Radiation Synthesis of Molecularly Imprinted Hydroxyethylmethacrylate-based Matrices for Glucose Recognition

Abstract

I n this study, 2-hydroxyethyl methacrylate (HEMA) was used as functional monomer and diethylene glycol diacrylate (DEGDA) and polyethylene glycol (200) diacrylate (PEG(200)DA) were used as crosslinking agents to imprint D(+)glucose. D(+)glucose imprinted polymers were prepared in the presence of dimethyl sulfoxide (DMSO) /isopropyl alcohol (IPA) (3/1, v/v) at room temperature, in the air by radiation-induced polymerization/ crosslinking. The control polymers were synthesized by the same procedure in the absence of D(+)glucose. In order to evaluate the recognition and separation properties of the imprinted system high performance liquid chromatography (HPLC) experiments were carried out where β (-) lactose, D(+)glucose and glycerol were used as analytes. To increase the affinity of the template to the stationary phase polarity of the mobile phase was decreased by the addition of acetonitrile into water. Optimum composition of acetonitrile/water (1/5 v/v) was determined according to the swelling experiments. The sizes of the cavities in the polymeric networks were determined by positron annihilation lifetime spectroscopy (PALS). The average radii of cavities were found as 0.254 and 0.279 nm for freeze-dried imprinted polymers prepared by using PEG(200)DA after swollen in water and acetonitrile/water mixture (1/5 by volume), respectively.

Keywords

• Molecularly imprinted polymers,poly(2-hydroxyethyl methacrylate),glucose recognition,gamma irradiation

References

1. B. Sellergren, Direct drug determination by selective sample enrichment on an imprinted polymer, Anal. Chem., 66 (1994) 1578-1582.
2. L. Fischer, R. Müller, B. Ekberg, K. Mosbach, Direct enantioseparation of beta-adrenergic blockers using a chiral stationary phase prepared by molecular imprinting, J. Am. Chem. Soc., 113 (1991) 9358-9360.
3. S.A. Piletsky, E.V. Piletskaya, A.V. Elgersma, K. Yano, I. Karube, Y.P. Parhometz, A.V. El’skaya, Atrazine sensing by molecularly imprinted membranes, Biosens. Bioelectron., 10 (1995) 959-964.
4. D. Kriz, K. Mosbach, Competitive amperometric morphine sensor based on an agarose immobilised molecularly imprinted polymer, Anal. Chim. Acta, 300 (1995) 71-75.
5. M. Kempe, K. Mosbach, Chiral recognition of Naprotected amino acids and derivatives in molecularly imprinted polymers, Int. J. Peptide Protein Res., 44 (1994) 603-606.
6. K. Haupt, Imprinted polymers: tailor-made mimics of antibodies and receptors, Chem. Commun., (2003) 171–178
7. Y. Ren, X. Wei, M. Zhang, Adsorption character for removal Cu(II) by magnetic Cu(II) Ion imprinted composite adsorbent, J. Hazard. Mater., 158 (2008) 14-22.
8. G. Sener, L. Uzun, A. Denizli, Lysine-promoted colorimetric response of gold nanoparticles: a simple assay for ultrasensitive mercury(II) detection, Anal. Chem., 86 (2014) 514-520.

9. A. Martín-Esteban, Molecularly imprinted polymers: new molecular recognition materials for selective solid-phase extraction of organic compounds, Fresenius J. Anal. Chem., 370 (2001) 795-802.
10. R.J. Umpleby, M. Bode, K.D. Shimizu, Measurement of the continuous distribution of binding sites in molecularly imprinted polymers, Analyst, 125 (2000) 1261–1265.
11. R.J. Umpleby, S.C. Baxter, Y. Chen, R.N. Shah, K.D. Shimizu, Characterization of molecularly imprinted polymers with the Langmuir-Freundlich isotherm, Anal. Chem., 3 (2001) 4584-4591.
12. G. Wulff, R. Grobe-Einsler, A. Sarhan, Enzymeanalogue built polymers, on the specificity distribution of chiral cavities prepared in synthetic polymers, Macromol. Chem., 178 (1977) 2817-2825.
13. A. Ersöz, A. Denizli, A. Ozcan, R. Say, Molecularly imprinted ligand-exchange recognition assay of glucose by quartz crystal microbalance, Biosens. Bioelectron., 20 (2005) 2197-2202.
14. P. Parmpi, P. Kofinas, biomimetic glucose recognition using molecularly imprinted polymer hydrogels, Biomaterials, 25 (2004) 1969-1973.
15. C. Chen, G. Chen, Z. Guan, D. Lee, F.H. Arnold, Polymeric sensor materials for glucose, Polym. Prepr., 37 (1996) 216-217.
16. H. Bodugoz, O. Güven, N.A. Peppas, Glucose recognition capabilities of hydroxyethyl methacrylatebased hydrogels containing poly(ethylene glycol) chains, J. Appl. Polym. Sci., 103 (2007) 432-441.
17. Z. Ateş, O. Güven, Radiation induced molecular imprinting of D-glucose onto poly(2-hydroxyethyl methacrylate) matrices using various crosslinking agents, Rad. Phys. Chem., 79 (2010) 219-222.
18. N. Djourelov, Z. Ateş, O. Güven, M. Misheva, T. Suzuki, Positron annihilation lifetime spectroscopy of molecularly imprinted hydroxyethyl methacrylate based polymers, Polymer, 48 (2007) 2692-2699.
19. C. Yu, K. Mosbach, Molecular imprinting utilizing an amide functional group for hydrogen bonding leading to highly efficient polymers, J. Org. Chem., 62 (1997) 4057-4064.
20. B. Sellergren, K.J. Shea, Influence of polymer morphology on the ability of imprinted network polymers to resolve enantiomers, J. Chromatogr., 635 (1993) 31-49.
21. J. Brandrup, E.H. Immergut, 1989. Polymer Handbook, third ed. John Wiley & Sons Inc., USA.
22. P.B. Rathi, Determination and evaluation of solubility parameter of satranidazole using dioxane-water system, Indian J. Pharm. Sci., 72 (2010) 671-674.
23. S.J. Tao, Positronium annihilation in molecular substances, J. Chem. Phys., 56 (1972) 5499-5510.
24. M. Eldrup, D. Lightbody, J.N. Sherwood, The temperature dependence of positron lifetimes in solid pivalic acid, Chem. Phys., 63 (1981) 51-58.
25. C. Ranganathaiah, 2010. Characterization of polymer nanocomposites by free-volume measurements, S., Thomas, G.E., Zaikov, S.V., Valsaraj, A.P. Meera, (Eds.), Recent advances in polymer nanocomposites: synthesis and characterisation, Taylor & Francis Group, New York, pp. 305-335.
26. G. Knowles, The reduced glucose permeability of the isolated malpighian tubules of the blowfly calliphora vomitoria, J. Exp. Biol., 62 (1975) 327-340.