Citation: DING Jian-Hua, XU Wen-Ping, ZHU Yu-Ling. Mixed-mode Solid Phase Extraction Coupled with High Performance Liquid Chromatography for Analysis of Non-steroidal Anti-inflammatory Drugs Residues in Bovine Milk[J]. Chinese Journal of Analytical Chemistry, ;2023, 51(6): 1013-1023. doi: 10.19756/j.issn.0253-3820.211239 shu

Mixed-mode Solid Phase Extraction Coupled with High Performance Liquid Chromatography for Analysis of Non-steroidal Anti-inflammatory Drugs Residues in Bovine Milk

School of Chemistry and Material Science, East China University of Technology, Nanchang 330013, China

Corresponding author: ZHU Yu-Ling, zyl9568@ecut.edu.cn
Received Date: 21 March 2021
Revised Date: 29 May 2023

Fund Project: Supported by the Department of Science and Technology of Jiangxi Province (No. 20192BBG7008) and the Doctoral Research Fund of East China University of Technology (No. DHBK2019145).

A imidazolium ionic liquid-functionalized silica (Sil-IL) was synthesized and used as mixed-mode sorbent for solid phase extraction (SPE) of non-steroidal anti-inflammatory drugs (NSAIDs, naproxen, ketoprofen, indoometacin and tolfenamic acid) residues from bovine milk. A method combining this mixed-mode SPE and high performance liquid chromatography-ultraviolet detector (HPLC-UV) was established for simultaneous analysis of four kinds of NSAIDs residues in bovine milk. The prepared Sil-IL was characterized by Fourier transform infrared spectra, Raman spectra and elemental analysis. Then the retention mechanism of NSAIDs on Sil-IL sorbent was explored and the parameters affecting the extraction efficiency were optimized. Experimental results showed that Sil-IL had good extraction selectivity and high extraction efficiency towards four kinds of NSAIDs. Meanwhile, the interaction between Sil-IL and NSAIDs was mainly hydrophobic and anion exchange interactions. Under optimal SPE conditions, good sensitivity was achieved with a limit of detection of 1.2-1.9 μg/kg. The method displayed good linear relationship in the concentration range of 3-1000 μg/L for ketoprofen, naproxen, indomethacin and 4-1000 μg/L for tolfenamic acid, with the correlation coefficient (R²) of 09996-0.9998. The intra-day and inter-day precision were 1.0%-3.0% and 1.9%-6.3%, respectively. The recoveries of four kinds of NSAIDs in bovine milk at two spiked levels were 90.8%-105.3% with relative standard deviations less than 6.1%. The established method was proved to be accurate, reliable, simple, sensitive and selective, and could be used for determination of NSAIDs residues in milk sample.
- Ionic liquid,
- Nonsteroidal anti-inflammatory drugs,
- Solid phase extraction,
- High performance liquid chromatography,
- Bovine milk
References
1. [1]
  VAN PAMEL E, DAESELEIRE E. Anal. Bioanal. Chem., 2015, 407(15):4485-4494.
2. [2]
3. [3]
4. [4]
  Commission Regulation (EU) No. 37/2010 of 22 December 2009 on Pharmacologically Active Substances and Their Classification Regarding Maximum Residue Limits in Foodstuffs of Animal Origin. Off. J. Eur. Union, L15:1-72.
5. [5]
6. [6]
  TARTAGLIA A, KABIR A, D'AMBROSIO F, RAMUNDO P, ULUSOY S, ULUSOY H I, MERONE G M, SAVINI F, D'OVIDIO C, GRAZIA U D, FURTON K G, LOCATELLI M. J. Chromatogr. B, 2020, 1144:122082.
7. [7]
  SEIDI S, SANATI S E. Microchim. Acta, 2019, 186(5):297.
8. [8]
  MIRZAJANI R, KARDANI F, RAMEZANI Z. Microchem. J., 2019, 144:270-284.
9. [9]
  LI W, HUANG L, GUO D, ZHAO Y, ZHU Y. J. Chromatogr. A, 2018, 1571:76-83.
10. [10]
11. [11]
  WANG Y, OU Y, XIE S, CHEN D, WANG X, PAN Y, WANG Y, HUANG L, CHENG G, QU W, LIU Z, TAO Y, YUAN Z. Food Anal. Methods, 2019, 12(6):1346-1368.
12. [12]
  SHISHOV A, NECHAEVA D, BULATOV A. Microchem. J., 2019, 150:104080.
13. [13]
  MARTA Z, BOBALY B, FEKETE J, MAGDA B, IMRE T, SZABO P T. J. Pharm. Biomed. Anal., 2018, 160:99-108.
14. [14]
  HUANG C, LI Y, YANG J, PENG J, TAN J, FAN Y, WANG L, CHEN J. Talanta, 2018, 190:15-22.
15. [15]
  REINHOLDS I, PUGAJEVA I, ZACS D, LUNDANES E, RUSKO J, PERKONS I, BARTKEVICS V. Environ. Monit. Assess., 2017, 189(11):568.
16. [16]
  KANG J W, PARK S J, PARK H C, GEDI V, SO B J, LEE K J. Appl. Biochem. Biotechnol., 2014, 174(1):1-5.
17. [17]
  GOKTAS E F, KABIL E, ABIOZ F. Drug. Test. Anal., 2020, 12(8):1065-1077.
18. [18]
  AVINO P, NOTARDONATO I, PASSARELLA S, RUSSO M V. Appl. Sci., 2020, 10(16):5441.
19. [19]
  JI Y, DU Z, ZHANG H, ZHANG Y. Anal. Methods, 2014, 6(18):7294-7304.
20. [20]
  JAFARI Z, HADJMOHAMMADI M R. Anal. Methods, 2020, 12(36):4429-4437.
21. [21]
  MEUCCI V, MINUNNI M, VANNI M, SGORBINI M, CORAZZA M, INTORRE L. Bioanalysis, 2014, 6(16):2147-2158.
22. [22]
  AZZOUZ A, JURADO-SANCHEZ B, SOUHAIL B, BALLESTEROS E. J. Agric. Food Chem., 2011, 59(9):5125-5132.
23. [23]
  GUC M, SCHROEDER G. Appl. Sci., 2020, 10(12):4217.
24. [24]
25. [25]
26. [26]
  BERTHOD A, RUIZ-ÁNGEL M J, CARDA-BROCH S. J. Chromatogr. A, 2018, 1559:2-16.
27. [27]
  TIAN M, YAN H, ROW K H. J. Chromatogr. B, 2009, 877(8-9):738-742.
28. [28]
  ZHU Y, ZHANG W, LI L, WU C, XING J. Anal. Methods, 2014, 6(7):2102-2111.
29. [29]
  JEDZINIAK P, SZPRENGIER-JUSZKIEWICZ T, PIETRUK K, SLEDZINSKA E, ZMUDZKI J. Anal. Bioanal. Chem., 2012, 403(10):2955-2963.
30. [30]
  KIBBEY C E, MEYERHOFF M E. Anal. Chem., 1993, 65(17):2189-2196.
1. [1]
  VAN PAMEL E, DAESELEIRE E. Anal. Bioanal. Chem., 2015, 407(15):4485-4494.
2. [2]
3. [3]
4. [4]
  Commission Regulation (EU) No. 37/2010 of 22 December 2009 on Pharmacologically Active Substances and Their Classification Regarding Maximum Residue Limits in Foodstuffs of Animal Origin. Off. J. Eur. Union, L15:1-72.
5. [5]
6. [6]
  TARTAGLIA A, KABIR A, D'AMBROSIO F, RAMUNDO P, ULUSOY S, ULUSOY H I, MERONE G M, SAVINI F, D'OVIDIO C, GRAZIA U D, FURTON K G, LOCATELLI M. J. Chromatogr. B, 2020, 1144:122082.
7. [7]
  SEIDI S, SANATI S E. Microchim. Acta, 2019, 186(5):297.
8. [8]
  MIRZAJANI R, KARDANI F, RAMEZANI Z. Microchem. J., 2019, 144:270-284.
9. [9]
  LI W, HUANG L, GUO D, ZHAO Y, ZHU Y. J. Chromatogr. A, 2018, 1571:76-83.
10. [10]
11. [11]
  WANG Y, OU Y, XIE S, CHEN D, WANG X, PAN Y, WANG Y, HUANG L, CHENG G, QU W, LIU Z, TAO Y, YUAN Z. Food Anal. Methods, 2019, 12(6):1346-1368.
12. [12]
  SHISHOV A, NECHAEVA D, BULATOV A. Microchem. J., 2019, 150:104080.
13. [13]
  MARTA Z, BOBALY B, FEKETE J, MAGDA B, IMRE T, SZABO P T. J. Pharm. Biomed. Anal., 2018, 160:99-108.
14. [14]
  HUANG C, LI Y, YANG J, PENG J, TAN J, FAN Y, WANG L, CHEN J. Talanta, 2018, 190:15-22.
15. [15]
  REINHOLDS I, PUGAJEVA I, ZACS D, LUNDANES E, RUSKO J, PERKONS I, BARTKEVICS V. Environ. Monit. Assess., 2017, 189(11):568.
16. [16]
  KANG J W, PARK S J, PARK H C, GEDI V, SO B J, LEE K J. Appl. Biochem. Biotechnol., 2014, 174(1):1-5.
17. [17]
  GOKTAS E F, KABIL E, ABIOZ F. Drug. Test. Anal., 2020, 12(8):1065-1077.
18. [18]
  AVINO P, NOTARDONATO I, PASSARELLA S, RUSSO M V. Appl. Sci., 2020, 10(16):5441.
19. [19]
  JI Y, DU Z, ZHANG H, ZHANG Y. Anal. Methods, 2014, 6(18):7294-7304.
20. [20]
  JAFARI Z, HADJMOHAMMADI M R. Anal. Methods, 2020, 12(36):4429-4437.
21. [21]
  MEUCCI V, MINUNNI M, VANNI M, SGORBINI M, CORAZZA M, INTORRE L. Bioanalysis, 2014, 6(16):2147-2158.
22. [22]
  AZZOUZ A, JURADO-SANCHEZ B, SOUHAIL B, BALLESTEROS E. J. Agric. Food Chem., 2011, 59(9):5125-5132.
23. [23]
  GUC M, SCHROEDER G. Appl. Sci., 2020, 10(12):4217.
24. [24]
25. [25]
26. [26]
  BERTHOD A, RUIZ-ÁNGEL M J, CARDA-BROCH S. J. Chromatogr. A, 2018, 1559:2-16.
27. [27]
  TIAN M, YAN H, ROW K H. J. Chromatogr. B, 2009, 877(8-9):738-742.
28. [28]
  ZHU Y, ZHANG W, LI L, WU C, XING J. Anal. Methods, 2014, 6(7):2102-2111.
29. [29]
  JEDZINIAK P, SZPRENGIER-JUSZKIEWICZ T, PIETRUK K, SLEDZINSKA E, ZMUDZKI J. Anal. Bioanal. Chem., 2012, 403(10):2955-2963.
30. [30]
  KIBBEY C E, MEYERHOFF M E. Anal. Chem., 1993, 65(17):2189-2196.
1. [1]
  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
2. [2]
  Fan Wu , Wenchang Tian , Jin Liu , Qiuting Zhang , YanHui Zhong , Zian Lin . Core-Shell Structured Covalent Organic Framework-Coated Silica Microspheres as Mixed-Mode Stationary Phase for High Performance Liquid Chromatography. University Chemistry, 2024, 39(11): 319-326. doi: 10.12461/PKU.DXHX202403031
3. [3]
  Siming Bian , Sijie Luo , Junjie Ou . Application of van Deemter Equation in Instrumental Analysis Teaching: A New Type of Core-Shell Stationary Phase. University Chemistry, 2025, 40(3): 381-386. doi: 10.12461/PKU.DXHX202406087
4. [4]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
5. [5]
  Zunxiang Zeng , Yuling Hu , Yufei Hu , Hua Xiao . Analysis of Plant Essential Oils by Supercritical CO₂Extraction with Gas Chromatography-Mass Spectrometry: An Instrumental Analysis Comprehensive Experiment Teaching Reform. University Chemistry, 2024, 39(3): 274-282. doi: 10.3866/PKU.DXHX202309069
6. [6]
  Wenjun Zheng . Application in Inorganic Synthesis of Ionic Liquids. University Chemistry, 2024, 39(8): 163-168. doi: 10.3866/PKU.DXHX202401020
7. [7]
  Mingyang Men , Jinghua Wu , Gaozhan Liu , Jing Zhang , Nini Zhang , Xiayin Yao . 液相法制备硫化物固体电解质及其在全固态锂电池中的应用. Acta Physico-Chimica Sinica, 2025, 41(1): 2309019-. doi: 10.3866/PKU.WHXB202309019
8. [8]
  Gaoyan Chen , Chaoyue Wang , Juanjuan Gao , Junke Wang , Yingxiao Zong , Kin Shing Chan . Heart to Heart: Exploring Cardiac CT. University Chemistry, 2024, 39(9): 146-150. doi: 10.12461/PKU.DXHX202402011
9. [9]
  Xiaowu Zhang , Pai Liu , Qishen Huang , Shufeng Pang , Zhiming Gao , Yunhong Zhang . Acid-Base Dissociation Equilibrium in Multiphase System: Effect of Gas. University Chemistry, 2024, 39(4): 387-394. doi: 10.3866/PKU.DXHX202310021
10. [10]
  Chongjing Liu , Yujian Xia , Pengjun Zhang , Shiqiang Wei , Dengfeng Cao , Beibei Sheng , Yongheng Chu , Shuangming Chen , Li Song , Xiaosong Liu . Understanding Solid-Gas and Solid-Liquid Interfaces through Near Ambient Pressure X-Ray Photoelectron Spectroscopy. Acta Physico-Chimica Sinica, 2025, 41(2): 100013-. doi: 10.3866/PKU.WHXB202309036
11. [11]
  Chunai Dai , Yongsheng Han , Luting Yan , Zhen Li , Yingze Cao . Ideological and Political Design of Solid-liquid Contact Angle Measurement Experiment. University Chemistry, 2024, 39(2): 28-33. doi: 10.3866/PKU.DXHX202306065
12. [12]
  Jiao CHEN , Yi LI , Yi XIE , Dandan DIAO , Qiang XIAO . Vapor-phase transport of MFI nanosheets for the fabrication of ultrathin b-axis oriented zeolite membranes. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 507-514. doi: 10.11862/CJIC.20230403
13. [13]
  Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO₃ for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
14. [14]
  Haiyang Zhang , Yanzhao Dong , Haojie Li , Ruili Guo , Zhicheng Zhang , Jiangjiexing Wu . Exploring the Integration of Chemical Engineering Principle Experiment with Cutting-Edge Research Achievements. University Chemistry, 2024, 39(10): 308-313. doi: 10.12461/PKU.DXHX202405035
15. [15]
  Feiya Cao , Qixin Wang , Pu Li , Zhirong Xing , Ziyu Song , Heng Zhang , Zhibin Zhou , Wenfang Feng . Magnesium-Ion Conducting Electrolyte Based on Grignard Reaction: Synthesis and Properties. University Chemistry, 2024, 39(3): 359-368. doi: 10.3866/PKU.DXHX202308094
16. [16]
  Yingran Liang , Fei Wang , Jiabao Sun , Hongtao Zheng , Zhenli Zhu . Construction and Application of a New Experimental Device for Determination of Alkaline Metal Elements by Plasma Atomic Emission Spectrometry Based on Solution Cathode Glow Discharge: An Alternative Approach for Fundamental Teaching Experiments in Emission Spectroscopy. University Chemistry, 2024, 39(5): 380-387. doi: 10.3866/PKU.DXHX202312024
17. [17]
  Aoyu Huang , Jun Xu , Yu Huang , Gui Chu , Mao Wang , Lili Wang , Yongqi Sun , Zhen Jiang , Xiaobo Zhu . Tailoring Electrode-Electrolyte Interfaces via a Simple Slurry Additive for Stable High-Voltage Lithium-Ion Batteries. Acta Physico-Chimica Sinica, 2025, 41(4): 100037-. doi: 10.3866/PKU.WHXB202408007
18. [18]
  Mei Yan , Rida Feng , Yerdos·Tohtarkhan , Biao Long , Li Zhou , Chongshen Guo . Expansion and Extension of Liquid Saturated Vapor Measurement Experiment. University Chemistry, 2024, 39(3): 294-301. doi: 10.3866/PKU.DXHX202308103
19. [19]
  Kexin Dong , Chuqi Shen , Ruyu Yan , Yanping Liu , Chunqiang Zhuang , Shijie Li . Integration of Plasmonic Effect and S-Scheme Heterojunction into Ag/Ag₃PO₄/C₃N₅ Photocatalyst for Boosted Photocatalytic Levofloxacin Degradation. Acta Physico-Chimica Sinica, 2024, 40(10): 2310013-. doi: 10.3866/PKU.WHXB202310013
20. [20]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056

Get Citation

PDF

XML

Metrics

PDF Downloads(15)
Abstract views(2046)
HTML views(117)

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

Mixed-mode Solid Phase Extraction Coupled with High Performance Liquid Chromatography for Analysis of Non-steroidal Anti-inflammatory Drugs Residues in Bovine Milk

References

Metrics

通讯作者: 陈斌, bchen63@163.com