https://dx.doi.org/10.4322/sc.2012.012
Molecularly imprinted polymers in sample preparation for organic compounds analysis: applications and trends
Santos, Mariane Gonçalves; Abrão, Lailah Cristina de Carvalho; Freitas, Lissara Aparecida de S.; Moraes, Gabriel De Oliveira Isac; Lima, Marcela Marília de; Figueiredo, Eduardo Costa
Palavras-chave: Molecularly imprinted polymers, MIP, sample preparation.
Resumo: Molecularly imprinted polymers are synthetic materials with molecular recognition ability. These materials are obtained by polymerization reactions that fix the functional monomers around the template molecule according with the binding groups and the stereochemistry of both molecules. The MIPs have been extensively used in several applications with emphasis for sample preparation procedures as solid phase extraction, solid phase microextraction, extraction by magnetic sorbents, microextraction by packed sorbent among others. So, the objective of this review is to present the novelty in MIP use for organic compounds extraction and point out the advantages of each application, as well as what is most promising in the evolution and improvement of each technique.
Referências Bibliográficas
1. Majores RE. An overview of sample preparation. LC-GC 1991; 9:16-20.
2. Smith RM. Before the injection - modern methods of sample preparation for separation techniques. Journal of Chromatography A 2003; 1000:3-27. https://dx.doi. org/10.1016/S0021-9673(03)00511-9
3. Kataoka H. New trends in sample preparation for clinical and pharmaceutical analysis. Trends in Analytical Chemistry 2003; 22:232-244. https://dx.doi. org/10.1016/S0165-9936(03)00402-3
4. Queiroz SCN, Collins CH, Jardim ICS. Métodos de extração e/ou concentração de compostos encontrados em fluidos biológicos para posterior determinação cromatográfica. Química Nova 2001; 24:68-76.
5. Papp R, Mullett WM, Kwong E. A method for the direct analysis of drug compounds in plasma using a single restricted access material (RAM) column. Journal of Pharmaceutical and Biomedical Analysis 2004.; 36:457-464. PMid:15522518. https://dx.doi. org/10.1016/j.jpba.2004.07.029
6. Anderson JA. High performance liquid chromatography (direct injection techniques). Clinical Chemistry 1993; 65: 434-443.
7. Pawliszyn J. Unified theory of extraction. In: Pawliszyn J, editor. Sampling and sample preparation for field and laboratory. Elsevier; 2002. p. 353.
8. Ramos L, Smith RM. Preface. Journal of Chromatography A 2007; 1152:1. https://dx.doi. org/10.1016/j.chroma.2007.03.041
9. Ramos L, Smith RM. Preface. Journal of Chromatography A 2007; 1153:1. https://dx.doi. org/10.1016/j.chroma.2007.03.041
10. Pedersen-Bjergaard S, Rasmussen KE. New sample preparation technologies. Analytical and Bioanalytical Chemistry 2009; 393:779 https://dx.doi.org/10.1007/ s00216-008-2493-y
11. Beltran A, Borrull F, Cormack PAG, Marce RM. Molecularly-imprinted polymers: useful sorbents for selective extractions. Trends in Analytical Chemistry 2010.; 29:1363-1375. https://dx.doi.org/10.1016/j. trac.2010.07.020
12. Polyakov MW. Adsorption properties and structure of silica gel. Russian Journal of Physical Chemistry 1931; 2.: 799-804.
13. Dickey FH.The Preparation of Specific Adsorbents. Proceedings of the National Academy of Sciences of the United States of America 1949; 35:227-229. https:// dx.doi.org/10.1073/pnas.35.5.227
14. Dickey FH. Specific Adsorption. The Journal of Physical Chemistry 1955; 59:695-707. https://dx.doi. org/10.1021/j150530a006
15. Wulff G, Sarhan A. Über die Anwendung von enzymanalog gebauten Polymeren zur Racemattrennung. Angewandte Chemie 1972; 84:341. https://dx.doi.org/10.1002/ange.19720840838
16. Arshady R, Mosbach K. Synthesis of substrateselective polymers by host-guest polymerization. Macromolecular Chemistry and Physics 1981; 182:687- 692.. https://dx.doi.org/10.1002/macp.1981.021820240
17. Norrlöw O, Glad M, Mosbach K. Acrylic polymer preparations containing recognition sites obtained by imprinting with substrates. Journal of Chromatography A 1984; 299:29-41. https://dx.doi.org/10.1016/S0021- 9673.(01)97819-7
18. Alexander C, Andersson HS, Andersson LI, Ansell RJ, Kirsch N, Nicholls IA et al. Molecular imprinting science and technology: a survey of the literature for the years up to and including 2003. Journal of Molecular Recognition 2006; 19:106-180. PMid:16395662. https:// dx.doi.org/10.1002/jmr.760
19. Andersson LI, Paprica A, Arvidsson T. A highly selective solid phase extraction sorbent for pre-concentration of sameridine made by molecular imprinting. Chromatographia 1997; 46:57-62. https:// dx.doi.org/10.1007/BF02490930
20. Walshe M, Howarth J, Kelly MT, O’Kennedy R, Smythet MR. The preparation of a molecular imprinted polymer to 7- hydroxycoumarin and its use as a solidphase extraction material Journal of Pharmaceutical and Biomedical Analysis 1997; 16:319-325. https:// dx.doi.org/10.1016/S0731-7085(97)00043-5
21. Masqué N, Marcé RM, Borrull F, Cormack PA, Sherrington DC. Synthesis and Evaluation of a Molecularly Imprinted Polymer for Selective On-Line Solid-Phase Extraction of 4-Nitrophenol from Environmental Water. Analytical Chemistry 2000; 72.:4122-4126. https://dx.doi.org/10.1021/ac0000628
22. Mayes AG, Mosbach K. Molecularly imprinted polymers: useful materials for analytical chemistry?. Trends in Analytical Chemistry 1997; 16:321-332. https://dx.doi.org/10.1016/S0165-9936(97)00037-X
23. Ye L, Mosbach K. The Technique of Molecular Imprinting - Principle, State of the Art, and Future Aspects. Journal of Inclusion Phenomena and Macrocyclic Chemistry 2001; 41:107-113. https://dx.doi. org/10.1023/A:1014498404292
24. Andersson LI. Molecular imprinting for drug bioanalysis: A review on the application of imprinted polymers to solid-phase extraction and binding assay. Journal of Chromatography B: Biomedical Sciences and Applications 2000a; 739:163-173. https://dx.doi. org/10.1016/S0378-4347(99)00432-6
25. Sellergren B. Direct Drug Determination by Selective Sample Enrichment on an Imprinted Polymer. Analytical Chemistry 1994; 66:1578-1582. https:// dx.doi.org/10.1021/ac00081a036
26. Vitor RV, Martins MCG, Figueiredo EC, Martins I. Application of molecularly imprinted polymer solidphase extraction for salivary cotinine. Analytical and Bioanalytical Chemistry 2011; 400:2109-2117. PMid:21448605. https://dx.doi.org/10.1007/s00216- 011.-4870-1
27. Javanbakhta M, Attaranb AM, Namjumanesha MH, Esfandyari-Manesha M, Akbari-Aderganic B. Solidphase extraction of tramadol from plasma and urine samples using a novel water-compatible molecularly imprinted polymer. Journal of Chromatography B 2010.; 878:1700-1706. PMid:20452295. https://dx.doi. org/10.1016/j.jchromb.2010.04.006
28. Gholivand MB, Khodadadian M. Rationally designed molecularly imprinted polymers for selective extraction of methocarbamol from human plasma. Talanta 2011; 85:1680-1688. PMid:21807239. https:// dx.doi.org/10.1016/j.talanta.2011.06.066
29. Yang J, Hu Y, Cai JB, Zhu XL, Su QD, Hu YQ et al. Selective hair analysis of nicotine by molecular imprinted solid-phase extraction: An application for evaluating tobacco smoke exposure. Food and Chemical Toxicology 2007; 45:896-903. PMid:17222493. https:// dx.doi.org/10.1016/j.fct.2006.11.010
30. Xie J, Chen L, Li C, Xu X. Selective extraction of functional components derived from herb in plasma by using a molecularly imprinted polymer based on 2,2-bis(hydroxymethyl)butanol trimethacrylate. Journal of Chromatography B 2003; 788:233-242. https://dx.doi.org/10.1016/S1570-0232(02)00796-1
31. El-Sheikh AH, Al-Quse RW, El-Barghouthi MI, Al-Masri FS. Derivatization of 2-chlorophenol with 4.-amino-anti-pyrine: A novel method for improving the selectivity of molecularly imprinted solid phase extraction of 2-chlorophenol from water.Talanta 2010.; 83:667-673. PMid:21111190. https://dx.doi. org/10.1016/j.talanta.2010.10.022
32. Dai C, Zhou X, Zhang Y, Liu S, Zhang J. Synthesis by precipitation polymerization of molecularly imprinted polymer for the selective extraction of diclofenac from water samples. Journal of Hazardous Materials 2011.; 198:175-181. PMid:22050930. https://dx.doi. org/10.1016/j.jhazmat.2011.10.027
33. Núñez L, Turiel E, Martin-Esteban A, Tadeo JL. Molecularly imprinted polymer for the extraction of parabens from environmental solid samples prior to their determination by high performance liquid chromatography-ultraviolet detection. Talanta 2010.; 80:1782-1788. PMid:20152411. https://dx.doi. org/10.1016/j.talanta.2009.10.023
34. Dong X, Wang N, Wang S, Zhang X, Fan Z. Synthesis and application of molecularly imprinted polymer on selective solid-phase extraction for the determination of monosulfuron residue in soil. Journal of Chromatography A 2004; 1057:13-19. PMid:15584218. https://dx.doi.org/10.1016/j.chroma.2004.09.036
35. Ferrer I, Lanza F, Tolokán A, Horvath V, Sellergren B, Horvai G et al. Selective Trace Enrichment of Chlorotriazine Pesticides from Natural Waters and Sediment Samples Using Terbuthylazine Molecularly Imprinted Polymers. Analytical Chemistry 2000; 72.:3934-3941. PMid:10959985. https://dx.doi. org/10.1021/ac000015f
36. Turiel E, Martín-Esteban A. Molecularly imprinted polymers for sample preparation: A review. Analytica Chimica Acta 2010; 668:87-99. PMid:20493285. https:// dx.doi.org/10.1016/j.aca.2010.04.019
37. Baggiani C, Baravalle P, Giovannoli C, Anfossi L, Giraudi G. Molecularly imprinted polymer/cryogel composites for solid-phase extraction of bisphenol A from river water and wine. Analytical and Bioanalytical Chemistry 2010; 397:815-822. PMid:20225052. https:// dx.doi.org/10.1007/s00216-010-3591-1
38. She Y, Cao W, Shi X, Lv X, Liu J, Wang R et al. Classspecific molecularly imprinted polymers for the selective extraction and determination of sulfonylurea herbicides in maize samples by high-performance liquid chromatography-tandem mass spectrometry. Journal of Chromatography B 2010; 878:2047- 2053.. PMid:20598653. https://dx.doi.org/10.1016/j. jchromb.2010.05.038
39. Shi X, Meng Y, Liu J, Sun A, Li D, Yao C et al. Groupselective molecularly imprinted polymer solid-phase extraction for the simultaneous determination of six sulfonamides in aquaculture products. Journal of Chromatography B 2011; 879:1071- 1076.. PMid:21459054. https://dx.doi.org/10.1016/j. jchromb.2011.03.019
40. Baggiani C, Baravalle P, Giraudi G, Tozzi C. Molecularly imprinted solid-phase extraction method for the high-performance liquid chromatographic analysis of fungicide pyrimethanil in wine. Journal of Chromatography A 2007; 1141:158-164. PMid:17178127. https://dx.doi.org/10.1016/j. chroma.2006.12.016
41. Turiel E, Tadeo JL, Cormack PAG, Martin-Esteban A. HPLC imprinted-stationary phase prepared by precipitation polymerisation for the determination of thiabendazole in fruit. Analyst 2005; 130:1601-1607. PMid:16284658. https://dx.doi.org/10.1039/b511031a
42. Mohamed R, Richoz-Payot J, Gremaud E, Mottier P, Yilmaz E, Tabet J-C et al. Advantages of Molecularly Imprinted Polymers LC-ESI-MS/MS for the Selective Extraction and Quantification of Chloramphenicol in Milk-Based Matrixes. Comparison with a Classical Sample Preparation. Analytical Chemistry 2007.; 79:9557-9565. PMid:18001131. https://dx.doi. org/10.1021/ac7019859
43. Andersson HS, Nicholls IA. A historical perspective of the development of molecular imprinting. In: Sellergren B, editor. Molecularly Imprinted Polymers: Man-made mimics of antibodies their applications in analytical chemistry. Elsevier; 2003. p. 1.
44. Silva RGC, Augusto F. Sol-gel molecular imprinted ormosil for solid-phase extraction of methylxanthines. Journal of Chromatography A 2006; 1114:216- 223.. PMid:16616927. https://dx.doi.org/10.1016/j. chroma.2006.03.073
45. Lin CI, Joseph AK, Chang CK, Wang YC, Lee YD. Synthesis of molecular imprinted organic-inorganic hybrid polymer binding caffeine. Analytica Chimica Acta 2003; 481:175-180. https://dx.doi.org/10.1016/ S0003-2670(03)00095-3
46. Li F, Li J, Zhang S. Molecularly imprinted polymer grafted on polysaccharide microsphere surface by the sol-gel process for protein recognition. Talanta 2004.; 74:1247-1255. PMid:18371777. https://dx.doi. org/10.1016/j.talanta.2007.08.032
47. Queirósa RB, Silva SO, Noronha JP, Frazão O, Jorge P, Aguilar G et al. Microcystin-LR detection in water by the Fabry-Pérot interferometer using an optical fibre coated with a sol-gel imprinted sensing membrane. Biosensors and Bioelectronics 2011; 26:3932-3937. PMid:21489775. https://dx.doi.org/10.1016/j. bios.2011.03.015
48. Li T, Chena PY, Niena PC, Lina CY, Vittal R, Lingb TR et al. Preparation of a novel molecularly imprinted polymer by the sol-gel process for sensing creatinine. Analytica Chimica Acta 2012; 711:83-90. https://dx.doi. org/10.1016/j.aca.2011.10.031
49. Golsefidia MA, Es’Haghia Z, Sarafraz-Yazdic A. Design, synthesis and evaluation of a molecularly imprinted polymer for hollow fiber-solid phase microextraction of chlorogenic acid in medicinal plants. Journal of Chromatography A 2012; 1229:24- 29.. PMid:22307151. https://dx.doi.org/10.1016/j. chroma.2012.01.019
50. Hu C-H, Chou T-C. Albumin molecularly imprinted polymer with high template affinity - Prepared by systematic optimization in mixed organic/aqueous media. Microchemical Journal 2009; 91:53-58. https:// dx.doi.org/10.1016/j.microc.2008.07.005
51. Navarroa V, Romeroa MG, Sánchez JFF, Cormack PAG, Carretero AS, Gutiérrez AF. Synthesis of caffeic acid molecularly imprinted polymer microspheres and high-performance liquid chromatography evaluation of their sorption properties. Journal of Chromatography A 2011; 1218:7289-7296. PMid:21889151. https:// dx.doi.org/10.1016/j.chroma.2011.08.043
52. Thibert V, Legeay P, ChapuisHugon F, Pichon V. 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 2012; 88:412- 419.. PMid:22265519. https://dx.doi.org/10.1016/j. talanta.2011.11.009
53. He J, Lv R, Zhan H, Wang H, Cheng J, Lu K et al. Preparation and evaluation of molecularly imprinted solid-phase micro-extraction fibers for selective extraction of phthalates in an aqueous sample. Analytica Chimica Acta 2010; 674:53- 58.. PMid:20638499. https://dx.doi.org/10.1016/j. aca.2010.06.018
54. Xu S, Liab J, Chen LJ. Molecularly imprinted coreshell nanoparticles for determination of trace atrazine by reversible addition-fragmentation chain transfer surface imprinting. Journal of Materials Chemistry 2011.; 21:4346-4351. https://dx.doi.org/10.1039/ c0jm03593a
55. Pan G, Ma Y, Zhang T, Guo X, Li C, Zhang H. Controlled synthesis of water-compatible molecularly imprinted polymer microspheres with ultrathin hydrophilic polymer shells via surface-initiated reversible addition-fragmentation chain transfer polymerization. Soft Matter 2011; 7:8428-8439. https:// dx.doi.org/10.1039/c1sm05497j
56. Kempe H, Kempe M. Development and Evaluation of Spherical Molecularly Imprinted Polymer Beads. Analytical Chemistry 2006; 78:3659-3666. PMid:16737221. https://dx.doi.org/10.1021/ac060068i
57. Walsh R, Osmani Q, Hughes H, Duggan P, McLoughlin P. Synthesis of imprinted beads by aqueous suspension polymerisation for chiral recognition of antihistamines. Journal of Chromatography B 2011.; 879:3523-3530. PMid:21982909. https://dx.doi. org/10.1016/j.jchromb.2011.09.036
58. López MMC, Pérez MCC, García MSD, Vilariãno JML, Rodríguez MVG, Losada LFB. Preparation, evaluation and characterization of quercetinmolecularly imprinted polymer for preconcentration and clean-up of catechins. Analytica Chimica Acta 2012.; 721:68-78. PMid:22405302. https://dx.doi. org/10.1016/j.aca.2012.01.049
59. Balamurugan K, Gokulakrishnan K, Prakasam T. Preparation and evaluation of molecularly imprinted polymer liquid chromatography column for the separation of Cathine enantiomers. Saudi Pharmaceutical Journal 2012; 20:53-61. https://dx.doi. org/10.1016/j.jsps.2011.06.004
60. Sambe H, Hoshina K, Haginaka J. Molecularly imprinted polymers for triazine herbicides prepared by multi-step swelling and polymerization method: Their application to the determination of methylthiotriazine herbicides in river water. Journal of Chromatography A 2007; 1152:130-137. PMid:16999969. https://dx.doi. org/10.1016/j.chroma.2006.09.003
61. Haginaka J. Molecularly imprinted polymers as affinity-based separation media for sample preparation. Journal of Separation Science 2009; 32.:1548-1565. PMid:19472278. https://dx.doi. org/10.1002/jssc.200900085
62. Soleimani M, Ghaderi S, Afshar MG, Soleimani S. Synthesis of molecularly imprinted polymer as a sorbent for solid phase extraction of bovine albumin from whey, milk, urine and serum. Microchemical Journal 2012; 100:1-7. https://dx.doi.org/10.1016/j. microc.2011.06.026
63. Vieira AC, Zampieri RA, Siqueira MEPB, Martins M, Figueiredo EC. Molecularly imprinted solidphase extraction and high-performance liquid chromatography with ultraviolet detection for the determination of urinary trans,trans-muconic acid: a comparison with ionic exchange extraction. Analyst 2012.; 137:2462-2469. PMid:22479697. https://dx.doi. org/10.1039/c2an16215f
64. Franqui LS, Vieira AC, Maia PP, Figueiredo EC. Extração de ácido trans-trans mucônico urinário com polímeros de impressão molecular e análise por cromatografia gasosa - espectrometria de massas. Química Nova. In press. PMid:11618007.
65. Khorrami AR, Rashidpur AJ. Design of a new cartridge for selective solid phase extraction using molecularly imprinted polymers: Selective extraction of theophylline from human serum samples. Biosensors and Bioelectronics 2009; 25:647-651. PMid:19157845. https://dx.doi.org/10.1016/j.bios.2008.11.033
66. Shi X, Liu J, Sun A, Li D, Chen J. Group-selective enrichment and determination of pyrethroid insecticides in aquaculture seawater via molecularly imprinted solid phase extraction coupled with gas chromatography-electron capture detection. Journal of Chromatography A 2012; 1227:60-66. PMid:22265776. https://dx.doi.org/10.1016/j.chroma.2012.01.012
67. Barros LA, Martins I, Rath S. A selective molecularly imprinted polymer-solid phase extraction for the determination of fenitrothion in tomatoes. Analytical and Bioanalytical Chemistry 2010; 397:1355-1361. PMid:20333363. https://dx.doi.org/10.1007/s00216- 010.-3629-4
68. Puoci F, Curcio M, Cirillo G, Iemma F, Spizzirri UG, Picci N. Molecularly imprinted solid-phase extraction for cholesterol determination in cheese products. Food Chemistry 2008; 106:836-842. https://dx.doi. org/10.1016/j.foodchem.2007.06.043
69. Jiang X, Zhao C, Jiang N, Zhang H, Liu M. Selective solid-phase extraction using molecular imprinted polymer for the analysis of diethylstilbestrol. Food Chemistry 2008; 108:1061-1067. https://dx.doi. org/10.1016/j.foodchem.2007.11.039
70. Figueiredo EC, Oliveira DM, Siqueira MEPB, Arruda MAZ. On-line molecularly imprinted solid-phase extraction for the selective spectrophotometric determination of nicotine in the urine of smokers. Analytica Chimica Acta 2009; 635:102-107. PMid:19200485. https://dx.doi.org/10.1016/j. aca.2008.12.045
71. Xu Z, Chen S, Huang W, Fang G, Pingzhu H, Wang S. Study on an on-line molecularly imprinted solidphase extraction coupled to high-performance liquid chromatography for separation and determination of trace estrone in environment. Analytical and Bioanalytical Chemistry 2009; 393:1273-1279. PMid:19104786. https://dx.doi.org/10.1007/s00216- 008.-2544-4
72. Feng Q, Zhao L, Yan W, Ji F, Wei Y, Lin J. Molecularly imprinted solid-phase extraction and flowinjection chemiluminescence for trace analysis of 2.,4-dichlorophenol in water samples. Analytical and Bioanalytical Chemistry 2008; 391:1073-1079. PMid:18425501. https://dx.doi.org/10.1007/s00216- 008.-2059-z
73. Figueiredo EC, Sparrapan R, Sanvido GB, Santos MG, Arruda MAZ, Eberlin MN. Quantitation of drugs via molecularly imprinted polymer solid phase extraction and electrospray ionization mass spectrometry: benzodiazepines in human plasma. Analyst 2011; 136.:3753-3757. PMid:21776492. https://dx.doi. org/10.1039/c1an15198c
74. Yan H, Qiao F, Row KH. Molecularly Imprinted Monolithic Column for Selective On-Line Extraction of Enrofloxacin and Ciprofloxacin from Urine. Chromatographia 2009; 70:1087-1093. https://dx.doi. org/10.1365/s10337-009-1244-3
75. Zhao C, Guan X, Liu X, Zhang H. Synthesis of molecularly imprinted polymer using attapulgite as matrix by ultrasonic irradiation for simultaneous on-line solid phase extraction and high performance liquid chromatography determination of four estrogens. Journal of Chromatography A 2012; 1229:72- 78.. https://dx.doi.org/10.1016/j.chroma.2012.01.042
76. Oliveira HM, Segundo MA, Lima JLFC, Miró M, Cerdà V. Exploiting automatic on-line renewable molecularly imprinted solid-phase extraction in lab-on-valve format as front end to liquid chromatography: application to the determination of riboflavin in foodstuffs. Analytical and Bioanalytical Chemistry 2010; 397:77-86. PMid:20191267. https:// dx.doi.org/10.1007/s00216-010-3522-1
77. Zhang Z, Zhang H, Hu Y, Yao S. Synthesis and application of multi-walled carbon nanotubesmolecularly imprinted sol-gel composite material for on-line solid-phase extraction and high-performance liquid chromatography determination of trace Sudan IV. Analytica Chimica Acta 2010; 661:173- 180.. PMid:20113732. https://dx.doi.org/10.1016/j. aca.2009.12.024
78. Xu Z, Fang G, Wang S. Molecularly imprinted solid phase extraction coupled to high-performance liquid chromatography for determination of trace dichlorvos residues in vegetables. Food Chemistry 2010.; 119:845-850. https://dx.doi.org/10.1016/j. foodchem.2009.08.047
79. Cacho C, Turiel E, Pérez-Conde C. Molecularly imprinted polymers: An analytical tool for the determination of benzimidazole compounds in water samples. Talanta 2009; 78:1029-1035. PMid:19269468. https://dx.doi.org/10.1016/j.talanta.2009.01.007
80. Melo LP, Queiroz MEC. Simultaneous analysis of parabens in cosmetic products by stir bar sorptive extraction and liquid chromatography. Journal of Separation Science 2010; 33:1849‑1855. PMid:20491059. https://dx.doi.org/10.1002/ jssc.201000024
81. Zhu X, Zhu Q. Molecular imprinted Nylon-6 stir bar as a novel extraction technique for enantioseparation of amino acids. Journal of Applied Polymer Science 2008; 109.:2665-2670. https://dx.doi.org/10.1002/app.27557
82. Gomez-Caballero A, Guerreiro A, Karim K, Piletsky S, Goicolea MA, Barrio RJ. Chiral imprinted polymers as enantiospecific coatings of stir bar sorptive extraction devices. Biosensors and Bioelectronics 2011; 28.:25‑32. PMid:21831628. https://dx.doi.org/10.1016/j. bios.2011.06.048
83. Yang L, Zhao X, Zhou J. Selective enrichment and determination of nicosulfuron in water and soil by a stir bar based on molecularly imprinted polymer coatings. Analytica Chimica Acta 2010; 670:72- 77.. PMid:20685419. https://dx.doi.org/10.1016/j. aca.2010.04.041
84. Wang S, Wei J, Hao T, Guo Z. Determination of ractopamine in pork by using electrochemiluminescence inhibition method combined with molecularly imprinted stir bar sorptive extraction. Journal of Electroanalytical Chemistry 2012.; 664:146-151. https://dx.doi.org/10.1016/j. jelechem.2011.11.011
85. Xu Z, Hu Y, Hu Y, Li G. Investigation of ractopamine molecularly imprinted stir bar sorptive extraction and its application for trace analysis of β2-agonists in complex samples. Journal of Chromatography A 2010.; 1217:3612-3618. PMid:20399437. https://dx.doi. org/10.1016/j.chroma.2010.03.046
86. Hu Y, Li J, Hu Y, Li G. Development of selective and chemically stable coating for stir bar sorptive extraction by molecularly imprinted technique. Talanta 2010; 82:464-470. PMid:20602921. https:// dx.doi.org/10.1016/j.talanta.2010.04.057
87. Xu Z, Song C, Hu Y, Li G. Molecularly imprinted stir bar sorptive extraction coupled with high performance liquid chromatography for trace analysis of sulfa drugs in complex samples. Talanta 2011; 85:97- 103.. PMid:21645676. https://dx.doi.org/10.1016/j. talanta.2011.03.041
88. Hu Y, Li J, Li G. Synthesis and application of a novel molecularly imprinted polymer-coated stir bar for microextraction of triazole fungicides in soil. Journal of Separation Science 2011; 34:1190‑1197. PMid:21491601. https://dx.doi.org/10.1002/ jssc.201100068
89. Zhang Z, Yang MJ, Pawliszyn J. Solid-Phase Microextraction. A Solvent-Free Alternative for Sample Preparation. Analytical Chemistry 1994.; 66:844A-853A. https://dx.doi.org/10.1021/ ac00089a001
90. Tamayo FG, Turiel E, Esteban AM. Molecularly imprinted polymers for solid-phase extraction and solid-phase microextraction: Recent developments and future trends. Journal of Chromatography A 2007.; 1152:32-40. PMid:17010356. https://dx.doi. org/10.1016/j.chroma.2006.08.095
91. Djozan D, Ebrahimi B, Mahkam M, Farajzadeh MA. Evaluation of a new method for chemical coating of aluminum wire with molecularly imprinted polymer layer. Application for the fabrication of triazines selective solid-phase microextraction fiber. Analytica Chimica Acta 2010; 674:40-48. PMid:20638497. https:// dx.doi.org/10.1016/j.aca.2010.06.006
92. Qiu L, Liua W, Huangb M, Zhanga L. Preparation and application of solid-phase microextraction fiber based on molecularly imprinted polymer for determination of anabolic steroids in complicated samples. Journal of Chromatography A 2010; 1217:7461‑7470. PMid:20965510. https://dx.doi.org/10.1016/j. chroma.2010.08.056
93. Prasad BB, Tiwari MP, Madhuri R, Sharma PS. Development of a highly sensitive and selective hyphenated technique (molecularly imprinted microsolid phase extraction fiber-molecularly imprinted polymer fiber sensor) for ultratrace analysis of folic acid. Analytica Chimica Acta 2010; 662:14‑22. PMid:20152260. https://dx.doi.org/10.1016/j. aca.2009.12.037
94. Hu X, Pana J, Hua Y, Li G. Preparation and evaluation of propranolol molecularly imprinted solid-phase microextraction fiber for trace analysis of β-blockers in urine and plasma samples. Journal of Chromatography A 2009; 1216:190-197. PMid:19084232. https://dx.doi. org/10.1016/j.chroma.2008.11.064
95. Djozan D, Ebrahimi B. Preparation of new solid phase micro extraction fiber on the basis of atrazinemolecular imprinted polymer: Application for GC and GC/MS screening of triazine herbicides in water, rice and onion. Analytica Chimica Acta 2008; 616:152- 159.. PMid:18482598. https://dx.doi.org/10.1016/j. aca.2008.04.037
96. Hu Y, Wang Y, Chen X, Hu Y, Li G. A novel molecularly imprinted solid-phase microextraction fiber coupled with high performance liquid chromatography for analysis of trace estrogens in fishery samples. Talanta 2010.; 80:2099-2105. PMid:20152458. https://dx.doi. org/10.1016/j.talanta.2009.11.015
97. Hu X, Daia G, Huanga J, Yea T, Fanb H, Youwena T et al. Molecularly imprinted polymer coated on stainless steel fiber for solid-phase microextraction of chloroacetanilide herbicides in soybean and corn. Journal of Chromatography A 2010; 1217:5875‑5882. PMid:20708736. https://dx.doi.org/10.1016/j. chroma.2010.07.011
98. Barahona F, Turiel E, Esteban AM. Supported liquid membrane-protected molecularly imprinted fibre for solid-phase microextraction of thiabendazole. Analytica Chimica Acta 2011; 694:83‑89. PMid:21565306. https://dx.doi.org/10.1016/j. aca.2011.03.052
99. Hu Y, Wang Y, Hu Y, Li G. Liquid-liquid-solid microextraction based on membrane-protected molecularly imprinted polymer fiber for trace analysis of triazines in complex aqueous samples. Journal of Chromatography A 2009; 1216:8304‑8311. PMid:19819459. https://dx.doi.org/10.1016/j. chroma.2009.09.063
100. Feng Q, Zhaoa L, Linb J. Molecularly imprinted polymer as micro-solid phase extraction combined with high performance liquid chromatography to determine phenolic compounds in environmental water samples. Analytica Chimica Acta 2009; 650:70- 76.. PMid:19720176. https://dx.doi.org/10.1016/j. aca.2009.04.016
101. Tarley CRT, Sotomayor LT, Kubota LT. Polímeros biomiméticos em química analítica. Parte 2: aplicações de MIP (“Molecularly Imprinted Polymers”) no desenvolvimento de sensores químicos. Química Nova 2005.; 28:1087-1101. https://dx.doi.org/10.1590/S0100- 40422005000600025.
102. Wang X, Maoa H, Huang W, Guan W, Zoub X, Pan J et al. Preparation of magnetic imprinted polymer particles via microwave heating initiated polymerization for selective enrichment of 2-amino-4-nitrophenol from aqueous solution. Chemical Engineering Journal 2011; 178.:85-92. https://dx.doi.org/10.1016/j.cej.2011.10.015
103. Wang X, Pan J, Guan W, Zou X, Huo P, Yan Y et al. Selective recognition of sesamol using molecularly imprinted polymers containing magnetic wollastonite. Journal of Separation Science 2011; 34:3287- 3294.. PMid:21997999. https://dx.doi.org/10.1002/ jssc.201100358
104. Pan J, Xu L, Dai J, Li X, Hang H, Huo P et al. Magnetic molecularly imprinted polymers based on attapulgite/ Fe3O4 particles for the selective recognition of 2.,4-dichlorophenol. Chemical Engineering Journal 2011.; 174:68-75. https://dx.doi.org/10.1016/j. cej.2011.08.046
105. Pan J, Yao H, Xu L, Ou H, Huo P, Li X, Yan Y. Selective Recognition of 2,4,6-Trichlorophenol by Molecularly Imprinted Polymers Based on Magnetic Halloysite Nanotubes Composites. The Journal of Physical Chemistry C 2011; 115:5440-5449. https://dx.doi. org/10.1021/jp111120x
106. Wang S, Li Y, Ding M, Wu X, Xu J, Wang R et al. Self-assembly molecularly imprinted polymers of 17.β-estradiol on the surface of magnetic nanoparticles for selective separation and detection of estrogenic hormones in feeds. Journal of Chromatography B 2011.; 879:2595-2600. PMid:21820977. https://dx.doi. org/10.1016/j.jchromb.2011.07.017
107. Ding M, Wu X, Yuan L, Wang S, Li Y, Wang R et al. Synthesis of core-shell magnetic molecularly imprinted polymers and detection of sildenafil and vardenafil in herbal dietary supplements. Journal of Hazardous Materials 2011; 191:177-183. PMid:21555181. https:// dx.doi.org/10.1016/j.jhazmat.2011.04.058
108. Hu Y, Li Y, Liu R, Tan W, Li G. Magnetic molecularly imprinted polymer beads prepared by microwave heating for selective enrichment of β-agonists in pork and pig liver samples. Talanta 2011; 84:462‑470. PMid:21376974. https://dx.doi.org/10.1016/j. talanta.2011.01.045
109. Zhang X, Chena L, Xua Y, Wanga H, Zenga Q, Zhaoa Q et al. Determination of β-lactam antibiotics in milk based on magnetic molecularly imprinted polymer extraction coupled with liquid chromatographytandem mass spectrometry. Journal of Chromatography B 2010; 878:3421-3426. PMid:21095165. https://dx.doi. org/10.1016/j.jchromb.2010.10.030
110. Gai QQ, Qua F, Zhanga T, Zhang Y. J. The preparation of bovine serum albumin surface-imprinted superparamagnetic polymer with the assistance of basic functional monomer and its application for protein separation. Journal of Chromatography A 2011.; 1218:3489-3495. PMid:21511265. https://dx.doi. org/10.1016/j.chroma.2011.03.069
111. Jing T, Xiaa H, Guanb Q, Lu W, Dai Q, Niu J et al. Rapid and selective determination of urinary lysozyme based on magnetic molecularly imprinted polymers extraction followed by chemiluminescence detection. Analytica Chimica Acta 2011; 692:73‑79. PMid:21501714. https://dx.doi.org/10.1016/j. aca.2011.02.057
112. Zhang Z, Tan W, Hu Y, Li G. Simultaneous determination of trace sterols in complicated biological samples by gas chromatography-mass spectrometry coupled with extraction using β-sitosterol magnetic molecularly imprinted polymer beads. Journal of Chromatography A 2011; 1218:4275- 4283.. PMid:21632061. https://dx.doi.org/10.1016/j. chroma.2011.05.022
113. Jing T, Du H, Dai Q, Xia H, Niu J, Hao Q et al. Magnetic molecularly imprinted nanoparticles for recognition of lysozyme. Biosensors and Bioelectronics 2010.; 26:301-306. PMid:20829022. https://dx.doi. org/10.1016/j.bios.2010.08.044
114. Wang X, Wanga L, Hea X, Zhanga Y, Chena L. A molecularly imprinted polymer-coated nanocomposite of magnetic nanoparticles for estrone recognition. Talanta 2009; 78:327-332. PMid:19203590. https:// dx.doi.org/10.1016/j.talanta.2008.11.024
115. Chen L, Zhanga X, Xua Y, Dub X, Sunb X, Suna L et al. Determination of fluoroquinolone antibiotics in environmental water samples based on magnetic molecularly imprinted polymer extraction followed by liquid chromatography-tandem mass spectrometry. Analytica Chimica Acta 2010; 662:31- 38.. PMid:20152262. https://dx.doi.org/10.1016/j. aca.2010.01.001
116. Chen L, Zhang X, Sun L, Xu Y, Zeng Q, Wang H et al. Fast and Selective Extraction of Sulfonamides from Honey Based on Magnetic Molecularly Imprinted Polymer. Journal of Agricultural and Food Chemistry 2009.; 57:10073-10080. PMid:19817457. https://dx.doi. org/10.1021/jf902257d
117. Chen L, Liu J, Zeng Q, Wang H, Yu A, Zhang H et al. Preparation of magnetic molecularly imprinted polymer for the separation of tetracycline antibiotics from egg and tissue samples. Journal of Chromatography A 2009; 1216:3710-3719. PMid:19268956. https:// dx.doi.org/10.1016/j.chroma.2009.02.044
118. Prieto A, Schrader S, Bauer C, Möder M. Synthesis of a molecularly imprinted polymer and its application for microextraction by packed sorbent for the determination of fluoroquinolone related compounds in water. Analytica Chimica Acta 2011; 685:146- 152.. PMid:21168563. https://dx.doi.org/10.1016/j. aca.2010.11.038
119. Prieto A, Vallejo A, Zuloaga O, Paschke A, Sellergen B, Schillinger E et al. Selective determination of estrogenic compounds in water by microextraction by packed sorbents and a molecularly imprinted polymer coupled with large volume injection-inport- derivatization gas chromatography-mass spectrometry. Analytica Chimica Acta 2011; 703.:PMid:21843673. https://dx.doi.org/10.1016/j. aca.2011.07.00741-51.
120. Qiao F, Sun H. J. Simultaneous extraction of enrofloxacin and ciprofloxacin from chicken tissue by molecularly imprinted matrix solid-phase dispersion. Journal of Pharmaceutical and Biomedical Analysis 2010.; 53:795-798. PMid:20619993. https://dx.doi. org/10.1016/j.jpba.2010.06.008
121. Hu Y, Liu R, Li R, Li G. Investigation of ractopamineimprinted polymer for dispersive solid-phase extraction of trace β-agonists in pig tissues. Journal of Separation Science 2010; 33:2017- 2025.. PMid:20533342. https://dx.doi.org/10.1002/ jssc.201000063
122. Guo L, Guan M, Zhao C, Zhang H. Molecularly imprinted matrix solid-phase dispersion for extraction of chloramphenicol in fish tissues coupled with high-performance liquid chromatography determination. Analytical and Bioanalytical Chemistry 2008.; 392:1431-1438. PMid:18949463. https://dx.doi. org/10.1007/s00216-008-2454-5
123. Sun H, Qiao F, Liu G, Liang S. Simultaneous isolation of six fluoroquinolones in serum samples by selective molecularly imprinted matrix solid-phase dispersion. Analytica Chimica Acta 2008; 625:154- 159.. PMid:18724989. https://dx.doi.org/10.1016/j. aca.2008.07.025
124. Yan H, Qiao F, Row KH. Molecularly Imprinted-Matrix Solid-Phase Dispersion for Selective Extraction of Five Fluoroquinolones in Eggs and Tissue. Analytical Chemistry 2007; 79:8242-8248. PMid:17918913. https://dx.doi.org/10.1021/ac070644q
125. Qiao F, Yan H. Simultaneous analysis of fluoroquinolones and xanthine derivatives in serum by molecularly imprinted matrix solid-phase dispersion coupled with liquid chromatography. Journal of Chromatography B 2011; 879:3551- 3555.. PMid:21978534. https://dx.doi.org/10.1016/j. jchromb.2011.09.040
126. Yan H, Wang H, Qiao J, Yang G. Molecularly imprinted matrix solid-phase dispersion combined with dispersive liquid-liquid microextraction for the determination of four Sudan dyes in egg yolk. Journal of Chromatography A 2011; 1218:2182- 2188.. PMid:21388626. https://dx.doi.org/10.1016/j. chroma.2011.02.042
127. Wang T, Tong J, Sun M, Chen L. Fast and selective extraction of chloramphenicol from soil by matrix solid-phase dispersion using molecularly imprinted polymer as dispersant. Journal of Separation Science 2011.; 34:1886-1892. PMid:21674791. https://dx.doi. org/10.1002/jssc.201100046
128. Boos KS, Fleischer CT. Multidimensional on-line solid-phase extraction (SPE) using restricted access materials (RAM) in combination with molecular imprinted polymers (MIP). Analytical Chemistry 2001.; 371:16-20. PMid:11605750. https://dx.doi. org/10.1007/s002160100831
129. Koeber R, Fleischer C, Lanza F, Boos KS, Sellergren B, Barcelo D. Evaluation of a Multidimensional Solid-Phase Extraction Platform for Highly Selective On-Line Cleanup and High-Throughput LC-MS Analysis of Triazines in River Water Samples Using Molecularly Imprinted Polymers. Analytical Chemistry 2001.; 73:2437-2444. PMid:11403283. https://dx.doi. org/10.1021/ac001483s
130. Haginaka J, Takehira H, Hosoya K, Tanaka N. Uniform-sized molecularly imprinted polymer for (S)-naproxen selectively modified with hydrophilic external layer. Journal of Chromatography A 1999; 849.:331-339. https://dx.doi.org/10.1016/S0021- 9673.(99)00570-1
131. Haginaka J, Sanbe H. Uniform-Sized Molecularly Imprinted Polymers for 2-Arylpropionic Acid Derivatives Selectively Modified with Hydrophilic External Layer and Their Applications to Direct Serum Injection Analysis. Analytical Chemistry 2000.; 72:5206-5210. PMid:11080865. https://dx.doi. org/10.1021/ac0005215
132. Hoshina K, Horiyama S, Matsunaga H, Haginaka J. Simultaneous determination of non-steroidal antiinflammatory drugs in river water samples by liquid chromatography-tandem mass spectrometry using molecularly imprinted polymers as a pretreatment column. Journal of Pharmaceutical and Biomedical Analysis 2011; 55:916-922. PMid:21470812. https:// dx.doi.org/10.1016/j.jpba.2011.03.014
133. Hoshina K, Horiyama S, Matsunaga H, Haginaka J. Molecularly imprinted polymers for simultaneous determination of antiepileptics in river water samples by liquid chromatography-tandem mass spectrometry. Journal of Chromatography A 2009; 1216:4957- 4962.. PMid:19439306. https://dx.doi.org/10.1016/j. chroma.2009.04.071
134. Sambe H, Hoshina K, Hosoya K, Haginaka J. Simultaneous determination of bisphenol A and its halogenated derivatives in river water by combination of isotope imprinting and liquid chromatographymass spectrometry. Journal of Chromatography A 2006.; 1134:16-23. PMid:16978634. https://dx.doi. org/10.1016/j.chroma.2006.08.072
135. Parisi OI, Cirillo G, Curcio M, Puoci F, Iemma F, Spizzirri UG et al. Surface modifications of molecularly imprinted polymers for improved template recognition in water media. Journal Of Polymer Research 2010; 17:355-362. https://dx.doi. org/10.1007/s10965-009-9322-7
136. Puoci F, Iemma F, Cirillo G, Curcio M, Parisi OI, Spizzirri UG et al. New restricted access materials combined to molecularly imprinted polymers for selective recognition/release in water media. European Polymer Journal 2009; 45:1634-1640. https://dx.doi. org/10.1016/j.eurpolymj.2009.01.021
137. Xu W, Su S, Jiang P, Wang H, Dong X, Zhang M. Determination of sulfonamides in bovine milk with column-switching high performance liquid chromatography using surface imprinted silica with hydrophilic external layer as restricted access and selective extraction material. Journal of Chromatography A 2010; 1217:7198-7207. PMid:20934183. https://dx.doi.org/10.1016/j. chroma.2010.09.035
138. Hua K, Zhang L, Zhang Z, Guo Y, Guo T. Surface hydrophilic modification with a sugar moiety for a uniform-sized polymer molecularly imprinted for phenobarbital in serum. Acta Biomaterialia 2011.; 7:3086-3093. PMid:21605708. https://dx.doi. org/10.1016/j.actbio.2011.05.006
139. Sergeyeva TA, Matuschewski H, Piletsky SA, Bendig J, Schedler U, Ulbricht M. Molecularly imprinted polymer membranes for substance-selective solidphase extraction from water by surface photo-grafting polymerization. Journal of Chromatography A 2001.; 907:89-99. https://dx.doi.org/10.1016/S0021- 9673.(00)01053-0
140. Pap B-T, Horváth V, Tolokán A, Horvai G, Sellergren B. Effect of solvents on the selectivity of terbutylazine imprinted polymer sorbents used in solid-phase extraction. Journal of Chromatography A 2002; 973:1- 12.. https://dx.doi.org/10.1016/S0021-9673(02)01084-1
141. Suedee C-R, Srichana T, Chuchome T, Kongmark U. Use of molecularly imprinted polymers from a mixture of tetracycline and its degradation products to produce affinity membranes for the removal of tetracycline from water. Journal of Chromatography B 2004.; 811:191-200. PMid:15522720.
142. Tan D-F, Deng M, Liu X, Zhao H, Li X, Quan X et al. Evaluation of a novel microextraction technique for aqueous samples: Porous membrane envelope filled with multiwalled carbon nanotubes coated with molecularly imprinted polymer. Journal of Separation Science 2011; 34:707-715. PMid:21312332. https:// dx.doi.org/10.1002/jssc.201000791
143. Zhong E-Q, Hu Y, Hu Y, Li G. Dynamic liquidliquid- solid microextraction based on molecularly imprinted polymer filaments on-line coupling to high performance liquid chromatography for direct analysis of estrogens in complex samples. Journal of Chromatography A 2012; 1241:13-20. PMid:22554413. https://dx.doi.org/10.1016/j.chroma.2012.04.017
144. Figueiredo EC, Sanvido GB, Arruda MAZ, Eberlin MN. Molecularly imprinted polymers as analyte sequesters and selective surfaces for easy ambient sonic-spray ionization. Analyst 2010; 135:726-730. PMid:20309446. https://dx.doi.org/10.1039/b923289c.