Synthesis of New Molecular Imprinted Polymer for Highly Recognition of Cholic Acid

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In this study, molecular imprinted polymers for highly selective recognition of cholic acid, which is a bile acid, were prepared. Acrylamide, methacrylic acid, methacrylamide were chosen as monomer for the production of molecularly imprinted polymers. Functional monomers were polymerized with various crosslinkers; ethylene glycol dimethacrylate (EGDMA), 1,4-butanediol diacrylate (BUT), trimethylpropane triacrylate (TMT) with target molecule (MIP-EGDMA, MIP-BUT and MIP TMT) and various MIPs were prepared. The cholic acid was removed from MIP with a suitable method. NIP polymers were synthesized without cholic acid (NIPEGDMA, NIP-BUT and NIP-TMT). For the characterization of synthesized polymers FTIR, DSC, TGA, SEM analyses were used. The parameters that affect the adsorption of target species on polymers such as temperature, pH, and concentration were evaluated. The selectivity and reusability studies were also investigated.

It is concluded that MIPs showed better adsorption capacity than NIPs for all solvents for cholic acid. The adsorption sequencing is MIP-TMT > MIP-BUT > MIP EGDMA. The maximum adsorption achieved with ethyl alcohol. The adsorption of cholic acid varies with chancing pH for all produced MIPs and NIPs. It is concluded that the adsorption of cholic acid is not affected by the temperature. The adsorption of cholic acid is followed as L type from Giles adsorption isotherms. The thermodynamic parameters are proved the physical nature of adsorption process. The studies conducted with deoxycholic acid, taurocholic acid that is homolog to cholic acid showed that produced MIPs are highly selective for cholic acid.

1. Guyton, A.C.; Hall, J.E. Textbook of Medical Physiology. WB Saunders Comp., Turkish press: USA, 2000, pp 827.

2. Mattern, S.; Matern, H.; Farthmann, H.; Gerok, W. Hepatic and extrahepatic elucuranidation of bile acids in man, characterization of bile acid uridine 5'-diphosphate-glucuronosyltransferase in hepatic, renal, and intestinal microsomes. J. Clin. Invest. 1984, 74, 402-410.

3. Hofmann, A.; Mysels, K. Bile acid solubility and precipitation in vitro and in vivo: the role of conjugation, pH, and Ca+2 ions, J. Lipid Res. 1992, 33, 617-626.

4. Rani, K.; Garg, P.; Pundir, C.S. Discrete analysis of bile acid in serum and bile with 3α-hydroxysteroid dehydrogenase and diaphorase immobilized onto alkylamine glass beads. Indian J. Biochem. Biophys. 2006, 43, 98-104.

5. Okutucu, B.; Önal, S. Molecularly imprinted polymers for separation of various sugars from human urine. Talanta 2011, 87, 74-79.

6. Li, S.; Huang, X.; Zheng, M.; Li, W. Molecularly imprinted polymers: modulating molecular recognition by a thermal phase transition in the binding framework. Anal. Bioanal. Chem. 2008, 392, 177-185.

7. Lu, Y.; Li, C.; Liu, X.; Huang, W. Molecular recognition through the exact placement of functional groups on non-covalent molecularly imprinted polymers. J. Chromatogr. A. 2002, 950, 89-97.

8. Mosbach, K.; Ramson, O. The emerging technique of molecular imprinting and its future impact on biotechnology. Biotechnol. 1996, 14, 163-170.

9. Wulff, G.; Poll, H.G. Influence of the structure of the binding sites on the selectivity for racemic resolution. Makromol. Chem. 1987, 188, 741-750.

10. Ramström, O.; Ansell, R.J. Molecular imprinting technology: challenges and prospects for the future. Chirality 1998, 10, 195-209.

11. Marty, J.D.; Mauzac, M. Molecular Imprinting: State of the Art and Perspectives. Adv. Polym. Sci. 2005, 172, 1-35.

12. Boonpangrak, S.; Whitcombe, M.J.; Prachayasittikul, V.; Mosbach, K.; Lei Ye, L. Preparation of molecularly imprinted polymers using nitroxide-mediated living radical polymerization. Biosens. Bioelectron. 2006, 22, 349-354.

13. Kriz, D.; Ramstroem, O.; Svensson, A.; Mosbach, K. Biomimetic sensor based on a molecularly imprinted polymer as a recognition element combined with fiber-optic detection. Anal. Chem. 1995, 67(13), 2142-2144.

14. Yavuz, H.; Karakoç, V.; Türkmen, D.; Say, R.; Denizli, A. 8-Synthesis of cholesterol imprinted polymeric particles. Int. J. Biol. Macromol. 2007, 41(1), 8-15.

15. Urban, J.; Jandera, P.; Schoenmakers, P. Preparation of monolithic columns with target mesopore-size distribution for potential use in size-exclusion chromatography. J. Chromatog. A. 2007, 1150, 279-289.

16. Seebach, A.; Seidel-Morgenstern, A. Enantioseparation on molecularly imprinted monoliths-preparation and adsorption isotherms. Anal. Chim. Acta 2007, 591, 57-62.

17. Lopez, M.; Perez, L.; Garcia, M.; Vilarino, J.; Rodriguez, M.; Losada, L. Preparation, evaluation and characterization of quercetin-molecularly imprinted polymer for preconcentration and clean-up of catechins. Anal. Chim. Acta 2012, 721, 68-78.

18. Baydemir, G.; Bereli, N.; Andaç, M.; Say, R.; Galaev, I.; Denizli, A. Supermacroporous poly(hydroxyethyl methacrylate) based cryogel with embedded bilirubin imprinted particles. React. Funct. Polym. 2009, 69, 36-42.

19. Piletsky, S.A.; Karim, K.; Piletska, E.V.; Day, C.J.; Freebairn, K.W.; Legge, C.; Turner, A.P.F. Recognition of ephedrine enantiomers molecularly imprinted polymers designed using a computational approach. Analyst. 2001, 126, 1826-1830.

20. Wang, Y.; Zhang, J.; Zhu, X.; Yu, A. Specific binding of cholic acid by cross-linked polymers prepared by the hybrid imprinting method. Polymer. 2007, 48, 5565-5571.

21. Roda, A.; Kricka, L.A.; DeLuca, M.; Hofmann, A.F. Bioluminescence measurement of primary bile acids using immobilized 7-hydroxy-steroid dehydrogenase: application to serum bile acids. J. Lipid Res. 1982, 23, 1354-1360.

22. Ewing Galen, W. Instrumental Methods of Chemical Analysis. Fourth edition. 1975, Tokyo, Japan.

23. Yang, L.; Xu, Y.; Su, Y.; Wu, J.; Zhao, K.; Chen, J.; Wang, M. FT-IR spectroscopic study on the variations of molecular structures of some carboxyl acids induced by free electron laser. Spectrochim. Acta A. 2005, 62, 1209-1215.

24. Peniche, C.; Argüelles-Monal, W.; Davidenko, N.; Sastre, R.; Gallardo, A.; Roman, J.S. Self-curing membranes of chitosan/PAA IPNs obtained by radical polymerization preparation characterization and interpolymer complexation. Biomaterials 1999, 20, 1869-1878.

25. Wang, Y.; Zhang, J.; Zhu, X.; Yu, A. Specific binding of cholic acid by cross-linked polymers prepared by the hybrid imprinting method. Polymer 2007, 48, 5565-5571.

26. Gao, B.; Lu, J.; Chen, Z.; Guo, J. Preparation and recognition performance of cholic acid-imprinted material prepared with novel surface-imprinting technique. Polymer. 2009, 50, 3275-3284.

27. Cabral, D.; Hamilton, J.; Small, D. M. The ionization behavior of bile acids in different aqueous environments. J. Lipid Res. 1986, 27, 334-343.

28. Giles, C.H.; Macewan, T.H.; Nakhwa, S.N.; Smith, D. Studies in adsorption part XI. A system of classification of solution adsorption isotherms and its use in diagnosis of adsorption mechanisms in measurement of specific surfaces areas of solids. J. Chem. Soc. 1960, 3973-3993.

29. Saraydın, D.; Karadağ, E. A comparison of adsorption isotherms of crosslinked poly(N-vinlypyrrolidone)/ Basic brown 1 binding System. Tr. J. of Chem. 1996, 20, 234-243.

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