Skip to main content
SpringerLink
Log in

Comparison of multi-recognition molecularly imprinted polymers for recognition of melamine, cyromazine, triamterene, and trimethoprim

  • Research Paper
  • Published:
Analytical and Bioanalytical Chemistry Aims and scope Submit manuscript

Abstract

Three fragmental templates, including 2,4-diamino-6-methyl-1,3,5-triazine (DMT), cyromazine (CYR), and trimethoprim (TME), were used to prepare the fragment molecularly imprinted polymers (FMIPs), respectively, in polar ternary porogen which was composed of ionic liquid ([BMIM]BF4), methanol, and water. The morphology, specific surface areas, and selectivity of the obtained FMIPs for fragmental analogues were systematically characterized. The experimental results showed that the FMIPs possessed the best specific recognition ability to the relative template and the greatest imprinting factor (IF) was 5.25, 6.69, and 7.11 of DMT on DMT-MIPs, CYR on CYR-MIPs, and TME on TME-MIPs, respectively. In addition, DMT-MIPs also showed excellent recognition capability for fragmental analogues including CYR, melamine (MEL), triamterene (TAT), and TME, and the IFs were 2.08, 3.89, 2.18, and 2.60, respectively. The effects of pH and temperature on the retention of the fragmental and structural analogues were studied in detail. Van’t Hoff analysis indicated that the retention and selectivity on FMIPs were an entropy-driven process, i.e., steric interaction. The resulting DMT-MIPs were used as a solid-phase extraction material to enrich CYR, MEL, TAT, and TME in different bio-matrix samples for high-performance liquid chromatography analysis. The developed method had acceptable recoveries (86.8–98.6 %, n = 3) and precision (2.7–4.6 %) at three spiked levels (0.05–0.5 μg g−1).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Chen LX, Xu SF, Li JH (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40(5):2922–2942

    Article  CAS  Google Scholar 

  2. Toth B, Horvai G (2012) Chromatography, solid-phase extraction, and capillary electrochromatography with MIPs. Top Curr Chem 325:267–306

    Article  CAS  Google Scholar 

  3. Kulsing C, Knob R, Macka M, Junor P, Boysen RI, Hearn MTW (2014) Molecular imprinted polymeric porous layers in open tubular capillaries for chiral separations. J Chromatogr A 1354(8):85–91

    Article  CAS  Google Scholar 

  4. Orozco J, Cortes A, Cheng G, Sattayasamisathit S, Gao W, Feng XM, Shen YF, Wang J (2013) Molecularly imprinted polymer-based catalytic micromotors for selective protein transport. J Am Chem Soc 135(14):5536–5539

    Article  Google Scholar 

  5. Li B, Xu JJ, Hall AJ, Haupt K, Bui BTS (2014) Water-compatible silica sol–gel molecularly imprinted polymer as a potential delivery system for the controlled release of salicylic acid. J Mol Recognit 27(9):559–565

    Article  CAS  Google Scholar 

  6. Fuchs Y, Soppera O, Mayes AG, Haupt K (2013) Holographic molecularly imprinted polymers for label-free chemical sensing. Adv Mater 25(4):566–570

    Article  CAS  Google Scholar 

  7. Chen FF, Xie XY, Shi YP (2013) Preparation of magnetic molecularly imprinted polymer for selective recognition of resveratrol in wine. J Chromatogr A 1300(26):112–118

    Article  CAS  Google Scholar 

  8. Kawaguchi M, Hayatsu Y, Nakata H, Ishii Y, Ito R, Saito K, Nakazawa H (2005) Molecularly imprinted solid phase extraction using stable isotope labeled compounds as template and liquid chromatography-mass spectrometry for trace analysis of bisphenol A in water sample. Anal Chim Acta 539(1–2):83–89

    Article  CAS  Google Scholar 

  9. Bognar J, Szucs J, Dorko Z, Horvath V, Gyurcsanyi RE (2013) Nanosphere lithography as a versatile method to generate surface-imprinted polymer films for selective protein recognition. Adv Funct Mater 23(37):4703–4709

    Article  CAS  Google Scholar 

  10. Cacho C, Turiel E, Martin-Esteban A, Ayala D, Perez-Conde C (2006) Semi-covalent imprinted polymer using propazine methacrylate as template molecule for the clean-up of triazines in soil and vegetable samples. J Chromatogr A 1114(2):255–262

    Article  CAS  Google Scholar 

  11. Berffren C, Bayoudh S, Sherrington D, Ensing K (2000) Use of molecularly imprinted solid-phase extraction for the selective clean-up of clenbuterol from calf urine. J Chromatogr A 889(1–2):105–110

    Google Scholar 

  12. Ellwanger A, Berggren C, Bayoudh S, Crecenzi C, Karlsson L, Owens PK, Ensing K, Cormack P, Sherrington D, Sellergren B (2001) Evaluation of methods aimed at complete removal of template from molecularly imprinted polymers. Analyst 126(6):784–792

    Article  CAS  Google Scholar 

  13. Kubo T, Kuroda K, Tominaga Y, Naito T, Sueyoshi K, Hosoya K, Otsuka K (2014) Effective determination of a pharmaceutical, sulpiride, in river water by online SPE-LC-MS using a molecularly imprinted polymer as a preconcentration medium. J Pharm Biomed 89(15):111–117

    Article  CAS  Google Scholar 

  14. Cleand D, McCluskey A (2013) The use of effective fragment potentials in the design and synthesis of molecularly imprinted polymers for the group recognition of PCBs. Org Biomol Chem 11(28):4646–4656

    Article  Google Scholar 

  15. Yan HY, Liu ST, Gao MM, Sun N (2013) Ionic liquids modified dummy molecularly imprinted microspheres as solid phase extraction materials for determination of clenbuterol and clorprenaline in urine. J Chromatogr A 1294(14):10–16

    Article  CAS  Google Scholar 

  16. Zhao XY, Zhang HW, Liang ZJ, Shu YP, Liang Y (2013) Selective recognition of triamterene in biological samples by molecularly imprinted monolithic column with a pseudo template employed. J Sep Sci 36(9–10):1501–1508

    Article  CAS  Google Scholar 

  17. Zaidi SA (2013) Dual-templates molecularly imprinted monolithic for the evaluation of serotonin and histamine in CEC. Electrophresis 34(9–10):1375–1382

    Article  CAS  Google Scholar 

  18. Jing T, Wang Y, Dai Q, Xia H, Niu JW, Hao QL, Mei SR, Zhou YK (2010) Preparation of mixed-templates molecularly imprinted polymers and investigation of the recognition ability for tetracycline antibiotics. Biosens Bioelectron 25(10):2218–2224

    Article  CAS  Google Scholar 

  19. Prasad BB, Jauhari D (2015) A dual-template biomimetic molecularly imprinted dendrimer-based piezoelectric sensor for ultratrace analysis of organochlorine pesticides. Sensor Actuators B Chem 207(Part A):542–551

    Article  CAS  Google Scholar 

  20. Wang XH, Fang QX, Liu SP, Chen L (2012) Preparation of a magnetic molecularly imprinted polymer with pseudo template for rapid simultaneous determination of cyromazine and melamine in bio-matrix samples. Anal Bioanal Chem 404(5):1555–1564

    Article  CAS  Google Scholar 

  21. Nezhadali A, Mojarrab M (2015) Fabrication of an electrochemical molecularly imprinted polymer triamterene sensor based on multivariate optimization using multi-walled carbon nanotubes. J Electroanal Chem 744(1):85–94

    Article  CAS  Google Scholar 

  22. Zhang HW, Guo JW, Li K, Wang WS, Wu YP, Lu QW, Zhai HY (2012) On-line determination of trimethoprim in human serum by molecularly imprinted monolithic column with melamine employed as analogue template. Chin J Anal Chem 40(5):699–704

    CAS  Google Scholar 

  23. Quaglis M, Chenon K, Hall AJ, Lorenti ED, Sellergren B (2001) Target analogue imprinted polymers with affinity for folic acid and related compounds. J Am Chem Soc 123(10):2146–2154

    Article  Google Scholar 

  24. He LM, Su YJ, Zheng YQ, Huang XH, Wu L, Liu YH, Zeng ZL, Chen ZL (2009) Novel cyromazine imprinted polymer applied to the solid-phase extraction of melamine from feed and milk samples. J Chromatogr A 1216(34):6196–6203

    Article  CAS  Google Scholar 

  25. Song XL, Li JH, Wang JT, Chen LX (2009) Quercetin molecularly imprinted polymers: preparation, recognition characteristics and properties as sorbent for solid-phase extraction. Talanta 80(2):694–702

    Article  CAS  Google Scholar 

  26. Pakade V, Lindahl S, Chimuka L, Turner C (2012) Molecularly imprinted polymers targeting quercetin in high-temperature aqueous solutions. J Chromatogr A 1230(23):15–23

    Article  CAS  Google Scholar 

  27. Ban L, Han X, Wang XH, Huang YP, Liu ZS (2013) Carprofen-imprinted monolith prepared by reversible addition-fragmentation chain transfer polymerization in room temperature ionic liquid. Anal Bioanal Chem 405(26):8597–8605

    Article  CAS  Google Scholar 

  28. Holland N, Frisby J, Owens E, Hughes H, Duggan P, McLoughlin P (2010) The influence of polymer morphology on the performance of molecularly imprinted polymers. Polymer 51(7):1578–1584

    Article  CAS  Google Scholar 

  29. Dauwe C, Sellergren B (1996) Influence of template basicity and hydrophobicity on the molecularly recognition properties of molecularly imprinted polymers. J Chromatogr A 753(2):191–200

    Article  CAS  Google Scholar 

  30. Gavazzini A, Marchetti N, Guzzinati R, Pasti L, Ciogli A, Gasprrini F, Lagana A (2014) Understanding mixed-mode retention mechanisms in liquid chromatography with hydrophobic stationary phase. Anal Chem 86(10):4919–4926

    Article  Google Scholar 

  31. Zhong DD, Huang YP, Xin XL, Liu ZS, Aisa HA (2013) Preparation of metallic pivot-based imprinted monolith for polar template. J Chromatogr B 934(1):109–116

    Article  CAS  Google Scholar 

  32. Bian M, Zhang Z, Yin H (2012) Effects and mechanism characterization of ionic liquids as mobile phase additives for the separation of matrine-type alkaloids by liquid chromatography. J Pharm Biomed 58(25):163–167

    Article  CAS  Google Scholar 

  33. Zhang YG, Song D, Lanni L, Shimizu K (2010) Importance of functional monomer dimerization in the molecular imprinting process. Macromolecules 43(15):6284–6294

    Article  CAS  Google Scholar 

  34. Caro E, Masque N, Mzcre RM, Borrul F, Comack PAG, Sherrington DC (2002) Non-covalent and semi-covalent molecularly imprinted polymers for selective on-line solid-phase extraction of 4-nitrophenol from water samples. J Chromatogr A 963(1–2):169–178

    Article  CAS  Google Scholar 

  35. Yang CX, Liu SS, Wang HF, Wang SW, Yan XP (2012) High-performance liquid chromatographic separation of position isomers using metal-organic framework MIL-53(Al) as the stationary phase. Analyst 137(1):133–139

    Article  CAS  Google Scholar 

  36. Kaszynska MS, Jaszczolt K, Witt D, Rachon J (2004) High-performance liquid chromatography of di- and trisubstituted aromatic positional isomers on 1,3-alternate 25,27-dipropoxy-26,28-bis-[3-propyloxy]-calix[4] arene-bonded silica gel stationary phase. J Chromatogr A 1055(1–2):21–28

    Article  Google Scholar 

  37. Sellergren B, Shea KJ (1995) Origin of peak asymmetry and the effect of temperature on solute retention in enantiomer separations on imprinted chiral stationary phases. J Chromatogr A 690(1):29–39

    Article  CAS  Google Scholar 

  38. Denderz N, Lehotay J, Cizmarik J, Cibulkova Z, Simon P (2012) Thermodynamic study of molecularly imprinted polymer used as the stationary phase in high performance liquid chromatography. J Chromatogr A 1235(27):77–83

    Article  CAS  Google Scholar 

  39. Dender N, Lehotay J (2012) Application of the Van’t Hoff dependences in the characterization of molecularly imprinted polymers for some phenolic acids. J Chromatogr A 1268(14):44–52

    Article  Google Scholar 

  40. Kim H, Kaczmarski K, Guiochon G (2006) Thermodynamic analysis of the heterogeneous binding sites of molecularly imprinted polymers. J Chromatogr A 1101(1–2):136–152

    Article  CAS  Google Scholar 

  41. Kim H, Guiochon G (2005) Thermodynamic functions and intraparticle mass transfer kinetics of structural analogues of a template on molecularly imprinted polymers in liquid chromatography. J Chromatogr A 1097(1–2):84–97

    Article  CAS  Google Scholar 

  42. Liu YQ, Hoshina K, Haginaka J (2010) Monodispersed, molecularly imprinted polymers for cinchonidine by precipitation polymerization. Talanta 80(5):1713–1718

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work was supported by the National Natural Science Foundation of China (Grant No. 21375096 and U1303202) and by the Hundred Talents Program of the Chinese Academy of Sciences.

Author information

Authors and Affiliations

  1. Tianjin Key Laboratory on Technologies Enabling Development of Clinical Therapeutics and Diagnostics (Theranostics), School of Pharmacy, Tianjin Medical University, 22 Qixiangtai Road, Heping District, Tianjin, 300070, China

    Xian-Hua Wang, Jing Zhang, Chao Peng, Qian Dong, Yan-Ping Huang & Zhao-Sheng Liu

Authors
  1. Xian-Hua Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jing Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chao Peng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Qian Dong
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yan-Ping Huang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zhao-Sheng Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zhao-Sheng Liu.

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

(PDF 399 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wang, XH., Zhang, J., Peng, C. et al. Comparison of multi-recognition molecularly imprinted polymers for recognition of melamine, cyromazine, triamterene, and trimethoprim. Anal Bioanal Chem 407, 7145–7155 (2015). https://doi.org/10.1007/s00216-015-8878-9

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00216-015-8878-9

Keywords

Search

Navigation