Citation: LIU Jun-Bo, TANG Shan-Shan, DAI Zheng-Qiang, WANG Yan, GAO Qian, JIN Rui-Fa. Computer Simulation and Experimental Investigations of Phenobarbital Molecular Imprinting System[J]. Chinese Journal of Structural Chemistry, ;2016, 35(12): 1840-1848. doi: 10.14102/j.cnki.0254-5861.2011-1238 shu

Computer Simulation and Experimental Investigations of Phenobarbital Molecular Imprinting System

LIU Jun-Bo ^a,*,, ,
TANG Shan-Shan ^a,*,, ,
DAI Zheng-Qiang ^a ,
WANG Yan ^a ,
GAO Qian ^a ,
JIN Rui-Fa ^b

a.
College of Resources and Environment, Jilin Agricultural University, Changchun 130118, China
b.
College of Chemistry and Chemical Engineering, Chifeng University, Chifeng 024000, China

Corresponding author: LIU Jun-Bo, liujb@mail.ccut.edu.cn TANG Shan-Shan, tangshanshan81@163.com
Received Date: 8 April 2016

Fund Project: Science and Technology Development Program of Jilin Province 20150101018JC and 20130206099SFNational Natural Science Foundation of China 21302062 and 21563002

Figures(5)

The interaction process between the phenobarbital (PHN) and acrylamide (AM) was studied using the M062X/6-31G(d,p) method. The PHN and AM were used as the template and functional monomer, respectively. The molecular electrostatic potential (MEP) was simulated for predicting the reactive sites. The atoms in molecules theory helped to reveal the imprinting mechanism and optimize the molar ratios for PHN and AM. The molecular imprinted polymers (MIPs) containing PHN were synthesized through the precipitation polymerization. The diameter range of the obtained MIPs was from 150 to 390 nm. According to the computational results, MIPs with the molar ratio of PHN and AM equal to 1:6 showed high selective adsorption for PHN. The apparent maximum adsorption quantity (Q_max) of MIPs toward PHN was 7.9 mg/g, and the Q_max of nonimprinted polymer microspheres (NIPs) was 3.2 mg/g. Herein, the studies can provide theoretical and experimental references for the controllable fabrication of MIPs.
- phenobarbital,
- acrylamide,
- molecular imprinting polymers,
- simulation,
- preparation
1. [1]
  Moein M. M, Javanbakht M, Karimi M, Akbari-Adergani B. Molecularly imprinted sol-gel nanofibers based solid phase microextraction coupled on-line with high performance liquidchromatography for selective determination of acesulfame[J]. Talanta, 2015,134:340-347. doi: 10.1016/j.talanta.2014.11.011
2. [2]
  Zhang Y. Q, Shan X, Gao X. Q. Development of a molecularly imprinted membrane for selective separation of flavonoids[J]. Sep. Purif. Technol, 2011,76:337-344. doi: 10.1016/j.seppur.2010.10.024
3. [3]
  Ji J, Zhou Z, Zhao X. L, Sun J. D, Sun X. L. Electrochemical sensor based on molecularly imprinted film at Au nanoparticles-carbon nanotubes modified electrode for determination of cholesterol[J]. Biosens. Bioelectron, 2015,66:590-595. doi: 10.1016/j.bios.2014.12.014
4. [4]
  Zhai H. Y, Su Z. H, Chen Z. G, Liu Z. P, Yuan K S, Huang L. Molecularly imprinted coated graphene oxide solid-phase extraction monolithic capillary column for selective extraction and sensitive determination of phloxine B in coffee bean[J]. Anal. Chim. Acta, 2015,865:16-21. doi: 10.1016/j.aca.2015.01.028
5. [5]
  Wyszomirski M, Prus W. Molecular modelling of a template substitute and monomers used in molecular imprinting for aflatoxin B1 micro-HPLC analysis[J]. Mol. Simulat, 2012,38:892-895. doi: 10.1080/08927022.2012.667876
6. [6]
  Luo D, Zhao Z, Zhang L, Wang Q, Wang J. On the structure of molecularly imprinted polymers by modifying charge on functional groups through molecular dynamics simulations[J]. Mol. Simulat, 2013,40:431-438.
7. [7]
  Su T. T, Liu J. B, Tang S. S, Chang H. B, Jin R. F. Theoretical study on the structures and properties of phenobarbital imprinted polymers.Chin[J]. J. Struct. Chem, 2014,33:1421-1430.
8. [8]
  Liu J. B, Shi Y, Tang S. S, Jin R. F. Theoretical and experimental research on the self-assembled system of molecularly imprinted polymers formed by salbutamol and methacrylic acid[J]. J. Sep. Sci, 2015,38:1065-1071. doi: 10.1002/jssc.201401309
9. [9]
  Mujahid A, Iqbal N, Afzal A. Bioimprinting strategies: from soft lithography to biomimetic sensors and beyond[J]. Biotechnol. Adv, 2013,31:1435-1447. doi: 10.1016/j.biotechadv.2013.06.008
10. [10]
  Hua K. C, Zhang L, Zhang Z. H, Guo Y, Guo T. Y. Surface hydrophilic modification with a sugar moiety for a uniform-sized polymer molecularly imprinted for phenobarbital in serum[J]. Acta Biomater, 2011,7:3086-3093. doi: 10.1016/j.actbio.2011.05.006
11. [11]
  Hu S. G, Wang S. W, He X. W. An amobarbital molecularly imprinted microsphere for selective solid-phase extraction of phenobarbital from human urine and medicines and their determination by high-performance liquid chromatography[J]. Analyst, 2003,128:1485-1489. doi: 10.1039/b310775b
12. [12]
  Yoshimatsu K, Reimhult K, Krozer A, Mosbacha K, Sodeb K, Yea L. Uniform molecularly imprinted microspheres and nanoparticles prepared by precipitation polymerization: the control of particle suitable for different analytical applications[J]. Anal. Chim. Acta, 2007,584:112-121. doi: 10.1016/j.aca.2006.11.004
13. [13]
  Sun J. N, Liu J. B, Tang S. S, Jin R. F. Theoretical researches on the self-assembly system of ciprofloxacin imprinted polymers[J]. Chin. J. Struct. Chem, 2013,32:1204-1210.
14. [14]
  Siripairoj W, Kaewchada A, Jaree A. Synthesis of molecularly imprinted polymers for the separation of gamma-oryzanol by using methacrylic acid as functional monomer[J]. J. Taiwan. Inst. Chem. E, 2014,45:338-346. doi: 10.1016/j.jtice.2013.06.035
15. [15]
  Gohary N. A. E, Madbouly A, Nashar R. M. E, Mizaikoff B. Synthesis and application of a molecularly imprinted polymer for the voltammetric determination of famciclovir[J]. Biosens. Bioelectron, 2015,65:108-114. doi: 10.1016/j.bios.2014.10.024
16. [16]
  Bai J. W, Zhong F. C, Liu X. Y, Zhang J. H. Preparation and evaluation of magnetic imprinted polymers for 2,4,6-trinitrotoluene by surface imprinting[J]. Poly. Int, 2014,63:1487-1493. doi: 10.1002/pi.2014.63.issue-8
17. [17]
  Wen Z, Ni T, Jia X, Wang G. P, Long W, Li X. L, Liao S, Hou D. Synthesis, recognition characteristics and properties of l-3-n-butylphthalide molecularly imprinted polymers as sorbent for solid-phase extraction through precipitation polymerization[J]. Mat. Sci. Eng. C, 2015,53:166-174. doi: 10.1016/j.msec.2015.04.034
18. [18]
  Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Baroe, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi I.; Gomperts R.; Martin R. L.; Fox D. J, Keith T, Al-Laham M. A, Peng C. Y, Nanayakkara A, Gonzalez C, Challacombe M, Gill P. M. W, Johnson B, Chen W, Wong M. W, Andres J. L, Gonzalez C, Head-Gordon M, Replogle E. S, Pople J. A.Gaussian 09, Revision A.2 Pittsburgh PA: Gaussian Inc, 2009.
19. [19]
  Bader R. F. W. A quantum theory of molecular structure and its applications[J]. Chem. Rev, 1991,91:893-928. doi: 10.1021/cr00005a013
20. [20]
  Bhawani Datt J, Anubha S, Poonam T, Sudha J. Molecular structure, vibrational spectra and HOMO, LUMO analysis of yohimbine hydrochloride by density functional theory and ab initio Hartree-Fock calculations[J]. Spectrochim. Acta Part A, 2011,82:270-278. doi: 10.1016/j.saa.2011.07.047
21. [21]
  Popelier P. L. A. Characterization of a dihydrogen bond on the basis of the electron density[J]. J. Phys. Chem. A, 1998,102:1873-1878. doi: 10.1021/jp9805048
1. [1]
  SU Ting-Ting , LIU Jun-Bo , TANG Shan-Shan , CHANG Hai-Bo , JIN Rui-Fa . Theoretical Study on the Structures and Properties of Phenobarbital Imprinted Polymers. Chinese Journal of Structural Chemistry, 2014, 33(10): 1421-1430.
2. [2]
  Yu Min WU , De Jun SUN , Tao WU , Chun Guang ZHANG . Synthesis and Characterization of the Terpolymer of Itaconic Acid with Acrylamide and 2-Acrylamido-2-methylpropanesulfonic Acid. Chinese Chemical Letters, 2001, 12(5): 411-412.
3. [3]
  Sheng Xian XU , Guo Qiang HU , Qing Yin WU , Yu Lin SONG . Preparation and Characterization of Molybdotungstoniobogermanic Acid. Chinese Chemical Letters, 1998, 9(5): 505-508.
4. [4]
  Qing Hai CAI , Yong Kui SHAN , Li Yi DAI , Bi Xia SU , Ming Yuan HE . Preparation and Characterization of New Type Ionic Liquids. Chinese Chemical Letters, 2003, 14(5): 523-524.
5. [5]
  Yu Ping WU , Chun Rong WAN , Chang Yin JIANG , Jian Jun LI , Yang Xing LI . Preparation of Anode Material for Lithium Ion Battery by Chemical Oxidation. Chinese Chemical Letters, 1999, 10(4): 339-340.
6. [6]
  De Jun LIU , Zi Xing SHAN , Rong WANG , Jin Gui QIN . Preparation for Supramolecular Complexes of Chiral Diols BDPDD, DMBDPD and BINOL with Some Prochiral Compounds. Chinese Chemical Letters, 2003, 14(4): 375-378.
7. [7]
  Qi Chun ZHANG , Pei Ji WU , Ke Jian JIANG , Rui Song DING , Yan Qiao WANG , Dao Ben ZHU . Preparation and Properties of (BEDT-TTF)₂Br3H₂O Salt. Chinese Chemical Letters, 1999, 10(2): 179-182.
8. [8]
  Dao Rong LI , Ling Na SUN , Chang Wen HU . Simple Preparation of the Photocatalyst of Sn²⁺-doped Titania. Chinese Chemical Letters, 2006, 17(8): 1089-1092.
9. [9]
  Yu ZHANG , Ming MA , Ning GU , Ling XU , Kun Ji CHEN . Preparation of Silver Nanoshells on Silica Particles by a Simple Two-step Process. Chinese Chemical Letters, 2004, 15(8): 1005-1008.
10. [10]
  Zhi Yong WANG , Chao JIANG , Ji Hui WU , Qing Xiang GUO . A Novel Palladium-Catalyzed Reaction and Its Application in Preparation of Derivatives of Stilbazols. Chinese Chemical Letters, 2001, 12(5): 399-402.
11. [11]
  Wei Liang XU , Ji Dong LIU , Yan Ping SUN . Preparation of a Cyclomaltoheptaose (β-cyclodextrin) Cross-linked Chitosan Derivative via Glyoxal or Glutaraldehyde. Chinese Chemical Letters, 2003, 14(7): 767-770.
12. [12]
  Jun ZHAO , Shu Feng CHEN , Xiao Tian LIANG . N-Arylindne 1,4-Cycloaddition Reaction.Preparation of Substituted Hexahydrofurol [3,2-c] quinolines. Chinese Chemical Letters, 1998, 9(11): 983-985.
13. [13]
  Zheng DUAN , Zhong Xian LI , Yang Jie WU . Iodine Mediated Efficient Formation of Ferrocenylcyanide in Aqueous Solution. Chinese Chemical Letters, 2006, 17(7): 880-882.
14. [14]
  Quan BAI , Yu KONG , Xin Du GENG . Studies on the Renaturation with Simultaneous Purification of Recombinant Human Proinsulin with Unit of Simultaneous Renaturation and Purification of Protein in Semi-preparative Scale. Chinese Chemical Letters, 2003, 14(8): 824-827.
15. [15]
  Tong Shuang LI , Zhan Hui ZHANG , Tong Shou JIN , Yu Lin LI . A Mild and Practical Procedure for Tetrahydropyranylation of Alcohols and Phenols Catalysed by Anhydrous Ferrous Sulfate. Chinese Chemical Letters, 1998, 9(3): 241-244.
16. [16]
  Ming Zhu LIU , Sheng Yi ZHANG , Yu Hua SHEN , Ming Liang ZHANG . Selenium Nanoparticles Prepared from Reverse Microemulsion Process. Chinese Chemical Letters, 2004, 15(10): 1249-1252.
17. [17]
  Yong YANG , Lei ZHANG , Wei FAN , Xiao Hong WANG , Bin LI , Jing Fu LIU . Synthesis of a New Polyoxometalate Loaded Stearic Acid Nanoparticles. Chinese Chemical Letters, 2004, 15(10): 1255-1257.
18. [18]
  YU Xiao-Bin , LIU Jun-Bo , YUAN Xing . Simulation and Preparation of Molecular Imprinting System with Atrazine as Template. Chinese Journal of Structural Chemistry, 2015, 34(4): 488-496. doi: 10.14102/j.cnki.0254-5861.2011-0603
19. [19]
  SU Qiong , ZHAO Qing , AN Xiao-Xin , WANG Yan-Bin , LI Xiao-Yan , DONG Wen-Kui . Syntheses, Crystal Structures, Hirshfeld Surface Analyses, Thermal and Fluorescent Properties of Cu(Ⅱ) and Ni(Ⅱ) Salamo-Type Complexes. Chinese Journal of Inorganic Chemistry, 2019, 35(3): 524-536. doi: 10.11862/CJIC.2019.042
20. [20]
  ZHU Zhaoyang , JIANG Aifeng , XIA Debin , WANG Ping , LIN Kaifeng , FAN Jizhuang , FAN Ruiqing , YANG Yulin . Stability of Aluminum Hydride Etherates and Its Solid-State Conversion to Alpha-Aluminum Hydride. Chinese Journal of Applied Chemistry, 2019, 36(9): 1069-1075. doi: 10.11944/j.issn.1000-0518.2019.09.190032

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