Journal of Pharmaceutical Analysis

2022, 12(3): ii-ii. doi: 10.1016/S2095-1779(22)00035-1

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Recent advances in quantum dots-based biosensors for antibiotics detection

Rui Ding, Yue Chen, Qiusu Wang, Zhengzhang Wu, Xing Zhang, Bingzhi Li, Lei Lin

2022, 12(3): 355-364. doi: 10.1016/j.jpha.2021.08.002

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Antibiotics are a category of chemical compounds used to treat bacterial infections and are widely applied in cultivation, animal husbandry, aquaculture, and pharmacy. Currently, residual antibiotics and their metabolites pose a potential risk of allergic reactions, bacterial resistance, and increased cancer incidence. Residual antibiotics and the resulting bacterial antibiotic resistance have been recognized as a global challenge that has attracted increasing attention. Therefore, monitoring antibiotics is a critical way to limit the ecological risks from antibiotic pollution. Accordingly, it is desirable to devise new analytical platforms to achieve efficient antibiotic detection with excellent sensitivity and specificity. Quantum dots (QDs) are regarded as an ideal material for use in the development of antibiotic detection biosensors. In this review, we characterize different types of QDs, such as silicon, chalcogenide, carbon, and other doped QDs, and summarize the trends in QD-based antibiotic detection. QD-based sensing applications are classified according to their recognition strategies, including molecularly imprinted polymers (MIPs), aptamers, and immunosensors. We discuss the advantages of QD-derived antibiotic sensors, including low cost, good sensitivity, excellent stability, and fast response, and illustrate the current challenges in this field.

Nanomagnet-facilitated pharmaco-compatibility for cancer diagnostics:Underlying risks and the emergence of ultrasmall nanomagnets

Divya S. Parimi, Yamini Gupta, Sreekar Marpu, Chandra S. Bhatt, Tharun K. Bollu, Anil K. Suresh

2022, 12(3): 365-379. doi: 10.1016/j.jpha.2021.11.002

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Cancer therapy is a fast-emerging biomedical paradigm that elevates the diagnostic and therapeutic potential of a nanovector for identification, monitoring, targeting, and post-treatment response analysis. Nanovectors of superparamagnetic iron oxide nanoparticles (SPION) are of tremendous significance in cancer therapy because of their inherited high surface area, high reactivity, biocompatibility, superior contrast, and magnetic and photo-inducibility properties. In addition to a brief introduction, we summarize various progressive aspects of nanomagnets pertaining to their production with an emphasis on sustainable biomimetic approaches. Post-synthesis particulate and surface alterations in terms of pharmaco-affinity, liquid accessibility, and biocompatibility to facilitate cancer therapy are highlighted. SPION parameters including particle contrast, core-fusions, surface area, reactivity, photosensitivity, photodynamics, and photothermal properties, which facilitate diverse cancer diagnostics, are discussed. We also elaborate on the concept of magnetism to selectively focus chemotherapeutics on tumors, cell sorting, purification of bioentities, and elimination of toxins. Finally, while addressing the toxicity of nanomaterials, the advent of ultrasmall nanomagnets as a healthier alternative with superior properties and compatible cellular interactions is reviewed. In summary, these discussions spotlight the versatility and integration of multi-tasking nanomagnets and ultrasmall nanomagnets for diverse cancer theragnostics.

Natural product-based radiopharmaceuticals:Focus on curcumin and its analogs, flavonoids, and marine peptides

Hendris Wongso

2022, 12(3): 380-393. doi: 10.1016/j.jpha.2021.07.006

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Natural products provide a bountiful supply of pharmacologically relevant precursors for the development of various drug-related molecules, including radiopharmaceuticals. However, current knowledge regarding the importance of natural products in developing new radiopharmaceuticals remains limited. To date, several radionuclides, including gallium-68, technetium-99m, fluorine-18, iodine-131, and iodine-125, have been extensively studied for the synthesis of diagnostic and therapeutic radiopharmaceuticals. The availability of various radiolabeling methods allows the incorporation of these radionuclides into bioactive molecules in a practical and efficient manner. Of the radiolabeling methods, direct radioiodination, radiometal complexation, and halogenation are generally suitable for natural products owing to their simplicity and robustness. This review highlights the pharmacological benefits of curcumin and its analogs, flavonoids, and marine peptides in treating human pathologies and provides a perspective on the potential use of these bioactive compounds as molecular templates for the design and development of new radiopharmaceuticals. Additionally, this review provides insights into the current strategies for labeling natural products with various radionuclides using either direct or indirect methods.

Phytochemicals targeting NF-κB signaling:Potential anti-cancer interventions

Akansha Chauhan, Asim Ul Islam, Hridayesh Prakash, Sandhya Singh

2022, 12(3): 394-405. doi: 10.1016/j.jpha.2021.07.002

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Nuclear factor κB (NF-κB) is a ubiquitous regulator of the signalome and is indispensable for various biological cell functions. NF-κB consists of five transcription factors that execute both cytoplasmic and nuclear signaling processes in cells. NF-κB is the only signaling molecule that governs both pro- and anti-apoptotic, and pro- and anti-inflammatory responses. This is due to the canonical and non-canonical components of the NF-κB signaling pathway. Together, these pathways orchestrate cancer-related inflammation, hyperplasia, neoplasia, and metastasis. Non-canonical NF-κB pathways are particularly involved in the chemoresistance of cancer cells. In view of its pivotal role in cancer progression, NF-κB represents a potentially significant therapeutic target for modifying tumor cell behavior. Several phytochemicals are known to modulate NF-κB pathways through the stabilization of its inhibitor, IκB, by inhibiting phosphorylation and ubiquitination thereof. Several natural pharmacophores are known to inhibit the nuclear translocation of NF-κB and associated pro-inflammatory responses and cell survival pathways. In view of this and the high degree of specificity exhibited by various phytochemicals for the NF-κB component, we herein present an in-depth overview of these phytochemicals and discuss their mode of interaction with the NF-κB signaling pathways for controlling the fate of tumor cells for cancer-directed interventions.

Physicochemical degradation of phycocyanin and means to improve its stability:A short review

Aïda Adjali, Igor Clarot, Zilin Chen, Eric Marchioni, Ariane Boudier

2022, 12(3): 406-414. doi: 10.1016/j.jpha.2021.12.005

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The cyanobacterium Arthrospira platensis, spirulina, is a source of pigments such as phycobiliprotein and phycocyanin. Phycocyanin is used in the food, cosmetics, and pharmaceutical industries because of its antioxidant, anti-inflammatory, and anticancer properties. The different steps involved in extraction and purification of this protein can alter the final properties. In this review, the stability of phycocyanin (pH, temperature, and light) is discussed, considering the physicochemical parameters of kinetic modeling. The optimal working pH range for phycocyanin is between 5.5 and 6.0 and it remains stable up to 45 ℃; however, exposure to relatively high temperatures or acidic pH decreases its half-life and increases the degradation kinetic constant. Phycobiliproteins are sensitive to light; preservatives such as mono- and di-saccharides, citric acid, or sodium chloride appear to be effective stabilizing agents. Encapsulation within nano- or micro-structured materials such as nanofibers, microparticles, or nanoparticles, can also preserve or enhance its stability.

A preparation strategy for protein-oriented immobilized silica magnetic beads with Spy chemistry for ligand fishing

Yu Yi, Jianming Hu, Shenwei Ding, Jianfeng Mei, Xudong Wang, Yanlu Zhang, Jianshu Chen, Guoqing Ying

2022, 12(3): 415-423. doi: 10.1016/j.jpha.2021.07.008

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Due to the complexity of bioactive ingredients in biological samples, the screening of target proteins is a complex process. Herein, a feasible strategy for directing protein immobilization on silica magnetic beads for ligand fishing based on SpyTag/SpyCatcher (ST/SC)-mediated anchoring is presented. Carboxyl functional groups on the surface of silica-coated magnetic beads (SMBs) were coupled with SC using the 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride/N-hydroxysulfosuccinimide method, named SC-SMBs. The green fluorescent protein (GFP), as the capturing protein model, was ST-labeled and anchored at a specific orientation onto the surface of SC-SMBs directly from relevant cell lysates via ST/SC self-ligation. The characteristics of the SC-SMBs were studied via electron microscopy, energy dispersive spectroscopy, and Fourier transform infrared spectroscopy. The spontaneity and site-specificity of this unique reaction were confirmed via electrophoresis and fluorescence analyses. Although the alkaline stability of ST-GFP-ligated SC-SMBs was not ideal, the formed isopeptide bond was unbreakable under acidic conditions (0.05 M glycine-HCl buffer, pH 1-6) for 2 h, under 20% ethanol solution within 7 days, and at most temperatures. We, therefore, present a simple and universal strategy for the preparation of diverse protein-functionalized SMBs for ligand fishing, prompting its usage on drug screening and target finding.

Compatibility and stability studies involving polymers used in fused deposition modeling 3D printing of medicines

Ihatanderson A. Silva, Ana Luiza Lima, Tais Gratieri, Guilherme M. Gelfuso, Livia L. Sa-Barreto, Marcilio Cunha-Filho

2022, 12(3): 424-435. doi: 10.1016/j.jpha.2021.09.010

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One of the challenges in developing three-dimensional printed medicines is related to their stability due to the manufacturing conditions involving high temperatures. This work proposed a new protocol for preformulation studies simulating thermal processing and aging of the printed medicines, tested regarding their morphology and thermal, crystallographic, and spectroscopic profiles. Generally, despite the strong drug-polymer interactions observed, the chemical stability of the model drugs was preserved under such conditions. In fact, in the metoprolol and Soluplus^® composition, the drug's solubilization in the polymer produced a delay in the drug decomposition, suggesting a protective effect of the matrix. Paracetamol and polyvinyl alcohol mixture, in turn, showed unmistakable signs of thermal instability and chemical decomposition, in addition to physical changes. In the presented context, establishing protocols that simulate processing and storage conditions may be decisive for obtaining stable pharmaceutical dosage forms using three-dimensional printing technology.

Nitrogen-doped carbon@TiO₂ double-shelled hollow spheres as an electrochemical sensor for simultaneous determination of dopamine and paracetamol in human serum and saliva

Hui Yang, Gongxun Cao, Yongjun Huang, Ye Lin, Fengying Zheng, Luxiu Lin, Fengjiao Liu, Shunxing Li

2022, 12(3): 436-445. doi: 10.1016/j.jpha.2021.08.005

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As the most commonly used antipyretic and analgesic drug, paracetamol (PA) coexists with neurotransmitter dopamine (DA) in real biological samples. Their simultaneous determination is extremely important for human health, but they also interfere with each other. In order to improve the conductivity, adsorption affinity, sensitivity, and selectivity of TiO₂-based electrochemical sensor, N-doped carbon@TiO₂ double-shelled hollow sphere (H-C/N@TiO₂) is designed and synthesized by simple alcoholic and hydrothermal method, using polystyrene sphere (PS) as a template. Meanwhile, TiO₂ hollow spheres (H-TiO₂) or N-doped carbon hollow spheres (H-C/N) are also prepared by the same method. H-C/N@TiO₂ has good conductivity, charge separation, and the highly enhanced and stable current responses for the detection of PA and DA. The detection limit and linear range are 50.0 nmol/L and 0.3-50 μmol/L for PA, 40.0 nmol/L and 0.3-50 μmol/L for DA, respectively, which are better than those of carbon-based sensors. Moreover, this electrochemical sensor, with high selectivity, strong anti-interference, high reliability, and long time durability, can be used for the simultaneous detection of PA and DA in human blood serum and saliva. The high electrochemical performance of H-C/N@TiO₂ is attributed to the multi-functional combination of different layers, because of good conductivity, absorption and electrons transfer ability from in-situ N-doped carbon and electrocatalytic activity from TiO₂.

Multiple rapid-responsive probes for hypochlorite detection based on dioxetane luminophore derivatives

Yingai Sun, Yuqi Gao, Chunchao Tang, Gaopan Dong, Pei Zhao, Dunquan Peng, Tiantian Wang, Lupei Du, Minyong Li

2022, 12(3): 446-452. doi: 10.1016/j.jpha.2021.10.001

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In recent years, various methods for detecting exogenous and endogenous hypochlorite have been studied, considering its essential role as a biomolecule. However, the existing technologies still pose obstacles such as their invasiveness, high costs, and complicated operation. In the current study, we developed a glow-type chemiluminescent probe, hypochlorite chemiluminescence probe (HCCL)-1, based on the scaffold of Schaap's 1,2-dioxetane luminophores. To better explore the physiological and pathological functions of hypochlorite, we modified the luminophore scaffold of HCCL-1 to develop several probes, including HCCL-2, HCCL-3, and HCCL-4, which amplify the response signal of hypochlorite. By comparing the luminescent intensities of the four probes using the IVIS^® system, we determined that HCCL-2 with a limit of detection of 0.166 μM has enhanced sensitivity and selectivity for tracking hypochlorite both in vitro and in vivo.

Highly sensitive electrochemical determination of rutin based on the synergistic effect of 3D porous carbon and cobalt tungstate nanosheets

Guangjun Feng, Yang Yang, Jiantao Zeng, Jun Zhu, Jingjian Liu, Lun Wu, Zhiming Yang, Guanyi Yang, Quanxi Mei, Qinhua Chen, Fengying Ran

2022, 12(3): 453-459. doi: 10.1016/j.jpha.2021.09.007

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Rutin, a flavonoid found in fruits and vegetables, is a potential anticancer compound with strong anticancer activity. Therefore, electrochemical sensor was developed for the detection of rutin. In this study, CoWO₄ nanosheets were synthesized via a hydrothermal method, and porous carbon (PC) was prepared via high-temperature pyrolysis. Successful preparation of the materials was confirmed, and characterization was performed by transmission electron microscopy, scanning electron microscopy, and X-ray photoelectron spectroscopy. A mixture of PC and CoWO₄ nanosheets was used as an electrode modifier to fabricate the electrochemical sensor for the electrochemical determination of rutin. The 3D CoWO₄ nanosheets exhibited high electrocatalytic activity and good stability. PC has a high surface-to-volume ratio and superior conductivity. Moreover, the hydrophobicity of PC allows large amounts of rutin to be adsorbed, thereby increasing the concentration of rutin at the electrode surface. Owing to the synergistic effect of the 3D CoWO₄ nanosheets and PC, the developed electrochemical sensor was employed to quantitively determine rutin with high stability and sensitivity. The sensor showed a good linear range (5-5000 ng/mL) with a detection limit of 0.45 ng/mL. The developed sensor was successfully applied to the determination of rutin in crushed tablets and human serum samples.

Characterization of multiple chemical components of GuiLingJi by UHPLC-MS and ¹H NMR analysis

Jingchao Shi, Xiaoxia Gao, Airong Zhang, Xuemei Qin, Guanhua Du

2022, 12(3): 460-469. doi: 10.1016/j.jpha.2021.09.013

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GuiLingJi (GLJ), a classic traditional Chinese medicine (TCM) formula, is composed of over 20 herbs, according to the Pharmacopeia of the People's Republic of China. Owing to its various activities, GLJ has been used in clinical settings for more than 400 years in China. However, the ambiguous chemical material basis limits the development of studies on the quality control and pharmacological mechanisms of GLJ. Therefore, comprehensive characterization of the multiple chemical components of GLJ is of great significance for the modernization of this formula. Given the great variety of herbs in GLJ, both UHPLC-MS and ¹H NMR techniques were employed in this study. In addition, solvent extraction with different polarities was used to eliminate signal interference and the concentration of trace components. A variety of MS analytic methods were also used, including implementation of a self-built compound database, diagnostic ion filtering, mass defect filtering, and Compound Discoverer 3.0 analysis software. Based on the above strategies, a total of 150 compounds were identified, including 5 amino acids, 13 phenolic acids and glycosides, 11 coumarins, 72 flavones, 20 triterpenoid and triterpenoid saponins, 23 fatty acids, and 6 other compounds. Moreover, 13 compounds were identified by ¹H NMR spectroscopy. The UHPLC-MS and ¹H NMR results supported and complemented each other. This strategy provides a rapid approach to analyzing and identifying the chemical composition of Chinese herbal prescriptions. The current study provides basis for further research on the quality control and pharmacological mechanism of GLJ.

Modifying current thin-film microextraction (TFME) solutions for analyzing prohibited substances:Evaluating new coatings using liquid chromatography

Łukasz Sobczak, Dominika Kołodziej, Krzysztof Goryński

2022, 12(3): 470-480. doi: 10.1016/j.jpha.2021.12.007

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For identifying and quantifying prohibited substances, solid-phase microextraction (SPME) continues to arouse interest as a sample preparation method. However, the practical implementation of this method in routine laboratory testing is currently hindered by the limited number of coatings compatible with the ubiquitous high-performance liquid chromatography (HPLC) systems. Only octadecyl (C₁₈) and polydimethylsiloxane/divinylbenzene ligands are currently marketed for this purpose. To address this situation, the present study evaluated 12 HPLC-compatible coatings, including several chemistries not currently used in this application. The stationary phases of SPME devices in the geometry of thin film-coated blades were prepared by applying silica particles bonded with various functional ligands (C₁₈, octyl, phenyl-hexyl, 3-cyanopropyl, benzenesulfonic acid, and selected combinations of these), as well as unbonded silica, to a metal support. Most of these chemistries have not been previously used as microextraction coatings. The 48 most commonly misused substances were selected to assess the extraction efficacy of each coating, and eight desorption solvent compositions were used to optimize the desorption conditions. All samples were analyzed using an HPLC system coupled with triple quadrupole tandem mass spectrometry. This evaluation enables selection of the best-performing coatings for quantifying prohibited substances and investigates the relationship between extraction efficacy and the physicochemical characteristics of the analytes. Ultimately, using the most suitable coatings is essential for trace-level analysis of chemically diverse prohibited substances.

Discussion on the dimerization reaction of penicillin antibiotics

Qizhang Wu, Xia Zhang, Jiaxin Du, Changqin Hu

2022, 12(3): 481-488. doi: 10.1016/j.jpha.2021.06.005

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Penicillins are one type of the most important antibiotics used in the clinic. Control of drug impurity profiles is an important part of ensuring drug safety. This is particularly important in penicillins where polymerization can lead to polymers as elicitors of passive cutaneous anaphylaxis. The current understanding of penicillin polymerization is based on reactions with amino groups, but no comprehensive mechanistic understanding has been reported. Here, we used theoretical calculations and column switching-LC/MS techniques to study penicillin dimerization. Ampicillin and benzylpenicillin were selected as representative penicillins with or without amino groups in the side chain, respectively. We identified four pathways by which this may occur and the energy barrier graphs of each reaction process were given. For benzylpenicillin without an amino group in the 6-side chain, dimerization mode A is the dominant mode, where the 2-carboxyl group of one molecule reacts with the β-lactam of another molecule. However, ampicillin with an amino group in the 6-side chain favors dimerization mode C, where the amino group of one molecule attacks the β-lactam of another molecule. These findings can lead to a polymer control approach to maintaining penicillin antibiotics in an active formulation.

Qualitative and quantitative evaluation of Flos Puerariae by using chemical fingerprint in combination with chemometrics method

Jing Han, Ke Xu, Quanxiang Yan, Wenwen Sui, Haotian Zhang, Sijie Wang, Zan Zhang, Ziyun Wei, Fei Han

2022, 12(3): 489-499. doi: 10.1016/j.jpha.2021.09.003

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In order to better control the quality of Flos Puerariae (FP), qualitative and quantitative analyses were initially performed by using chemical fingerprint and chemometrics methods in this study. First, the fingerprint of FP was developed by HPLC and the chemical markers were screened out by similarity analysis (SA), hierarchical clustering analysis (HCA), principal components analysis (PCA), and orthogonal partial least squares discriminant analysis (OPLS-DA). Next, the chemical constituents in FP were profiled and identified by HPLC coupled to Fourier transform ion cyclotron resonance mass spectrometry (HPLC-FT-ICR MS). Then, the characteristic constituents in FP were quantitatively analyzed by HPLC. As a result, 31 common peaks were assigned in the fingerprint and 6 of them were considered as qualitative markers. A total of 35 chemical constituents were detected by HPLC-FT-ICR MS and 16 of them were unambiguously identified by comparing retention time, UV absorption wavelength, accurate mass, and MS/MS data with those of reference standards. Subsequently, the contents of glycitin, genistin, tectoridin, glycitein, genistein, and tectorigenin in 13 batches of FP were detected, ranging from 0.4438 to 11.06 mg/g, 0.955 to 1.726 mg/g, 9.81 to 57.22 mg/g, 3.349 to 41.60 mg/g, 0.3576 to 0.989 mg/g, and 2.126 to 9.99 mg/g, respectively. In conclusion, fingerprint analysis in combination with chemometrics methods could discover chemical markers for improving the quality control standard of FP. It is expected that the strategy applied in this study will be valuable for further quality control of other traditional Chinese medicines.

A strategy of screening and binding analysis of bioactive components from traditional Chinese medicine based on surface plasmon resonance biosensor

Diya Lv, Jin Xu, Minyu Qi, Dongyao Wang, Weiheng Xu, Lei Qiu, Yinghua Li, Yan Cao

2022, 12(3): 500-508. doi: 10.1016/j.jpha.2021.11.006

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Elucidating the active components of traditional Chinese medicine (TCM) is essential for understanding the mechanisms of TCM and promote its rational use as well as TCM-derived drug development. Recent studies have shown that surface plasmon resonance (SPR) technology is promising in this field. In the present study, we propose an SPR-based integrated strategy to screen and analyze the major active components of TCM. We used Radix Paeoniae Alba (RPA) as an example to identify the compounds that can account for its anti-inflammatory mechanism via tumor necrosis factor receptor type 1 (TNF-R1). First, RPA extraction was analyzed using an SPR-based screening system, and the potential active ingredients were collected, enriched, and identified as paeoniflorin and paeonol. Next, the affinity constants of paeoniflorin and paeonol were determined as 4.9 and 11.8 μM, respectively. Then, SPR-based competition assays and molecular docking were performed to show that the two compounds could compete with tumor necrosis factor-α (TNF-α) while binding to the subdomain 1 site of TNF-R1. Finally, in biological assays, the two compounds suppressed cytotoxicity and apoptosis induced by TNF-α in the L929 cell line. These findings prove that SPR technology is a useful tool for determining the active ingredients of TCM at the molecular level and can be used in various aspects of drug development. The SPR-based integrated strategy is reliable and feasible in TCM studies and will shed light on the elucidation of the pharmacological mechanism of TCM and facilitate its modernization.

MIL-53-based homochiral metal-organic framework as a stationary phase for open-tubular capillary electrochromatography

Xiaodong Sun, Bing Niu, Qi Zhang, Qin Chen

2022, 12(3): 509-516. doi: 10.1016/j.jpha.2021.12.004

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Homochiral metal-organic frameworks (MOFs) have attracted considerable attention in many fields of research, such as chiral catalysis and chiral chromatography. However, only few homochiral MOFs can be effectively used in capillary electrochromatography (CEC) and their performances are far from adequate. In this study, we successfully synthesized achiral nanocrystalline MIL-53. A facile post-synthetic modification strategy was then implemented to functionalize the product, yielding a homochiral MOF:l-His-NH-MIL-53. This MOF was then employed as a chiral coating in open-tubular CEC mode (OT-CEC), and, as such, it exhibited high enantioselectivities for several racemic drugs. The homochiral MOF and the fabricated capillary coating were systematically characterized using transmission electron microscopy, scanning electron microscopy (with energy-dispersive X-ray spectrometry), Fourier-transform infrared spectroscopy, X-ray diffractometry, thermogravimetric analysis, circular dichroism spectroscopy, Brunauer-Emmett-Teller surface area measurements, and X-ray photoelectron spectroscopy. This study is expected to provide a new strategy for the design and establishment of MOF-based chiral OT-CEC systems.

2022 Vol. 12, No. 3