Citation: ZHAO Na, HU Xiao-Ling, GUAN Ping, SONG Ren-Yuan, TIAN Tian, ZHANG Xiang-Rong. Preparation of Erythromycin-Imprinted Polymeric Microspheres by Emulsion Polymerization and Their Adsorption Properties[J]. Acta Physico-Chimica Sinica, ;2014, 30(1): 121-128. doi: 10.3866/PKU.WHXB201311272 shu

Preparation of Erythromycin-Imprinted Polymeric Microspheres by Emulsion Polymerization and Their Adsorption Properties

1.
The Key Laboratory of Space Applied Physics and Chemistry, Ministry of Education, School of Natural and Applied Science, Northwestern Polytechnical University, Xi'an 710072, P. R. China

Received Date: 18 September 2013
Available Online: 27 November 2013
Fund Project: 国家自然科学基金(21174111)资助项目 (21174111)

Uniform molecularly imprinted polymeric microspheres (EM-MIPMs) were prepared by emulsion polymerization using erythromycin as the template molecule, methacrylic acid (MAA) as the functional monomer, and ethylene glycol dimethacrylate (EDMA) and sodium dodecylbenzene sulfonate (SBS) as the cross-linker and emulsifier, respectively. The obtained erythromycin-MAA complexes were characterized using ultraviolet (UV) absorption spectroscopy, Fourier-transform infrared (FTIR) spectroscopy, and ¹H nuclear magnetic resonance (NMR) spectroscopy. The results showed that erythromycin-MAA complexes were obtained by cooperative hydrogen-bonding interactions. The surface features and thermal stability of the EM-MIPMs were investigated using scanning electron microscopy (SEM) and thermal gravimetric analysis (TGA). The average diameter of the EM-MIPMs was 4.24 μm, larger than non-imprinted polymeric microspheres. They exhibited excellent thermal stability. Kinetic, equilibrium adsorption, and selectivity adsorption experiments (solid-phase extraction) were used to evaluate the binding properties and molecule recognition characteristics of EM-MIPMs for erythromycin. The experimental kinetic data were well described by a pseudo-second-order kinetic model. Erythromycin binding was examined using the Langmuir and Freundlich isotherm models. The EM-MIPMs had an excellent affinity for erythromycin. The equilibrium experimental data for the EM-MIPMs fitted the Langmuir isotherm well, and the binding amount reached 0.242 mmol·g^-1. Furthermore, solid-phase extraction experiments demonstrated that the EM-MIPMs had a higher affinity for the target molecules than for roxithromycin and erythromycin ethylsuccinate.
- Erythromycin,
- Molecularly imprinted microsphere,
- Adsorption,
- Binding property
1. [1]
  
  (1) Scorrano, S.; Lon , L.; Vasapollo, G. Anal. Chim. Acta 2010,659, 167. doi: 10.1016/j.aca.2009.11.046
2. [2]
  (2) Zhang, Z. D.; Zheng, S. J.; Yang, J.;Wang,W. M.; Liu, B. Z.;Zhu, X. L. Chinese Journal of Chemical Physics 2013, 26 (3),361. [张志丹, 郑赛晶, 杨俊, 王维妙, 刘百战, 朱晓兰. 化学物理学报, 2013, 26 (3), 361.] doi: 10.1063/1674-0068/26/03/361-368
3. [3]
  (3) Geng, L. N.; Kang, N.; Ning, Z. Y.;Wu, L. Q.; Li, Y.; Sun, L.Q.; Luo, A. Q. Acta Phys. -Chim. Sin. 2008, 24 (1), 25. [耿利娜, 康宁, 宁周云, 武利庆, 李琰, 孙立权, 罗爱芹. 物理化学学报, 2008, 24 (1), 25.] doi: 10.3866/PKU.WHXB20080105
4. [4]
  (4) Qiu, Z. Y.; Zhong, S. A. Acta Chim. Sin. 2010, 68 (3), 246. [邱增英, 钟世安. 化学学报, 2010, 68 (3), 246.]
5. [5]
  (5) Huang, Y. H.; Xu, Y.; Du, B. B.; He, Q. H.; Cao, Y. S. Chin. J. Anal. Chem. 2012, 40 (7), 1011. [黄运红, 许扬, 杜碧柏, 何庆华, 曹郁生. 分析化学, 2012, 40 (7), 1011.] doi: 10.1016/S1872-2040(11)60558-6
6. [6]
  (6) Chen, Z. D.;Wei, J. X.;Wang,W. C.; Kong, Y. Chin. Chem. Lett. 2010, 21 (3), 353.
7. [7]
  (7) Curcio, M.; Puoci, F.; Cirillo, G.; Iemma, F.; Spizzirri, U. G.;Picci, N. J. Agric. Food Chem. 2010, 58 (22), 11883. doi: 10.1021/jf102936p
8. [8]
  (8) Sellergren, B.; Karmalkar, R. N.; Shea, K. J. J. Org. Chem.2000, 65 (13), 4009. doi: 10.1021/jo000014n
9. [9]
  (9) Men, J. Y.; Gao, B. J.; Chen, Z. P.; Yao, L. Acta Chim. Sin. 2012,70 (21), 2273. [门吉英, 高保娇, 陈志萍, 么兰. 化学学报,2012, 70 (21), 2273.] doi: 10.6023/A12070402
10. [10]
  (10) Ornelasa, M.; Loureiroa, D.; Araújoa, M. J.; Marquesa, E.; Dias-Cabralb, C.; Azenhaa, M.; Silva, F. J. Chromatogr. A 2013, 1297 (5), 138.
11. [11]
  (11) Dvorakova, G.; Haschick, R.; Chiad, K.; Klapper, M.; Müllen,K.; Biffis, A. Macromol. Rapid Commun. 2010, 31 (23),2035. doi: 10.1002/marc.201000406
12. [12]
  (12) Xu, Z. F.;Wen, G.; Kuang, D. Z.; Zhang, F. X.; Tang, S. P.J. Environ. Sci. Heal. B 2013, 48 (5), 336. doi: 10.1080/03601234.2013.742372
13. [13]
  (13) Li, J. J.; Yang, M.; Huo, D. Q.; Hou, C. J.; Li, X. L.;Wang, G.M.; Feng, D. J. Sep. Sci. 2013, 36 (6), 1142. doi: 10.1002/jssc.201200869
14. [14]
  (14) Dai, J. D.; Pan, J. M.; Xu, L. C.; Li, X. X.; Zhou, Z. P.; Zhang,R. X.; Yan, Y. S. J. Hazard. Mater. 2012, 205-206, 179.
15. [15]
  (15) Rodríguez, E.; Navarro-Villoslada, F.; Benito-Peñña, E.;Marazuela, M. D.; Moreno-Bondi, M. C. Anal. Chem. 2011, 83 (6), 2046. doi: 10.1021/ac102839n
16. [16]
  (16) He, J.; Tang, H. Z.; You, L. Q.; Yuan, L. L.; Liu, Z. M.; Zhu, J.;Lu, K.; Chen, X. Z. Chromatographia 2013, 76 (15-16), 959.
17. [17]
  (17) Geng, L. Y.; Kou, X.; Lei, J. D.; Su, H. J.; Ma, G. H.; Su, Z. G.J. Chem. Technol. Biot. 2012, 87 (5), 635. doi: 10.1002/jctb.v87.5
18. [18]
  (18) Kou, X.; Geng, L. Y.; Lei, J. D.; Ma, G. H.; Su, Z. G. The Chinese Journal of Process Engineering 2011, 11 (3), 481.[寇星, 耿立媛, 雷建都, 马光辉, 苏志国. 过程工程学报,2011, 11 (3), 481.]
19. [19]
  (19) Guan, P.; Hu, X. L.; Hao, M. Y. J. Funct. Mater. 2010, 41 (z2),379. [管萍, 胡小玲, 郝明燕. 功能材料, 2010, 41 (z2), 379.]
20. [20]
  (20) Hu, X. L.; Guan, P.; Zhu, L.; Zhang, X. L. Preparation Methodof Macrolide Antibiotics Molecularly Imprinted PolymerMicrospheres. CN Patent 101507916A, 2009-08-19. [胡小玲,管萍, 朱丽, 张新丽. 大环内酯类抗生素分子印迹聚合物微球的制备方法. 中国: CN101507916A[P], 2009-08-19.]
21. [21]
  (21) Song, R. Y.; Hu, X. L.; Guan, P.; Yin, Y. N.; Zhu, L. Ion Exchange and Adsorption 2013, 29 (2), 97. [宋任远, 胡小玲,管萍, 尹亚楠, 朱丽. 离子交换与吸附, 2013, 29 (2), 97. ]
22. [22]
  (22) Andersson, H. S.; Nicholls, I. A. Bioorg. Chem. 1997, 25 (3),203. doi: 10.1006/bioo.1997.1067
23. [23]
  (23) Li, Q.; Yue, Q. Y.; Su, Y.; Gao, B. Y.; Sun, H. J. Chem. Eng. J.2010, 158 (3), 489. doi: 10.1016/j.cej.2010.01.033
24. [24]
  (24) Greluk, M.; Hubicki, Z. Chem. Eng. J. 2010, 162 (3), 919. doi: 10.1016/j.cej.2010.06.043
25. [25]
  (25) Pan, J. M.; Yao, H.; Xu, L. C.; Ou, H. X.; Huo, P.W.; Li, X. X.;Yan, Y. S. J. Phys. Chem. C 2011, 115 (13), 5440. doi: 10.1021/jp111120x
26. [26]
  (26) Li, X. X.; Pan, J. M.; Dai, J. D.; Dai, X. H.; Xu, L. C.;Wei, X.;Hang, H.; Li, C. X.; Liu, Y. Chem. Eng. J. 2012, 198-199, 503.
27. [27]
  (27) Abramian, L.; El-Rassy, H. Chem. Eng. J. 2009, 150 (2-3), 403.doi: 10.1016/j.cej.2009.01.019
28. [28]
  (28) Zhang, Z. Z.; Zhang, Z. B.; Fernández, Y.; Menénde, J. A.; Niu,H.; Peng, J. H.; Zhang, L. B.; Guo, S. H. Appl. Surf. Sci. 2010,256 (8), 2569. doi: 10.1016/j.apsusc.2009.10.106
29. [29]
  (29) Zhou, L. C.; Meng, X. G.; Li, J. M.; Hu,W.; Liu, B.; Du, J. Acta Phys. -Chim. Sin. 2012, 28 (7), 1615. [周良春, 孟祥光, 李建梅, 胡伟, 刘波, 杜娟. 物理化学学报, 2012, 28 (7),1615.] doi: 10.3866/PKU.WHXB201204282
1. [1]
  Jingke LIU , Jia CHEN , Yingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060
2. [2]
  Peng XU , Shasha WANG , Nannan CHEN , Ao WANG , Dongmei YU . Preparation of three-layer magnetic composite Fe₃O₄@polyacrylic acid@ZiF-8 for efficient removal of malachite green in water. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 544-554. doi: 10.11862/CJIC.20230239
3. [3]
  Zeyu XU , Anlei DANG , Bihua DENG , Xiaoxin ZUO , Yu LU , Ping YANG , Wenzhu YIN . Evaluation of the efficacy of graphene oxide quantum dots as an ovalbumin delivery platform and adjuvant for immune enhancement. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1065-1078. doi: 10.11862/CJIC.20240099
4. [4]
  Jing Wang , Pingping Li , Yuehui Wang , Yifan Xiu , Bingqian Zhang , Shuwen Wang , Hongtao Gao . Treatment and Discharge Evaluation of Phosphorus-Containing Wastewater. University Chemistry, 2024, 39(5): 52-62. doi: 10.3866/PKU.DXHX202309097
5. [5]
  Guang Huang , Lei Li , Dingyi Zhang , Xingze Wang , Yugai Huang , Wenhui Liang , Zhifen Guo , Wenmei Jiao . Cobalt’s Valor, Nickel’s Foe: A Comprehensive Chemical Experiment Utilizing a Cobalt-based Imidazolate Framework for Nickel Ion Removal. University Chemistry, 2024, 39(8): 174-183. doi: 10.3866/PKU.DXHX202311051
6. [6]
  Jiarong Feng , Yejie Duan , Chu Chu , Dezhen Xie , Qiu'e Cao , Peng Liu . Preparation and Application of a Streptomycin Molecularly Imprinted Electrochemical Sensor: A Suggested Comprehensive Analytical Chemical Experiment. University Chemistry, 2024, 39(8): 295-305. doi: 10.3866/PKU.DXHX202401016
7. [7]
  Xiaosong PU , Hangkai WU , Taohong LI , Huijuan LI , Shouqing LIU , Yuanbo HUANG , Xuemei LI . Adsorption performance and removal mechanism of Cd(Ⅱ) in water by magnesium modified carbon foam. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1537-1548. doi: 10.11862/CJIC.20240030
8. [8]
  Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014
9. [9]
  Shuanglin TIAN , Tinghong GAO , Yutao LIU , Qian CHEN , Quan XIE , Qingquan XIAO , Yongchao LIANG . First-principles study of adsorption of Cl₂ and CO gas molecules by transition metal-doped g-GaN. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1189-1200. doi: 10.11862/CJIC.20230482
10. [10]
  Youlin SI , Shuquan SUN , Junsong YANG , Zijun BIE , Yan CHEN , Li LUO . Synthesis and adsorption properties of Zn(Ⅱ) metal-organic framework based on 3, 3', 5, 5'-tetraimidazolyl biphenyl ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1755-1762. doi: 10.11862/CJIC.20240061
11. [11]
  Qianqian Zhong , Yucui Hao , Guotao Yu , Lijuan Zhao , Jingfu Wang , Jian Liu , Xiaohua Ren . Comprehensive Experimental Design for the Preparation of the Magnetic Adsorbent Based on Enteromorpha Prolifera and Its Utilization in the Purification of Heavy Metal Ions Wastewater. University Chemistry, 2024, 39(8): 184-190. doi: 10.3866/PKU.DXHX202312013
12. [12]
  Xinyu Yin , Haiyang Shi , Yu Wang , Xuefei Wang , Ping Wang , Huogen Yu . Spontaneously Improved Adsorption of H₂O and Its Intermediates on Electron-Deficient Mn^(3+δ)+ for Efficient Photocatalytic H₂O₂ Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312007-. doi: 10.3866/PKU.WHXB202312007
13. [13]
  Shasha Ma , Zujin Yang , Jianyong Zhang . Facile Synthesis of FeBTC Metal-Organic Gel and Its Adsorption of Cr₂O₇²⁻: A Physical Chemistry Innovation Experiment. University Chemistry, 2024, 39(8): 314-323. doi: 10.3866/PKU.DXHX202401008
14. [14]
  Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
15. [15]
  Zijian Jiang , Yuang Liu , Yijian Zong , Yong Fan , Wanchun Zhu , Yupeng Guo . Preparation of Nano Zinc Oxide by Microemulsion Method and Study on Its Photocatalytic Activity. University Chemistry, 2024, 39(5): 266-273. doi: 10.3866/PKU.DXHX202311101
16. [16]
  Peiling Li , Qing Feng , Hongling Yuan , Qin Wang . Live Interview Recording about the Penicillin Family. University Chemistry, 2024, 39(9): 122-127. doi: 10.3866/PKU.DXHX202311022
17. [17]
  Yuhao SUN , Qingzhe DONG , Lei ZHAO , Xiaodan JIANG , Hailing GUO , Xianglong MENG , Yongmei GUO . Synthesis and antibacterial properties of silver-loaded sod-based zeolite. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 761-770. doi: 10.11862/CJIC.20230169
18. [18]
  Rui Gao , Ying Zhou , Yifan Hu , Siyuan Chen , Shouhong Xu , Qianfu Luo , Wenqing Zhang . Design, Synthesis and Performance Experiment of Novel Photoswitchable Hybrid Tetraarylethenes. University Chemistry, 2024, 39(5): 125-133. doi: 10.3866/PKU.DXHX202310050
19. [19]
  Fang Niu , Rong Li , Qiaolan Zhang . Analysis of Gas-Solid Adsorption Behavior in Resistive Gas Sensing Process. University Chemistry, 2024, 39(8): 142-148. doi: 10.3866/PKU.DXHX202311102
20. [20]
  Kai Yang , Gehua Bi , Yong Zhang , Delin Jin , Ziwei Xu , Qian Wang , Lingbao Xing . Comprehensive Polymer Chemistry Experiment Design: Preparation and Characterization of Rigid Polyurethane Foam Materials. University Chemistry, 2024, 39(4): 206-212. doi: 10.3866/PKU.DXHX202308045

Get Citation

PDF

XML

Metrics

PDF Downloads(574)
Abstract views(884)
HTML views(19)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142