Abstract
The aim of this work was to prepare lactose imprinted polymer and study of its selectivity for the recognition of different mono- and disaccharides. A series of molecularly imprinted polymers (MIPs) against lactose were synthesized and their binding properties were compared with a Blank non-imprinted polymer. Methacrylamide (MAAM) and ethylene glycol dimethacrylate were used as functional monomer and cross-linker, respectively. Dimethylsulfoxide was also applied as polymerization solvent. Different lactose:MAAM ratios were applied and optimized MIP was selected in a conventional batch adsorption study. The dissociation constant and maximum binding sites of polymer were determined using the Scatchard analysis. The selectivity of MIP for different mono- and disaccharides was also evaluated. The results indicated that the shape of cavity and orientation of functional monomers in binding sites and the spatial arrangement of hydroxyl groups in saccharide structure were responsible for the selectivity of lactose imprinted polymer.
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Abbreviations
- AIBN:
-
2,2′-Azo-bis-iso-butyronitrile
- BF:
-
Binding factor
- B max :
-
Maximum binding sites
- EGDMA:
-
Ethylene glycol dimethacrylate
- K D :
-
Dissociation constant
- MAAM:
-
Methacrylamide
References
B. Okutucu, S. Onal, A. Telefoncu, Talanta 78, 1190 (2009)
S.L. Flitsch, R.V. Ulijn, Nature 421, 219 (2003)
P. Sears, C.H. Wong, Angew. Chem. Int. Ed. Engl. 38, 2300 (1999)
P. Sears, C.H. Wong, Cell. Mol. Life Sci. 54, 223 (1998)
A. Varki, Glycobiology 3, 97 (1993)
R.D. Palmiter, Nature 221, 912 (1969)
J. Babu, S. Kumar, P. Babu, J.H. Prasad, U.C. Ghoshal, Am. J. Clin. Nutr. 91, 140 (2010)
B.T. Cooper, Lancet 1, 465 (1985)
P. Jellema, F.G. Schellevis, D.A. van der Windt, C.M. Kneepkens, H.E. van der Horst, QJM 103, 555 (2010)
D.A. Savaiano, C.J. Boushey, G.P. McCabe, J. Nutr. 136, 1107 (2006)
T. Sahi, Scand. J. Gastroenterol. Suppl. 202, 7 (1994)
S.A. Mohajeri, S.A. Ebrahimi, J. Sep. Sci. 31, 3595 (2008)
S.A. Mohajeri, H. Hosseinzadeh, F. Keyhanfar, J. Aghamohammadian, J. Sep. Sci. 33, 2302 (2010)
S.A. Mohajeri, G. Karimi, M.R. Khansari, Anal. Chim. Acta 683, 143 (2010)
S.A. Mohajeri, G. Karimi, J. Aghamohammadian, M.R. Khansari, J. Appl. Polym. Sci. 121, 3590 (2011)
S.A. Mohajeri, B. Malaekeh-Nikouei, H. Sadegh, Drug Dev. Ind. Pharm. 38, 616 (2012)
B. Rezaei, S. Mallakpour, O. Rahmanian, J. Iran. Chem. Soc. 7, 1004 (2010)
M.S. Tehrani, M.T. Vardini, P.A. Azar, S.W. Husain, J. Iran. Chem. Soc. 7, 759 (2010)
H. Zhang, L. Ye, K. Mosbach, J. Mol. Recognit. 19, 248 (2006)
B. Okutucu, S. Onal, Talanta 87, 74 (2011)
S. Striegler, M. Dittel, Anal. Chim. Acta 484, 53 (2003)
P. Parmpi, P. Kofinas, Biomaterials 25, 1969 (2004)
Y. Yoshimi, A. Narimatsu, K. Nakayama, S. Sekine, K. Hattori, K. Sakai, J. Artif Organs 12, 264 (2009)
C. Kirk, M. Jensen, C.N. Kjaer, M.M. Smedskjaer, K.L. Larsen, R. Wimmer, D. Yu, Biosens. Bioelectron. 25, 623 (2009)
G.L. Miller, Anal. Chem. 31, 426 (1959)
M. Dubois, K.A. Gilles, J.K. Hamilton, P.A. Rebers, F. Smith, Anal. Chem. 28, 350 (1956)
G. Wulff, Angew. Chem. Int. Ed. 34, 1812 (1995)
R. Rajkumar, A. Warsinke, H. Mohwald, F.W. Scheller, M. Katterle, Biosens. Bioelectron. 22, 3318 (2007)
S. Shinkai, M. Takeuchi, Biosens. Bioelectron. 20, 1250 (2004)
J.L. Dashnau, K.A. Sharp, J.M. Vanderkooi, J. Phys. Chem. B 109, 24152 (2005)
T. Pap, G. Horvai, J. Chromatogr. A 1034, 99 (2004)
H.W. Sun, F.X. Qiao, G.Y. Liu, J. Chromatogr. A 1134, 194 (2006)
Z. Xu, D. Kuang, L. Liu, Q. Deng, J. Pharm. Biomed. Anal. 45, 54 (2007)
Z. Sun, W. Schussler, M. Sengl, R. Niessner, D. Knopp, Anal. Chim. Acta 620, 73 (2008)
Y. Liu, K. Hoshina, J. Haginaka, Talanta 80, 1713 (2010)
A. Ersoz, A. Denizli, A. Ozcan, R. Say, Biosens. Bioelectron. 20, 2197 (2005)
W. Wang, S. Gao, B. Wang, Org. Lett. 1, 1209 (1999)
J. Nilsson, P. Spegel, S. Nilsson, J. Chromatogr. B Analyt. Technol. Biomed. Life Sci. 804, 3 (2004)
R. Suedee, T. Srichana, R. Chotivatesin, G.P. Martin, Drug Dev. Ind. Pharm. 28, 545 (2002)
Acknowledgments
We gratefully acknowledge the Vice Chancellor of Research, Mashhad University of Medical Sciences for financial support through the grant number 88819. The results described in this paper were part of a PharmD student’s thesis.
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The authors have declared no conflict of interest.
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Hadizadeh, F., Zakerian, A. & Mohajeri, S.A. Non-covalently lactose imprinted polymers and recognition of saccharides in aqueous solutions. J IRAN CHEM SOC 10, 207–212 (2013). https://doi.org/10.1007/s13738-012-0142-z
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DOI: https://doi.org/10.1007/s13738-012-0142-z