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Comparison of different approaches for direct coupling of solid-phase microextraction to Mass spectrometry for drugs of abuse analysis in plasma

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Journal of Pharmaceutical Analysis 2023年第2期13卷 216-222页

作者： Wei Zhou Martyna N.Wieczorek Runshan Will Jiang Janusz Pawliszyn Department of Chemistry University of WaterlooWaterlooONN2L 3G1Canada Faculty of Food Science and Nutrition Poznan University of Life SciencesPoznanPoland

The direct coupling of solid-phase microextraction(SPME)to Mass spectrometry(MS)(SPME-MS)has proven to be an effective method for the fast screening and quantitative analysis of compounds in complex matrices such as blood and plasma.In recent years,our lab has developed three novel SPME-MS techniques:SPME-microfluidic open interface-MS(SPME-MOI-MS),coated blade spray-MS(CBS-MS),and SPME-probe electrospray ionization-MS(SPME-PESI-MS).The fast and high-throughput nature of these SPME-MS technologies makes them attractive options for point-of-care analysis and anti-doping testing.However,all these three techniques utilize different SPME geometries and were tested with different MS instruments.Lack of comparative data makes it difficult to determine which of these methodologies is the best option for any given application.This work fills this gap by making a comprehensive comparison of these three technologies with different SPME devices including SPME fibers,CBS blades,and SPME-PESI probes and SPME-liquid chromatography-MS(SPME-LC-MS)for the analysis of drugs of abuse using the same MS instrument.Furthermore,for the first time,we developed different desorption chambers for MOI-MS for coupling with SPME fibers,CBS blades,and SPME-PESI probes,thus illustrating the universality of this approach.In total,eight analytical methods were developed,with the experimental data showing that all the SPME-based methods provided good analytical performance with R^(2)of linearities larger than 0.9925,accuracies between 81%and 118%,and good precision with an RSD%≤13%.

关键词： Solid-phase microextraction Mass spectrometry Microfluidic open interface Coated blade spray Probe electrospray ionization Drug of abuse

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Identification,structure elucidation and origin of a common pyridinium-thiocyanate intermediate in electrospray Mass spectrometry among the benziamidazole-class proton pump inhibitors

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Journal of Pharmaceutical Analysis 2023年第6期13卷 683-688页

作者： Dong Sun Chunyu Wang Yanxia Fan Jingkai Gu Research Center for Drug Metabolism School of Life SciencesJilin UniversityChangchun130012China State Key Laboratory of Supramolecular Structure and Materials Jilin UniversityChangchun130012China Beijing Institute of Drug Metabolism Beijing102209China Jilin Institute for Drug Control Changchun130033China

During the analysis of benziamidazole-class irreversible proton pump inhibitors,an unusual mass spectral response with the mass-to-charge ratio at[Mt10]t intrigued us,as it couldn't be assigned to any literature known relevant structure,intermediate or adduct ion.Moreover,this mysterious mass pattern of[Mt10]t has been gradually observed by series of marketed proton pump inhibitors,viz.omeprazole,pantoprazole,lansoprazole and rabeprazole.All the previous attempts to isolate the corresponding component were unsuccessful.The investigation of present work addresses this kind of signal to a pyridinium thiocyanate mass spectral intermediate(10),which is the common fragment ion of series of labile aggregates.The origin of such aggregates can be traced to the reactive intermediates formed by acid-promoted degradation.These reactive intermediates tend to react with each other and give raise series of complicated aggregates systematically in a water/acetonitrile solution by electrospray ionization.The structure of the corresponding pyridinium thiocyanate species of omeprazole(10a)has been eventually characterized with the help of synthetic specimen(10a′).Our structural proposal as well as its origin was supported by in situ nuclear magnetic resonance,chemical derivatization and colorimetric experiments.

关键词： Proton pump inhibitor Mass spectrometry Electrospray ionization Pseudo-molecular ion Pyridinium thiocyanate

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Nylon 6-cellulose composite hosted in a hypodermic needle: Biofluid extraction and analysis by ambient Mass spectrometry in a single device

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Journal of Pharmaceutical Analysis 2023年第11期13卷 1346-1352页

作者： Jaime Millan-Santiago Rafael Lucena Soledad Cardenas Affordable and Sustainable Sample Preparation(AS2P)Research Group Analytical Chemistry DepartmentChemical Institute for Energy and Environment(IQUEMA)University of CordobaE-14071CordobaSpain

This study proposes a hypodermic needle(HN)as a sorbent holder and an electrospray(ESI)emitter,thus combining extraction and analysis in a single device.A novel nylon 6-cellulose(N6-Cel)composite sorbent is proposed to extract methadone from oral fluid samples.The cellulosic substrate provides the composite with high porosity,permitting the flow-through of the sample,while the polyamide contributes to the extraction of the analyte.The low price of the devices(considering the holder and the sorbent)contributes to the affordability of the method,and their small size allows easy transportation,opening the door to on-site extractions.Under the optimum conditions,the analyte can be determined by high-resolution ambient ionization Mass spectrometry at a limit of detection(LOD)as low as 0.3 mg/L and precision(expressed as relative standard deviation,RSD)better than 9.3%.The trueness,expressed as relative recovery(RR),ranged from 90%to 109%.As high-resolution mass spectrometers are not available in many laboratories,the method was also adapted to low-resolution spectrometers.In this sense,the direct infusion of the eluates in a triple quadrupole-Mass spectrometry provided an LOD of 2.2 mg/L.The RSD was better than 5.3%,and the RR ranged from 96%to 121%.

关键词： ESI emitter Mass spectrometry Hypodermic needle Composite Methadone

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Rapid and sensitive analysis of trace b-blockers by magnetic solidphase extraction coupled with Fourier transform ion cyclotron resonance Mass spectrometry

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Journal of Pharmaceutical Analysis 2022年第2期12卷 293-300页

作者： Xue Xiao Kaili He Ya-Jun Hou Zhangmin Xiang Yunyun Yang Guangdong Provincial Key Laboratory of Chemical Measurement and Emergency Test Technology Guangdong Provincial Engineering Research Center for Ambient Mass SpectrometryInstitute of AnalysisGuangdong Academy of Sciences(China National Analytical CenterGuangzhou)Guangzhou510070China

A rapid and sensitive method for analyzing trace b-blockers in complex biological samples,which involved magnetic solid-phase extraction(MSPE)coupled with Fourier transform ion cyclotron resonance Mass spectrometry(FTICR-MS),was developed.Novel nanosilver-functionalized magnetic nanoparticles with an interlayer of poly(3,4-dihydroxyphenylalanine)(polyDOPA@Ag-MNPs)were synthesized and used as MSPE adsorbents to extract trace b-blockers from biological samples.After extraction,the analytes loaded on the polyDOPA@Ag-MNPs were desorbed using an organic solvent and analyzed by FTICR-MS.The method was rapid and sensitive,with a total detection procedure of less than 10 min as well as limits of detection and quantification in the ranges of 3.5-6.8 pg/mL and 11.7-22.8 pg/mL,respectively.The accuracy of the method was also desirable,with recoveries ranging from 80.9%to 91.0%following the detection of analytes in human blood samples.All the experimental results demonstrated that the developed MSPE-FTICR-MS method was suitable for the rapid and sensitive analysis of trace b-blockers in complex biological samples.

关键词： β-blockers Magnetic solid-phase extraction Nanosilver-functionalized magnetic nanoparticles Poly(3,4-dihydroxyphenylalanine) Fourier transform ion cyclotron resonance Mass spectrometry

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Profiling the Bisecting N-acetylglucosamine Modification in Amniotic Membrane via Mass spectrometry

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Genomics, Proteomics & Bioinformatics 2022年第4期20卷 648-656页

作者： Qiushi Chen Yuanliang Zhang Keren Zhang Jie Liu Huozhen Pan Xinran Wang Siqi Li Dandan Hu Zhilong Lin Yun Zhao Guixue Hou Feng Guan Hong Li Siqi Liu Yan Ren BGI-Shenzhen Shenzhen 518083China Joint International Research Laboratory of Glycobiology and Medical Chemistry College of Life SciencesNorthwest UniversityXi’an 710069China Shenzhen Seventh People's Hospital Shenzhen 518081China Institute of Interdisciplinary Integrative Medicine Research Shanghai University of Traditional Chinese MedicineShanghai 201203China

Bisecting N-acetylglucosamine(GlcNAc),a GlcNAc linked to the coreβ-mannose residue via aβ1,4 linkage,is a special type of N-glycosylation that has been reported to be involved in various biological processes,such as cell adhesion and fetal development.This N-glycan structure is abundant in human trophoblasts,which is postulated to be resistant to natural killer cellmediated cytotoxicity,enabling a mother to nourish a fetus without rejection.In this study,we hypothesized that the human amniotic membrane,which serves as the last barrier for the fetus,may also express bisected-type glycans.To test this hypothesis,glycomic analysis of the human amniotic membrane was performed,and bisected N-glycans were detected.Furthermore,our proteomic data,which have been previously employed to explore human missing proteins,were analyzed and the presence of bisecting GlcNAc-modified peptides was confirmed.A total of 41glycoproteins with 43 glycopeptides were found to possess a bisecting GlcNAc,and 25 of these glycoproteins were reported to exhibit this type of modification for the first time.These results provide insights into the potential roles of bisecting GlcNAc modification in the human amniotic membrane,and can be beneficial to functional studies on glycoproteins with bisecting GlcNAc modifications and functional studies on immune suppression in human placenta.

关键词： Glycan Glycoprotein Amniotic membrane Bisecting N-acetylglucosamine Mass spectrometry

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Mass spectrometry analysis of intact protein N-glycosylation signatures of cells and sera in pancreatic adenocarcinomas

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Journal of Zhejiang University-Science B(Biomedicine & Biotechnology) 2024年第1期25卷 51-64页

作者： Mingming XU Zhaoliang LIU Wenhua HU Ying HAN Zhen WU Sufeng CHEN Peng XIA Jing DU Xumin ZHANG Piliang HAO Jun XIA Shuang YANG Center for Clinical Mass spectrometry College of Pharmaceutical SciencesSoochow UniversitySuzhou215123China School of Life Science and Technology ShanghaiTech UniversityShanghai201210China State Key Laboratory of Genetic Engineering Department of BiochemistrySchool of Life SciencesFudan UniversityShanghai200438China Department of Clinical Laboratory Center Zhejiang Provincial People’s HospitalPeople’s Hospital of Hangzhou Medical CollegeHangzhou310014China

Pancreatic cancer is among the most malignant cancers,and thus early intervention is the key to better survival outcomes.However,no methods have been derived that can reliably identify early precursors of development into malignancy.Therefore,it is urgent to discover early molecular changes during pancreatic tumorigenesis.As aberrant glycosylation is closely associated with cancer progression,numerous efforts have been made to mine glycosylation changes as biomarkers for diagnosis;however,detailed glycoproteomic information,especially site-specific N-glycosylation changes in pancreatic cancer with and without drug treatment,needs to be further explored.Herein,we used comprehensive solid-phase chemoenzymatic glycoproteomics to analyze glycans,glycosites,and intact glycopeptides in pancreatic cancer cells and patient sera.The profiling of N-glycans in cancer cells revealed an increase in the secreted glycoproteins from the primary tumor of MIA PaCa-2 cells,whereas human sera,which contain many secreted glycoproteins,had significant changes of glycans at their specific glycosites.These results indicated the potential role for tumor-specific glycosylation as disease biomarkers.We also found that AMG-510,a small molecule inhibitor against Kirsten rat sarcoma viral oncogene homolog(KRAS)G12C mutation,profoundly reduced the glycosylation level in MIA PaCa-2 cells,suggesting that KRAS plays a role in the cellular glycosylation process,and thus glycosylation inhibition contributes to the anti-tumor effect of AMG-510.

关键词： Pancreatic cancer Glycosylation Biomarker Glycoproteomics Mass spectrometry

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In-situ generation and global property profiling of metal nanoclusters by ultraviolet laser dissociation-Mass spectrometry

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Science China Chemistry 2022年第6期65卷 1196-1203页

作者： Zheyi Liu Zhaoxian Qin Chaonan Cui Zhixun Luo Bing Yang You Jiang Can Lai Zhipeng Wang Xiaolei Wang Xiang Fang Gao Li Fangjun Wang Chunlei Xiao Xueming Yang State Key Laboratory of Molecular Reaction Dynamics Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian116023China CAS Key Laboratory of Separation Sciences for Analytical Chemistry Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian116023China State Key Laboratory of Catalysis Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian116023China State Key Laboratory for Structural Chemistry of Unstable and Stable Species Institute of ChemistryChinese Academy of SciencesBeijing100190China Dalian National Laboratory for Clean Energy Dalian Institute of Chemical PhysicsChinese Academy of SciencesDalian116023China National Institute of Metrology Beijing100013China University of Chinese Academy of Sciences Beijing100049China

Metal nanoclusters are promising nanomaterials with unique properties, but only a few ones with specific numbers of metal atoms can be obtained and studied up to now. In this study, we establish a new paradigm of in-situ generation and global study of metal nanoclusters with different sizes, constitutions, and charge states, including both accurate constitution characterization and global activity profiling. The complex mixtures of metal nanoclusters are produced by employing single-pulsed 193-nm laser dissociation of monolayer-protected cluster(MPC) precursors within a high-resolution Mass spectrometry(HRMS). More than400 types of bare gold nanoclusters including novel multiply charged(2+ and 3+), S-/P-doped, and silver alloy ones can be efficiently generated and accurately characterized. A distinct size(1 to 142 atoms)-and charge(1+ to 3+)-hierarchy reactivity is clearly observed for the first time. This global cluster study might greatly promote the developments and applications of novel metal nanoclusters.

关键词： metal nanocluster ultraviolet laser dissociation Mass spectrometry global property profiling size-and charge-hierarchy

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Graphene as adsorbent for highly efficient extraction of modified nucleosides in urine prior to liquid chromatography-tandem Mass spectrometry analysis

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Chinese Chemical Letters 2024年第4期35卷 490-495页

作者： Cheng Guo Xiaoxiao Zhang Xiujuan Hong Yiqiu Hu Lingna Mao Kezhi Jiang Cancer Institute(Key Laboratory of Cancer Prevention and Intervention China National Ministry of Education)The Second Affiliated HospitalZhejiang University School of MedicineHangzhou 310009China Cancer Center Zhejiang UniversityHangzhou 310058China Key Laboratory of Organosilicon Chemistry and Material Technology College of Material Chemistry and Chemical EngineeringHangzhou Normal UniversityHangzhou 311121China Department of General Practice The Second Affiliated HospitalZhejiang University School of MedicineHangzhou 310009China

RNA modifications have been involved in numerous biological processes, and aberrations of these modifications are tightly associated with various diseases including cancer. Herein, we developed graphenebased solid-phase extraction and robust ultra performance liquid chromatography-tandem Mass spectrometry(UPLC-MS/MS) combined with stable isotope-dilution for simultaneous enrichment and accurate determination of 17 modified nucleosides in human urine. We found graphene could effectively adsorb various modified nucleosides in human urine samples. With this method, we identified and quantified these modified nucleosides in urine samples collected from lung cancer patients and healthy controls.We revealed that the levels of 12 modified nucleosides were all diminished in urine from lung cancer patients, compared with healthy controls. It is worth noting that we demonstrated, for the first time, the presence of 5,2-O-dimethyluridine(m~5U_m) in human urine. Together, we established a robust analytical method for simultaneous determinations of 17 modified nucleosides in human urine, and our results revealed a close correlation between the concentrations of urinary modified nucleosides and the occurrence of lung cancer, implying the potential applications of these modified nucleosides as noninvasive biomarkers for the early detection of lung cancer. Moreover, this study will stimulate future investigations on the regulatory roles of RNA modifications in the initiation and progression of lung cancer.

关键词： Mass spectrometry RNA modification Modified nucleosides Graphene Biomarker Urine

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Tracking gassing behavior in pouch cell by operando on-line electrochemical Mass spectrometry

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Journal of Energy Chemistry 2023年第9期84卷 286-291页

作者： Haitang Zhang Jianken Chen Baodan Zhang Xiaohong Wu Zhengang Li Leiyu Chen Junhao Wang Xiaoyu Yu Haiyan Luo Jiyuan Xue Yu-Hao Hong Yu Qiao Shi-Gang Sun State Key Laboratory of Physical Chemistry of Solid Surfaces iChEM(Collaborative Innovation Center of Chemistry for Energy Materials)Department of ChemistryCollege of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005FujianChina Fujian Science&Technology Innovation Laboratory for Energy Materials of China(Tan Kah Kee Innovation Laboratory) Xiamen 361005FujianChina

As the rapid development of more powerful and safer lithiumion batteries, the mechanism study of gases evolution is attacking more and more attention in recent years. Especially under overcharge/discharge and/or high-... 详细信息

关键词： Pouch cell Operando characterization Mass spectrometry Lithium-ion batteries Gassing behavior

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Tuning Solvent Composition to Enhance the Stability of Metal Clusters in Mass spectrometry

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Chinese Journal of Structural Chemistry 2022年第4期41卷 34-39页

作者： Yingzi Han Yihuang Jiang Jing Jeanne Yang Shuichao Lin Zichao Tang Lansun Zheng State Key Laboratory of Physical Chemistry of Solid Surface College of Chemistry and Chemical EngineeringXiamen UniversityXiamen 361005China

Electrospray ionization time-of-flight Mass spectrometry(ESI-TOF-MS)has been recognized as a powerful technique for studying metal clusters’chemical composition and reaction mechanisms.It is a great challenge in Mass spectrometry analysis to maintain the metal cluster molecules intact without fragmentation,which is achieved in this work by using mixed solvents to change the interaction between cluster molecules and solvent molecules,further affecting the fragmentation behaviors of the metal cluster in MS.Theoretical analysis reveals that the stability of the[(C)Au_(6)Ag_(2)(C_(18)H_(14)ONP)_(6)]^(4+)cluster in ESI-TOF-MS is related to the strength of the chemical bonds between its own atoms and the bonding between the solvent and the cluster molecules.

关键词： metal cluster Mass spectrometry fragmentation stability hydrogen bond

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