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Microchimica Acta

, 185:247 | Cite as

Molecularly imprinted polymers for the detection of illegal drugs and additives: a review

  • Deli Xiao
  • Yue Jiang
  • Yanping Bi
Review Article
  • 456 Downloads

Abstract

This review (with 154 refs.) describes the current status of using molecularly imprinted polymers in the extraction and quantitation of illicit drugs and additives. The review starts with an introduction into some synthesis methods (lump MIPs, spherical MIPs, surface imprinting) of MIPs using illicit drugs and additives as templates. The next section covers applications, with subsections on the detection of illegal additives in food, of doping in sports, and of illicit addictive drugs. A particular focus is directed towards current limitations and challenges, on the optimization of methods for preparation of MIPs, their applicability to aqueous samples, the leakage of template molecules, and the identification of the best balance between adsorption capacity and selectivity factor. At last, the need for convincing characterization methods, the lack of uniform parameters for defining selectivity, and the merits and demerits of MIPs prepared using nanomaterials are addressed. Strategies are suggested to solve existing problems, and future developments are discussed with respect to a more widespread use in relevant fields.

Graphical abstract

This review gives a comprehensive overview of the advances made in molecularly imprinting of polymers for use in the extraction and quantitation of illicit drugs and additives. Methods for syntheses, highlighted applications, limitations and current challenges are specifically addressed.

Keywords

Illicit drugs Molecular imprinting Polymerization Sports doping Surface imprinting Trace substance 

Notes

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Grant No. 81402899) and Shandong Provincial Natural Science Foundation, China (No. ZR2014HP020).

Compliance with ethical standards

The author(s) declare that they have no competing interests.

Supplementary material

604_2018_2735_MOESM1_ESM.docx (586 kb)
ESM 1 (DOCX 586 kb)

References

  1. 1.
    Mccall AK, Bade R, Kinyua J, Lai FY, Thai PK, Covaci A, Bijlsma L, Van Nuijs AL, Ort C (2016) Critical review on the stability of illicit drugs in sewers and wastewater samples. Water Res 88:933–947CrossRefGoogle Scholar
  2. 2.
    Martel M (2002) Drug diplomacy in the twentieth century: an international history. Review of: McAllister, W.B. Drug diplomacy in the twentieth century: an international history. New York: Routledge, 2000. Histoire sociale. Social history 70:543–5Google Scholar
  3. 3.
    Drugs, Public Policy G (2010) Drug policy and the public good: a summary of the book. Addiction 7:1137–1145CrossRefGoogle Scholar
  4. 4.
    Farr SL, Hutchings YL, Ondersma SJ, Creanga AA (2014) Brief interventions for illicit drug use among peripartum women. Am J Obstet Gynecol 4:336–343CrossRefGoogle Scholar
  5. 5.
    Jones HE, Hickman M, Kasprzyk-Hordern B, Welton NJ, Baker DR, Ades AE (2014) Illicit and pharmaceutical drug consumption estimated via wastewater analysis. Part B: placing back-calculations in a formal statistical framework. Sci Total Environ 487:642–650CrossRefGoogle Scholar
  6. 6.
    El Ansari W, Vallentin-Holbech L, Stock C (2015) Predictors of illicit drug/s use among university students in Northern Ireland, Wales and England. Glob J Health Sci 4:18–29Google Scholar
  7. 7.
    Nieschlag E, Vorona E (2015) Doping with anabolic androgenic steroids (AAS): adverse effects on non-reproductive organs and functions. Rev Endocr Metab Disord 3:199–211CrossRefGoogle Scholar
  8. 8.
    Van Den Broek I, Blokland M, Nessen MA, Sterk S (2015) Current trends in mass spectrometry of peptides and proteins: application to veterinary and sports-doping control. Mass Spectrom Rev 6:571–594CrossRefGoogle Scholar
  9. 9.
    Mosbach K (1994) Molecular imprinting. Trends Biochem Sci 1:9–14CrossRefGoogle Scholar
  10. 10.
    Pauling L (1940) A theory of the structure and process of formation of antibodies. J Am Chem Soc 10:2643–2657CrossRefGoogle Scholar
  11. 11.
    Haupt K (2003) Peer reviewed: molecularly imprinted polymers: the next generation. Anal Chem 17:376 A–383 AGoogle Scholar
  12. 12.
    Wulff G (2013) Fourty years of molecular imprinting in synthetic polymers: origin, features and perspectives. Microchim Acta 15:1359–1370CrossRefGoogle Scholar
  13. 13.
    Yu D, Hu X, Wei S, Wang Q, He C, Liu S (2015) Dummy molecularly imprinted mesoporous silica prepared by hybrid imprinting method for solid-phase extraction of bisphenol A. J Chromatogr A 1396:17–24CrossRefGoogle Scholar
  14. 14.
    Yang J, Li Y, Wang J, Sun X, Cao R, Sun H, Huang C, Chen J (2015) Molecularly imprinted polymer microspheres prepared by Pickering emulsion polymerization for selective solid-phase extraction of eight bisphenols from human urine samples. Anal Chim Acta 872:35–45CrossRefGoogle Scholar
  15. 15.
    Wu X, Liang S, Ge X, Lv Y, Sun H (2015) Synthesis and evaluation of dummy molecularly imprinted microspheres for the specific solid-phase extraction of six anthraquinones from slimming tea. J Sep Sci 8:1263–1270CrossRefGoogle Scholar
  16. 16.
    He J, Song L, Chen S, Li Y, Wei H, Zhao D, Gu K, Zhang S (2015) Novel restricted access materials combined to molecularly imprinted polymers for selective solid-phase extraction of organophosphorus pesticides from honey. Food Chem 187:331–337CrossRefGoogle Scholar
  17. 17.
    Chen W, Xue M, Xue F, Mu X, Xu Z, Meng Z, Zhu G, Shea KJ (2015) Molecularly imprinted hollow spheres for the solid phase extraction of estrogens. Talanta 140:68–72CrossRefGoogle Scholar
  18. 18.
    Wongniramaikul W, Choodum A, Dennany L, Daeid NN (2012) A comprehensive chromatographic comparison of amphetamine and methylamphetamine extracted from river water using molecular imprinted polymers and without the need for sample derivatization. J Sep Sci 23:3332–3339CrossRefGoogle Scholar
  19. 19.
    Shaikh H, Memon N, Khan H, Bhanger MI, Nizamani SM (2012) Preparation and characterization of molecularly imprinted polymer for di(2-ethylhexyl) phthalate: application to sample clean-up prior to gas chromatographic determination. J Chromatogr A 1247:125–133CrossRefGoogle Scholar
  20. 20.
    Nolvachai Y, Kulsing C, Boysen RI, Hearn MTW, Marriott PJ (2014) Miniaturized molecularly imprinted polymer extraction method for the gas chromatographic analysis of flavonoids. J Sep Sci 8:1018–1025CrossRefGoogle Scholar
  21. 21.
    Liu J, Zhang L, Song LLH, Liu Y, Tang H, Li Y (2015) Synthesis of metronidazole-imprinted molecularly imprinted polymers by distillation precipitation polymerization and their use as a solid-phase adsorbent and chromatographic filler. J Sep Sci 7:1172–1178CrossRefGoogle Scholar
  22. 22.
    Lian Z, Wang J (2012) Molecularly imprinted polymer for selective extraction of malachite green from seawater and seafood coupled with high-performance liquid chromatographic determination. Mar Pollut Bull 12:2656–2662CrossRefGoogle Scholar
  23. 23.
    Pacheco JG, Castro M, Machado S, Barroso MF, Nouws HPA, Delerue-Matos C (2015) Molecularly imprinted electrochemical sensor for ochratoxin a detection in food samples. Sensors Actuators B Chem 215:107–112CrossRefGoogle Scholar
  24. 24.
    Li Y, Zhao X, Li P, Huang Y, Wang J, Zhang J (2015) Highly sensitive Fe3O4 nanobeads/graphene-based molecularly imprinted electrochemical sensor for 17 beta-estradiol in water. Anal Chim Acta 884:106–113CrossRefGoogle Scholar
  25. 25.
    Lenain P, De Saeger S, Mattiasson B, Hedstrom M (2015) Affinity sensor based on immobilized molecular imprinted synthetic recognition elements. Biosens Bioelectron 69:34–39CrossRefGoogle Scholar
  26. 26.
    Gholivand MB, Karimian N (2015) Fabrication of a highly selective and sensitive voltammetric ganciclovir sensor based on electropolymerized molecularly imprinted polymer and gold nanoparticles on multiwall carbon nanotubes/glassy carbon electrode. Sensors Actuators B Chem 215:471–479CrossRefGoogle Scholar
  27. 27.
    Foguel MV, Ton X-A, Zanoni MVB, Sotomayor MDPT, Haupt K, Bui BTS (2015) A molecularly imprinted polymer-based evanescent wave fiber optic sensor for the detection of basic red 9 dye. Sensors Actuators B Chem 218:222–228CrossRefGoogle Scholar
  28. 28.
    Da Silva H, Pacheco J, Silva J, Viswanathan S, Delerue-Matos C (2015) Molecularly imprinted sensor for voltammetric detection of norfloxacin. Sensors Actuators B Chem 219:301–307CrossRefGoogle Scholar
  29. 29.
    Caro E, Marce RM, Borrull F, Cormack PG, Sherrington DC (2006) Application of molecularly imprinted polymers to solid-phase extraction of compounds from environmental and biological samples. Trac-Trends in Anal Chemi 2:143–154CrossRefGoogle Scholar
  30. 30.
    Hilt JZ, Byrne ME (2004) Configurational biomimesis in drug delivery: molecular imprinting of biologically significant molecules. Adv Drug Deliv Rev 11:1599–1620CrossRefGoogle Scholar
  31. 31.
    Dramou P, Zuo P, He H, Pham-Huy LA, Zou W, Xiao D, Pham-Huy C (2013) Development of novel amphiphilic magnetic molecularly imprinted polymers compatible with biological fluids for solid phase extraction and physicochemical behavior study. J Chromatogr A 1317:110–120CrossRefGoogle Scholar
  32. 32.
    Meng L, Meng P, Zhang Q, Wang Y (2013) Fast screening of ketamine in biological samples based on molecularly imprinted photonic hydrogels. Anal Chim Acta 771:86–94CrossRefGoogle Scholar
  33. 33.
    Zhang Z, Tan W, Hu Y, Li G (2011) Simultaneous determination of trace sterols in complicated biological samples by gas chromatography-mass spectrometry coupled with extraction using beta-sitosterol magnetic molecularly imprinted polymer beads. J Chromatogr A 28:4275–4283CrossRefGoogle Scholar
  34. 34.
    Zhao M, Chen X, Zhang H, Yan H, Zhang H (2014) Well-defined hydrophilic molecularly imprinted polymer microspheres for efficient molecular recognition in real biological samples by facile RAFT coupling chemistry. Biomacromolecules 5:1663–1675CrossRefGoogle Scholar
  35. 35.
    Baggiani C, Anfossi L, Baravalle P, Giovannoli C, Giraudi G, Barolo C, Viscardi G (2009) Determination of banned Sudan dyes in food samples by molecularly imprinted solid phase extraction-high performance liquid chromatography. J Sep Sci 19:3292–3300CrossRefGoogle Scholar
  36. 36.
    Xu Z, Hu Y, Hu Y, Li G (2010) Investigation of ractopamine molecularly imprinted stir bar sorptive extraction and its application for trace analysis of β 2-agonists in complex samples. J Chromatogr A 22:3612–3618CrossRefGoogle Scholar
  37. 37.
    Hu Y, Li Y, Liu R, Tan W, Li G (2011) Magnetic molecularly imprinted polymer beads prepared by microwave heating for selective enrichment of β-agonists in pork and pig liver samples. Talanta 84 (2):462-470Google Scholar
  38. 38.
    Dai J, Pan J, Xu L, Li X, Zhou Z, Zhang R, Yan Y (2012) Preparation of molecularly imprinted nanoparticles with superparamagnetic susceptibility through atom transfer radical emulsion polymerization for the selective recognition of tetracycline from aqueous medium. J Hazard Mater 1:179–188CrossRefGoogle Scholar
  39. 39.
    Zhan J, Fang G, Yan Z, Pan M, Liu C, Wang S (2013) Preparation of a semicovalent, molecularly surface imprinted polymer for the rapid determination of trace acid orange II in food and environmental samples. Anal Bioanal Chem 19:6353–6363CrossRefGoogle Scholar
  40. 40.
    Hu C, Deng J, Zhao Y, Xia L, Huang K, Ju S, Xiao N (2014) A novel core-shell magnetic nano-sorbent with surface molecularly imprinted polymer coating for the selective solid phase extraction of dimetridazole. Food Chem 5:366–373CrossRefGoogle Scholar
  41. 41.
    Su X, Li X, Li J, Liu M, Lei F, Tan X, Li P, Luo W (2015) Synthesis and characterization of core-shell magnetic molecularly imprinted polymers for solid-phase extraction and determination of Rhodamine B in food. Food Chem 171:292–297.  https://doi.org/10.1016/j.foodchem.2014.09.024
  42. 42.
    Han Q, Xin S, Zhu W, Zhu C, Zhou X, Jiang H (2016) Magnetic sensing film based on Fe 3 O 4 @Au-GSH molecularly imprinted polymers for the electrochemical detection of estradiol. Biosens Bioelectron 79:180–186CrossRefGoogle Scholar
  43. 43.
    Wu L, Lin Z, Zhong HP, Chen XM , Huang ZY (2017) Rapid determination of malachite green in water and fish using a fluorescent probe based on CdTe quantum dots coated with molecularly imprinted polymer. Sensors and Actuators B: Chemical 239:69-75Google Scholar
  44. 44.
    Qiu L, Liu W, Huang M, Zhang L (2010) Preparation and application of solid-phase microextraction fiber based on molecularly imprinted polymer for determination of anabolic steroids in complicated samples. J Chromatogr A 48:7461CrossRefGoogle Scholar
  45. 45.
    Fang G , Lu J, Pan M, Li W, Ren L, Wang S (2011) Substitution of Antibody with Molecularly Imprinted Film in Enzyme-Linked Immunosorbent Assay for Determination of Trace Ractopamine in Urine and Pork Samples. Food Analytical Methods 4 (4):590-597Google Scholar
  46. 46.
    Deng DL, Zhang JY, Chen C, Hou XL, Su YY, Wu L (2012) Monolithic molecular imprinted polymer fiber for recognition and solid phase microextraction of ephedrine and pseudoephedrine in biological samples prior to capillary electrophoresis analysis. J Chromatogr A 2:195CrossRefGoogle Scholar
  47. 47.
    Zhong Q, Hu Y, Li G (2013) A novel protocol for molecularly imprinted polymer filaments online coupled to GC-MS for the determination of androgenic steroids in urine. J Sep Sci 24:3903CrossRefGoogle Scholar
  48. 48.
    Zhang Q, Jing L, Zhang J, Ren Y, Wang Y, Wang Y, Wei T, Liedberg B (2014) Surface plasmon resonance sensor for femtomolar detection of testosterone with water-compatible macroporous molecularly imprinted film. Anal Biochem 1:7–14CrossRefGoogle Scholar
  49. 49.
    Tan Y, Jing L, Ding Y, Wei T (2015) A novel double-layer molecularly imprinted polymer film based surface plasmon resonance for determination of testosterone in aqueous media. Applied Surface Science 342:84-91Google Scholar
  50. 50.
    Ray JV, Mirata F, Pérollier C, Arotcarena M, Bayoudh S, Resmini M (2016) Smart coumarin-tagged imprinted polymers for the rapid detection of tamoxifen. Anal Bioanal Chem 7:1855–1861CrossRefGoogle Scholar
  51. 51.
    Gong CB, Wei YB, Liu LT, Zheng AX, Yang YH, Chow CF, Tang Q (2017) Photoresponsive hollow molecularly imprinted polymer for trace triamterene in biological samples. Materials Science & Engineering C 76:568–578Google Scholar
  52. 52.
    Lin CI, Joseph AK, Chang CK, Wang YC, Yu DL (2003) Synthesis of molecular imprinted organic–inorganic hybrid polymer binding caffeine. Anal Chim Acta 2:175–180CrossRefGoogle Scholar
  53. 53.
    Ho KC, Yeh WM, Tung TS, Liao JY (2005) Amperometric detection of morphine based on poly(3,4-ethylenedioxythiophene) immobilized molecularly imprinted polymer particles prepared by precipitation polymerization. Anal Chim Acta 1:90–96CrossRefGoogle Scholar
  54. 54.
    Madrakian T, Afkhami A, Mahmood-Kashani H, Ahmadi M (2013) Superparamagnetic surface molecularly imprinted nanoparticles for sensitive solid-phase extraction of tramadol from urine samples. Talanta 4:255CrossRefGoogle Scholar
  55. 55.
    Rezaei B, Foroughi-Dehnavi S, Ensafi AA (2015) Fabrication of electrochemical sensor based on molecularly imprinted polymer and nanoparticles for determination trace amounts of morphine. Ionics 10:1–12Google Scholar
  56. 56.
    Chantada-Vázquez MP, Sánchez-González J, Peña-Vázquez E, Tabernero MJ, Bermejo AM, Bermejo-Barrera P, Moreda-Piñeiro A (2016) Synthesis and characterization of novel molecularly imprinted polymer – coated Mn-doped ZnS quantum dots for specific fluorescent recognition of cocaine. Biosens. Bioelectron Supplement C:213–221CrossRefGoogle Scholar
  57. 57.
    Rodríguez J, Castañeda G, Contento AM, Muñoz L (2012) Direct and fast determination of paclitaxel, morphine and codeine in urine by micellar electrokinetic chromatography. J Chromatogr A 30:66–72CrossRefGoogle Scholar
  58. 58.
    Chericoni S, Stefanelli F, Iannella V, Giusiani M (2014) Simultaneous determination of morphine, codeine and 6-acetyl morphine in human urine and blood samples using direct aqueous derivatisation: validation and application to real cases. J Chromatogr B 4:127–132CrossRefGoogle Scholar
  59. 59.
    Deiminiat B, Rounaghi GH, Arbab-Zavar MH (2017) Development of a new electrochemical imprinted sensor based on poly-pyrrole, sol–gel and multiwall carbon nanotubes for determination of tramadol. Sensors and Actuators B: Chemical 238:651-659Google Scholar
  60. 60.
    Blomgren A, Berggren C, Holmberg A, Larsson F, Sellergren B, Ensing K (2002) Extraction of clenbuterol from calf urine using a molecularly imprinted polymer followed by quantitation by high-performance liquid chromatography with UV detection. J Chromatogr A 1:157–164CrossRefGoogle Scholar
  61. 61.
    Harun N, Anderson RA, Cormack PA (2010) Analysis of ketamine and norketamine in hair samples using molecularly imprinted solid-phase extraction (MISPE) and liquid chromatography–tandem mass spectrometry (LC-MS/MS). Anal Bioanal Chem 7:2449CrossRefGoogle Scholar
  62. 62.
    Sorribes-Soriano A, Esteve-Turrillas FA, Armenta S, De LGM, Herrero-Martínez JM (2017) Cocaine abuse determination by ion mobility spectrometry using molecular imprinting. J Chromatogr A 1481:23–30Google Scholar
  63. 63.
    Zhai H, Huang L, Chen Z, Su Z, Yuan K, Liang G, Pan Y (2017) Chip-based molecularly imprinted monolithic capillary array columns coated GO/SiO2 for selective extraction and sensitive determination of rhodamine B in chili powder. Food Chem 214:664–669CrossRefGoogle Scholar
  64. 64.
    Yuan K, Wang J, Zhai H, Chen Z, Huang L, Su Z (2015) Sensitive determination of rose bengal in brown sugar by a molecularly imprinted solid-phase extraction monolithic capillary column coupled with capillary electrophoresis. Anal Methods 19:8297–8303CrossRefGoogle Scholar
  65. 65.
    Lin Z, Wang D, Zhang H, Li L, Huang Z, Shen J, Lin Y (2016) Extraction and determination of malachite green from aquatic products based on molecularly imprinted polymers. Separation Science & Technology 10:1684–1689Google Scholar
  66. 66.
    Du T, Cheng J, Wu M, Wang X, Zhou H, Cheng M (2014) An in situ immobilized pipette tip solid phase microextraction method based on molecularly imprinted polymer monolith for the selective determination of difenoconazole in tap water and grape juice. J Chromatogr B Analyt Technol Biomed Life Sci 1:104–109CrossRefGoogle Scholar
  67. 67.
    Wang P, Liu X, Su X, Zhu R (2015) Sensitive detection of β-agonists in pork tissue with novel molecularly imprinted polymer extraction followed liquid chromatography coupled tandem mass spectrometry detection. Food Chem 184:72–79CrossRefGoogle Scholar
  68. 68.
    Lian ZR, Wang JT (2013) Study of molecularly imprinted solid-phase extraction of gonyautoxins 2,3 in the cultured dinoflagellate Alexandrium tamarense by high-performance liquid chromatography with fluorescence detection. Environ Pollut 182:385–391CrossRefGoogle Scholar
  69. 69.
    Zhang Z, Cheng Z, Zhang CF, Wang H, Li J (2011) Precipitation polymerization of molecularly imprinted polymers for recognition of melamine molecule. J Appl Polym Sci 2:962–967Google Scholar
  70. 70.
    Yan H, Liu S, Gao M, Sun N (2013) Ionic liquids modified dummy molecularly imprinted microspheres as solid phase extraction materials for the determination of clenbuterol and clorprenaline in urine. J Chromatogr A 11:10–16CrossRefGoogle Scholar
  71. 71.
    Li L, Lin ZZ, Chen XM, Zhang HY, Lin YD, Lai ZZ, Huang ZY (2015) Molecularly imprinted polymers for extraction of malachite green from fish samples prior to its determination by HPLC. Microchim Acta 9–10:1791–1796CrossRefGoogle Scholar
  72. 72.
    Wei F, Xu G, Wu Y, Wang X, Yang J, Liu L, Zhou P, Hu Q (2016) Molecularly imprinted polymers on dual-color quantum dots for simultaneous detection of norepinephrine and epinephrine. Sensors Actuators B Chem 229:38–46CrossRefGoogle Scholar
  73. 73.
    Guan G, Zhang Z, Wang Z, Liu B, Gao D, Xie C (2007) Single-hole hollow polymer microspheres toward specific high-capacity uptake of target species. Adv Mater 17:2370CrossRefGoogle Scholar
  74. 74.
    Zhao Q, Li H, Xu Y, Zhang F, Zhao J, Wang L, Hou J, Ding H, Li Y, Jin H, Ding L (2015) Determination triazine pesticides in cereal samples based on single-hole hollow molecularly imprinted microspheres. J Chromatogr A 1376:26–34CrossRefGoogle Scholar
  75. 75.
    Ren D, He J, Zhang H (2014) Synthesis, characterization and evaluation of hollow molecularly imprinted polymers for Sudan I. Anal Methods 9:3079CrossRefGoogle Scholar
  76. 76.
    Zhao M, Zhang C, Zhang Y, Guo X, Yan H, Zhang H (2014) Efficient synthesis of narrowly dispersed hydrophilic and magnetic molecularly imprinted polymer microspheres with excellent molecular recognition ability in a real biological sample. Chem Commun 17:2208–2210CrossRefGoogle Scholar
  77. 77.
    Ma Y, Zhang Y, Zhao M, Guo X, Zhang H (2012) Efficient synthesis of narrowly dispersed molecularly imprinted polymer microspheres with multiple stimuli-responsive template binding properties in aqueous media. Chem Commun 50:6217–6219CrossRefGoogle Scholar
  78. 78.
    Ma Y, Pan G, Zhang Y, Guo X, Zhang H (2013) Narrowly dispersed hydrophilic molecularly imprinted polymer nanoparticles for efficient molecular recognition in real aqueous samples Including River water, milk, and bovine serum. Angew Chem Int Ed 5:1511–1514CrossRefGoogle Scholar
  79. 79.
    Jin Y, Jiang M, Shi Y, Lin Y, Peng Y, Dai K, Lu B (2008) Narrowly dispersed molecularly imprinted microspheres prepared by a modified precipitation polymerization method. Anal Chim Acta 1:105–113CrossRefGoogle Scholar
  80. 80.
    Liu Y, Huang Y, Liu J, Wang W, Liu G, Zhao R (2012) Superparamagnetic surface molecularly imprinted nanoparticles for water-soluble pefloxacin mesylate prepared via surface initiated atom transfer radical polymerization and its application in egg sample analysis. J Chromatogr A 13:15–21CrossRefGoogle Scholar
  81. 81.
    Tao J, Gao XD, Peng W, Yan W, Lin YF, Hu XZ, Hao QL, Zhou YK, Mei SR (2009) Determination of trace tetracycline antibiotics in foodstuffs by liquid chromatography-tandem mass spectrometry coupled with selective molecular-imprinted solid-phase extraction. Anal Bioanal Chem 8:2009–2018Google Scholar
  82. 82.
    Long C, Mai Z, Yang Y, Zhu B, Xu X, Lu L, Zou X (2009) Determination of multi-residue for malachite green, gentian violet and their metabolites in aquatic products by high-performance liquid chromatography coupled with molecularly imprinted solid-phase extraction. J Chromatogr A 12:2275–2281CrossRefGoogle Scholar
  83. 83.
    Luo X, Li C, Duan Y, Zhang H, Zhang D, Zhang C, Sun G, Sun X (2015) Molecularly imprinted polymer prepared by Pickering emulsion polymerization for removal of acephate residues from contaminated waters. J Appl Polym Sci 133:15Google Scholar
  84. 84.
    Chen H, Son S, Zhang F, Yan J, Li Y, Ding H, Ding L (2015) Rapid preparation of molecularly imprinted polymers by microwave-assisted emulsion polymerization for the extraction of florfenicol in milk. J Chromatogr B 1:32–38CrossRefGoogle Scholar
  85. 85.
    Qiao F, Du J (2013) Rapid screening of clenbuterol hydrochloride in chicken samples by molecularly imprinted matrix solid-phase dispersion coupled with liquid chromatography. J Chromatogr B 3:136CrossRefGoogle Scholar
  86. 86.
    Xu ZX, Fang GZ, Wang S (2010) Molecularly imprinted solid phase extraction coupled to high-performance liquid chromatography for determination of trace dichlorvos residues in vegetables. Food Chem 2:845–850CrossRefGoogle Scholar
  87. 87.
    Sun XL, He XW, Zhang YK, Chen LX (2009) Determination of tetracyclines in food samples by molecularly imprinted monolithic column coupling with high performance liquid chromatography. Talanta 3:926–934CrossRefGoogle Scholar
  88. 88.
    Sun X, He J, Cai G, Lin A, Zheng W, Liu X, Chen L, He X, Zhang Y (2010) Room temperature ionic liquid-mediated molecularly imprinted polymer monolith for the selective recognition of quinolones in pork samples. J Sep Sci 23–24:3786CrossRefGoogle Scholar
  89. 89.
    Hu X, Cai Q, Fan Y, Ye T, Cao Y, Guo C (2012) Molecularly imprinted polymer coated solid-phase microextraction fibers for determination of Sudan I-IV dyes in hot chili powder and poultry feed samples. J Chromatogr A 1:39–46CrossRefGoogle Scholar
  90. 90.
    Tan L, He R, Chen K, Peng R, Huang C, Yang R, Tang Y (2016) Ultra-high performance liquid chromatography combined with mass spectrometry for determination of aflatoxins using dummy molecularly imprinted polymers deposited on silica-coated magnetic nanoparticles. Microchim Acta 4:1469–1477CrossRefGoogle Scholar
  91. 91.
    Wang P, Su X, Shi L, Yuan Y (2016) An aptamer based assay for the β-adrenergic agonist ractopamine based on aggregation of gold nanoparticles in combination with a molecularly imprinted polymer. Microchim Acta 11:2899–2905CrossRefGoogle Scholar
  92. 92.
    Claude B, Morin P, Bayoudh S, De CJ (2008) Interest of molecularly imprinted polymers in the fight against doping. Extraction of tamoxifen and its main metabolite from urine followed by high-performance liquid chromatography with UV detection. J Chromatogr A 1196-1197:81–88CrossRefGoogle Scholar
  93. 93.
    Wang XH, Xie LF, Dong Q, Liu HL, Huang YP, Liu ZS (2015) Synthesis of monodisperse molecularly imprinted microspheres with multi-recognition ability via precipitation polymerization for the selective extraction of cyromazine, melamine, triamterene and trimethoprim. J Chromatogr B Analyt Technol Biomed Life Sci 1007:127–131CrossRefGoogle Scholar
  94. 94.
    Ambrosini S, Shinde S, De LE, Sellergren B (2012) Glucuronide directed molecularly imprinted solid-phase extraction: isolation of testosterone glucuronide from its parent drug in urine. Analyst 1:249–254CrossRefGoogle Scholar
  95. 95.
    Gurtova O, Ye L, Chmilenko F (2013) Potentiometric propranolol-selective sensor based on molecularly imprinted polymer. Anal Bioanal Chem 1:287CrossRefGoogle Scholar
  96. 96.
    Da Silva ATM, De Oliveira HL, Silva CF, Fonseca MC, Pereira TFD, Nascimento CS, De Figueiredo EC, Borges KB (2017) Efficient molecularly imprinted polymer as a pipette-tip solid-phase sorbent for determination of carvedilol enantiomers in human urine. J Chromatogr B 1061-1062:399–410CrossRefGoogle Scholar
  97. 97.
    Tse SBB, Haupt K (2011) Preparation and evaluation of a molecularly imprinted polymer for the selective recognition of testosterone--application to molecularly imprinted sorbent assays. J Mol Recognit Jmr 6:1123Google Scholar
  98. 98.
    Ahmadi F, Rezaei H, Tahvilian R (2012) Computational-aided design of molecularly imprinted polymer for selective extraction of methadone from plasma and saliva and determination by gas chromatography. J Chromatogr A 24:9–19CrossRefGoogle Scholar
  99. 99.
    Turson M, Zhuang XL, Liu HN, Jiang P, Dong XC (2009) Evaluation of the clenbuterol imprinted monolithic column prepared by reversible addition-fragmentation chain transfer polymerization. Chin Chem Lett 9:1136–1140CrossRefGoogle Scholar
  100. 100.
    Tehrani MS, Vardini MT, Azar PA, Husain SW (2010) Molecularly imprinted polymer based PVC-membrane-coated graphite electrode for the determination of metoprolol. J Iran Chem Soc 3:759–769CrossRefGoogle Scholar
  101. 101.
    Khodadadian M, Ahmadi F (2010) Computer-assisted design and synthesis of molecularly imprinted polymers for selective extraction of acetazolamide from human plasma prior to its voltammetric determination. Talanta 4–5:1446CrossRefGoogle Scholar
  102. 102.
    Nezhadali A, Mojarrab M (2014) Computational study and multivariate optimization of hydrochlorothiazide analysis using molecularly imprinted polymer electrochemical sensor based on carbon nanotube/polypyrrole film. Sensors Actuators B Chem 1:829–837CrossRefGoogle Scholar
  103. 103.
    Djozan D, Farajzadeh MA, Sorouraddin SM, Baheri T (2012) Molecularly imprinted-solid phase extraction combined with simultaneous derivatization and dispersive liquid–liquid microextraction for selective extraction and preconcentration of methamphetamine and ecstasy from urine samples followed by gas chromatogr. J Chromatogr A 14:24–31CrossRefGoogle Scholar
  104. 104.
    Meng L, Meng P, Zhang Q, Wang Y (2013) Fast screening of ketamine in biological samples based on molecularly imprinted photonic hydrogels. Anal Chim Acta 7:86–94CrossRefGoogle Scholar
  105. 105.
    Thibert V, Legeay P, Chapuishugon F, Pichon V (2012) Synthesis and characterization of molecularly imprinted polymers for the selective extraction of cocaine and its metabolite benzoylecgonine from hair extract before LC-MS analysis. Talanta 1:412–419CrossRefGoogle Scholar
  106. 106.
    Ganjavi F, Ansari M, Kazemipour M, Zeidabadinejad L (2017) Computer-aided design and synthesis of a highly selective molecularly imprinted polymer for the extraction and determination of buprenorphine in biological fluids. J Sep Sci 15:3175–3182Google Scholar
  107. 107.
    Atlabachew M, Torto N, Chandravanshi BS, Rediabshiro M, Chigome S, Mothibedi K, Combrinck S (2016) A (−) norephedrine-based molecularly imprinted polymer for the solid-phase extraction of psychoactive phenylpropylamino alkaloids from Khat (Catha edulis Vahl. Endl.) chewing leaves. Biomed Chromatogr 7:1007–1015CrossRefGoogle Scholar
  108. 108.
    Lendoiro E, De CA, Fernández-Vega H, Cela-Pérez MC, López-Vilariño JM, González-Rodríguez MV, Cruz A, López-Rivadulla M (2014) Molecularly imprinted polymer for selective determination of Δ9-tetrahydrocannabinol and 11-nor-Δ9-tetrahydrocannabinol carboxylic acid using LC-MS/MS in urine and oral fluid. Anal Bioanal Chem 15:3589–3597Google Scholar
  109. 109.
    Nestić M, Babić S, Pavlović DM, Sutlović D (2013) Molecularly imprinted solid phase extraction for simultaneous determination of Δ9-tetrahydrocannabinol and its main metabolites by gas chromatography-mass spectrometry in urine samples. Forensic Sci Int 1–3:317CrossRefGoogle Scholar
  110. 110.
    Djozan D (2007) Preparation and evaluation of solid-phase microextraction fibers based on monolithic molecularly imprinted polymers for selective extraction of diacetylmorphine and analogous compounds. J Chromatogr A 1–2:16–23CrossRefGoogle Scholar
  111. 111.
    Javanbakht M, Attaran AM (2010) Solid-phase extraction of tramadol from plasma and urine samples using a novel water-compatible molecularly imprinted polymer. J Chromatogr B Analyt Technol Biomed Life Sci 20:1700CrossRefGoogle Scholar
  112. 112.
    Javanbakht M, Moein MM, Akbariadergani B (2012) On-line clean-up and determination of tramadol in human plasma and urine samples using molecularly imprinted monolithic column coupling with HPLC. J Chromatogr B 23:49–54CrossRefGoogle Scholar
  113. 113.
    Azodi-Deilami S, Abdouss M, Hasani SA (2010) Preparation and utilization of a molecularly imprinted polymer for solid phase extraction of tramadol. Cent Eur J Chem 4:861–869Google Scholar
  114. 114.
    Zhang H, Liu G, Chai C (2012) A novel amperometric sensor based on screen-printed electrode modified with multi-walled carbon nanotubes and molecularly imprinted membrane for rapid determination of ractopamine in pig urine. Chin J Anal Chem 2:103–110Google Scholar
  115. 115.
    Li X, Li M, Li J, Lei F, Su X, Liu M, Li P, Tan X (2014) Synthesis and characterization of molecularly imprinted polymers with modified rosin as a cross-linker and selective SPE-HPLC detection of basic orange II in foods. Anal Methods 16:6397–6406CrossRefGoogle Scholar
  116. 116.
    Tse SBB, Merlier F, Haupt K (2010) Toward the use of a molecularly imprinted polymer in doping analysis: selective preconcentration and analysis of testosterone and epitestosterone in human urine. Anal Chem 11:4420–4427Google Scholar
  117. 117.
    Morante-Zarcero S, Sierra I (2012) Simultaneous enantiomeric determination of propranolol, metoprolol, pindolol, and atenolol in natural waters by HPLC on new polysaccharide-based stationary phase using a highly selective molecularly imprinted polymer extraction. Chirality 10:860–866CrossRefGoogle Scholar
  118. 118.
    Dulaurent S, Balkhi SE, Poncelet L, Gaulier JM, Marquet P, Saint-Marcoux F (2016) QuEChERS sample preparation prior to LC-MS/MS determination of opiates, amphetamines, and cocaine metabolites in whole blood. Anal Bioanal Chem 5:1467–1474CrossRefGoogle Scholar
  119. 119.
    Nie J, Zhang DW, Tie C, Zhou YL, Zhang XX (2013) A label-free DNA hairpin biosensor for colorimetric detection of target with suitable functional DNA partners. Biosens Bioelectron 49C:236–242CrossRefGoogle Scholar
  120. 120.
    Johansen SS, Bhatia HM (2007) Quantitative analysis of cocaine and its metabolites in whole blood and urine by high-performance liquid chromatography coupled with tandem mass spectrometry. J Chromatogr B 1–2:338–344CrossRefGoogle Scholar
  121. 121.
    Berg T, Lundanes E, Christophersen AS, Strand DH (2009) Determination of opiates and cocaine in urine by high pH mobile phase reversed phase UPLC-MS/MS. J Chromatogr B 4:421–432CrossRefGoogle Scholar
  122. 122.
    Hua M, Tao M, Wang P, Zhang Y, Wu Z, Chang Y, Yang Y (2010) Label-free electrochemical cocaine aptasensor based on a target-inducing aptamer switching conformation. Analytical Sciences the International Journal of the Japan Society for Analytical Chemistry 12:1265CrossRefGoogle Scholar
  123. 123.
    Fernández P, Morales L, Vázquez C, Bermejo AM, Tabernero MJ (2006) HPLC-DAD determination of opioids, cocaine and their metabolites in plasma. Forensic Sci Int 1:31CrossRefGoogle Scholar
  124. 124.
    Lachenmeier K, Musshoff F, Madea B (2006) Determination of opiates and cocaine in hair using automated enzyme immunoassay screening methodologies followed by gas chromatographic–mass spectrometric (GC–MS) confirmation. Forensic Science International 2:189–199Google Scholar
  125. 125.
    Qiu L, Zhou H, Zhu W, Qiu L, Jiang J, Shen G, Yu R (2013) A novel label-free fluorescence aptamer-based sensor method for cocaine detection based on isothermal circular strand-displacement amplification and graphene oxide absorption. New J Chem 12:3998–4003CrossRefGoogle Scholar
  126. 126.
    Sánchez-González J, Tabernero MJ, Bermejo AM, Bermejo-Barrera P, Moreda-Piñeiro A (2015) Porous membrane-protected molecularly imprinted polymer micro-solid-phase extraction for analysis of urinary cocaine and its metabolites using liquid chromatography - tandem mass spectrometry. Anal Chim Acta 898:50–59CrossRefGoogle Scholar
  127. 127.
    Ma C, Wang W, Yang Q, Shi C, Cao L (2011) Cocaine detection via rolling circle amplification of short DNA strand separated by magnetic beads. Biosens Bioelectron 7:3309–3312CrossRefGoogle Scholar
  128. 128.
    Hilton JP, Nguyen TH, Pei R, Stojanovic M, Lin Q (2011) A microfluidic affinity sensor for the detection of cocaine. Sensors Actuators A Phys 2:241–246CrossRefGoogle Scholar
  129. 129.
    Taghdisi SM, Danesh NM, Emrani AS, Ramezani M, Abnous K (2015) A novel electrochemical aptasensor based on single-walled carbon nanotubes, gold electrode and complimentary strand of aptamer for ultrasensitive detection of cocaine. Biosens Bioelectron 73:245–250CrossRefGoogle Scholar
  130. 130.
    Emrani AS, Danesh NM, Ramezani M, Taghdisi SM, Abnous K (2016) A novel fluorescent aptasensor based on hairpin structure of complementary strand of aptamer and nanoparticles as a signal amplification approach for ultrasensitive detection of cocaine. Biosens Bioelectron 79:288–293CrossRefGoogle Scholar
  131. 131.
    Li Y, Ji X, Liu B (2011) Chemiluminescence aptasensor for cocaine based on double-functionalized gold nanoprobes and functionalized magnetic microbeads. Anal Bioanal Chem 1:213CrossRefGoogle Scholar
  132. 132.
    Tagliaro F, Antonioli C, De BZ, Ghielmi S, Marigo M (1994) Reversed-phase high-performance liquid chromatographic determination of cocaine in plasma and human hair with direct fluorimetric detection. J Chromatogr A 1–2:207–215CrossRefGoogle Scholar
  133. 133.
    Alizadeh T, Ganjali MR, Zare M, Norouzi P (2010) Development of a voltammetric sensor based on a molecularly imprinted polymer (MIP) for caffeine measurement. Electrochim Acta 5:1568–1574CrossRefGoogle Scholar
  134. 134.
    Djozan D, Farajzadeh MA, Sorouraddin SM, Baheri T (2011) Synthesis and application of high selective monolithic fibers based on molecularly imprinted polymer for SPME of trace methamphetamine. Chromatographia 9:975–983CrossRefGoogle Scholar
  135. 135.
    Liu LK, Yang WM, Wan-Zhen XU, Zhou ZP, Liu H, Yan YS (2014) Molecular simulation assisted design and preparation of magnetic molecularly imprinted polymers and their characteristics. Chin J Anal Chem 2:249–257CrossRefGoogle Scholar
  136. 136.
    Lin LQ, Li YC, Fu Q, He LC, Zhang J, Zhang QQ (2006) Preparation of molecularly imprinted polymer for sinomenine and study on its molecular recognition mechanism. Polymer 11:3792–3798CrossRefGoogle Scholar
  137. 137.
    Pace SJ, Nguyen E, Baria MP, Mojica E-RE (2015) Use of computational modeling in preparation and evaluation of surface imprinted xerogels for binding tetracycline. Microchim Acta 1:69–76CrossRefGoogle Scholar
  138. 138.
    Ahmadi F, Karamian E (2014) Computational aided-molecular imprinted polymer Design for Solid Phase Extraction of Metaproterenol from plasma and determination by voltammetry using modified carbon nanotube electrode. Iran J Pharm Res Ijpr 2:417Google Scholar
  139. 139.
    Xu J, Zhang Y, Wu K, Zhang L, Ge S, Yu J (2017) A molecularly imprinted polypyrrole for ultrasensitive voltammetric determination of glyphosate. Microchim Acta 7:1959–1967CrossRefGoogle Scholar
  140. 140.
    Wen Y, Liao X, Deng C, Liu G, Yan Q, Li L, Wang X (2017) Imprinted voltammetric streptomycin sensor based on a glassy carbon electrode modified with electropolymerized poly(pyrrole-3-carboxy acid) and electrochemically reduced graphene oxide. Microchim Acta 3:935–941CrossRefGoogle Scholar
  141. 141.
    Rachkov A, Minoura N (2001) Towards molecularly imprinted polymers selective to peptides and proteins. The epitope approach. Biochim Biophys Acta 1–2:255–266CrossRefGoogle Scholar
  142. 142.
    Wang S, Li Y, Ding M, Wu X, Xu J, Wang R, Wen T, Huang W, Zhou P, Ma K (2011) Self-assembly molecularly imprinted polymers of 17β-estradiol on the surface of magnetic nanoparticles for selective separation and detection of estrogenic hormones in feeds. J Chromatogr B Analyt Technol Biomed Life Sci 25:2595–2600CrossRefGoogle Scholar
  143. 143.
    Qiao L, Gan N, Hu F, Wang D, Lan H, Li T, Wang H (2014) Magnetic nanospheres with a molecularly imprinted shell for the preconcentration of diethylstilbestrol. Microchim Acta 11:1341–1351CrossRefGoogle Scholar
  144. 144.
    Hou J, Li H, Wang L, Zhang P, Zhou T, Ding H, Ding L (2016) Rapid microwave-assisted synthesis of molecularly imprinted polymers on carbon quantum dots for fluorescent sensing of tetracycline in milk. Talanta 146:34–40CrossRefGoogle Scholar
  145. 145.
    Zhang Z, Li J, Song X, Ma J, Chen L (2014) Hg2+ ion-imprinted polymers sorbents based on dithizone-Hg2+ chelation for mercury speciation analysis in environmental and biological samples. RSC Adv 87:46444–46453CrossRefGoogle Scholar
  146. 146.
    He C, Liu F, Li K, Liu H (2006) Molecularly imprinted polymer film grafted from porous silica for selective recognition of testosterone. Anal Lett 2:275–286CrossRefGoogle Scholar
  147. 147.
    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 9–10:1501–1508CrossRefGoogle Scholar
  148. 148.
    Xu S, Chen L, Li J, Qin W, Ma J (2011) Preparation of hollow porous molecularly imprinted polymers and their applications to solid-phase extraction of triazines in soil samples. J Mater Chem 32:12047–12053CrossRefGoogle Scholar
  149. 149.
    Zhang Y, Li Y, Hu Y, Li G, Chen Y (2010) Preparation of magnetic indole-3-acetic acid imprinted polymer beads with 4-vinylpyridine and β-cyclodextrin as binary monomer via microwave heating initiated polymerization and their application to trace analysis of auxins in plant tissues. J Chromatogr A 47:7337–7344CrossRefGoogle Scholar
  150. 150.
    Zhang W, Qin L, He XW, Li WY, Zhang YK (2009) Novel surface modified molecularly imprinted polymer using acryloyl-beta-cyclodextrin and acrylamide as monomers for selective recognition of lysozyme in aqueous solution. J Chromatogr A 21:4560–4567CrossRefGoogle Scholar
  151. 151.
    Yan H, Cheng X, Sun N (2013) Synthesis of multi-core-shell magnetic molecularly imprinted microspheres for rapid recognition of dicofol in tea. J Agric Food Chem 11:2896–2901CrossRefGoogle Scholar
  152. 152.
    Long Z, Xu W, Yi L, Qiu H (2016) Nanosilica-based molecularly imprinted polymer nanoshell for specific recognition and determination of rhodamine B in red wine and beverages. J Chromatogr B 1029–1030:230–238Google Scholar
  153. 153.
    Long Z, Xu W, Peng Y, Lu Y, Luo Q, Qiu H (2016) Highly selective coextraction of rhodamine B and dibenzyl phthalate based on high-density dual-template imprinted shells on silica microparticles. J Sep Sci 2:506–513Google Scholar
  154. 154.
    Li YH, Yang T, Qi XL, Qiao YW, Deng AP (2008) Development of a group selective molecularly imprinted polymers based solid phase extraction of malachite green from fish water and fish feed samples. Anal Chim Acta 2:317–325CrossRefGoogle Scholar

Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of Analytical ChemistryChina Pharmaceutical UniversityNanjingChina
  2. 2.Key Laboratory of Biomedical Functional MaterialsChina Pharmaceutical UniversityNanjingChina
  3. 3.School of Pharmaceutical SciencesTaishan Medical UniversityTai’anPeople’s Republic of China

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