Targeted extraction of active compounds from natural products by molecularly imprinted polymers

• Authors: Antonelle Pardo , Laetitia Mespouille , Philippe Dubois , Pierre Duez , Bertrand Blankert
• Languages of publication: EN

Abstracts

EN

One of the most promising separation techniques that have emerged during the last decade is based on the use of molecularly imprinted polymers (MIPs). MIPs are stable polymers that possess specific cavities designed for a template molecule, endowed with excellent selectivity compared to regular solid phase extraction techniques. Molecularly imprinted solid-phase extraction (MISPE) has already shown a high efficiency for the sample preparation from complex matrices. Natural products received huge attention in recent years. Indeed, the application of MISPE for the screening of natural products appears extremely interesting not only for the selective extraction of a target compound but also for the concomitant discovery of new drug candidates, promising sources of therapeutic benefits. In the present review, examples of recognition and separation of active components from natural extracts are emphasized. MIPs are very promising materials to mimic the recognition characteristics exhibited by enzymes or receptors although further developments are necessary to fully exploit their wide potential.

Keywords

EN

Molecularly imprinted polymers; Solid-phase extraction; Pharmaceutical analysis; Screening

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2012
• Volume: 10
• Issue: 3
• Pages: 751-765

Dates

published

1 - 6 - 2012

online

23 - 3 - 2012

Contributors

author

Antonelle Pardo

author

Laetitia Mespouille

• Laboratory of Polymeric and Composite Materials (LPMC), Faculty of Sciences, University of Mons — UMONS, 7000, Mons, Belgium

author

Philippe Dubois

• Laboratory of Polymeric and Composite Materials (LPMC), Faculty of Sciences, University of Mons — UMONS, 7000, Mons, Belgium

author

Pierre Duez

• Laboratory of Therapeutic Chemistry and Pharmacognosy, Faculty of Medicine and Pharmacy, University of Mons — UMONS, 7000, Mons, Belgium

author

Bertrand Blankert

• Laboratory of Pharmaceutical Analysis, Faculty of Medicine and Pharmacy, University of Mons — UMONS, 7000, Mons, Belgium

References

• [1] P.M. Dewick, Medicinal Natural Products, A biosynthetic approach, 2nd Edition (John Wiley & Sons, Chichester, 2001)
• [2] C.W. Huck, G.K. Bonn, J. Chromatogr. A 885, 51 (2000) http://dx.doi.org/10.1016/S0021-9673(00)00333-2[Crossref]
• [3] X. Xiaojie, Z. Lili, C. Lirong, J. Chromatogr. B. 804, 61 (2004) http://dx.doi.org/10.1016/j.jchromb.2004.02.012[Crossref]
• [4] G. Wulff, A. Sarhan, Angew. Chem. 84, 364 (1972) http://dx.doi.org/10.1002/ange.19720840838[Crossref]
• [5] R. Arshady, K. Mosbach, Makromolekul. Chem. 182, 687 (1982) http://dx.doi.org/10.1002/macp.1981.021820240[Crossref]
• [6] E. Turiel, A. Martin-Esteban, Anal. Bioanal. Chem. 378, 1876 (2004) http://dx.doi.org/10.1007/s00216-003-2331-1[Crossref]
• [7] V.B. Kandimalla, H. Ju, Anal. Bioanal. Chem. 380, 587 (2004) http://dx.doi.org/10.1007/s00216-004-2793-9[Crossref]
• [8] C. He, Y. Long, J. Pan, K. Li, F. Liu, J. Biochem. Bioph. Meth. 70, 133 (2007) http://dx.doi.org/10.1016/j.jbbm.2006.07.005[Crossref]
• [9] G. Vlatakis, L.I. Andersson, R. Müller, K. Mosbach, Nature 361, 645 (1993) http://dx.doi.org/10.1038/361645a0[Crossref]
• [10] O. Ramström, L. Ye, K. Mosbach, Chem. Biol. 3, 471 (1996) http://dx.doi.org/10.1016/S1074-5521(96)90095-2[Crossref]
• [11] W.H. Ali, D. Derrien, F. Alix, C. Pérollier, O. Lépine, S. Bayoudh, F. Chapuis-Hugon, V. Pichon, J. Chromatogr. A 1217, 6668 (2010) http://dx.doi.org/10.1016/j.chroma.2010.04.071[Crossref]
• [12] P. Lucci, D. Derrien, F. Alix, C. Pérollier, S. Bayoudh, Anal. Chim. Acta 672, 15 (2010) http://dx.doi.org/10.1016/j.aca.2010.03.010[Crossref]
• [13] J. Svenson, I.A. Nicholls, Anal. Chim. Acta 435, 19 (2001) http://dx.doi.org/10.1016/S0003-2670(00)01396-9[Crossref]
• [14] X. Zhuang, X. Dong, S. Ma, T. Zhang, J. Chromatogr. Sci. 46, 739 (2008) [Crossref]
• [15] O. Brüggemann, K. Haupt, L. Ye, E. Yilmaz, K. Mosbach, J. Chromatogr. A 889, 15 (2000) http://dx.doi.org/10.1016/S0021-9673(00)00350-2[Crossref]
• [16] L. Ye, K. Haupt, Anal. Bioanal. Chem. 378, 1887 (2004) http://dx.doi.org/10.1007/s00216-003-2450-8[Crossref]
• [17] C. Alexander, H.S. Andersson, L.I. Andersson, R.J. Ansell, N. Kirsch, I.A. Nicholls, J. O’Mahony, M.J. Whitcombe, J. Mol. Recognit. 19, 106 (2006) http://dx.doi.org/10.1002/jmr.760[Crossref]
• [18] C. Alvarez-Lorenzo, A. Concheiro, J. Chromatogr. B. 804, 231 (2004) http://dx.doi.org/10.1016/j.jchromb.2003.12.032[Crossref]
• [19] B. Sellergren, Anal. Chem. 66, 1578 (1994) http://dx.doi.org/10.1021/ac00081a036[Crossref]
• [20] G. Cirillo, M. Curcio, O.I. Parisi, F. Puoci, F. Iemma, U.G. Spizzirri, D. Restuccia, N. Picci, Food Chem. 125, 1058 (2011) http://dx.doi.org/10.1016/j.foodchem.2010.09.077[Crossref]
• [21] G. Karasova, J. Lehotay, J. Sadecka, I. Skacani, M. Lachova, J. Sep. Sci. 28, 2468 (2005) http://dx.doi.org/10.1002/jssc.200500190[Crossref]
• [22] C. Yu, K. Mosbach, J. Org. Chem. 62, 4057 (1997) http://dx.doi.org/10.1021/jo961784v[Crossref]
• [23] J. Xie, L. Zhu, H. Luo, L. Zhou, C. Li, X. Xu, J. Chromatogr. A 934, 1 (2001) http://dx.doi.org/10.1016/S0021-9673(01)01294-8[Crossref]
• [24] L. Zhu, L. Chen, X. Xu, Anal. Chem. 75, 6381 (2003) http://dx.doi.org/10.1021/ac026371a[Crossref]
• [25] L. Zhu, X. Xu, J. Chromatogr. A 991, 151 (2003) http://dx.doi.org/10.1016/S0021-9673(03)00207-3[Crossref]
• [26] S.-G. Hu, L. Li, X.-W. He, J. Chromatogr. A 1062, 31 (2005) http://dx.doi.org/10.1016/j.chroma.2004.11.036[Crossref]
• [27] H. Cao, J.B. Xiao, M. Xu, Macromol. Res. 14, 324 (2006) http://dx.doi.org/10.1007/BF03219089[Crossref]
• [28] B. Sellergren, J. Wieschemeyer, K.-S. Boos, D. Seidel, Chem. Mater. 10, 4037 (1998) http://dx.doi.org/10.1021/cm980730u[Crossref]
• [29] K. Tanabe, T. Takeuchi, J. Matsui, K. Ikebukuro, K. Yano, I. Karube, Chem. Commun. 2303 (1995) [Crossref]
• [30] P. Manesiotis, A.J. Hall, J. Courtois, K. Irgum, B. Sellergren, Angew. Chem. Int. Ed. 44, 3902 (2005) http://dx.doi.org/10.1002/anie.200500342[Crossref]
• [31] Z. Guo, L. Zhang, C. Song, X. Zhang, Analyst 136, 3016 (2011) http://dx.doi.org/10.1039/c1an15281e[Crossref]
• [32] Z.-F. Guo, T.-T. Guo, M. Guo, Anal. Chim. Acta 612, 136 (2008) http://dx.doi.org/10.1016/j.aca.2008.02.039[Crossref]
• [33] B. Sellergren, Makromol. Chem. 190, 2703 (1989) http://dx.doi.org/10.1002/macp.1989.021901104[Crossref]
• [34] X. Song, J. Li, J. Wang, L. Chen, Talanta 80, 694 (2009) http://dx.doi.org/10.1016/j.talanta.2009.07.051[Crossref]
• [35] Y. Zhang, D. Song, L.M. Lanni, K.D. Shimizu, Macromolecules 43, 6284 (2010) http://dx.doi.org/10.1021/ma101013c[Crossref]
• [36] B. Sellergren, L.I. Andersson, Methods 22, 92 (2000) http://dx.doi.org/10.1006/meth.2000.1040[Crossref]
• [37] G. Wulff, Angew. Chem. Int. Ed. 34, 1812 (1995) http://dx.doi.org/10.1002/anie.199518121[Crossref]
• [38] R. Simon, M.E. Collins, D.A. Spivak, Anal. Chim. Acta 591, 7 (2007) http://dx.doi.org/10.1016/j.aca.2006.12.045[Crossref]
• [39] D.A. Spivak, R. Simon, J. Campbell, Anal. Chim. Acta 504, 23 (2004) http://dx.doi.org/10.1016/S0003-2670(03)00946-2[Crossref]
• [40] M. Kempe, Anal. Chem. 68, 1948 (1996) http://dx.doi.org/10.1021/ac9512160[Crossref]
• [41] H.S. Andersson, J.G. Karlsson, S.A. Piletsky, A.-C. Koch-Schmidt, K. Mosbach, I.A. Nicholls, J. Chromatogr. A 848, 39 (1999) http://dx.doi.org/10.1016/S0021-9673(99)00483-5[Crossref]
• [42] H. Kim, D.A. Spivak, J. Am. Chem. Soc. 125, 11269 (2003) http://dx.doi.org/10.1021/ja0361502[Crossref]
• [43] C. Crescenzi, S. Bayoudh, P.A.G. Cormack, T. Klein, K. Ensing, Anal. Chem. 73, 2171 (2001) http://dx.doi.org/10.1021/ac0014360[Crossref]
• [44] X. Feás, J.A. Seijas, M.P. Vázquez-Tato, P. Regal, A. Cepeda, C. Fente, Anal. Chim. Acta 631, 237 (2009) http://dx.doi.org/10.1016/j.aca.2008.10.054[Crossref]
• [45] Å. Zander, P. Findlay, T. Renner, B. Sellergren, A. Swietlow, Anal. Chem. 70, 3304 (1998) http://dx.doi.org/10.1021/ac971272w[Crossref]
• [46] A. Ellwanger, C. Berggren, S. Bayoudh, C. Crecenzi, L. Karlsson, P.K. Owens, K. Ensing, P. Cormack, D. Sherrington, B. Sellergren, Analyst 126, 784 (2001) http://dx.doi.org/10.1039/b009693h[Crossref]
• [47] J.D. Marty, M. Tizra, M. Mauzac, I. Rico-Lattes, A. Lattes, Macromolecules 32, 8674 (1999) http://dx.doi.org/10.1021/ma990592+[Crossref]
• [48] K.J. Shea, D.Y. Sasaki, G.J. Stoddard, Macromolecules 22, 1722 (1989) http://dx.doi.org/10.1021/ma00194a037[Crossref]
• [49] I. Gavrilovic, K. Mitchell, A.D. Brailsford, D.A. Cowan, A.T. Kicman, R.J. Ansell, Steroids 76, 478 (2011) http://dx.doi.org/10.1016/j.steroids.2011.01.004[Crossref]
• [50] R. Simon, S. Houck, D.A. Spivak, Anal. Chim. Acta 542, 104 (2005) http://dx.doi.org/10.1016/j.aca.2005.03.048[Crossref]
• [51] M. Sibrian-Vazquez, D.A. Spivak, Macromolecules 36, 5105 (2003) http://dx.doi.org/10.1021/ma025710z[Crossref]
• [52] M. Sibrian-Vazquez, D.A. Spivak, J. Am. Chem. Soc. 126, 7827 (2004) http://dx.doi.org/10.1021/ja038961b[Crossref]
• [53] A. Guyot, M. Bartholin, Prog. Polym. Sci. 8, 277 (1982) http://dx.doi.org/10.1016/0079-6700(82)90002-8[Crossref]
• [54] D. Horák, F. Švec, M. Bleha, J. Kalal, Angew. Makromol. Chem. 95, 109 (1981) http://dx.doi.org/10.1002/apmc.1981.050950108[Crossref]
• [55] B. Sellergren, K.J. Shea, J. Chromatogr. A 635, 31 (1993) http://dx.doi.org/10.1016/0021-9673(93)83112-6[Crossref]
• [56] D.A. Spivak, Adv. Drug Deliver. Rev. 57, 1779 (2005) http://dx.doi.org/10.1016/j.addr.2005.07.012[Crossref]
• [57] F.B. Kaabi, V. Pichon, LCGC North America 25, 732 (2007)
• [58] S.A. Piletsky, E.V. Piletskaya, T.L. Panasyuk, A.V. El’skaya, R. Levi, I. Karube, G. Wulff, Macromolecules 31, 2137 (1998) http://dx.doi.org/10.1021/ma970818d[Crossref]
• [59] A. Kugimiya, T. Takeuchi, J. Matsuib, K. Ikebukuro, K. Yano, I. Karube, Anal. Lett. 29, 1099 (1996) http://dx.doi.org/10.1080/00032719608001461[Crossref]
• [60] I. Mijangos, F. Navarro-Villoslada, A. Guerreiro, E. Piletska, I. Chianella, K. Karim, A. Turner, S. Piletsky, Biosens. Bioelectron. 22, 381 (2006) http://dx.doi.org/10.1016/j.bios.2006.05.012[Crossref]
• [61] J.-M. Lin, T. Nakagama, K. Uchiyama, T. Hobo, J. Pharm. Biomed. Anal. 15, 1351 (1997) http://dx.doi.org/10.1016/S0731-7085(96)02013-4[Crossref]
• [62] Q. Fu, Q. Fang, B. Feng, S. Sun, W. Du, E. Amut, A. Xiao, C. Chang, J. Chromatogr. B. 879, 894 (2011) http://dx.doi.org/10.1016/j.jchromb.2011.02.041[Crossref]
• [63] L.-q. Lin, J. Zhang, Q. Fu, L.-c. He, Y.-c. Li, Anal. Chim. Acta 561, 178 (2006) http://dx.doi.org/10.1016/j.aca.2006.01.011[Crossref]
• [64] T. Takeuchi, J. Haginaka, J. Chromatogr. B. 728, 1 (1999) http://dx.doi.org/10.1016/S0378-4347(99)00057-2[Crossref]
• [65] B. Dirion, Z. Cobb, E. Schillinger, L.I. Andersson, B. Sellergren, J. Am. Chem. Soc. 125, 15101 (2003) http://dx.doi.org/10.1021/ja0355473[Crossref]
• [66] F.G. Tamayo, J.L. Casillas, A. Martin-Esteban, Anal. Chim. Acta 482, 165 (2003) http://dx.doi.org/10.1016/S0003-2670(03)00213-7[Crossref]
• [67] X. Yin, Q. Liu, Y. Jiang, Y. Luo, Spectrochim. Acta A. 79, 191 (2011) http://dx.doi.org/10.1016/j.saa.2011.02.034[Crossref]
• [68] Y. Yuan, Y. Wang, M. Huang, R. Xu, H. Zeng, C. Nie, J. Kong, Anal. Chim. Acta 695, 63 (2011) http://dx.doi.org/10.1016/j.aca.2011.04.007[Crossref]
• [69] J.-P. Lai, X.-W. He, Y. Jiang, F. Chen, Anal. Bioanal. Chem. 375, 264 (2003)
• [70] T. Kubo, M. Nomachi, K. Nemoto, T. Sano, K. Hosoya, N. Tanaka, K. Kaya, Chim. Acta 577, 1 (2006) http://dx.doi.org/10.1016/j.aca.2006.06.028[Crossref]
• [71] B. Claude, P. Morin, M. Lafosse, A.-S. Belmont, K. Haupt, Talanta 75, 344 (2008) http://dx.doi.org/10.1016/j.talanta.2007.11.037[Crossref]
• [72] X. Zhu, Q. Cao, N. Hou, G. Wang, Z. Ding, Anal. Chim. Acta 561, 171 (2006) http://dx.doi.org/10.1016/j.aca.2006.01.009[Crossref]
• [73] A. MartÍn-Esteban, Fresen. J. Anal. Chem. 370, 795 (2001) http://dx.doi.org/10.1007/s002160100854[Crossref]
• [74] X. Dong, W. Wang, S. Ma, H. Sun, Y. Li, J. Guo, J. Chromatogr. A 1070, 125 (2005) http://dx.doi.org/10.1016/j.chroma.2005.03.017[Crossref]
• [75] X. Dong, H. Sun, X. Lu, H. Wang, S. Liu, N. Wang, Analyst 127, 1427 (2002) http://dx.doi.org/10.1039/b202295h[Crossref]
• [76] J. Matsui, M. Okada, M. Tsuruoka, T. Takeuchi, Anal. Commun. 34, 85 (1997) http://dx.doi.org/10.1039/a700103g[Crossref]
• [77] I. Ferrer, F. Lanza, A. Tolokan, V. Horvath, B. Sellergren, G. Horvai, D. Barceló, Anal. Chem. 72, 3934 (2000) http://dx.doi.org/10.1021/ac000015f[Crossref]
• [78] W.-H. Zhou, X.-C. Guo, H.-Q. Zhao, S.-X. Wu, H.-H. Yang, X.-R. Wang, Talanta 84, 777 (2011) http://dx.doi.org/10.1016/j.talanta.2011.02.004[Crossref]
• [79] E. Turiel, A. Martín-Esteban, Anal. Chim. Acta 668, 87 (2010) http://dx.doi.org/10.1016/j.aca.2010.04.019[Crossref]
• [80] S. Ma, X. Zhuang, H. Wang, H. Liu, J. Li, X. Dong, Anal. Lett. 40, 321 (2007) http://dx.doi.org/10.1080/00032710600867689[Crossref]
• [81] W.M. Mullett, E.P.C. Lai, Anal. Chem. 70, 3636 (1998) http://dx.doi.org/10.1021/ac980264s[Crossref]
• [82] W. M. Mullett, E. P. C. Lai, B. Sellergren, Anal. Commun. 36, 217 (1999) http://dx.doi.org/10.1039/a902509j[Crossref]
• [83] N. Masqué, R.M. Marcé, F. Borrull, P.A.G. Cormack, D.C. Sherrington, Anal. Chem. 72, 4122 (2000) http://dx.doi.org/10.1021/ac0000628[Crossref]
• [84] G. Theodoridis, C.K. Zacharis, P.D. Tzanavaras, D.G. Themelis, A. Economou, J. Chromatogr. 1030, 69 (2004) http://dx.doi.org/10.1016/j.chroma.2003.12.036[Crossref]
• [85] M. Huang, W. Pang, J. Zhang, S. Lin, J. Hu, J. Pharm. Biomed. Anal. 58, 12 (2012) http://dx.doi.org/10.1016/j.jpba.2011.09.010[Crossref]
• [86] E. Caro, R.M. Marcé, P.A.G. Cormack, D.C. Sherrington, F. Borrull, J. Chromatogr. A 995, 233 (2003) http://dx.doi.org/10.1016/S0021-9673(03)00543-0[Crossref]
• [87] P. Lucci, O. Núñez, M.T. Galceran, J. Chromatogr. A 1218, 4828 (2011) http://dx.doi.org/10.1016/j.chroma.2011.02.007[Crossref]
• [88] J. Xie, L. Zhu, X. Xu, Anal. Chem. 74, 2352 (2002) http://dx.doi.org/10.1021/ac015755i[Crossref]
• [89] W. Bi, M. Tian, K.H. Row, J. Chromatogr. A (2011) In press
• [90] D.L. Rathbone, Adv. Drug Deliver. Rev. 57, 1854 (2005) http://dx.doi.org/10.1016/j.addr.2005.07.017[Crossref]
• [91] K. Sreenivasan, J. Appl. Polym. Sci. 82, 889 (2001) http://dx.doi.org/10.1002/app.1920[Crossref]
• [92] D.L. Rathbone, A. Ali, P. Antonaki, S. Cheek, Biosens. Bioelectron. 20, 2353 (2005) http://dx.doi.org/10.1016/j.bios.2005.01.009[Crossref]
• [93] B. Claude, P. Morin, M. Lafosse, A.-S. Belmont, K. Haupt, Talanta 75, 344 (2008) http://dx.doi.org/10.1016/j.talanta.2007.11.037[Crossref]
• [94] C. Lopez, B. Claude, P. Morin, J.P. Max, R. Pena, J.P. Ribet, Anal. Chim. Acta 683, 198 (2011) http://dx.doi.org/10.1016/j.aca.2010.09.051[Crossref]
• [95] H. Guo, K. Liu, Y. Liu, B. Fang, M. Liu, L. He, Z. Zeng, J. Chromatogr. B. 879, 181 (2011) http://dx.doi.org/10.1016/j.jchromb.2010.11.041[Crossref]
• [96] C.-Y. Chen, C.-H. Wang, A.-H. Chen, Talanta 84, 1038 (2011) http://dx.doi.org/10.1016/j.talanta.2011.03.009[Crossref]
• [97] N. Pérez-Moral, A.G. Mayes, Anal. Chim. Acta 504, 15 (2004) http://dx.doi.org/10.1016/S0003-2670(03)00533-6[Crossref]
• [98] B. Danielsson, Adv. Biochem. Eng. Biotechnol. 109, 97 (2008)
• [99] A. Beltran, F. Borrull, R.M. Marcé, P.A.G. Cormack, TrAC, Trends Anal. Chem. 29, 1363 (2010) http://dx.doi.org/10.1016/j.trac.2010.07.020[Crossref]
• [100] A. Poma, A.P.F. Turner, S.A. Piletsky, Trends Biotech. 28, 629 (2010) http://dx.doi.org/10.1016/j.tibtech.2010.08.006[Crossref]

Identifiers

DOI

10.2478/s11532-012-0018-1