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Preparation and Application of a Molecularly Imprinted Monolith for Specific Recognition of Domoic Acid

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Preparation and Application of a Molecularly Imprinted Monolith for Specific Recognition of Domoic Acid Analytical and Bioanalytical Chemistry https://doi.org/10.1007/s00216-017-0843-3 RESEARCH PAPER Preparation and application of a molecularly imprinted monolith for specific recognition of domoic acid Fan Yang1 & Ruirui Wang1 & Guangshui Na 1 & Qilun Yan1 & Zhongsheng Lin1 & Zhifeng Zhang1 Received: 14 September 2017 /Revised: 19 November 2017 /Accepted: 18 December 2017 # Springer-Verlag GmbH Germany, part of Springer Nature 2018 Abstract In this work, a molecularly imprinted monolithic column was synthesized by a facile procedure and was applied for specific recognition of domoic acid, an amnesic shellfish poison. The poly(4-vinylpyridine-co-ethylene glycol dimethacrylate) molecu- larly imprinted monolith was synthesized in a stainless steel column by in situ polymerization. Pentane-1,3,5-tricarboxylic acid was used as a dummy imprinting template instead of the highly toxic and expensive target molecule. It is the first time that a molecularly imprinted monolith is introduced for separation and detection of domoic acid. After optimizing the preparation conditions, the prepared imprinted monolith was systematically characterized and exhibited excellent stability and permeability as a HPLC stationary phase. The results of chromatographic analysis demonstrated that the molecularly imprinted monolith exhibited specific retention and selective recognition toward domoic acid, with an imprinted factor up to 3.77. Furthermore, the molecularly imprinted monolith was successfully applied for selective enrichment of domoic acid from biological samples. Keywords Molecular imprinting . Monolith . Domoic acid . High performance liquid chromatography Introduction low in seawater and biological samples, a reliable and sensitive analytical method for DA detection is urgently needed. To date, Domoic acid (DA) is a neurotoxinaminoacidwhichispro- several analytical methods have been reported for monitoring of duced by several species of marine single-celled diatoms of the DA in shellfish, phytoplankton, and seawater, such as enzyme- genus Pseudo-nitzschia and accumulates in crustaceans, fish, linked immunosorbent assay (ELISA) [6, 7], capillary electro- and shellfish [1]. As a major amnesic shellfish poisoning toxin, phoresis (CE) [8, 9], capillary electrochromatography (CEC) DA can bioaccumulate in filter-feeding marine organisms, and [10], high performance liquid chromatography (HPLC) the ingestion of these DA-contaminated seafood may lead to coupled with ultraviolet detection or mass spectrometry poisoning symptoms such as vomiting, diarrhea, abdominal [11–14], and so on. Compared with other DA detection cramps, headache, and dizziness. In severe cases, the victim methods, HPLC had the advantages of being accurate, sensi- may experience trouble breathing, seizures, permanent loss of tive, stable, and reliable, and was considered to be the most short-term memory, even coma or death [2–4]. DA is consid- widely used analytical method for DA detection. ered as a significant risk to not only public health but also the Molecular imprinting is known as a technique for synthesis stability of aquaculture and shellfish harvesting industries [5]. of tailor-made recognition materials by polymerization of suit- Many countries have carried out DA monitoring programs to able functional monomers and cross-linkers in the presence of ensure consumer protection and sustainable development of template [15]. After removal of the template from the polymer, marine economy. Since the concentration of DA is extremely molecularly imprinted polymers (MIPs) are obtained with rec- ognition cavities complementary to the template in shape, size, and functional groups, which can selectively recognize the tem- plate. Due to the remarkable selectivity and specific recognition * Fan Yang toward the target molecule, MIPs have gained great interest and [email protected] been widely applied in fields of separation processes, micro reactors, catalysis, biosensors, and so on [16–18]. In recent 1 Key Laboratory for Ecological Environment in Coastal Areas (SOA), years, molecularly imprinted materials were specifically de- National Marine Environmental Monitoring Center, No.42, Linghe Street, Dalian, Liaoning 116023, China signed as affinity absorbents to remove low-level DA from Yang F. et al. complex samples [19–24]. Lotierzo et al. [19], using DA as Experimental template, synthesized a molecularly imprinted polymer film by direct photo-grafting on a gold chip. Considering the high Materials and chemicals toxicity and high cost of DA, some dummy imprinting tem- plates were chosen as DA substitutes. Kubo et al. [20]usedo- 4-Vinylpyridine (4-VP) and DA were obtained from Sigma phthalic acid as an alternative template to prepare molecularly Aldrich (St. Louis, USA). Ethylene glycol dimethacrylate imprintedpolymerstowardtoDA,whichprovidedtwosimilar (EDMA) was obtained from Acros Organics (NJ, USA). neighboring carboxylic acid groups to simulate DA during the 2,2′-Azobisisobutyronitrile (AIBN) and benzoic acid were ob- imprinting process. Subsequently, they investigated a Bthree- tained from J&K Chemical (Beijing, China). PTA was from point^ recognition of DA by using pentane-1,3,5-tricarboxylic Tokyo Chemical Research Institute (Tokyo, Japan). Toluene acid (PTA) as imprinting template. By comparing with other and dodecanol were obtained from Kemiou Chemical structural analogues of DA, PTA was proved to be the opti- Reagent Co., Ltd. (Tianjin, China). Deionized water was pu- mized dummy template. The PTA-MIPs exhibited the highest rified using a Milli-Q water purification system (Millipore, selective recognition ability for DA and was successfully used Milford, MA, USA). Other reagents used were of analytical as solid-phase extraction (SPE) medium to selective enrichment grade or better. Stainless steel columns (100 mm × 4.6 mm of DA [21]. Zhou et al. [22] prepared MIP toward to DA by i.d.) were supplied by Hongtai Chromatogram Equipment bulk polymerization method, and used it as SPE sorbent for Co., Ltd. (Dalian, China). selective extraction of DA from seafood samples. These result- ed MIP materials have shown good selectivity toward to DA. Instruments However, when using MIPs as SPE sorbent before further anal- ysis, a tedious preparation procedure of packed columns is HPLC was used to investigate the adsorption and recognition needed, such as grinding, sieving, and column packing, which properties of the MIP monoliths. All the chromatographic ex- leads to time-consuming, poor reproducibility, and material periments were performed by using a Thermo Finnigan loss. Surveyor HPLC system (Thermo Fisher Scientific, USA), Monolith is a separation media that consist of a single, which consisted of a Surveyor LC pump, an Auto Sampler, continuous, integrated interconnecting porous skeleton with- and a PDA detector. Data acquisition and processing were out interparticular voids. As a new generation of stationary controlled by Xcalibur software system. The scanning elec- phase, monolithic column has shown significant advantages tron micrographic (SEM) images of the monoliths were ob- comparing with conventional particle-packed column, such as tained by a Nova NanoSEM 450 microscope (FEI, USA). easy preparation, versatile surface modification, fast mass- Pore size distribution measurements of the monoliths were transfer kinetics, and higher permeability [25]. With a bimodal conducted on an AutoPoreIV 9500 mercury intrusion porous structure comprising macropores and mesopores, porosimetry (Micrometritics, Norcross, GA, USA). Fourier- monoliths show both high permeability and large surface area transform infrared (FT-IR) spectra (4000 to 400 cm−1)in for interaction with analytes. Molecularly imprinted monolith- KBr were recorded using a NEXUS FT-IR spectrophotometer ic column (MIP monolith), which integrates high selectivity of (Thermo Nicolet, USA). Elemental analysis of the monolith molecularly imprinted technology and high efficiency of was performed by a CHNOS elemental analyzer (Vario monolithic column, has attracted significant interest as station- MICRO, Elementar, Germany). ary phase of HPLC and CEC for the fast and online isolation of desired analytes [26, 27]. It is important to explore MIP Preparation of organic polymer-based MIP monolith monolith in sample pretreatment and chromatographic sepa- ration of amnesic shellfish poisoning toxin. The MIP monolith was prepared using PTA as dummy tem- In this work, a MIP monolith was synthesized and applied plate in a stainless steel column by in situ polymerization for specific recognition of DA. To the best of our knowledge, under the optimal conditions. Briefly, the template molecule it is the first time to introduce MIP monolith for the separation PTA (10 mg) and functional monomer 4-VP (0.1 mL) were and detection of DA. Due to the high toxic and high cost of dissolved in a binary porogenic solvent, which consisted of DA, PTA was chosen as an alternative template during the 175 μL toluene and 1.575 mL dodecanol. Then cross-linker imprinting process. 4-Vinylpyridine and ethylene glycol EDMA (0.70 mL) and initiator of the polymerization reaction dimethacrylate were used as functional monomer and cross- AIBN (1 wt%) were added in the above solution stepwise. The linker respectively during the in situ polymerization process. polymerization mixture was sonicated for 3 min in order to The synthesis procedure was simple, facile, and cost efficient. obtain homogeneous solution, and purged with nitrogen for The resultant monolith was systematically
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