Hui-Jia, WANG Xing-Yan, LI Ze-Hong, GAO Rui-Xia. Construction of Boric Acid Affinity Magnetic Molecularly Imprinted Polymer and Its Application in Selective Extraction of Rutin[J]. Chinese Journal of Analytical Chemistry, ;2023, 51(4): 600-610. doi: 10.19756/j.issn.0253-3820.221587 shu

Construction of Boric Acid Affinity Magnetic Molecularly Imprinted Polymer and Its Application in Selective Extraction of Rutin

School of Chemistry, Xi'an Jiaotong University, Xi'an 710049, China

Corresponding author: GAO Rui-Xia, ruixiagao@xjtu.edu.cn
Received Date: 29 November 2022
Revised Date: 12 January 2023

Fund Project: Supported by the Natural Science Foundation of Shaanxi Province, China (Nos. 2020JM-066, 2020JQ-019).

Molecularly imprinted polymers (MIPs), known as ″artificial antibodies″, are widely used in extraction and separation of natural pharmaceutical active ingredients due to the high selectivity. To enhance the extraction efficiency and the affinity of imprinted pores for target molecules, a novel type of boronic acid-affinity magnetic molecularly imprinted polymers (RT-PBA/MMIPs) was prepared using phenylboronic acid (PBA)-modified magnetic spheres (PBA/MSN) as the carrier, RT as the template molecule, and dopamine (DA) as the functional monomer, while boronic acid affinity and two-step template immobilization strategies were synergistically applied at the same time. Through a series of physical and chemical characterizations, it was verified that the prepared RT-PBA/MMIPs had uniform particle size, stable crystal form, and excellent magnetic properties. Meanwhile, kinetic, thermodynamic and selective adsorption experiments demonstrated that RT-PBA/MMIPs had fast adsorption speed (6 min to reach adsorption equilibrium), high adsorption capacity (Q=2.04 mg/g), and good selectivity (IF=2.43) and reusability (the adsorption efficiency was higher than 94.43% after 6 adsorptiondesorption cycles). In addition, RT-PBA/MMIPs were used as a solid-phase extraction adsorbent in combination with high performance liquid chromatography to achieve efficient extraction and enrichment of RT from Sophora japonica with recoveries of 83.1%-92.3%. In a word, the developed RT-PBA/MMIPs showed good practical application prospects and were expected to be used for the rapid and selective separation and extraction of RT as well as other active ingredients of natural medicines.
- Boronic acid affinity,
- Two-step template immobilization,
- Magnetic surface molecularly imprinted polymers,
- Specific recognition,
- Rutin
1. [1]
  MUVHULAWA N, DLUDLA P V, ZIQUBU K, MTHEMBU S X H, MTHIYANE F, NKAMBULE B B, MAZIBUKOMBEJE S E. Pharmacol. Res., 2022, 178:106163.
2. [2]
  WANG Z, DING Z, LI Z, DING Y, JIANG F, LIU J. Microb. Pathog., 2021, 159:105121.
3. [3]
  LI Y, QIN R, YAN H, WANG F, HUANG S, ZHANG Y, ZHONG M, ZHANG W, WANG Z. J. Nutr. Biochem., 2018, 51:91-98.
4. [4]
  RAHMAN F, TABREZ S, ALI R, ALQAHTANI A S, AHMED M Z, RUB A. J. Tradit. Complementary Med., 2021, 11(2):173-179.
5. [5]
  BAJEROVÁ P, ADAM M, BAJER T, VENTURA K. J. Sep. Sci., 2014, 37(7):835-844.
6. [6]
  LIU H, JIAO Z, LIU J, ZHANG C, ZHENG X, LAI S, CHEN F, YANG H. Food Anal. Methods, 2013, 6(3):781-788.
7. [7]
  FANG X, WANG Y, WANG J, ZHANG J, WANG X. J. Sep. Sci., 2013, 36(16):2672-2679.
8. [8]
  GU H, CHEN F, ZHANG Q, ZANG J. J. Chromatogr. B, 2016, 1014:45-55.
9. [9]
10. [10]
11. [11]
  ZENG H, WANG Y, NIE C, KONG J, LIU X. Analyst, 2012, 137(10):2503-2512.
12. [12]
  HE P, ZHU H, MA Y, LIU N, NIU X, WEI M, PAN J. Chem. Eng. J., 2019, 367:55-63.
13. [13]
  ZHANG H, SONG H, TIAN X, WANG Y, HAO Y, WANG W, GAO R, YANG W, KE Y S, TANG Y. Microchim. Acta, 2021, 188(1):17.
14. [14]
  UYGUN Z O, UYGUN H D E. Electroanalysis, 2020, 32(2):226-229.
15. [15]
16. [16]
  MATTEINI P, AGATI G, PINELLI P, GOTI A. Monatsh Chem., 2011, 142(9):885-893.
17. [17]
  JIN Y, WANG T, LI Q, WANG F, LI J. Talanta, 2022, 239:123084.
18. [18]
19. [19]
  ZHANG M, ZHANG X, HE X, CHEN L, ZHANG Y. Nanoscale, 2012, 4(10):3141-3147.
20. [20]
  SONG H J, WANG C F, ZHANG H P, YAO L, ZHANG J J, GAO R X, TANG X S, CHONG T, LIU W P, TANG Y H. Colloid. Surf., B, 2019, 182:110375.
21. [21]
  ZHANG Z, ZHANG X, NIU D, LI Y, SHI J. J. Hazard. Mater., 2017, 328:160-169.
22. [22]
  XIE X, HU Q, KE R, ZHEN X, BU Y, WANG S. Chem. Eng. J., 2019, 371:130-137.
23. [23]
  WANG L, LI J, WANG J, GUO X, WANG X, CHOO J, CHEN L. J. Colloid Interface Sci., 2019, 541:376-386.
24. [24]
  LI G, AHN W S, ROW K H. J. Sep. Sci., 2016, 39(23):4465-4473.
25. [25]
  FU Y, CHEN Z, YU H, YUE Y, DI D. J. Appl. Polym. Sci., 2012, 123(2):903-912.
26. [26]
  PENG L, WANG Y, ZENG H, YUAN Y. Analyst, 2011, 136(4):756-763.
27. [27]
  WANG F, NI X, ZHANG J, ZHANG Q, JIA H, HE H, DRAMOU P. Food Chem., 2022, 381:132275.
1. [1]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . Remarkable Photocatalytic H₂O₂ Production Efficiency over Ultrathin g-C₃N₄ Nanosheet with Large Surface Area and Enhanced Crystallinity by Two-Step Calcination. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-0. doi: 10.3866/PKU.WHXB202406019
2. [2]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
3. [3]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
4. [4]
  Yangrui Xu , Yewei Ren , Xinlin Liu , Hongping Li , Ziyang Lu . NH₂-UIO-66 Based Hydrophobic Porous Liquid with High Mass Transfer and Affinity Surface for Enhancing CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(11): 2403032-0. doi: 10.3866/PKU.WHXB202403032
5. [5]
  Yuxia Luo , Xiaoyu Xie , Fangfang Chen . 药物递送魔法师——分子印迹聚合物. University Chemistry, 2025, 40(8): 202-210. doi: 10.12461/PKU.DXHX202409129
6. [6]
  Meihui Cai , Yi Huang , Xingxing Ma , Qiuling Song . Exploring the Mysteries of the Petasis-Boronic Acid-Mannich Reaction. University Chemistry, 2025, 40(11): 184-190. doi: 10.12461/PKU.DXHX202412054
7. [7]
  Gengyuan Li , Yexin Wang , Song Gao , Shangda Jiang . Advances in Light-Induced Spin Polarization of Magnetic Molecules. University Chemistry, 2025, 40(12): 87-94. doi: 10.12461/PKU.DXHX202509112
8. [8]
  Jiarong Feng , Yejie Duan , Chu Chu , Dezhen Xie , Qiu'e Cao , Peng Liu . Preparation and Application of a Streptomycin Molecularly Imprinted Electrochemical Sensor: A Suggested Comprehensive Analytical Chemical Experiment. University Chemistry, 2024, 39(8): 295-305. doi: 10.3866/PKU.DXHX202401016
9. [9]
  Kaimin WANG , Na HE , Shiyi LI , Xuling BAI , Weiqing SUN , Yanqing YE , Yulu MA . Synthesis, Hirshfeld surface analysis and properties of two Zn(Ⅱ)/Ni(Ⅱ) coordination polymers. Chinese Journal of Inorganic Chemistry, 2026, 42(1): 55-64. doi: 10.11862/CJIC.20250178
10. [10]
  Yuhui Yang , Jintian Luo , Biao Zuo . A Teaching Approach to Polymer Surface and Interface in Undergraduate Polymer Physics Courses. University Chemistry, 2025, 40(4): 126-130. doi: 10.12461/PKU.DXHX202408056
11. [11]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
12. [12]
  Songmei Ma , Ying Zhang , Gang Liu , Wenlong Xu . Comprehensive Experiment Teaching Exploration and Practice in Polymeric Materials Integrating Research-Driven Learning, Creativity-Enhanced Competency, and Science-Education Synergy: A Case Study of Machine Learning-Assisted Intelligent Handwriting Recognition System. University Chemistry, 2026, 41(1): 289-297. doi: 10.12461/PKU.DXHX202509083
13. [13]
  Rui Li , Jiayu Zhang , Anyang Li . Two Levels of Understanding of Chemical Bonds: a Case of the Bonding Model of Hypervalent Molecules. University Chemistry, 2024, 39(2): 392-398. doi: 10.3866/PKU.DXHX202308051
14. [14]
  Yuan Chun , Yongmei Liu , Fuping Tian , Hong Yuan , Shu'e Song , Wanchun Zhu , Yunchao Li , Zhongyun Wu , Xiaokui Wang , Yunshan Bai , Li Wang , Jianrong Zhang , Shuyong Zhang . Suggestions on Operating Specifications of Physical Chemistry Experiment: Measurement of Colloidal and Surface Chemical Properties, Molecular Structure and Properties. University Chemistry, 2025, 40(5): 178-188. doi: 10.12461/PKU.DXHX202503053
15. [15]
  Baohua LÜ , Yuzhen LI . Anisotropic photoresponse of two-dimensional layered α-In₂Se₃(2H) ferroelectric materials. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1911-1918. doi: 10.11862/CJIC.20240105
16. [16]
  Qiuting Zhang , Fan Wu , Jin Liu , Zian Lin . Chromatographic Stationary Phase and Chiral Separation Using Frame Materials. University Chemistry, 2025, 40(4): 291-298. doi: 10.12461/PKU.DXHX202405174
17. [17]
  Renjie Xue , Chao Ma , Jing He , Xuechao Li , Yanning Tang , Lifeng Chi , Haiming Zhang . Catassembly in the Host-Guest Recognition of 2D Metastable Self-Assembled Networks. Acta Physico-Chimica Sinica, 2024, 40(9): 2309011-0. doi: 10.3866/PKU.WHXB202309011
18. [18]
  Tianrong Zhu , Fan Yu , Yuhang Liu , Haiyi Xu , Tingting Ma , Ming Li , Yuhang Xue , Yazhen Wang , Aihua Li , Biao Xiao , Xiaolun Peng . Intelligent Visualization, Precise Iodometry: Color Recognition-based Indirect Iodometric Method for Copper Determination. University Chemistry, 2026, 41(1): 264-275. doi: 10.12461/PKU.DXHX202503096
19. [19]
  Yuejiao Wang , Quanxing Mao , Junshuo Cui , Xiaogeng Feng , Xiaohong Chang , Zhenning Lou , Ying Xiong . 颜色识别式人工智能融入混合碱滴定实验的应用. University Chemistry, 2026, 41(1): 107-113. doi: 10.12461/PKU.DXHX202506020
20. [20]
  Xin XIONG , Qian CHEN , Quan XIE . First principles study of the photoelectric properties and magnetism of La and Yb doped AlN. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1519-1527. doi: 10.11862/CJIC.20240064

Get Citation

PDF

XML

Metrics

PDF Downloads(18)
Abstract views(2535)
HTML views(166)

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