表面印迹聚合物的制备及其在药物分离分析中的应用
|
摘要
表面分子印迹技术是在载体表面上发生聚合反应,将分子识别位点建立在载体的外层或者表面。从而使表面分子印迹聚合物具有结合速度快、识别选择性强、结合容量高、提高印迹材料的效率等优点。近年来表面分子印迹技术在药物分离分析中的应用引起人们的关注。简要介绍了表面分子印迹聚合物的原理及4种制备方法(溶胶-凝胶法、接枝共聚法、牺牲载体法、聚合加膜法、活性可控自由基聚合法),并对其在药物分离分析的4个方面(中药提取分离中;药物传感器方面;手性药物拆分中;药物释放中)的应用进行了综述。
The surface molecular imprinting technique is to polymerize and establish the molecular recognition site on the outer layer or surface of the carrier. As a result, the surface molecularly imprinted polymers have the advantages of fast binding speed, strong identification selectivity, high binding capacity and improved efficiency of imprinted materials. In this paper, the principle of surface molecularly imprinted polymers and four preparation methods(sol-gel method, graft copolymerization method, sacrificial carrier method, polymerization plus membrane method, active controllable free radical polymerization) were briefly introduced. Four aspects of drug separation and analysis(traditional Chinese medicine extraction and separation; drug sensors; chiral drug resolution; the application) in drug release was reviewed.
The surface molecular imprinting technique is to polymerize and establish the molecular recognition site on the outer layer or surface of the carrier. As a result, the surface molecularly imprinted polymers have the advantages of fast binding speed, strong identification selectivity, high binding capacity and improved efficiency of imprinted materials. In this paper, the principle of surface molecularly imprinted polymers and four preparation methods(sol-gel method, graft copolymerization method, sacrificial carrier method, polymerization plus membrane method, active controllable free radical polymerization) were briefly introduced. Four aspects of drug separation and analysis(traditional Chinese medicine extraction and separation; drug sensors; chiral drug resolution; the application) in drug release was reviewed.
引文
[1] Wulff G, Sarhan A, Zabrocki K,et al. Enzyme-analogue built polymers, 4. On the synthesis of polymers containing chiral cavities and their use for the resolution of racemates[J]. Makromol Chemistry, 2003,178(10):2799-2816.
[2] Vlatakis G, Andersson L I, Muller R, et al. Drug assay using antibody mimics made by molecular imprinting[J]. Nature, 1993, 361(6413):645-647.
[3] Chen L, Wang R, Cui L, et al. Preparation of five high-purity iridoid glycosides from Gardenia jasminoides Eills by molecularly imprinted solid-phase extraction integrated with preparative liquid chromatography [J]. Journal of Separation Science, 2018, 41(13): 2759-2766.
[4] Poole C F. New trends in solid-phase extraction[J]. Trends Anal Chem, 2003, 22(6): 362-373.
[5] Puoci F, Garreffa C, Iemma F, et al. Molecularly imprinted solid phase extraction for detection of sudan I in food matrices [J]. Food Chemistry, 2005, 93(2):349-353.
[6] Battal D, Akgonullu S, Yalcin M S, et al. Molecularly imprinted polymer based quartz crystal microbalance sensor system for sensitive and label-free detection of synthetic cannabinoids in urine [J]. Biosensors & Bioelectronics, 2018, 111:10-17.
[7] Afsarimanesh N, Mukhopadhyay S C, Kruger M, et al. Molecularly imprinted polymer-based electrochemical biosensor for bone loss detection [J]. IEEE Transactions on Bio-medical Engineering, 2018, 65(6): 1264-1271.
[8] Liu Yanli, Li Xiaojun, He Xiaorong, et al.The fabrication of molecularly imprinted electochemical sensor and its application in protein detection[J].Chemical Industry and Engineering Progress,2018,36(9):2533-2539(in Chinese).刘艳丽,李小军,贺晓荣,等.分子印迹电化学传感器制备及在蛋白质检测上的应用[J].化工进展,2018,36(9): 2533-2539.
[9] Lin C I, Joseph A K, Chang C K, et al. Synthesis of molecular imprinted organic-inorganic hybrid polymer binding caffeine [J]. Analytica Chimica Acta, 2003, 481(2): 175-180.
[10] Bonomi P, Servant A, Resmini M, et al. Modulation of imprinting efficiency in nanogels with catalytic activity in the Kemp elimination [J]. Journal of Molecular Recognition Jmr, 2012, 25(6): 352.
[11] Puoci F, Cirillo G, Curcio M, et al. Molecularly imprinted polymers in drugdelivery: state of art and future perspectives.[J]. Expert Opinion on Drug Delivery, 2011, 8(10):1379-1393.
[12] Chen H, Zhang W, Yang N, et al. Chitosan-based surface molecularly imprinted polymer microspheres for sustained release of sinomenine hydrochloride in aqueous media[J]. Appl Biochem Biotechnol, 2018, 185: 370-384.
[13] Li Y, Xiang R, Horvath, C, et al. Capillary electrochromatography of peptides on a neutral porous monolith with annular electroosmotic flow generation[J]. Electrophoresis, 2004, 25: 545-553.
[14] Wongniramaikul W, Choodum A, Dennany L, et al.A comprehensive chromatographic comparison of amphetamine and methylamphetamine extracted from river water using molecular imprinted polymers and without the need for sample derivatization[J]. J Sep Sci,2012,35:3332-3339.
[15] Philip C, Devaky K S. Multiwalled carbon nanotubes with surface grafted transition state analogue imprints as chymotrypsin mimics for the hydrolysis of amino acid esters: synthesis and kinetic studies [J]. Molecular Catalysis, 2017, 436:276-84.
[16] Yu H, Koide H, Urakami T, et al. Recognition, neutralization and clearance of target peptides in the blood stream of living mice by molecular imprinted polymer nanoparticles: a plastic antibody [J]. Journal of the American Chemical Society, 2010, 132(19): 6644-6645.
[17] Turner N W, Jeans C W, Brain K R, et al. From 3D to 2D: a review of the molecular imprinting of proteins[J]. Biotechnol Progr, 2006,22(6): 1474-1489.
[18] Jiao Jiaqi, Xue Yanbin, Yang Huizhen, et al. Application and prospect of molecular imprinting technology in drug extraction field [J]. Chinese Remedies And Clinics, 2018,18(2):214-218(in Chinese).焦佳琪,薛燕斌,杨慧珍, 等.分子印迹技术在药物提取领域的应用和展望[J].中国药物与临床,2018,18(2):214-218.
[19] Liu Renyong. Preparation of surface molecular imprinted polymers and its application in herdicide residlles detecction[D].Hefei: University of Science and Technology of China, 2009(in Chinese). 刘仁勇. 表面分子印记聚合物的制备及其在农残检测中的应用[D].合肥: 中国科学技术大学,2009.
[20] Huang J, Wu Y, Cong J, et al. Selective and sensitive glycoprotein detection via a biomimetic electrochemical sensor based on surface molecular imprinting and boronate-modified reduced graphene oxide [J]. Sensors and Actuators B: Chemical, 2018, 259:1-9.
[21] Rong Q, Zhang Y, Lyu T, et al. Highly selective and sensitive methanol gas sensor based on molecular imprinted silver-doped LaFeO3 core-shell and cage structures [J]. Nanotechnology, 2018, 29(14): 145503.
[22] Zheng X F, Lian, Q, Yang H, et al.Surface molecularly imprinted polymer of chitosan grafted poly(methyl methacrylate) for 5-fluorouracil and controlled release[J].Sci Rep,2016,6:214-219.
[23] Gao B, Li Y, Cui K, et al. Molecularly imprinted membrane with innovative structure and high performance for chiral separation of amino acids [J]. International Journal of Polymeric Materials and Polymeric Biomaterials, 2017, 67(8): 517-27.
[24] Ouyang R, Lei J, Ju H, et al. Surface molecularly imprinted nanowire for protein specific recognition [J]. Chemical Communications, 2008, 44: 5761-5763.
[25] Xu W Z, Zhou W, Xu P P, et al. A molecularly imprinted polymer based on TiO2 as a sacrificial support for selective recognition of dibenzothiophene [J]. Chemical Engineering Journal, 2011, 172(1): 191-198.
[26] Liu P, Zhang X, Xu W, et al. Electrochemical sensor for the determination of brucine in human serum based on molecularly imprinted poly-o-phenylenediamine/SWNTs composite film [J]. Sensors and Actuators B: Chemical, 2012, 163(1): 84-89.
[27] Wei Shoulian, Su Xuxian, Wang Hongwu, et al.Study and application of acid orangeⅡ sensor based on molecularly imprinted electropolymerized membrance[J]. Journal of Instrumental Analysis,2014, 33(6): 683-687(in Chinese).韦寿莲, 苏绪贤, 汪洪武, 等. 基于分子印迹电聚合膜的酸性橙Ⅱ传感器的研究及应用[J]. 分析测试学报, 2014, 33(6): 683-687.
[28] Li Y, Zhou W H, Yang H H, et al. Grafting of molecularly imprinted polymers from the surface of silica gel particles via reversible addition-fragmentation chain transfer polymerization: a selective sorbent for theophylline [J]. Talanta, 2009, 79(2): 141-145.
[29] Wu Y, Yan Y, Pan J, et al. Fabrication and evaluation of molecularly imprinted regenerated cellulose composite membranes via atom transfer radical polymerization [J]. Chinese Chemical Letters, 2014, 25(2): 273-278.
[30] Luo J, Chen N, Yang Z, et al. Determination of active ingredients in Chinese medicine danning tablets using dispersion solid-phase extraction by molecular imprinting nanomaterials coupled with HPLC-DAD [J]. Analytical Methods, 2017, 9(17): 2585-2589.
[31] Wan Y, Wang M, Fu Q, et al. Novel dual functional monomers based molecularly imprinted polymers for selective extraction of myricetin from herbal medicines[J].J Chromatogr B Analyt Technol Biomed Life Sci,2018,1097:1-9.
[32] Chen F F, Xie X Y, Shi Y P, et al. Magnetic molecularly imprinted polymer for the detection of rhaponticin in Chinese patent medicines [J]. Journal of Chromatography A, 2012, 1252:8-14.
[33] Tan K, Ma Q, Luo J, et al. Water-dispersible molecularly imprinted nanohybrids via co-assembly of carbon nanotubes with amphiphilic copolymer and photocrosslinking for highly sensitive and selective paracetamol detection [J]. Biosensors & Bioelectronics, 2018, 117(71):3-9.
[34] Ou S H, Pan L S, Jow J J, et al. Molecularly imprinted electrochemical sensor, formed on Ag screen-printed electrodes, for the enantioselective recognition of d and l phenylalanine[J].Biosens Bioelectron,2018,105:143-145.
[35] Essousi H, Barhoumi H. Electroanalytical application of molecular imprinted polyaniline matrix for dapsone determination in real pharmaceutical samples [J]. Journal of Electroanalytical Chemistry, 2018, 818(13):1-9.
[36] Wang Y F, Jin H X, Wang Y G, et al.Synthesis and characterization of magnetic molecularly imprinted polymer for the enrichment of ofloxacin enantiomers in fish samples[J].Molecules,2016,21(7):3-14.
[37] Tan Qi. Adsorption and separation of chiral drugs (S)-naproxen with novel surface moleculary imprinted polymer[D].Xiangtan: Xiangtan University, 2016(in Chinese).谭琦. 新型表面分子印迹聚合物对手性药物(S)-萘普生的吸附分离[D].湘潭: 湘潭大学,2016.
[38] Lai Shenzhi. Preparation of sueface imprinted materials and study on separation of amlodipine drugs[D]. Hunan: Xiangtan University,2016(in Chinese). 赖申枝. 表面印迹材料的制备及用于氨氯地平药物的手性分离研究[D].湘潭:湘潭大学,2017.
[39] Mao C, Xie X, Liu X. et al.The controlled drug release by pH-sensitive molecularly imprinted nanospheres for enhanced antibacterial activity[J]. Mater Sci Eng C Mater Biol Appl,2017,77:84-91.
[40] Madadian-Bozorg N, Zahedi P, Shamsi M, et al. Poly (methacrylic acid)-based molecularly imprinted polymer nanoparticles containing 5-fluourouracil used in colon cancer therapy potentially [J]. Polymers for Advanced Technologies, 2018, 29(8): 2401-2409.
[41] Chen H, Zhang W, Yang N, et al. Chitosan-based surface molecularly imprinted polymer microspheres for sustained sustained release of sinomenine hydrochloride in aqueous media[J].Appl Biochem Biote-chnol, 2018, 185(2):370-384.
[2] Vlatakis G, Andersson L I, Muller R, et al. Drug assay using antibody mimics made by molecular imprinting[J]. Nature, 1993, 361(6413):645-647.
[3] Chen L, Wang R, Cui L, et al. Preparation of five high-purity iridoid glycosides from Gardenia jasminoides Eills by molecularly imprinted solid-phase extraction integrated with preparative liquid chromatography [J]. Journal of Separation Science, 2018, 41(13): 2759-2766.
[4] Poole C F. New trends in solid-phase extraction[J]. Trends Anal Chem, 2003, 22(6): 362-373.
[5] Puoci F, Garreffa C, Iemma F, et al. Molecularly imprinted solid phase extraction for detection of sudan I in food matrices [J]. Food Chemistry, 2005, 93(2):349-353.
[6] Battal D, Akgonullu S, Yalcin M S, et al. Molecularly imprinted polymer based quartz crystal microbalance sensor system for sensitive and label-free detection of synthetic cannabinoids in urine [J]. Biosensors & Bioelectronics, 2018, 111:10-17.
[7] Afsarimanesh N, Mukhopadhyay S C, Kruger M, et al. Molecularly imprinted polymer-based electrochemical biosensor for bone loss detection [J]. IEEE Transactions on Bio-medical Engineering, 2018, 65(6): 1264-1271.
[8] Liu Yanli, Li Xiaojun, He Xiaorong, et al.The fabrication of molecularly imprinted electochemical sensor and its application in protein detection[J].Chemical Industry and Engineering Progress,2018,36(9):2533-2539(in Chinese).刘艳丽,李小军,贺晓荣,等.分子印迹电化学传感器制备及在蛋白质检测上的应用[J].化工进展,2018,36(9): 2533-2539.
[9] Lin C I, Joseph A K, Chang C K, et al. Synthesis of molecular imprinted organic-inorganic hybrid polymer binding caffeine [J]. Analytica Chimica Acta, 2003, 481(2): 175-180.
[10] Bonomi P, Servant A, Resmini M, et al. Modulation of imprinting efficiency in nanogels with catalytic activity in the Kemp elimination [J]. Journal of Molecular Recognition Jmr, 2012, 25(6): 352.
[11] Puoci F, Cirillo G, Curcio M, et al. Molecularly imprinted polymers in drugdelivery: state of art and future perspectives.[J]. Expert Opinion on Drug Delivery, 2011, 8(10):1379-1393.
[12] Chen H, Zhang W, Yang N, et al. Chitosan-based surface molecularly imprinted polymer microspheres for sustained release of sinomenine hydrochloride in aqueous media[J]. Appl Biochem Biotechnol, 2018, 185: 370-384.
[13] Li Y, Xiang R, Horvath, C, et al. Capillary electrochromatography of peptides on a neutral porous monolith with annular electroosmotic flow generation[J]. Electrophoresis, 2004, 25: 545-553.
[14] Wongniramaikul W, Choodum A, Dennany L, et al.A comprehensive chromatographic comparison of amphetamine and methylamphetamine extracted from river water using molecular imprinted polymers and without the need for sample derivatization[J]. J Sep Sci,2012,35:3332-3339.
[15] Philip C, Devaky K S. Multiwalled carbon nanotubes with surface grafted transition state analogue imprints as chymotrypsin mimics for the hydrolysis of amino acid esters: synthesis and kinetic studies [J]. Molecular Catalysis, 2017, 436:276-84.
[16] Yu H, Koide H, Urakami T, et al. Recognition, neutralization and clearance of target peptides in the blood stream of living mice by molecular imprinted polymer nanoparticles: a plastic antibody [J]. Journal of the American Chemical Society, 2010, 132(19): 6644-6645.
[17] Turner N W, Jeans C W, Brain K R, et al. From 3D to 2D: a review of the molecular imprinting of proteins[J]. Biotechnol Progr, 2006,22(6): 1474-1489.
[18] Jiao Jiaqi, Xue Yanbin, Yang Huizhen, et al. Application and prospect of molecular imprinting technology in drug extraction field [J]. Chinese Remedies And Clinics, 2018,18(2):214-218(in Chinese).焦佳琪,薛燕斌,杨慧珍, 等.分子印迹技术在药物提取领域的应用和展望[J].中国药物与临床,2018,18(2):214-218.
[19] Liu Renyong. Preparation of surface molecular imprinted polymers and its application in herdicide residlles detecction[D].Hefei: University of Science and Technology of China, 2009(in Chinese). 刘仁勇. 表面分子印记聚合物的制备及其在农残检测中的应用[D].合肥: 中国科学技术大学,2009.
[20] Huang J, Wu Y, Cong J, et al. Selective and sensitive glycoprotein detection via a biomimetic electrochemical sensor based on surface molecular imprinting and boronate-modified reduced graphene oxide [J]. Sensors and Actuators B: Chemical, 2018, 259:1-9.
[21] Rong Q, Zhang Y, Lyu T, et al. Highly selective and sensitive methanol gas sensor based on molecular imprinted silver-doped LaFeO3 core-shell and cage structures [J]. Nanotechnology, 2018, 29(14): 145503.
[22] Zheng X F, Lian, Q, Yang H, et al.Surface molecularly imprinted polymer of chitosan grafted poly(methyl methacrylate) for 5-fluorouracil and controlled release[J].Sci Rep,2016,6:214-219.
[23] Gao B, Li Y, Cui K, et al. Molecularly imprinted membrane with innovative structure and high performance for chiral separation of amino acids [J]. International Journal of Polymeric Materials and Polymeric Biomaterials, 2017, 67(8): 517-27.
[24] Ouyang R, Lei J, Ju H, et al. Surface molecularly imprinted nanowire for protein specific recognition [J]. Chemical Communications, 2008, 44: 5761-5763.
[25] Xu W Z, Zhou W, Xu P P, et al. A molecularly imprinted polymer based on TiO2 as a sacrificial support for selective recognition of dibenzothiophene [J]. Chemical Engineering Journal, 2011, 172(1): 191-198.
[26] Liu P, Zhang X, Xu W, et al. Electrochemical sensor for the determination of brucine in human serum based on molecularly imprinted poly-o-phenylenediamine/SWNTs composite film [J]. Sensors and Actuators B: Chemical, 2012, 163(1): 84-89.
[27] Wei Shoulian, Su Xuxian, Wang Hongwu, et al.Study and application of acid orangeⅡ sensor based on molecularly imprinted electropolymerized membrance[J]. Journal of Instrumental Analysis,2014, 33(6): 683-687(in Chinese).韦寿莲, 苏绪贤, 汪洪武, 等. 基于分子印迹电聚合膜的酸性橙Ⅱ传感器的研究及应用[J]. 分析测试学报, 2014, 33(6): 683-687.
[28] Li Y, Zhou W H, Yang H H, et al. Grafting of molecularly imprinted polymers from the surface of silica gel particles via reversible addition-fragmentation chain transfer polymerization: a selective sorbent for theophylline [J]. Talanta, 2009, 79(2): 141-145.
[29] Wu Y, Yan Y, Pan J, et al. Fabrication and evaluation of molecularly imprinted regenerated cellulose composite membranes via atom transfer radical polymerization [J]. Chinese Chemical Letters, 2014, 25(2): 273-278.
[30] Luo J, Chen N, Yang Z, et al. Determination of active ingredients in Chinese medicine danning tablets using dispersion solid-phase extraction by molecular imprinting nanomaterials coupled with HPLC-DAD [J]. Analytical Methods, 2017, 9(17): 2585-2589.
[31] Wan Y, Wang M, Fu Q, et al. Novel dual functional monomers based molecularly imprinted polymers for selective extraction of myricetin from herbal medicines[J].J Chromatogr B Analyt Technol Biomed Life Sci,2018,1097:1-9.
[32] Chen F F, Xie X Y, Shi Y P, et al. Magnetic molecularly imprinted polymer for the detection of rhaponticin in Chinese patent medicines [J]. Journal of Chromatography A, 2012, 1252:8-14.
[33] Tan K, Ma Q, Luo J, et al. Water-dispersible molecularly imprinted nanohybrids via co-assembly of carbon nanotubes with amphiphilic copolymer and photocrosslinking for highly sensitive and selective paracetamol detection [J]. Biosensors & Bioelectronics, 2018, 117(71):3-9.
[34] Ou S H, Pan L S, Jow J J, et al. Molecularly imprinted electrochemical sensor, formed on Ag screen-printed electrodes, for the enantioselective recognition of d and l phenylalanine[J].Biosens Bioelectron,2018,105:143-145.
[35] Essousi H, Barhoumi H. Electroanalytical application of molecular imprinted polyaniline matrix for dapsone determination in real pharmaceutical samples [J]. Journal of Electroanalytical Chemistry, 2018, 818(13):1-9.
[36] Wang Y F, Jin H X, Wang Y G, et al.Synthesis and characterization of magnetic molecularly imprinted polymer for the enrichment of ofloxacin enantiomers in fish samples[J].Molecules,2016,21(7):3-14.
[37] Tan Qi. Adsorption and separation of chiral drugs (S)-naproxen with novel surface moleculary imprinted polymer[D].Xiangtan: Xiangtan University, 2016(in Chinese).谭琦. 新型表面分子印迹聚合物对手性药物(S)-萘普生的吸附分离[D].湘潭: 湘潭大学,2016.
[38] Lai Shenzhi. Preparation of sueface imprinted materials and study on separation of amlodipine drugs[D]. Hunan: Xiangtan University,2016(in Chinese). 赖申枝. 表面印迹材料的制备及用于氨氯地平药物的手性分离研究[D].湘潭:湘潭大学,2017.
[39] Mao C, Xie X, Liu X. et al.The controlled drug release by pH-sensitive molecularly imprinted nanospheres for enhanced antibacterial activity[J]. Mater Sci Eng C Mater Biol Appl,2017,77:84-91.
[40] Madadian-Bozorg N, Zahedi P, Shamsi M, et al. Poly (methacrylic acid)-based molecularly imprinted polymer nanoparticles containing 5-fluourouracil used in colon cancer therapy potentially [J]. Polymers for Advanced Technologies, 2018, 29(8): 2401-2409.
[41] Chen H, Zhang W, Yang N, et al. Chitosan-based surface molecularly imprinted polymer microspheres for sustained sustained release of sinomenine hydrochloride in aqueous media[J].Appl Biochem Biote-chnol, 2018, 185(2):370-384.