留言板

尊敬的读者、作者、审稿人, 关于本刊的投稿、审稿、编辑和出版的任何问题, 您可以本页添加留言。我们将尽快给您答复。谢谢您的支持!

姓名
邮箱
手机号码
标题
留言内容
验证码

分子印迹聚合物修饰氧化石墨烯用于选择性识别槲皮素

赵小峰,  段菲菲,  崔培培,  杨永珍,  刘旭光,  侯相林

downloadPDF
文章导航 > 新型炭材料  > 2018 >  33(6): 529-543
赵小峰, 段菲菲, 崔培培, 杨永珍, 刘旭光, 侯相林. 分子印迹聚合物修饰氧化石墨烯用于选择性识别槲皮素. 新型炭材料, 2018, 33(6): 529-543. doi: 10.1016/S1872-5805(18)60355-5
引用本文: 赵小峰, 段菲菲, 崔培培, 杨永珍, 刘旭光, 侯相林. 分子印迹聚合物修饰氧化石墨烯用于选择性识别槲皮素. 新型炭材料, 2018, 33(6): 529-543. doi: 10.1016/S1872-5805(18)60355-5
shu
ZHAO Xiao-feng, DUAN Fei-fei, CUI Pei-pei, YANG Yong-zhen, LIU Xu-guang, HOU Xiang-lin. A molecularly-imprinted polymer decorated on graphene oxide for the selective recognition of quercetin. New Carbon Mater., 2018, 33(6): 529-543. doi: 10.1016/S1872-5805(18)60355-5
Citation: ZHAO Xiao-feng, DUAN Fei-fei, CUI Pei-pei, YANG Yong-zhen, LIU Xu-guang, HOU Xiang-lin. A molecularly-imprinted polymer decorated on graphene oxide for the selective recognition of quercetin. New Carbon Mater., 2018, 33(6): 529-543. doi: 10.1016/S1872-5805(18)60355-5
shu

分子印迹聚合物修饰氧化石墨烯用于选择性识别槲皮素

doi: 10.1016/S1872-5805(18)60355-5
  • 1.

    太原理工大学 新材料界面科学与工程教育部重点实验室, 山西 太原 030024;

  • 2.

    太原理工大学 化学化工学院, 山西 太原 030024;

  • 3.

    太原理工大学 新材料工程技术研究中心, 山西 太原 030024;

  • 4.

    中国科学院山西煤炭化学研究所 山西省生物炼制工程技术研究中心, 山西 太原 030001

基金项目: 国家自然科学基金（U1610255，U1607120）；山西省科技创新重点团队（2015013002-10，201605D131045-10）；山西省研究生教育创新项目（2016SY018）.
详细信息
    作者简介:

    赵小峰,硕士研究生.E-mail:18734143706@163.com

    通讯作者:

    刘旭光,教授.E-mail:liuxuguang@tyut.edu.cn;杨永珍,教授.E-mail:yyztyut@126.com;侯相林,研究员.E-mail:houxianglin@sxicc.ac.cn

  • 中图分类号: TB33

A molecularly-imprinted polymer decorated on graphene oxide for the selective recognition of quercetin

  • 1.

    Key Laboratory of Interface Science and Engineering in Advanced Materials(Taiyuan University of Technology), Ministry of Education, Taiyuan 030024, China;

  • 2.

    College of Chemistry and Chemical Engineering, Taiyuan University of Technology, Taiyuan 030024, China;

  • 3.

    Research Center on Advanced Materials Science and Technology, Taiyuan University of Technology, Taiyuan 030024, China;

  • 4.

    Shanxi Engineering Research Center of Biorefinery, Institute of Coal Chemistry, Chinese Academy of Sciences, Taiyuan 030001, China

Funds: National Natural Science Foundation of China (U1610255, U1607120); Shanxi Provincial Key Innovative Research Team in Science and Technology (2015013002-10, 201605D131045-10); Postgraduate Innovation Program of Shanxi Province (2016SY018).

    摘要
  • 摘要: 利用分子模拟技术设计槲皮素（Qu）印迹预组装体系，确定功能单体的种类及其与Qu的作用比例；在此基础上，采用自由基聚合法制备分子印迹聚合物修饰的氧化石墨烯（GO/MIP），并通过傅里叶变换红外光谱仪、元素分析仪、拉曼光谱仪、热重分析仪、扫描电子显微镜和原子力显微镜系统分析所制GO/MIP复合材料的形貌和结构。静态吸附实验的结果表明，在298 K下，GO/MIP复合材料对Qu的动力学吸附平衡时间和吸附量分别为30 min和30.61 mg g-1。此外，准二级动力学模型和Langmuir吸附等温模型可较好地描述GO/MIP复合材料对Qu的吸附行为。混合黄酮类化合物溶液中进行的竞争吸附实验的结果说明，相对Qu而言，GO/MIP复合材料对结构类似物山奈酚和芦丁的相对选择性系数分别为1.966和3.557。所制GO/MIP复合材料提高了表面MIPs用于选择性识别多酚类化合物的能力，为制备用于天然产物中特异性检测和快速分离黄酮的表面MIPs提供指导意义。
    Abstract: A molecularly-imprinted polymer decorated on graphene oxide (GO/MIP) was designed with the aid of molecular modeling to select an appropriate functional monomer and to optimize its ratio to an imprinting molecule of quercetin (Qu) for the selective adsorption of Qu. The GO/MIP was prepared by free radical polymerization on the surface of GO using a functional monomer of 4-vinylpyridine at its optimal molar ratio to Qu of 4:1. The GO/MIP was characterized by Fourier transform infrared spectroscopy, elemental analysis, Raman spectroscopy, thermogravimetric analysis, scanning electron microscopy, atomic force microscopy and adsorption measurements. Results indicate that the equilibrium time and adsorption capacity of the GO/MIP towards Qu are 30 min and 30.61 mg g-1 at 298 K, respectively and the adsorption data are well described by a pseudo-second-order kinetic model and the Langmuir isotherm model. From competing adsorption tests in a solution containing three flavonoids (Qu, kaempferol and rutin), the GO/MIP displays an excellent recognition ability for Qu with faster adsorption kinetics than bulk MIP without GO, and has highest adsorption capacity and selectivity for Qu among the three flavonoids, which is superior to un-imprinted polymer.
    • HTML全文
  • 下载: 全尺寸图片 幻灯片
    • 参考文献(54)
  • Tim Cushnie T P, Lamb Andrew J. Antimicrobial activity of flavonoids[J]. Int J Antimicrob Ag, 2005, 26:343-356.
    Song X L, Li J H, Wang J T, et al. Quercetin molecularly imprinted polymers:Preparation, recognition characteristics and properties as sorbent for solid-phase extraction[J]. Talanta, 2009, 80:694-702.
    Russo N, Toscano M, Uccella N. Semiempirical molecular modeling into quercetin reactive site:Structural, conformational, and electronic features[J]. J Agr Food Chem, 2000, 48:3232-3237.
    De Souza K C B, Schapoval E E S, Bassani V L. LC determination of flavonoids:Separation of quercetin, luteolin and 3-O-methylquercetin in Achyrocline satureioides preparations[J]. J Pharmaceut Biomed, 2002, 28:771-777.
    Fasolo D, Schwingel L, Holzschuh M, et al. Validation of an isocratic LC method for determination of quercetin and methylquercetin in topical nanoemulsions[J]. J Pharmaceut Biomed, 2007, 44:1174-1177.
    Hartonen K, Parshintsev J, Sandberg K, et al. Isolation of flavonoids from aspen knotwood by pressurized hot water extraction and comparison with other extraction techniques[J]. Talanta, 2007:74, 32-38.
    Stenger F C, Cechinel-Filho V, Meyre-Silva C, et al. Synthesis of laurylchitosan and its use in the separation of flavonoids from Aleurites moluccana by matrix solid-phase dispersion[J]. Chromatographia, 2009, 69:183-187.
    Mitani K, Narimatsu S, Kataoka H. Determination of daidzein and genistein in soybean foods by automated on-line in-tube solid-phase microextraction coupled to high-performance liquid chromatography[J]. J Chromatogr A, 2003, 986:169-177.
    Zhang X F, Du X Z, Huang X, et al. Creating protein-imprinted self-assembled monolayers with multiple binding sites and biocompatible imprinted cavities[J]. J Am Chem Soc, 2013, 135:9248-9251.
    Abbate V, Bassindale A R, Brandstadt K F, et al. Biomimetic catalysis at silicon centre using molecularly imprinted polymers[J]. J Catal, 2011, 284:68-76.
    Xie J C, Zhu L L, Luo H P, et al. Direct extraction of specific pharmacophoric flavonoids from gingko leaves using a molecularly imprinted polymer for quercetin[J]. J Chromatogr A, 2001, 934:1-11.
    Molinelli A, Weiss R, Mizaikoff B. Advanced solid phase extraction using molecularly imprinted polymers for the determination of quercetin in red wine[J]. J Agr Food Chem, 2002, 50:1804-1808.
    Sun S, Zhang M Q, Li Y J, et al. A molecularly imprinted polymer with incorporated graphene oxide for electrochemical determination of quercetin[J]. Sensors, 2013, 13:5493-5506.
    Mao Y, Bao Y, Gan S Y, et al. Electrochemical sensor for dopamine based on a novel graphene-molecular imprinted polymers composite recognition element[J]. Biosens Bioelectron, 2011, 28:291-297.
    Pakade V, Lindahl S, Chimuka L, et al. Molecularly imprinted polymers targeting quercetin in high-temperature aqueous solutions[J]. J Chromatogr A, 2012, 1230:15-23.
    Pardoa A, Mespouille L, Blankert B, et al. Quercetin-imprinted chromatographic sorbents revisited:Optimization of synthesis and rebinding protocols for application to natural resources[J]. J Chromatogr A, 2014, 1364:128-139.
    Luo J, Jiang S S, Liu X Y. Efficient one-pot synthesis of mussel-inspired molecularly imprinted polymer coated graphene for protein-specific recognition and fast separation[J]. J Phys Chem C, 2013, 117:18448-18456.
    Yang Y Z, Liu X G, Xu B S. Recent advances in molecular imprinting technology for the deep desulfurization of fuel oils[J]. New Carbon Mater, 2014, 29, 1-14.
    Gao B J, Zhang Y Y, Chen T. Designing and preparing of quercetin surface-imprinted material and its molecular recognition characteristics[J]. J Appl Polym Sci, 2014, 131:41112.
    Hong Y S, Chen L G. Extraction of quercetin from Herba Lysimachiae by molecularly imprinted-matrix solid phase dispersion[J]. J Chromatogr B, 2013, 941:38-44.
    Chen F F, Xie X Y, Shi Y P. Preparation of magnetic molecularly imprinted polymer for selective recognition of resveratrol in wine[J]. J Chromatogr A, 2013, 1300:112-118.
    Xia Y Q, Guo T Y, Song M D, et al. Selective separation of quercetin by molecular imprinting using chitosan beads as functional matrix[J]. React Funct Polym, 2006, 66:1734-1740.
    Liu Q, Shi J, Jiang G. Application of graphene in analytical sample preparation[J]. Trac-Trend Anal Chem, 2012, 37:1-11.
    Li Y, Li X, Dong C K, et al. A graphene oxide-based molecularly imprinted polymer platform for detecting endocrine disrupting chemicals[J]. Carbon, 2010, 48:3427-3433.
    Zeng Y B, Zhou Y, Kong L, et al. A novel composite of SiO2-coated graphene oxide and molecularly imprinted polymers for electrochemical sensing dopamine[J]. Biosens Bioelectron, 2013, 45:25-33.
    Duan F F, Chen C Q, Wang G Z, et al. Efficient adsorptive removal of dibenzothiophene by graphene oxide-based surface molecularly imprinted polymer[J]. RSC Adv, 2014, 4:1469.
    Luo J, Cong J J, Liu J, et al. A facile approach for synthesizing molecularly imprinted graphene for ultrasensitive and selective electrochemical detecting 4-nitrophenol[J]. Anal Chim Acta, 2015, 864:74-84.
    Liu S C, Pan J M, Zhu H J, et al. Graphene oxide based molecularly imprinted polymers with double recognition abilities:the combination of covalent boronic acid and traditional non-covalent monomers[J]. Chem Eng J, 2016, 290:220-231.
    Chen F F, Zhao W F, Zhang J, et al. Magnetic two-dimensional molecularly imprinted materials for the recognition and separation of proteins[J]. Phys Chem Chem Phys, 2016, 18:718-725.
    Liu J B, Wang Y, Su T T, et al. Theoretical and experimental studies on the performances of barbital-imprinted systems[J]. J Sep Sci, 2015, 38:4105-4110.
    Ma P F, Yang W M, Fan T, et al. Surface imprinted polymers for oil denitrification with the combination of computational simulation and multi-template molecular imprinting[J]. Polym Adv Technol, 2015, 26:476-486.
    HummersJr W S, Offeman R E. Preparation of graphitic oxide[J]. J Am Chem Soc, 1958, 80:1339.
    O'Mahony J, Wei S T, Molinelli A, et al. Imprinted polymeric materials. Insight into the nature of prepolymerization complexes of quercetin imprinted polymers[J]. Anal Chem, 2006, 78:6187-6190.
    Li L F, Chen L, Zhang H, et al. Temperature and magnetism bi-responsive molecularly imprinted polymers:preparation, adsorption mechanism and properties as drug delivery system for sustained release of 5-fluorouracil[J]. Mat Sci Eng C, 2016, 61:158-168.
    Fu Q, Sanbe H, Kagawa C, et al. Uniformly sized molecularly imprinted polymer for (S)-nilvadipine. Comparison of chiral recognition ability with HPLC chiral stationary phases based on a protein[J]. Anal Chem, 2003, 75:191-198.
    Uzuriaga-Sánchez R J, Khan S, Wong A, et al. Magnetically separable polymer (Mag-MIP) for selective analysis of biotin in food samples[J]. Food Chem, 2016, 190:460-467.
    Kozlowska M, Goclon J, Rodziewicz P. Intramolecular hydrogen bonds in low-molecular-weight polyethylene glycol[J]. Chem Phys Chem, 2016, 17:1143-1153.
    Bondi A. Van der Waals volumes and radii[J]. J Phys Chem, 1964, 68:441-451.
    Aparicio S. A systematic computational study on flavonoids[J]. Int J Mol Sci, 2010, 11:2017-2038.
    García G, Atilhan M, Aparicio S. Flavonol-carbon nanostructure hybrid systems:A DFT study on the interaction mechanism and UV/Vis features[J]. Phys Chem Chem Phys, 2016, 18:4760-4771.
    Schniepp H C, Li J L, McAllister M J. Functionalized single graphene sheets derived from splitting graphite oxide[J]. J Phys Chem B, 2006, 110:8535-8539.
    Park S, Ruoff R S. Chemical methods for the production of graphenes[J]. Nat Nanotechnol, 2009, 4:217-224.
    Stankovich S, Piner R D, Nguyen S T, et al. Synthesis and exfoliation of isocyanate-treated graphene oxide nanoplatelets[J]. Carbon, 2006, 44:3342-3347.
    Xu S F, Li J H, Chen L X. Molecularly imprinted core-shell nanoparticles for determination of trace atrazine by reversible addition-fragmentation chain transfer surface imprinting[J]. J Mater Chem, 2011, 21:4346-4351.
    Sadeghi S, Jahani M. Selective solid-phase extraction using molecular imprinted polymer sorbent for the analysis of Florfenicol in food samples[J]. Food Chem, 2013, 141:1242-1251.
    Duan F F, Chen C Q, Chen L, et al. Preparation and evaluation of water-compatible surface molecularly imprinted polymers for selective adsorption of bisphenol A from aqueous solution[J]. Ind Eng Chem Res, 2014, 53:14291-14300.
    Bourlinos A B, Gournis D, Petridis D, et al. Graphite oxide:Chemical reduction to graphite and surface modification with primary aliphatic amines and amino acids[J]. Langmuir, 2003, 19:6050-6055.
    McAllister M J, Li J L, Adamson D H, et al. Single sheet functionalized graphene by oxidation and thermal expansion of graphite[J]. Chem Mater, 2007, 19:4396-4404.
    Kou L, Gao C. Making silica nanoparticle-covered graphene oxide nanohybrids as general building blocks for large-area superhydrophilic coatings[J]. Nanoscale, 2011, 3:519-528.
    Kudin K N, Ozbas B, Schniepp H C, et al. Raman spectra of graphite oxide and functionalized graphene sheets[J]. Nano Lett, 2008, 8, 36-41.
    Zeng Y B, Zhou Y, Zhou T S, et al. A novel composite of reduced graphene oxide and molecularly imprinted polymer for electrochemical sensing 4-nitrophenol[J]. Electrochim Acta, 2014, 130:504-511.
    Baydemir G, Andac M, Bereli N, et al. Selective removal of bilirubin from human plasma with bilirubin-Imprinted particles[J]. Ind Eng Chem Res, 2007, 46:2843-2852.
    Duan F F, Chen C Q, Zhao X F, et al. Water-compatible surface molecularly imprinted polymers with synergy of bi-functional monomers for enhanced selective adsorption of bisphenol A from aqueous solution[J]. Environ Sci-Nano, 2016, 3:213-222.
    Chen J X, Lei S, Xie Y Y, et al. Fabrication of high-performance magnetic lysozyme-imprinted microsphere and its NIR-responsive controlled release property[J]. ACS Appl Mater Inter, 2015, 7:28606-28615.
    • 相关文章
    • 施引文献
  • 资源附件(0)
  • 加载中
WeChat 点击查看大图
图(1)
计量
  • 文章访问数:  416
  • HTML全文浏览量:  103
  • PDF下载量:  176
  • 被引次数: 0
出版历程
  • 收稿日期:  2018-08-12
  • 录用日期:  2018-12-27
  • 修回日期:  2018-11-03
  • 刊出日期:  2018-12-28

目录

    /

    返回文章
    返回

    地　　址： 山西省太原市迎泽区桃园南路27号邮政编码：030001

    电话/传真：0351-2025254

    电子邮件： tcl@sxicc.ac.cn

    版权所有 © 《新型炭材料（中英文）》编辑部 本系统由 北京仁和汇智信息技术有限公司 开发   百度统计