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Synthesis, characterization and adsorption behavior of sinapic acid imprinted polymer via precipitation polymerization

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Abstract

A cost-effective and eco-friendly approach for extraction and clean-up of sinapic acid was developed via the use of molecularly imprinted polymers (MIPs). Acetonitrile/methanol (5:1) was used as the porogenic solvent system, sinapic acid as the template, methacrylic acid as the functional monomer and ethylene glycol dimethacrylate as the cross-linking agent were used to prepare MIPs via precipitation polymerization. A series of MIPs were synthesized with variable template: monomer: cross-linker mole ratios: 1:4:20, 1:8:20 and 1:8:32. Polymers were characterized by complementary methods: scanning electron microscopy (SEM), dynamic light scattering (DLS), gas adsorption analysis, infrared absorption spectroscopy (FT-IR) and thermogravimetric analysis (TGA). The batch rebinding experiments were conducted to evaluate polymer performance in terms of relative binding affinity towards the template. The initial concentration and solution pH strongly affect the binding capacity of polymers in aqueous media. Moreover, the fabricated MIPs were successfully applied for extraction of sinapic acid from rapeseed meal extract.

A schematic of molecularly imprinted polymer for extraction of sinapic acid from aqueous solutions

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References

  1. Danquah MK, Aruei RC, Wilson LD (2018) Phenolic pollutant uptake properties of molecular templated polymers containing β-cyclodextrin. J Phys Chem 122(17):4748–4757

    Article  CAS  Google Scholar 

  2. Kibechu RW, Mamo MA, Msagati TAM, Sampath S, Mambab BB (2014) Synthesis and application of reduced graphene oxide and molecularly imprinted polymers composite in chemo sensor for trichloroacetic acid detection in aqueous solution. Phys Chem Earth 76–78:49–53

    Article  Google Scholar 

  3. Suwanwong Y, Kulkeratiyut S, Prachayasittikul V, Boonpangrak S (2014) Effects of polymerization methods and functional monomers on curcumin imprinted polymer properties. Sep Sci Technol 49:1086–1095

    Article  CAS  Google Scholar 

  4. Lee S-H, Doong R-A (2012) Adsorption and selective recognition of 17ß-estradiol by molecularly imprinted polymers. J Polym Res 19. https://doi.org/10.1007/s10965-012-9939-9

  5. Parisi OI, Cirillo G, Curcio M, Puoci F, Iemma F, Spizzirri UG, Picci N (2010) Surface modifications of molecularly imprinted polymers for improved template recognition in water media. J Polym Res 17:355–362

    Article  CAS  Google Scholar 

  6. Yang W-L, Huang S-M, Wu Q-Z, He J-F (2014) Properties evaluation and separation application of naringin-imprinted polymers prepared by a covalent imprinting method based on boronate ester. J Polym Res 21(4). https://doi.org/10.1007/s10965-014-0383-x

  7. Ahmad AL, Lah NFC, Low SC (2018) Configuration of molecular imprinted polymer for electrochemical atrazine detection. J Polym Res 25

  8. Mathew D, Thomas B, Devaky KS (2019) Design, synthesis and characterization of enzyme-analogue-built polymer catalysts as artificial hydrolases. Artificial Cells, Nanomedicine, and Biotechnology 47(1):1149–1172

    Article  CAS  PubMed  Google Scholar 

  9. Sinha AS, Khandavilli U, O'Connor E, Deadman BJ, Maguire AR, Lawrence SE (2015) Novel co-crystals of the nutraceutical sinapic acid. CrystEngComm 17:4832–4841

    Article  CAS  Google Scholar 

  10. Nićiforović N, Abramovič H (2014) Sinapic acid and its derivatives: natural sources and bioactivity. Compr Rev Food Sci Food Saf 13(1):34–51

    Article  Google Scholar 

  11. Quinn L, Gray SG, Meaney S, Finn S, Kenny O, Hayes M (2017) Sinapinic and protocatechuic acids found in rapeseed: isolation, characterisation and potential benefits for human health as functional food ingredients. Irish Journal of Agricultural and Food Research 56:104–119

    Article  CAS  Google Scholar 

  12. Biorefineries, Springer International Publishing, Switzerland 2019

    Google Scholar 

  13. Flourat AL, Willig G, Teixeira ARS, Allais F (2019) Eco-friendly extraction of sinapine from residues of mustard production. Front Sustain Food Syst 3. https://doi.org/10.3389/fsufs.2019.00012

  14. Sinichi S, Siañez AVL, Diosady LL (2019) Recovery of phenolic compounds from the by-products of yellow mustard protein isolation. Food Res Int 115:460–466

    Article  CAS  PubMed  Google Scholar 

  15. Sharma S, Sharma AK, Verma S, Dodiya HS (2014) Edible oil refinery waste water treatment by using effluent treatment plant. International Journal of Chemical Studies, International Journal of Chemical Studies 2(3):36–42

    Google Scholar 

  16. Soto ML, Moure A, Domínguez H, Parajo JC (2011) Recovery, concentration and purification of phenolic compounds by adsorption: a review. J Food Eng 105:1–27

    Article  CAS  Google Scholar 

  17. Kraljic K, Škevin D, Barišic L, Kovacevic M, Obranovic M, Jurcevic I (2015) Changes in 4-vinylsyringol and other phenolics during rapeseed oil refining. Food Chem 187:236–242

    Article  CAS  PubMed  Google Scholar 

  18. Huang Y-J, Chang R, Zhu Q-J (2018) Synthesis and characterization of a molecularly imprinted polymer of spermidine and the exploration of its molecular recognition properties. Polymers 10(12). https://doi.org/10.3390/polym10121389

  19. Jianfeng H, Lan L, Guilan Y, Qinying D (2006) Preparation, characterization and properties studies of quinine-imprinted polymer in the aqueous phase. Frontiers of Chemistry in China 2:211–216

    Google Scholar 

  20. Lu Y, Zhu Y, Zhang Y, Wang K (2019) Synthesizing vitamin E molecularly imprinted polymers via precipitation polymerization. Journal of Chemical Engineering Data 64(3):1045–1050

    Article  CAS  Google Scholar 

  21. Ma L, Tang L, Li R-S, Huang Y-P, Liu Z-S (2015) Water-compatible molecularly imprinted polymers prepared using metal-organic gel as porogen. RSC Advances 5:84601–84609

    Article  CAS  Google Scholar 

  22. Smyk B (2002) Fluorescence study of sinapic acid interaction with bovine serum albumin and egg albumin. J Fluoresc 13(4):349–356

    Article  Google Scholar 

  23. Pardeshi S, Singh SK (2016) Precipitation polymerization: A versatile tool for preparing Molecularly Imprinted Polymer beads for chromatography applications. RSC Advances 6:23525–23536

    Article  CAS  Google Scholar 

  24. Edwin J, Romano F, So RC, Donne SW, Holdsworth CI (2016) Preparation and binding evaluation of histamine-imprinted microspheres via conventional thermal and RAFT-mediated free- radical polymerization. ACS Omega 1:518–531

    Article  Google Scholar 

  25. Barros LAd, Pereira LA, Custódiob R, Rath S (2014) A novel computational approach for development of highly selective fenitrothion imprinted polymer: theoretical predictions and experimental validations. Journal of the Brazilian Chemical Society 25(4):619–628

    Google Scholar 

  26. Pluhar B, Zienerb U, Mizaikoff B (2013) Surface imprinting of pepsin via miniemulsion polymerization. J Mater Chem B 1:5489–5495

    Article  CAS  PubMed  Google Scholar 

  27. Zayas H, Holdsworth CI, Bowyerb MC, McCluskey A (2014) Evaluation of 4-substituted styrenes as functional monomers for the synthesis of theophyllinespecific molecularly imprinted polymers. Organic & Biomolecular Chemistry 12:6994–7003

    Article  CAS  Google Scholar 

  28. Parisi OI, Ruffo M, Malivindi R, Vattimo AF, Pezzi V, Puoci F (2020) Molecularly imprinted polymers (MIPs) as theranostic systems for sunitinib controlled release and self-monitoring in cancer therapy. Pharmaceutics 12(1). https://doi.org/10.3390/pharmaceutics12010041

  29. Trotta F, Caldera F, Cavalli R, Soster M, Riedo C, Biasizzo M, Barretta GU, Balzano F, Brunella V (2016) Molecularly imprinted cyclodextrin nanosponges for the controlled delivery of L-DOPA: perspectives for the treatment of Parkinson’s disease. Expert Opinion on Drug Delivery 13:1671–1680

    Article  CAS  PubMed  Google Scholar 

  30. Booker K, Holdsworth CI, Bowyer M, Mccluskey A (2011) Ionic liquids as porogens in the synthesis of molecularly imprinted polymers, in: S. Handy (Ed.), Applications of Ionic Liquids in Science and Technology. InTech 197–212

  31. Yue J, Wang Z, Chen J, Zheng M, Wang Q, Lou X (2019) Investigation of pore structure characteristics and adsorption characteristics of coals with different destruction types. Adsorption Science & Technology 7-8:623–648

    Article  Google Scholar 

  32. Lanfredi S, Nobre MAL, Poon PS, Matos J (2020) Hybrid material based on an amorphous-carbon matrix and ZnO/Zn for the solar photocatalytic degradation of basic blue 41. Molecules 25(1). https://doi.org/10.3390/molecules25010096

  33. Murray A, Örmeci B (2018) Competitive effects of humic acid and wastewater on adsorption of Methylene Blue dye by activated carbon and non-imprinted polymers. Int J Environ Sci 66:310–317

  34. Jiang L, Lu R, Ye L (2019) Towards detection of glycoproteins using molecularly imprinted nanoparticles and boronic acid-modified fluorescent probe. Polymers 11(1):173

    Article  PubMed Central  Google Scholar 

  35. Yoon S-K, Lee J-C, Lee S, Choi S-H, Kim H-J, Park H-J, Kang H-D (2006) Synthesis of molecularly imprinted polymer (MIP) by radiation-induced polymerization and separation of ferulic acid from rice oil using MIP-packed column. Analytical Science & Technology 19(3):218–225

    Google Scholar 

  36. Zhang W, She X, Wang L, Fan H, Zhou Q, Huang X, Tang JZ (2017) Preparation, characterization and application of a molecularly imprinted polymer for selective recognition of sulpiride. Materials 10(5). https://doi.org/10.3390/ma10050475

  37. Fathi Til R, Alizadeh-Khaledabad M, Mohammadi R, Pirsaa S, Wilson LD (2020) Molecular imprinted polymers for the controlled uptake of sinapic acid from aqueous media. Food and Function 11:895–906

    Article  CAS  PubMed  Google Scholar 

  38. Jiang D, Sun X, Zhang Y (2012) Preparation and application of acrylamide molecularly imprinted composite solid-phase extraction materials. Anal Methods 4:3760–3766

    Article  Google Scholar 

  39. Chow ALJ, Bhawani SA (2016) Synthesis and characterization of molecular imprinting polymer microspheres of cinnamic acid: extraction of cinnamic acid from spiked blood plasma. International Journal of Polymer Science Volume 2016. https://doi.org/10.1155/2016/5671507

  40. Granado VLV, Rudnitskaya A, Oliveira J, Gomes MTSdR (2012) Design of molecularly imprinted polymers for diphenylamine sensing. Talanta 94:133–139

  41. Douglas Kinghorn Y-WCA, Pan L (2010) Natural products as sweeteners and sweetness modifiers. In: Mander H-WLL (ed) Comprehensive natural products II: chemistry and biology. Elsevier Science, Oxford, U.K.

    Google Scholar 

  42. Zhao W-R, Kang T-F, Lu L-P, Cheng S-Y (2018) Magnetic surface molecularly imprinted poly(3-aminophenylboronic acid) for selective capture and determination of diethylstilbestrol. RSC Adv 8:13129–13141

    Article  CAS  Google Scholar 

  43. Dai C, Zhang J, Zhang Y, Zhou X, Liu S (2013) Application of molecularly imprinted polymers to selective removal of clofibric acid from water. PLoS One 8(10). https://doi.org/10.1371/journal.pone.0078167

  44. Sánchez-Polo M, Gala IV, López-Peñalver JJ, Rivera-utrilla J (2015) Molecular imprinted polymer to remove tetracycline from aqueous solutions. Microporous Mesoporous Mater 203:32–40

    Article  Google Scholar 

  45. Michailof C, Manesiotis P, Panayiotou C (2008) Synthesis of caffeic acid and p-hydroxybenzoic acid molecularly imprinted polymers and their application for the selective extraction of polyphenols from olive mill waste waters. J Chromatogr A 1182:25–33

    Article  CAS  PubMed  Google Scholar 

  46. Rodrigues ASS, Aguiar APd, Aguiarb MRMPd, Maria LCdS (2007) Quaternization reaction of 2-vinylpyridine and 4-vinylpyridine network copolymers for 4-nitrophenol adsorption. Journal of the Brazilian Chemical Society 18(2):431–436

    Article  CAS  Google Scholar 

  47. Farrington K, Regan F (2007) Investigation of the nature of MIP recognition: the development and characterisation of a MIP for ibuprofen. Biosens Bioelectron 22:1138–1146

    Article  CAS  PubMed  Google Scholar 

  48. Yu P, Sun Q, Tan Z, Meng M, Pan J, Yan Y, Li C (2015) Magnetic molecularly imprinted polymer beads obtained by suspension polymerization for the adsorption of 2,4,6-trichlorophenol from an aqueous solution in a fixed-bed column. Adsorption Science & Technology 33(3):321–336

    Article  CAS  Google Scholar 

  49. Surikumaran H, Mohamad S, Sarih NM (2014) Molecular imprinted polymer of methacrylic acid functionalised β-cyclodextrin for selective removal of 2,4-dichlorophenol. Int J Mol Sci 15:6111–6136

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. Liu X, Wu F, Au C, Tao Q, Pi M, Zhang W (2018) Synthesis of molecularly imprinted polymer by suspension polymerization for selective extraction of p-hydroxybenzoic acid from water. J Appl Polym Sci 136(3). https://doi.org/10.1002/app.46984

  51. Asman S, Yusof NA, Abdullah AH, Haron MJ (2011) Synthesis and characterization of a molecularly imprinted polymer for methylene blue. Asian J Chem 23(11):4786–4794

    CAS  Google Scholar 

  52. Javanbakht M, Namjumanesh MH, Akbari-adergani B (2009) Molecularly imprinted solid-phase extraction for the selective determination of bromhexine in human serum and urine with high performance liquid chromatography. Talanta 80:133–138

    Article  CAS  PubMed  Google Scholar 

  53. Díaz-Alvarez M, Turiel E, Martín-Esteban A (2019) Molecularly imprinted polymer monolith containing magnetic nanoparticles for the stir-bar sorptive extraction of thiabendazole and carbendazim from orange samples. Anal Chim Acta 1045:117–122

    Article  PubMed  Google Scholar 

  54. Ye H, Chen X, Feng Z (2017) Preparations of magnetic molecularly imprinted polymer for selective recognition and determination of 4-methylimidazole in soft beverage by high performance liquid chromatography. Adsorption Science & Technology 35(1–2):37–54

    Article  CAS  Google Scholar 

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Acknowledgements

Authors gratefully acknowledge the financial supports from the University of Tabriz and the Urmia University. LDW acknowledges the support of the Government of Canada through the Natural Sciences and Engineering Research Council of Canada (NSERC; Discovery Grant RGPIN 2016-06197). R. Fathi Til acknowledges the support of Urmia University through the VRS program at the University of Saskatchewan for facilitation of this collaborative research project.

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Authors and Affiliations

  1. Department of Food Science and Technology, Faculty of Agriculture, Urmia University, Urmia, Iran

    Roya Fathi Til, Mohammad Alizadeh-Khaledabad & Sajad Pirsa

  2. Polymer Research Laboratory, Department of Organic and Biochemistry, Faculty of Chemistry, University of Tabriz, Tabriz, Iran

    Reza Mohammadi

  3. Department of Chemistry, University of Saskatchewan, 110 Science Place, Saskatoon, Saskatchewan, S7N 5C9, Canada

    Lee D. Wilson

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  1. Roya Fathi Til
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  2. Reza Mohammadi
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Correspondence to Reza Mohammadi or Mohammad Alizadeh-Khaledabad.

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Fathi Til, R., Mohammadi, R., Alizadeh-Khaledabad, M. et al. Synthesis, characterization and adsorption behavior of sinapic acid imprinted polymer via precipitation polymerization. J Polym Res 27, 235 (2020). https://doi.org/10.1007/s10965-020-02213-2

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