Preparation of molecularly imprinted polymer microspheres via atom transfer radical precipitation polymerization

The first combined use of atom transfer radical polymerization (ATRP) and precipitation polymerization in the molecular imprinting field is described. The utilized polymerization technique, namely atom transfer radical precipitation polymerization (ATRPP), provides MIP microspheres with obvious molecular imprinting effects towards the template, fast template binding kinetics and an appreciable selectivity over structurally related compounds. The living chain propagation mechanism in ATRPP results in MIP spherical particles with diameters (number‐average diameter D_n ≈ 3 μm) much larger than those prepared via traditional radical precipitation polymerization (TRPP). In addition, the MIP microspheres prepared via ATRPP have also proven to show significantly higher high‐affinity binding site densities on their surfaces than the MIP generated via TRPP, while the binding association constants K_a and apparent maximum numbers N_max of the high‐affinity sites as well as the specific template bindings are almost the same in the two cases. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 3257–3270, 2009     

Preparation and evaluation of a macroporous molecularly imprinted hybrid silica monolithic column for recognition of proteins by high performance liquid chromatography

A novel type of macroporous molecularly imprinted hybrid silica monolithic column was first developed for recognition of proteins. The macroporous silica-based monolithic skeleton was synthesized in a 4.6 mm i.d. stainless steel column by a mild sol–gel process with methyltrimethoxysilane (MTMS) as a sole precursor, and then vinyl groups were introduced onto the surface of the silica skeleton by chemical modification of γ-methacryloxypropyltrimethoxysilane (γ-MAPS). Subsequently, the molecularly imprinted polymer (MIP) coating was copolymerized and anchored onto the surface of the silica monolith. Bovine serum albumin (BSA) and lysozyme (Lyz), which differ greatly in molecular size, isoelectric point, and charge, were representatively selected for imprinted templates to evaluate recognition property of the hybrid silica-based MIP monolith. Some important factors, such as template–monomer molar ratio, total monomer concentration and crosslinking density, were systematically investigated. Under the optimum conditions, the obtained hybrid silica-based MIP monolith showed higher binding affinity for template than its corresponding non-imprinted (NIP) monolith. The imprinted factor (IF) for BSA and Lyz reached 9.07 and 6.52, respectively. Moreover, the hybrid silica-based MIP monolith displayed favorable binding characteristics for template over competitive protein. Compared with the imprinted silica beads for stationary phase and in situ organic polymer-based hydrogel MIP monolith, the hybrid silica MIP monolith exhibited higher recognition, stability and lifetime.     

A novel molecularly imprinted method with computational simulation for the affinity isolation and knockout of baicalein from Scutellaria baicalensis

A novel molecularly imprinted polymer (MIP) was synthesized by precipitation polymerization with baicalein (BAI) as the template and used as solid‐phase extraction (SPE) adsorbent, aiming at the affinity isolation and selective knockout of BAI from Scutellaria baicalensis Georgi (SB). We used computational simulation to predict the optimal functional monomer, polymerization solvent and molar ratio of template to functional monomer. Characterization and performance tests revealed that MIP exhibited uniform spherical morphology, rapid binding kinetics, and higher adsorption capacity for BAI compared with nonimprinted polymer (NIP). The application of MIP in SPE coupled with high‐performance liquid chromatography to extract BAI from SB showed excellent recovery (94.3%) and purity (97.0%). Not only the single BAI compound, but also the BAI‐removed SB extract was obtained by one‐step process. This new method is useful for isolation and knockout of key bioactive compounds from herbal medicines. Copyright © 2015 John Wiley & Sons, Ltd.     

Preparation of molecular imprinted polymer with quaternary ammonium groups as recognition sites for separation of pig cyclophilin 18 and bovine serum albumin

We introduce a new type of molecular imprinted polymer (MIP) with immobilized assistant recognition polymer chains (ARPCs) to create effective recognition sites. In this work, cloned pig cyclophilin 18 (pCyP18) and BSA were used as templates, respectively. The template protein was selectively assembled with ARPCs from the library which consists of numerous limited length polymer chains with randomly distributed recognition sites of the quaternary ammonium cationic groups and immobilizing sites. The assemblies of protein and ARPCs were adsorbed by macroporous microspheres and immobilized by cross‐linking polymerization. After removing the templates, the two kinds of synthesized MIPs were used to adsorb cloned pCyP18 and BSA from protein mixtures respectively and both showed high selectivity. It confirms that this new method is suitable to separate proteins of both low and high molecular weight. The extended experiment on adsorption of natural pCyP18 from cytosol shows that the obtained MIP using cloned protein as template can be used to enrich natural protein of low content.     

Surface plasmon resonance sensor chips for the recognition of bovine serum albumin via electropolymerized molecularly imprinted polymers

In this paper,a surface plasmon resonance(SPR)sensor chip for detection of bovine serum album(BSA)was prepared by electropolymerization of 3-aminophenylboronic acid(3-APBA)based on molecularly imprinted polymer(MIP)technique.The surface morphology of MIP and non-imprinted(NIP)flms were characterized by scanning electroscopy(SEM).SEM images exhibited nanoscale cavities formed on the MIP films surface homogeneously due to the removal of BSA templates.The effects of pH,ion strength of rebinding BSA,the specific binding and selective recognition were studied for MIP films.Results indicated that the BSA-imprinted films exhibited a good adsorption of template protein(0.02–0.8 mg/mL)in0.05 mol/L sodium phosphate buffer at pH 5.0 with the limit of detection(LOD)of 0.02 mg/mL.     

Thermosensitive molecularly imprinted hydrogel cross‐linked with N‐malely chitosan for the recognition and separation of BSA

A novel temperature‐sensitive molecularly imprinted hydrogel composed of N‐isopropylacrylamide and acrylamide has been prepared by using free‐radical polymerization and was cross‐linked by modified water‐soluble N‐maley chitosan in aqueous solution. BSA (pI 4.9, MW 66.0 kDa) was used as the template protein. The produced hydrogels were characterized by environmental SEM to reveal the microcosmic morphology. A microporous structure was only found in the imprinted hydrogel, while no obvious microporous structure was found in nonimprinted hydrogels. The lower critical solution temperature of the hydrogels was 34°C, and the optimal binding conditions were tested, namely, the adsorption equilibrium time of 6 h and initial BSA concentration of 1.0 mg/mL. The adsorption capacity Q_max was determined by Langmuir isotherm plots and was 5.72 mg/g for imprinted hydrogel and 1.18 mg/g for nonimprinted hydrogels. A separation factor (β) of 4 was obtained when bovine hemoglobin (pI 6.9, MW 64.0 kDa) was selected as the particular reference protein. Molecular weights and pIs were chosen to investigate the selectivity of the hydrogels. It was shown that the shape memory and the size effect were the major factors for the recognition. This imprinted hydrogel was used to specifically adsorb the BSA from the protein mixture.     

Molecularly imprinted hydrogel displaying reduced non‐specific binding and improved protein recognition

A novel approach for enhancing protein recognition in molecularly imprinted hydrogel (MIH) is presented. This approach was developed based on the hypothesis that the number of specific binding sites created in the previously described MIH is very small, thus attempts to enhance the capacity result in most cases in additional non‐specific binding and loss of selectivity. Thus, blocking the non‐specific binding sites could lead to higher capacities and better selectivity. To test this hypothesis, MIH interpenetrating networks designed to block non‐specific binding sites were synthesized using two separate stages of polymerization. Re‐binding of the template protein (lysozyme) and a competitor protein (cytochrome C) was measured, and the results were compared with the similar experiment performed using a control non‐imprinted hydrogel and a “conventional” MIH. The imprinting efficacy of the MIH interpenetrating network was found to be much higher than that of the controls. Furthermore, competitive adsorption assays have demonstrated the superiority of the new formulation.     

Bovine serum albumin recognition via thermosensitive molecular imprinted macroporous hydrogels prepared at two different temperatures

A novel temperature-sensitive molecular imprinted hydrogel composed of 2-acrylamido-2-methyl-propanosulfonic acid (AMPS), N-isopropylacrylamide (NIPAm) and acrylamide (AAm) has been prepared by free-radical cross-linking copolymerization in aqueous solution under two different temperatures (25 °C and −20 °C). Bovine serum albumin (BSA, pI 4.9, MW 66.0 kDa) is used as the template protein. The influence of the external temperature stimuli on the affinity of the hydrogels was investigated, and the optimal binding conditions were tested. The adsorption capacity (Q_max) and association constant (K) for the specific interaction between the hydrogel and the template protein were determined by Langmuir isotherm plots. Several types of reference protein, which are different in molecular weights and isoelectric points were chosen to investigate the selectivity of the hydrogels. It was shown that the shape memory and the charge effect were the major factors for the recognition. This imprinted hydrogel was used to specifically adsorb the BSA from the protein mixture and real sample, which demonstrated its potential selectivity.     

液晶分子印迹整体柱的制备及其分子识别热力学

液晶分子印迹聚合物(MIPs)因刚性液晶单体的加入而在超低交联度水平下也能印迹和识别模板分子,有效解决了传统MIPs因高交联度造成的位点包埋、结合容量低、传质慢等问题。尽管液晶MIPs具有如此独特的优势,但却面临着由于交联度的大幅度降低而导致印迹效果下降的问题。为了研究液晶MIPs的结合特性,制备具有良好印迹效果的低交联液晶MIPs,该文通过二次接枝聚合,制备了一系列不同交联度的液晶分子印迹整体柱,用高效液相色谱法研究了聚合参数与印迹整体柱亲和性的关系。实验中选用三羟甲基丙烷三甲基丙烯酸酯(TRIM)为交联剂,以甲苯和十二醇为致孔剂合成整体柱骨架,并在此基础上以(S)-萘普生为模板,加入液晶单体4-氰基苯基单环己基乙烯(CPCE)进行二次聚合接枝。实验中系统考察了流动相中乙腈比例及缓冲液pH值对色谱保留的影响,结果发现液晶单体的加入使得MIPs对萘普生保留控制机制由原来的氢键作用变为了疏水作用;通过动态吸附实验得到的突破曲线经前沿分析及对吸附等温线Langmuir、Freundlich和Scatchard分析拟合,发现交联度为15%时液晶MIPs印迹因子最大(3.78)、非均一性最强,且特异性吸附量高于非特异性吸附量。液晶MIPs的计量置换模型(SDM-R)分析表明,液晶印迹整体柱对模板分子的总亲和力(ln A=0.645)明显高于其类似物;而从空间匹配程度看,与液晶印迹整体柱空间匹配程度最高的是酮洛芬而非模板分子,但液晶印迹整体柱对酮洛芬的总亲和力(ln A=0.242)不及模板分子的一半,表明在本低交联液晶印迹系统中,空间效应不是决定印迹系统识别能力的主要因素。进一步的分离热力学研究发现,低交联液晶印迹柱的|ΔΔH|<T|ΔΔS|,而交联度为70%的非液晶MIPs柱的|ΔΔH|>T|ΔΔS|,表明液晶MIPs的分离过程是一个熵控制过程,而常规无液晶MIPs的分离过程是一个焓控制过程。上述结果表明,液晶单体的加入改变了MIPs的识别机制,适当的低交联度可显著提高液晶MIPs的识别性能,因此液晶MIPs这些特质有望使其成为新一代的MIPs。     

Study on the Binding Characteristic of Methamidophos‐Specific Molecularly Imprinted Polymer and the Interactions between Template and Monomers

A new molecularly imprinted polymer (MIP) was prepared using methamidophos (MAP) as the template molecule based on non‐covalent interaction. The complexes formed between template and monomers before polymerization were characterized by ¹H NMR titration test, FT‐IR and UV spectrometry study. These studies indicated that a 1:2 molecular complex formed dominantly between MAP and functional monomers. A model mainly involving cooperative hydrogen interaction was proposed by exact placement of functional groups. Association constant was estimated to be 2.894 × 10⁶ L²/mol². When the initial concentration of MAP was 1.0 mmol L^?1, the affinity capacity of MIP was 4.23 times that of NIP. The binding performance of MIP was modeled with the Freundlich isotherm (FI) and the total number of binding sites was calculated to be 33.97 μmol/g. The MIP showed great homogeneity with a heterogeneity index of m = 0.7356. The specificity of MIP was investigated by single‐analyte binding and molecularly imprinted solid‐phase extraction (MISPE) assays using MAP and other structurally related organophorous pesticides (OPPs). The results indicated that the MIP had a marked preference for MAP.     

Preparation of molecularly imprinted polymers via atom transfer radical “bulk” polymerization

The first application of atom transfer radical “bulk” polymerization (ATRBP) in molecular imprinting is described, which provides molecularly imprinted polymers (MIPs) with obvious imprinting effects towards the template, very fast binding kinetics, and an appreciable selectivity over structurally related compounds. In comparison with the MIP prepared via the normally used traditional “bulk” free radical polymerization (BFRP), the MIPs obtained via ATRBP showed somewhat lower binding capacities and apparent maximum numbers N_max for high‐affinity sites as well as quite similar binding association constants K_a for high‐affinity sites and high‐affinity site densities, in contrast with the previous reports (e.g., nitroxide/iniferter‐mediated “bulk” polymerization provided MIPs with improved properties). This is tentatively ascribed to the occurrence of rather fast gelation process in ATRBP, which greatly restricted the mobility of the chemical species, leading to a heavily interrupted equilibrium between dormant species and active radicals and heterogeneous polymer networks. In addition, the general applicability of ATRBP was also confirmed by preparing MIPs for different templates. This work clearly demonstrates that applying controlled radical polymerizations (CRPs) in molecular imprinting not always benefits the binding properties of the resultant MIPs, which is of significant importance for the rational use of CRPs in generating MIPs with improved properties. © 2009 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 532–541, 2010     

Preparation and characterization of protein molecularly imprinted polysiloxane using mesoporous calcium silicate as matrix by sol–gel technology

Calcium silicate particles containing mesoporous SiO₂ on the surface (CaSiO₃@SiO₂) were prepared by acid modification of calcium silicate with diluted hydrochloric acid. Bovine serum albumin (BSA) molecularly imprinted polysiloxane (MIP) was synthesized using silane as the functional monomer, BSA as the template and CaSiO₃@SiO₂ particles as the matrix in an aqueous phase. SEM, granulometry, FT-IR and BET analysis were used to characterize the protein MIP. Influence factors on the rebinding capacity of the MIP were investigated, such as the pH in treating CaSiO₃, eluent type and silane proportion. The mass of BSA loading and rebinding on CaSiO₃@SiO₂ and MIP was investigated. The adsorption and recognition properties of the MIP were evaluated and the results showed that the MIP exhibited an obvious improvement in terms of rebinding capacity for BSA as compared with non-imprinted polysiloxane (NIP). BSA imprinted polysiloxane could recognize the template protein by using Lys, Ova, Hb, and Glo as control proteins, and the selectivity factor (β) was above 2.3. The rebinding capacity of BSA imprinted polysiloxane for BSA reached 81.31 mg/g, which was 2.25 times of NIP.     

Synthesis and Adsorption Study of BSA Surface Imprinted Polymer on CdS Quantum Dots

A new bovine serum albumin (BSA) surface imprinting method was developed by the in-corporation of quantum dots (QDs) into molecularly imprinted polymers (MIP), which can offer shape selectivity. Preparation and adsorption conditions were optimized. Physical ap-pearance of the QDs and QDs-MIP particles was illustrated by scanning electron microscope images. Photoluminescence emission of CdS was quenched when rebinding of the template.The quenching of photoluminescence emissions is presumably due to the fluorescence reso-nance energy transfer between quantum dots and BSA template molecules. The adsorption is compiled with Langmuir isotherm, and chemical adsorption is the rate-controlling step.The maximum adsorption capacity could reach 226.0 mg/g, which is 142.4 mg/g larger than that of undoped BSA MIP. This study demonstrates the validity of QDs coupled with MIP technology for analyzing BSA.     

橄榄醇分子印迹聚合物的制备及评价(英文)

以橄榄醇为模板分子,α-甲基丙烯酸(MAA)为功能单体,乙二醇二甲基丙烯酸酯(EDMA)为交联剂,甲苯和十二醇为溶剂,通过本体聚合法制备了橄榄醇分子印迹聚合物。利用平衡结合实验、扫描电镜(SEM)及红外光谱(FTIR)对分子印迹聚合物(MIP)进行了表征,并用该聚合物进行了加标麦麸中橄榄醇的固相萃取(SPE)研究。平衡结合实验表明MIP对模板分子具有更好的识别性。Scatchard分析表明对橄榄醇分子的吸附存在2类不同结合位点,其中高亲和力结合位点和低亲和力结合位点的解离常数分别为0.021和1.002 mmol/L,相应的最大表观结合量分别为18.74和135.9 μmol/g。在优化的固相萃取条件下,MIP固相萃取柱对加标麦麸中橄榄醇的回收率达到97.8%~98.8%,相对标准偏差为2.8%~4.2%(n=5),线性范围为0.1~100 mg/L,检出限(S/N=3)为0.062 mg/L。与非印迹聚合物(NIP)柱及市售聚苯乙烯/二乙烯基苯(PLS)柱相比,MIP柱的选择性更强,回收率更高,纯化效果更好。     

Preparation and characterization of molecularly imprinted organic–inorganic hybrid materials by sol–gel processing for selective recognition of ibuprofen

This work adopted semi-covalent imprinting to prepare molecularly imprinted polymers (MIP) with ibuprofen, a non-steroidal anti-inflammatory drug, as template by sol–gel processing, which is characterized by both the high affinity of covalent binding and the mild operation conditions of non-covalent rebinding. A functional monomer, which was used to synthesize the monomer-imprinted molecule complex, was prepared by multi-step synthesis for the first time. MIP was characterized by Fourier transform IR spectrum and nitrogen adsorption. Thin-layer chromatography separation was used to evaluate the specific molecular recognition ability of MIP. In addition, dynamic and thermodynamic studies on MIP imprinting ibuprofen were undertaken. The results of equilibrium rebinding experiments showed that MIP exhibited good adsorption capacity for ibuprofen. Scatchard analysis illustrated that the template-polymer system shows only one-site binding behavior with a dissociation constant of 1.84 mmol L^?1. Dynamic adsorption exhibited pseudo-second-order kinetics. The positive value of ΔH^θ and the negative values of ΔG^θ demonstrated that the binding system for MIP is endothermic and spontaneous.     

Uniform molecularly imprinted microspheres and nanoparticles prepared by precipitation polymerization: the control of particle size suitable for different analytical applications

Molecularly imprinted polymers (MIPs) are being increasingly used as selective adsorbents in different analytical applications. To satisfy the different application purposes, MIPs with well controlled physical forms in different size ranges are highly desirable. For examples, MIP nanoparticles are very suitable to be used to develop binding assays and for microfluidic separations, whereas MIP beads with diameter of 1.5-3 μm can be more appropriate to use in new analytical liquid chromatography systems. Previous studies have demonstrated that imprinted microspheres and nanoparticles can be synthesized using a simple precipitation polymerization method. Despite that the synthetic method is straightforward, the final particle size obtained has been difficult to adjust for a given template. In this work, we initiated to study new synthetic conditions to obtain MIP beads with controllable size in the nano- to micro-meter range, using racemic propranolol as a model template. Varying the composition of the cross-linking monomer allowed the particle size of the MIP beads to be altered in the range of 130 nm to 2.4 μm, whereas the favorable binding property of the imprinted beads remained intact. The chiral recognition sites were further characterized with equilibrium binding analysis using tritium-labeled (S)-propranolol as a tracer. In general, the imprinted sites displayed a high chiral selectivity: the apparent affinity of the (S)-imprinted sites for (S)-propranolol was 20 times that of for (R)-propranolol. Compared to previously reported irregular particles, the chiral selectivity of competitive radioligand binding assays developed from the present imprinted beads has been increased by six to seven folds in an optimized aqueous solvent.     

Constituting of a new surface‐initiating system on polymeric microspheres and preparation of basic protein surface‐imprinted material in aqueous solution

In this work, a new surface‐initiating system was constituted on the surfaces of cross‐linked polyvinyl alcohol (CPVA) microspheres, and on this basis, papain surface‐imprinted material was successfully prepared in aqueous solution. CPVA microspheres were modified with chlorethamin as reagent, and so a mass of primary amino group was introduced onto CPVA microspheres. Whereupon, a surface initiating system (−NH₂/S₂O₈²⁻) was formed at the interface between the microspheres and aqueous solution, in which papain as template protein, 4‐styrene sulfonate (SSS) as functional monomer, N,N′‐methylenebisacrylamide (MBA) as cross‐linker and (NH₄)₂S₂O₈ as initiator were all dissolved. In neutral solution, the polypeptide chains of papain as a basic protein were positively charged, and the molecules of anionic monomer SSS would spontaneously gather around papain polypeptide chain, forming complex by right of strong electrostatic interaction. The free radicals produced on CPVA microspheres initiated the monomer SSS around papain polypeptide chain and the cross‐linker MBA to produce graft/cross‐linking polymerization, and at the same time, papain macromolecules were embed in the cross‐linked networks. As a result, the graft/cross‐linking polymerizing of SSS and the molecule imprinting of papain were synchronously carried out, and papain surface‐imprinted material, MIP‐PSSS/CPVA microspheres, was obtained. The experimental results show that the papain surface‐imprinted material has excellent binding affinity and high recognition selectivity for papain. The binding capacity of MIP‐PSSS/CPVA microspheres for papain reaches 44 mg/g, and relative to another basic protein, trypsin (TRY) as contrast protein, the selectivity coefficient of MIP‐PSSS/CPVA microspheres for papain is 14.35, displaying very high recognition specificity.     

One‐pot synthesis of surface‐functionalized molecularly imprinted polymer microspheres by iniferter‐induced “living” radical precipitation polymerization

This article describes for the first time the development of a new polymerization technique by introducing iniferter‐induced “living” radical polymerization mechanism into precipitation polymerization and its application in the molecular imprinting field. The resulting iniferter‐induced “living” radical precipitation polymerization (ILRPP) has proven to be an effective approach for generating not only narrow disperse poly(ethylene glycol dimethacrylate) microspheres but also molecularly imprinted polymer (MIP) microspheres with obvious molecular imprinting effects towards the template (a herbicide 2,4‐dichlorophenoxyacetic acid (2,4‐D)), rather fast template rebinding kinetics, and appreciable selectivity over structurally related compounds. The binding association constant K_a and apparent maximum number N_max for the high‐affinity sites of the 2,4‐D imprinted polymer were determined by Scatchard analysis and found to be 1.18 × 10⁴ M^?1 and 4.37 μmol/g, respectively. In addition, the general applicability of ILRPP in molecular imprinting was also confirmed by the successful preparation of MIP microspheres with another template (2‐chloromandelic acid). In particular, the living nature of ILRPP makes it highly useful for the facile one‐pot synthesis of functional polymer/MIP microspheres with surface‐bound iniferter groups, which allows their direct controlled surface modification via surface‐initiated iniferter polymerization and is thus of great potential in preparing advanced polymer/MIP materials. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 48: 3217–3228, 2010     

Adsorption Isotherms of Quercetin and Catechin Compounds on Quercetin-MIP

A molecular imprinted polymer(MIP)was prepared with quercetin as the template and methacrylic acid(MAA)as the functional monomer.Acetonitrile and methanol were used as the porogen with ethylene glycol dimethacrylate(EGDMA)as the crosslinker and 2,2'-azobis(isobutyronitrile)(AIBN)as the initiator.The experimental parameters of the equilibrium isotherms were estimated via linear and nonlinear regression analyses.The linear equation as the functions of the adsorption concentration of the single compound in its solution and the competitive adsorption of the single compound in its mixed compounds solution was then expressed,and the adsorption equilibrium data were correlated to Langmuir and Freundlich isotherm models.The mixture compounds show competitive adsorption on the specific binding sites of quercetin-MIP.Furthermore,the competitive Langmuir isotherms were applied to the mixture compounds.The adsorption concentrations of quercetin,( )catechin( C),and(-)epicatechin(EC)on the quercetin molecular imprinted polymer were compared.The quercetin-imprinted polymer shows extraordinarily higher adsorption ability for quercetin than for the two catechin compounds that were also assessed.     

Selective recognition of 4-nitrophenol from aqueous solution by molecularly imprinted polymers with functionalized tetratitanate whisker composites as support

Three kinds of molecularly imprinted polymers (MIPs) were obtained with surface molecular imprinting technique on functionalized potassium tetratitanate whisker (F-PTW). The results of adsorption experiments indicated that MIP prepared using PTW modified with N-(2-aminoethyl)-3-(trimethoxysilyl)propylamine (AAPTS) (F-PTW A) as support [MIP(1)] was superior to the other two polymers, then MIP(1) was selected to analyze the 4-nitrophenol (4-NP) adsorption process from aqueous solution in this study. AAPTS offered hydrophilic exterior that allowed to self-assemble with the template 4-NP through intermolecular interaction rather than based on the interactions between the functional monomers and template. Equilibrium adsorption data were analyzed by the Langmuir and Freundlich isotherm models at various temperatures. Kinetic properties were successfully investigated by pseudo-first-order model, pseudo-second-order model, intraparticle diffusion equation, initial adsorption rate, half-adsorption time. A diffusion-controlled process as the essential adsorption rate-controlling step was also proposed. The performance of such imprinted polymer was further demonstrated by high-performance liquid chromatography, and the results showed that the selectivity of MIP(1) exhibited higher affinity for template 4-NP over competitive phenolic compounds than that of non-imprinted polymer NIP(1). MIP(1) could be reused four times without significant loss in the adsorption capacity.