Abstract
A macromolecular crowding-assisted liquid-crystalline molecularly imprinted monolith (LC-MIM) was prepared successfully for the first time. The imprinted stationary phase was synthesized with polymethyl methacrylate (PMMA) or polystyrene (PS) as the crowding agent, 4-cyanophenyl dicyclohexyl propylene (CPCE) as the liquid-crystal monomer, and hydroquinidine as the pseudo-template for the chiral separation of cinchona alkaloids in HPLC. A low level of cross-linker (26 %) has been found to be sufficient to achieve molecular recognition on the crowding-assisted LC-MIM due to the physical cross-linking of mesogenic groups in place of chemical cross-linking, and baseline separation of quinidine and quinine could be achieved with good resolution (R s = 2.96), selectivity factor (α = 2.16), and column efficiency (N = 2650 plates/m). In contrast, the LC-MIM prepared without crowding agents displayed the smallest diastereoselectivity (α = 1.90), while the crowding-assisted MIM with high level of cross-linker (80 %) obtained the greatest selectivity factor (α = 7.65), but the lowest column efficiency (N = 177 plates/m).
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References
Wulff G (2002) Chem Rev 102:1–27
Cheong WJ, Ali F, Choi JH, Lee JOK, Sung KY (2013) Talanta 106:45–59
Barahona F, Turiel E, Martín-Esteban A (2011) J Chromatogr A 1218:7065–7070
Turiel E, Martín-Esteban A (2009) J Sep Sci 32:3278–3284
Shimizu KD, Stephenson CJ (2010) Curr Opin Chem Biol 14:743–753
Resmini M (2012) Anal Bioanal Chem 402:3021–3026
Cunliffe D, Kirby A, Alexander C (2005) Adv Drug Deliv Rev 57:1836–1853
Courtois J, Fischer G, Sellergren B, Irgum K (2006) J Chromatogr A 1109:92–99
Matsui J, Goji S, Murashima T, Miyoshi D, Komai S, Shigeyasu A, Kushida T, Miyazawa T, Yamada T, Tamaki K, Sugimoto N (2007) Anal Chem 79:1749–1757
John Ellis R (2001) Trends Biochem Sci 26:597–604
Minton AP (2000) Curr Opin Struct Biol 10:34–39
Miyoshia D, Sugimoto N (2008) Biochimie 90:1040–1051
Piletsky SA, Piletskaya EV, Panasyuk TL, El’Skaya AV, Levi R, Karube I, Wulff G (1998) Macromolecules 31:2137–2140
Marty JD, Tizra M, Mauzac M, Rico-Lattes I, Lattes A (1999) Macromolecules 32:8674–8677
Marty JD, Labadie L, Mauzac M, Fournier C, Rico-Lattes I, Lattes A (2004) Mol Cryst Liq Cryst 411:561–566
Marty JD, Mauzac M, Fournier C, Rico-Lattes I, Lattes A (2002) Liq Cryst 29:529–536
Binet C, Ferr’ere S, Lattes A, Laurent E, Marty JD, Mauzac M, Mingotaud AF, Palaprat G, Weyland M (2007) Anal Chim Acta 591:1–6
Weyland M, Ferrere S, Lattes A, Mingotaud AF, Mauzac M (2008) Liq Cryst 35:219–231
Binet C, Bourrier D, Dilhan M, Estève D, Ferrère S, Garrigue JC, Granier H, Lattes A, Gué AM, Mauzac M, Mingotaud AF (2006) Talanta 69:757–762
Liu X, Zong HY, Huang YP, Liu ZS (2013) J Chromatogr A 1309:84–89
Wei ZH, Mu LN, Pang QQ, Huang YP, Liu ZS (2012) J Chromatogr A 1237:115–121
Ban L, Zhao L, Deng BL, Huang YP, Liu ZS (2013) Anal Bioanal Chem 405:2245–2253
Mu LN, Wang XH, Zhao L, Huang YP, Liu ZS (2011) J Chromatogr A 1218:9236–9243
Li XX, Bai LH, Wang H, Wang J, Huang YP, Liu ZS (2012) J Chromatogr A 1251:141–147
Shi XX, Xu L, Duan HQ, Huang YP, Liu ZS (2011) Electrophoresis 32:1348–1356
Li XX, Hao LF, Huang YP, Duan HQ, Liu ZS (2012) Polym Eng Sci 52:1440–1449
Nandanan E, Sudalai A, Ravindranathan T (1997) Tetrahedron Lett 38:2577–2580
Matsui J, Kato T, Takeuchi T, Suzukit M, Yokoyama K, Tamiya E, Karube I (1993) Anal Chem 65:2223–2224
Kim H, Guiochon G (2005) Anal Chem 77:93–102
Andersson HS, Karlsson JG, Piletsky SA, Koch-Schmidt AC, Mosbach K, Nicholls IA (1999) J Chromatogr A 848:39–49
Sellergren B, Shea KJ (1993) J Chromatogr A 635:31–49
Haginaka J, Kagawa C (2003) Anal Sci 19:39–42
Sellergren B, Shea KJ (1995) J Chromatogr A 690:29–39
Kiisters E, Loux V, Schmid E, Floersheim P (1994) J Chromatogr A 666:421–432
Piletsky SA, Mijangos I, Guerreiro A, Piletska EV, Chianella I, Karim K, Turner APF (2005) Macromolecule 38:1410–1416
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This work was supported by the National Natural Science Foundation of China (Grant Nos. 21375096 and U1303202).
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Zhang, C., Zhang, J., Huang, YP. et al. Macromolecular crowding-assisted fabrication of liquid-crystalline imprinted polymers. Anal Bioanal Chem 407, 2923–2931 (2015). https://doi.org/10.1007/s00216-015-8510-z
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DOI: https://doi.org/10.1007/s00216-015-8510-z