Skip to main content
SpringerLink
Log in

A comprehensive theoretical study of structural optimization, interaction energies calculations and solvent effects between ractopamine and functional monomers in molecular imprinting polymers

  • Original Paper
  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Abstract

A theoretical study on the interaction of the ractopamine (RAC) with functional monomers in the formation of imprinted polymers was investigated by means of quantum chemical calculations. In the present work, all structural optimization, interaction energies calculations and solvent effects were performed using density functional theory (DFT) method. The obtained data from five systems were used to evaluate the ability to form non-covalently bonded monomer–template complexes under vacuum and the different solvents conditions. These systems were presented by the following monomers: acrylic acid (AA), methacrylic acid (MAA), trifluoromethylacrylic acid (TFMAA), acrylamide (AAm) and methylacrylamide (MAAm). The solvent effects of pre-polymerization were considered using the solvation model based on density (SMD) in five solvents (toluene, chloroform, methanol, acetonitrile and dimethyl sulphoxide (DMSO) in this work. The results were evaluated through the solvation energy and the reaction energetics. Computer simulation of the interaction between the ractopamine and functional monomers indicated that although TFMAA has a strong interaction with the template in comparison to other complex forms in gas phase; it possesses non-specific interaction with the ractopamine molecule in solution. Moreover, MAAm was suitable for imprinting ractopamine, because the strongest interaction occurred between ractopamine and MAAm with a polymerization ratio of 1:4 in DMSO. The values of ΔG and ΔE were 26.30 and 40.51 kcal mol−1, respectively. This work may be useful for providing information for the choice of suitable functional monomer and proper solvent in the preparation of RAC molecularly imprinted polymers.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  1. Li TF, Yao T, Zhang C, Liu GY, She YX, Jin MJ, Jin F, Wang SS, Shao H, Wang J (2016) Electrochemical detection of ractopamine based on a molecularly imprinted poly-o-phenylenediamine/gold nanoparticle–ionic liquid–graphene film modified glass carbon electrode. RSC Adv 6:66949–66956

    Article  CAS  Google Scholar 

  2. Yang F, Wang PL, Wang RG, Zhou Y, Su XO, He YJ, Shi L, Yao DS (2015) Label free electrochemical aptasensor for ultrasensitive detection of ractopamine. Biosens Bioelectron 77:347–352

    Article  Google Scholar 

  3. MOA Regulation 176, Ministry of Agriculture, P.R. China. 2002

  4. Commission decision, 1996/23/EC. Off J Eur Commun L125:10

  5. Shishani E, Chai SC, Jamokha S, Aznar G, Hoffman MK (2003) Determination of ractopamine in animal tissues by liquid chromatography-fluorescence and liquid chromatography/tandem mass spectrometry. Anal Chim Acta 483:137–145

    Article  CAS  Google Scholar 

  6. Zhang LY, Chang BY, Dong T, He PL, Yang WJ, Wang ZY (2009) Simultaneous determination of salbutamol, ractopamine, and clenbuterol in animal feeds by SPE and LC–MS. J Chromatogr Sci 47:324–328

    Article  CAS  Google Scholar 

  7. Wang L, Li YQ, Zhou YK, Yang Y (2010) Determination of four β2-agonists in meat, liver and kidney by GC–MS with dual internal standards. Chromatographia 71:737–739

    Article  CAS  Google Scholar 

  8. Vulić A, Pleadin J, Perši N, Milić D, Radeck W (2012) UPLC–MS/MS determination of ractopamine residues in retinal tissue of treated food-producing pigs. J Chromatogr B 895–896:102–107

    Google Scholar 

  9. Tang C, Zhang J, Li L, Zhao Q, Bu D (2014) Ractopamine residues in urine, plasma and hair of cattle during and after treatment. J Anal Toxicol 38:149–154

    Article  CAS  Google Scholar 

  10. Zhang Y, Wang FX, Fang L, Wang S, Fang GZ (2009) Rapid determination of ractopamine residues in edible animal products by enzyme-linked immunosorbent assay: development and investigation of matrix effects. J Biomed Biotechnol 12:269–281

    Google Scholar 

  11. Wang WY, Zhang YL, Wang JY, Shi X, Ye JN (2010) Determination of β-agonists in pig feed, pig urine and pig liver using capillary electrophoresis with electrochemical detection. Meat Sci 85:302–305

    Article  CAS  Google Scholar 

  12. Yang X, Feng B, Yang P, Ding YL, Chen Y, Fei JJ (2014) Electrochemical determination of toxic ractopamine at an ordered mesoporous carbon modified electrode. Food Chem 145:619–624

    Article  CAS  Google Scholar 

  13. Chen D, Yang M, Zheng NJ, Xie N, Liu DL, Xie CF, Yao DS (2016) A novel aptasensor for electrochemical detection of ractopamine, clenbuterol, salbutamol, phenylethanolamine and procaterol. Biosens Bioelectron 80:525–531

    Article  CAS  Google Scholar 

  14. Figueiredo L, Erny GL, Santos L, Alves A (2016) Applications of molecularly imprinted polymers to the analysis and removal of personal care products: a review. Talanta 146:754–765

    Article  CAS  Google Scholar 

  15. Chen L, Wang X, Lu W, Wu X, Li J (2016) Molecular imprinting: perspectives and applications. Chem Soc Rev 45:2137–2211

    Article  CAS  Google Scholar 

  16. Zhong SA, Kong YY, Zhou L, Zhou CY, Zhang XN, Wang Y (2014) Efficient conversion of myricetin from Ampelopsis grossedentata extracts and its purification by MIP–SPE. J Chromatogr B 945–946:39–45

    Article  Google Scholar 

  17. Jiang TH, Zhao LX, Chu BL, Feng QZ, Yan W, Lin JM (2009) Molecularly imprinted solid-phase extraction for the selective determination of 17β-estradiol in fishery samples with high performance liquid chromatography. Talanta 78:442–447

    Article  CAS  Google Scholar 

  18. Benito-Peña E, Martins S, Orellana G, Moreno-Bondi MC (2008) Water-compatible molecularly imprinted polymer for the selective recognition of fluoroquinolone antibiotics in biological samples. Anal Bioanal Chem 393:235–245

    Article  Google Scholar 

  19. Liang RN, Song DA, Zhang RM, Qin W (2010) Potentiometric sensing of neutral species based on a uniform-sized molecularly imprinted polymer as a receptor. Angew Chem Int Ed 49:2556–2559

    Article  CAS  Google Scholar 

  20. Alizadeh T, Zare M, Ganjali MR, Norouzi P, Tavana B (2010) A new molecularly imprinted polymer (MIP)-based electrochemical sensor for monitoring 2,4,6-trinitrotoluene (TNT) in natural waters and soil samples. Biosens Bioelectron 25:1166–1172

    Article  CAS  Google Scholar 

  21. Kimmel DW, Leblanc G, Meschievitz ME, Cliffel DE (2012) Electrochemical sensors and biosensors. Anal Chem 84:685–707

    Article  CAS  Google Scholar 

  22. Yannopoulos SI, Lyberatos G, Theodossiou N, Wang L, Valipour M, Tamburrino A, Angelakis AN (2015) Evolution of water lifting devices (pumps) over the centuries worldwide. Water 7:5031–5060

    Article  Google Scholar 

  23. Isarankura-Na-Ayudhya C, Nantasenamat C, Buraparuangsang P, Piacham T, Ye L, Bülow L, Prachayasittikul V (2008) Computational insights on sulfonamide imprinted polymers. Molecules 13:3077–3091

    Article  CAS  Google Scholar 

  24. Yañez F, Chianella I, Piletsky SA, Concheiro A, Alvarez-Lorenzo C (2010) Computational modeling and molecular imprinting for the development of acrylic polymers with high affinity for bile salts. Anal Chim Acta 659:178–185

    Article  Google Scholar 

  25. Liu J, Dai Z, Li B, Tang S, Jin R (2014) Utilization of theoretical studies of the imprinting ratio to guide experimental research into the molecular imprinted polymers formed using enrofloxacin and methacrylic acid. J Mol Model 20:1–10

    Google Scholar 

  26. Nicholls IA, Chavan S, Golker K, Karlsson BC, Olsson GD, Rosengren AM, Suriyanarayanan S, Wiklander JG (2015) Theoretical and computational strategies for the study of the molecular imprinting process and polymer performance. Adv Biochem Eng Biotechnol 150:25–50

    CAS  Google Scholar 

  27. Cowen T, Karim K, Piletsky S (2016) Computational approaches in the design of synthetic receptors—a review. Anal Chim Acta 14:1969–1998

    Google Scholar 

  28. Valipour M (2013) Increasing irrigation efficiency by management strategies: cutback and surge irrigation. J Agric Biol Sci 8:35–43

    Google Scholar 

  29. Valipour M, Mousavi SM, Valipour R, Rezaei E (2013) A new approach for environmental crises and its solutions by computer modeling. The 1st international conference on environmental crises and its solutions, Kiseh Island, Iran

  30. Valipour M (2015) Study of different climatic conditions to assess the role of solar radiation in reference crop evapotranspiration equations. Arch Agron Soil Aci 61:679–694

    Article  Google Scholar 

  31. Valipour M (2016) Optimization of neural networks for precipitation analysis in a humid region to detect drought and wet year alarms. Meteorol Appl 23:91–100

    Article  Google Scholar 

  32. Valipour M (2016) How much meteorological information is necessary to achieve reliable accuracy for rainfall estimations? Agriculture 6:53

    Article  Google Scholar 

  33. Ghani NTA, Nashar RME, Abdel-Haleem FM, Madbouly A (2016) Computational design, synthesis and application of a new selective molecularly imprinted polymer for electrochemical detection. Electroanal 28:1530–1538

    Article  Google Scholar 

  34. Qiu XZ, Xu XY, Liang Y, Hua YB, Guo HS (2016) Fabrication of a molecularly imprinted polymer immobilized membrane with nanopores and its application in determination of β-agonists in pork samples. J Chromatogr A 1429:79–85

    Article  CAS  Google Scholar 

  35. Azimi A, Javanbakht M (2014) Computational prediction and experimental selectivity coefficients for hydroxyzine and cetirizine molecularly imprinted polymer based potentiometric sensors. Anal Chim Acta 812:184–190

    Article  CAS  Google Scholar 

  36. Barros LAD, Pereira LA, Custódio R, Rath S (2014) A novel computational approach for development of highly selective fenitrothion imprinted polymer: theoretical predictions and experimental validations. J Braz Chem Soc 25:619–628

    Google Scholar 

  37. Torkashvand M, Gholivand MB, Taherkhani F (2015) Fabrication of an electrochemical sensor based on computationally designed molecularly imprinted polymer for the determination of mesalamine in real samples. Mater Sci Eng C 55:209–217

    Article  CAS  Google Scholar 

  38. Karimian N, Gholivand MB, Taherkhani F (2015) Computational design and development of a novel voltammetric sensor for minoxidil detection based on electropolymerized molecularly imprinted polymer. J Electroanal Chem 740:45–52

    Article  CAS  Google Scholar 

  39. Fonseca MC, Nascimento CS, Borges KB (2016) Theoretical investigation on functional monomer and solvent selection for molecular imprinting of tramadol. Chem Phys Lett 645:174–179

    Article  CAS  Google Scholar 

  40. Simon S, Duran M, Dannenberg JJ (1996) How does basis set superposition error change the potential surfaces for hydrogen-bonded dimers? J Chem Phys 105:11024–11031

    Article  CAS  Google Scholar 

  41. Boys SF, Bernardi F (2002) Calculation of small molecular interactions by differences of separate total energies—some procedures with reduced errors. Mol Phys 19:553–566

    Article  Google Scholar 

  42. Barone V, Cossi M (1998) Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J Phys Chem A 102:1995–2001

    Article  CAS  Google Scholar 

  43. Marenich AV, Cramer CJ, Truhlar DG (2009) Universal solvation model based on solute electron density and on a continuum model of the solvent defined by the bulk dielectric constant and atomic surface tensions. J Phys Chem B 113:6378–6396

    Article  CAS  Google Scholar 

  44. Ahmadi F, Rezaei H, Tahvilian R (2012) Computational-aided design of molecularly imprinted polymer for selective extraction of methadone from plasma and saliva and determination by gas chromatography. J Chromatogr A 1270:9–19

    Article  CAS  Google Scholar 

  45. Frisch MJ, Trucks GW, HB Schlegel, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Jr, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2009) Gaussian 09, Revision A.02. Gaussian, Inc., Wallingford

  46. Meng SC, Li W, Yin XL, Xie JM (2013) A comprehensive theoretical study of the hydrogen bonding interactions and microscopic solvation structures of a pyridyl-urea-based hydrogelator in aqueous solution. Comput Theor Chem 1006:76–84

    Article  CAS  Google Scholar 

  47. Boonseng S, Roffe GW, Spencer J, Cox H (2015) The nature of the bonding in symmetrical pincer palladacycles. Dalton Trans 44:7570–7577

    Article  CAS  Google Scholar 

  48. Needham P (2013) Hydrogen bonding: homing in on a tricky chemical concept. Stud His Philos Sci 44:51–65

    Article  Google Scholar 

  49. Wu LQ, Sun BW, Li YZ, Chang WB (2003) Study properties of molecular imprinting polymer using a computational approach. Analyst 128:944–949

    Article  CAS  Google Scholar 

  50. Wu HY, Cui CC, Song QJ, Wang HJ, Wu AP (2009) Theoretical study of the peroxidation of chlorophenols in gas phase and aqueous solutions. J Mol Struct Theochem 916:86–90

    Article  CAS  Google Scholar 

  51. Madikizela LM, Mdluli PS, Chimuka L (2016) Experimental and theoretical study of molecular interactions between 2-vinyl pyridine and acidic pharmaceuticals used as multi-template molecules in molecularly imprinted polymer. React Funct Polym 103:33–43

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (31601549, U1507115 and 21605061), the Natural Science of Jiangsu Province (BK20161362), the Natural Science Fund for Colleges and Universities in Jiangsu Province (16KJB150045), China Postdoctoral Science Foundation (2016M601747) and was sponsored by Qing Lan Project of the Higher Education Institutions of Jiangsu Province.

Author information

Authors and Affiliations

  1. Zhenjiang Key Laboratory of Functional Chemistry, Institute of Medicine and Chemical Engineering, Zhenjiang College, Zhenjiang, 212003, China

    Haiyan Wu, Jicheng Xu & Yan Jiang

  2. School of Environment and Safety Engineering, Jiangsu University, Zhenjiang, 212013, China

    Haiyan Wu

  3. School of Chemistry and Chemical Engineering, Jiangsu University, Zhenjiang, 212013, China

    Xin Li, Suci Meng, Wenchi Zhang & Fengxian Qiu

Authors
  1. Haiyan Wu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xin Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Suci Meng
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Jicheng Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Wenchi Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yan Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Fengxian Qiu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Fengxian Qiu.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, H., Li, X., Meng, S. et al. A comprehensive theoretical study of structural optimization, interaction energies calculations and solvent effects between ractopamine and functional monomers in molecular imprinting polymers. Polym. Bull. 75, 1981–1996 (2018). https://doi.org/10.1007/s00289-017-2140-x

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00289-017-2140-x

Keywords

Search

Navigation