Determination of Effective Functional Monomer and Solvent for R(+)-Cathinone Imprinted Polymer Using Density Functional Theory and Molecular Dynamics Simulation Approaches
Andrian Saputra(1), Karna Wijaya(2), Ria Armunanto(3), Lisa Tania(4), Iqmal Tahir(5*)
(1) Department of Chemical Education, Faculty of Teacher Training and Education, University of Lampung, Bandar Lampung 35145, Indonesia
(2) Austrian-Indonesian Center for Computational Chemistry, Department of Chemistry, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(3) Austrian-Indonesian Center for Computational Chemistry, Department of Chemistry, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(4) Department of Chemical Education, Faculty of Teacher Training and Education, University of Lampung, Bandar Lampung 35145, Indonesia
(5) Austrian-Indonesian Center for Computational Chemistry, Department of Chemistry, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(*) Corresponding Author
Abstract
Determination of effective functional monomer and solvent for R(+)-cathinone imprinted polymer through modeling has been done using density functional theory (DFT) and molecular dynamics (MD) simulation approaches. The selection criteria of the best monomer and solvent are based on the classical potential energy (ΔEMM) from molecular dynamics simulation and confirmed further by quantum potential energy (ΔEDFT) from DFT calculation. The DFT calculation was performed in B3LYP exchange-correlation functional within the 6-31G(d) basis set of function including Polarizable Continuum Model (PCM) solvation effect. From this research, it is obtained that N,N’-methylene bis acrylamide and chloroform are respectively the best candidates for effective functional monomer and solvent, for the synthesis of R(+)-cathinone imprinted polymer.
Keywords
Full Text:
Full Text PDFReferences
[1] Jones, S., Fileccia, E.L., Murphy, M., Fowler, M.J., King, M.V., Shortall, S.E., Wigmore, P.M., Green, A.R., Fone, K.C., and Ebling, F.J., 2014, Cathinone increases body temperature, enhances locomotor activity, and induces striatal c-fos expression in the Siberian hamster, Neurosci. Lett., 559, 34–38.
[2] Correll, D., 2013, Development of a Rapid SPME/GC-MS Method for the Detection and Quantification of Synthetic Cathinones in Oral Fluid, Theses, Trinity College, Hartford.
[3] Santali, E.Y., Cadogan, A.K., Daeid, N.N., Savage, K.A., and Sutcliffe, O.B., 2011, Synthesis, full chemical characterisation and development of validated methods for the quantification of (±)-4′-methylmethcathinone (mephedrone): A new “legal high”, J. Pharm. Biomed. Anal., 56 (2), 246–255.
[4] Sellergren, B., and Allender, C., 2005, Molecularly imprinted polymers: A bridge to advanced drug delivery, Adv. Drug Delivery Rev., 57 (12), 1733–1741.
[5] Danielsson, B., 2008, Artificial receptors, Adv. Biochem. Eng. Biotechnol., 109, 97–122.
[6] Bakas, I., Oujji, N.B., Moczko, E., Istamboulie, G., Piletsky, S., Piletska, E., Ait-Addi, E., Ait-Ichou, I., Noguer, T., and Rouillon, R., 2013, Computational and experimental investigation of molecular imprinted polymers for selective extraction of dimethoate and its metabolite omethoate from olive oil, J. Chromatogr. A, 1274, 13–18.
[7] Nicholls, I.A., Karlsson, B.C.G., Olsson, G.D., and Rosengren, A.M., 2013, Computational strategies for the design and study of molecularly imprinted materials, Ind. Eng. Chem. Res., 52 (39), 13900–13909.
[8] Wei, S., Jakusch, M., and Mizaikoff, B., 2007, Investigating the mechanisms of 17β-estradiol imprinting by computational prediction and spectroscopic analysis, Anal. Bioanal. Chem., 389 (2), 423–431.
[9] Gholivand, M.B., Torkashvand, M., and Malekzadeh, G., 2012, Fabrication of an electrochemical sensor based on computationally designed molecularly imprinted polymers for determination of cyanazine in food samples, Anal. Chim. Acta, 713, 36–44.
[10] Saputra, A., Wijaya, K., Ahmad, M.N., and Tahir, I., 2013, Penggunaan metode semiempirik AM1 untuk pemilihan monomer fungsional efektif pada prasintesis polimer tercetak diazinon, VALENSI, 3 (1), 1–9.
[11] Del Sole, R., Lazzoi, M.R., Arnone, M., Della Sala, F., Cannoletta, D., and Vasapollo, G., 2009, Experimental and computational studies on non-covalent imprinted microspheres as recognition system for nicotinamide molecules, Molecules, 14 (7), 2632–2649.
[12] Dong, C., Li, X., Guo, Z., and Qi, J., 2009, Development of a model for the rational design of molecular imprinted polymer: Computational approach for combined molecular dynamics/quantum mechanics calculations, Anal. Chim. Acta, 647 (1), 117–124.
[13] Albrecht, M., 2007, Supramolecular chemistry-general principles and selected examples from anion recognition and metallosupramolecular chemistry, Naturwissenschaften, 94 (12), 951–966.
[14] Manali, K., Monojit, D., and Sukla, V.J., 2012, Solvent effect on extraction of Gallic acid from Amalaki churna (Emblica officinalis Gaertn.) to reduce matrix effect using HPTLC and UV-spectroscopy with 12 different nature solvents, IRJP, 3 (6), 155–158.
[15] García, E.S., 2006, Computational Study of Weakly Interacting Complexes, Dissertation, Fakultät für Chemie Ruhr-Universität Bochum, Bochum.
[16] Karim, K., Breton, F., Rouillon, R., Piletska, E.V., Guereiro, A., Chianella, I., and Piletsky, S.A., 2005, How to find effective functional monomers for effective molecularly imprinted polymers?, Adv. Drug Delivery Rev., 57 (12), 1795–1808.
[17] van der Spoel, D., Lindahl, E., Hess, B., van Buuren, A.R., Apol, E., Meulenhoff, P.J., Tieleman, D.P., Sijbers, A.L.T.M., Feenstra, K.A., van Drunen, R., and Berendsen, H.J.C., 2010, Gromacs User Manual version 4.5.6., www.gromacs.org.
[18] Humphrey, W., Dalke, A., and Schulten, K., 1996, VMD: Visual molecular dynamics, J. Mol. Graphics, 14 (1), 33–38.
[19] Oostenbrink, C., Villa, A., Mark, A.E., and van Gunsteren, W.F., 2004, A biomolecular force field based on the free enthalpy of hydration and solvation: The GROMOS force-field parameter sets 53A5 and 53A6, J. Comput. Chem., 25 (13), 1656–1676.
[20] Schüttelkopf, A.W., and van Aalten, D.M., 2004, PRODRG: A tool for high-throughput crystallography of protein-ligand complexes, Acta Crystallogr., Sect. D: Biol. Crystallogr., 60 (Pt 8), 1355–1363.
[21] Tomasi, J., Mennucci, B., and Cammi, R., 2005, Quantum mechanical continuum solvation models, Chem. Rev., 105 (8), 2999–3093.
DOI: https://doi.org/10.22146/ijc.24311
Article Metrics
Abstract views : 2697 | views : 2588Copyright (c) 2017 Indonesian Journal of Chemistry
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.
Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.
View The Statistics of Indones. J. Chem.