Abstract
A novel surface imprinting polymer based on magnetic carbon nanotubes was prepared using dendritic polyethyleneimine as functional monomer to amplify the number of imprinted cavities. The characteristics of resulting polymers were evaluated by transmission electron microscopy (TEM), X-ray diffraction (XRD), Fourier-transform infrared spectroscopy (FT-IR), and vibrating sample magnetometer (VSM). Results suggest that magnetic nanoparticles are deposited onto the surface of multiwalled carbon nanotubes and the imprinted shell is coated on the surface of magnetic carbon nanotubes with a thickness of approximately 8 nm. Magnetic imprinted polymers are sensitive to magnetic fields and can be easily separated within 3 s using an external magnet. The adsorption results indicate that the obtained imprinted polymers have fast kinetics, an ultrahigh adsorption capacity of 479.9 mg g−1, and satisfactory selectivity towards the template molecule. The prepared materials have excellent stability with no obvious deterioration after six adsorption–regeneration cycles. In addition, a method for determination of gallic acid (GA) in pomegranate rind was developed, using a combination of the prepared polymers used as solid-phase extraction (SPE) sorbents and high-performance liquid chromatography (HPLC) for rapid isolation and determination of GA. The limit of detection of the proposed method is 0.001 μg mL−1, and the intra and inter-day relative standard deviations (RSDs) are lower than 3.8 % and 5.3 %, respectively. The recoveries of GA from pomegranate rind extract are in the range 98.2–103.6 % with RSDs lower than 4.3 %.
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References
Saxena HO, Faridi U, Srivastava S, Kumar JK, Darokar MP, Luqman S, Chanotiya CS, Krishna V, Negi AS, Khanuja SPS (2008) Gallic acid-based indanone derivatives as anticancer agents. Bioorg Med Chem Lett 18:3914–3918
Li D, Liu ZJ, Yuan Y, Liu YW, Niu FL (2015) Green synthesis of gallic acid-coated silver nanoparticles with high antimicrobial activity and low cytotoxicity to normal cells. Process Biochem 50:357–366
Badhani B, Sharma N, Kakkar R (2015) Gallic acid: a versatile antioxidant with promising therapeutic and industrial applications. RSC Adv 5:27540–27557
Chuang CY, Liu HC, Wu LC, Chen CY, Chang JT, Hsu SL (2010) Gallic acid induces apoptosis of lung fibroblasts via a reactive oxygen species-dependent ataxia telangiectasia mutated-p53 activation pathway. J Agric Food Chem 58:2943–2951
Ramamurthy G, Krishnamoorthy G, Sastry TP, Mandal AB (2014) Rationalized method to enhance the chromium uptake in tanning process: role of Gallic acid. Clean Techn Environ Policy 16:647–654
Rouchon V, Bernard S (2015) Mapping iron gall ink penetration within paper fibres using scanning transmission X-ray microscopy. J Anal At Spectrom 30:635–641
Chen LX, Xu SF, Li JH (2011) Recent advances in molecular imprinting technology: current status, challenges and highlighted applications. Chem Soc Rev 40:2922–2942
Du W, Fu Q, Zhao G, Huang P, Jiao YY, Wu H, Luo ZM, Chang C (2013) Dummy-template molecularly imprinted solid phase extraction for selective analysis of ractopamine in pork. Food Chem 139:24–30
Liu M, Li XY, Li JJ, Su XM, Wu ZY, Li PF, Lei FH, Tan XC, Shi ZW (2015) Synthesis of magnetic molecularly imprinted polymers for the selective separation and determination of metronidazole in cosmetic samples. Anal Bioanal Chem 407:3875–3880
He HL, Gu XL, Shi LY, Hong JL, Zhang HJ, Gao YK, Du SH, Chen LN (2015) Molecularly imprinted polymers based on SBA-15 for selective solid-phase extraction of baicalein from plasma samples. Anal Bioanal Chem 407:509–519
Li JH, Dong RC, Wang XY, Xiong H, Xu SF, Shen DZ, Song XL, Chen LX (2015) One-pot synthesis of magnetic molecularly imprinted microspheres by RAFT precipitation polymerization for the fast and selective removal of 17b-estradiol. RSC Adv 5:10611–10618
Xie XY, Pan XY, Han SL, Wang SC (2015) Development and characterization of magnetic molecularly imprinted polymers for the selective enrichment of endocrine disrupting chemicals in water and milk samples. Anal Bioanal Chem 407:1735–1744
Zhang Z, Li JH, Fu JQ, Chen LX (2014) Fluorescent and magnetic dual-responsive coreshell imprinting microspheres strategy for recognition and detection of phycocyanin. RSC Adv 4:20677–20685
Du J, He MF, Wang XM, Fan H, Wei YM (2014) Facile preparation of boronic acid functionalized magnetic nanoparticles with a high capacity and their use in the enrichment of cis-diol-containing compounds from plasma. Biomed Chromatogr 29:312–320
Sayar O, Akbarzadeh Torbati N, Saravani H, Mehrani K, Behbahani A, Moghadam Zadeh HR (2014) A novel magnetic ion imprinted polymer for selective adsorption of trace amounts of lead(II) ions in environment samples. J Ind Eng Chem 20:2657–2662
Shi SY, Guo JF, You QP, Chen XQ, Zhang YP (2014) Selective and simultaneous extraction and determination of hydroxybenzoic acids in aqueous solution by magnetic molecularly imprinted polymers. Chem Eng J 243:485–493
Ma GF, Chen LG (2014) Development of magnetic molecularly imprinted polymers based on carbon nanotubes-application for trace analysis of pyrethroids in fruit matrices. J Chromatogr A 1329:1–9
Ning FJ, Peng HL, Li JH, Chen LX, Xiong H (2014) Molecularly imprinted polymer on magnetic graphene oxide for fast and selective extraction of 17beta-estradiol. J Agric Food Chem 62:7436–7443
Wang RY, Wang Y, Xue C, Wen TT, Wu JH, Hong JL, Zhou XM (2013) Selective separation and enrichment of glibenclamide in health foods using surface molecularly imprinted polymers prepared via dendritic grafting of magnetic nanoparticles. J Sep Sci 36:1015–1021
Wan L, Wang XF, Zhu WQ, Zhang C, Song AH, Sun CS, Jiang TY, Wang SL (2015) Folate-polyethyleneimine functionalized mesoporous carbon nanoparticles for enhancing oral bioavailability of paclitaxel. Int J Pharm 484:207–217
Lee MS, Lee SY, Park SJ (2015) Preparation and characterization of multi-walled carbon nanotubes impregnated with polyethyleneimine for carbon dioxide capture. Int J Hydrogen Energ 40:3415–3421
Dissing U, Mattiasson B (1998) Integrated removal of nucleic acids and recovery of LDH from homogenate of beef heart by affinity precipitation. Bioseparation 7:221–229
Khoobi M, Motevalizadeh SF, Asadgol Z, Forootanfar H, Shafiee A, Faramarzi MA (2015) Polyethyleneimine-modified superparamagnetic Fe3O4 nanoparticles for lipase immobilization: Characterization and application. Mater Chem Phys 149–150:77–86
Gao J, Sun SP, Zhu WP, Chung TS (2014) Polyethyleneimine (PEI) cross-linked P84 nanofiltration (NF) hollow fiber membranes for Pb2+ removal. J Membrane Sci 452:300–310
Gao RX, Zhang LL, HaoY CXH, Tang YH (2014) Specific removal of protein using protein imprinted polydopamine shells on modified amino functionalized magnetic nanoparticles. RSC Adv 4:64514–64524
Jiang B, Yang KG, Zhao Q, Wu Q, Liang Z, Zhang LH, Peng XJ, Zhang YK (2012) Hydrophilic immobilized trypsin reactor with magnetic graphene oxide as support for high efficient proteome digestion. J Chromatogr A 1254:8–13
Xiao DL, Dramou P, Xiong NQ, He H, Yuan DH, Dai H, Li H, He XM, Peng J, Li N (2013) Preparation of molecularly imprinted polymers on the surface of magnetic carbon nanotubes with a pseudo template for rapid simultaneous extraction of four fluoroquinolones in egg samples. Analyst 138:3287–3296
Pardeshi S, Dhodapkar R, Kumar A (2014) Molecularly imprinted microspheres and nanoparticles prepared using precipitation polymerisation method for selective extraction of gallic acid from Emblica officinalis. Food Chem 146:385–393
Hu X, Xie LW, Guo JF, Li H, Jiang XY, Zhang YP, Shi SY (2015) Hydrophilic gallic acid-imprinted polymers over magnetic mesoporoussilica microspheres with excellent molecular recognition ability in aqueous fruit juices. Food Chem 179:206–212
Acknowledgements
The authors are grateful for financial support from the National Natural Science Foundation of China (No. 21305107), the Fundamental Research Funds for the Central Universities (Nos. xjj2013041, 08142034), and China Postdoctoral Science Foundation (No. 2014M562388).
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Hao, Y., Gao, R., Liu, D. et al. Selective extraction of gallic acid in pomegranate rind using surface imprinting polymers over magnetic carbon nanotubes. Anal Bioanal Chem 407, 7681–7690 (2015). https://doi.org/10.1007/s00216-015-8930-9
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DOI: https://doi.org/10.1007/s00216-015-8930-9