Hydrophilic interaction chromatography-multiple reaction monitoring mass spectrometry method for basic building block analysis of low molecular weight heparins prepared through nitrous acid depolymerization

Journal of Chromatography A - Tập 1479 - Trang 121-128 - 2017
Xiaojun Sun1,2, Zhimou Guo3, Mengqi Yu1, Chao Lin4, Anran Sheng1, Zhiyu Wang5, Robert J. Linhardt2, Lianli Chi1
1National Glycoengineering Research Center, Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, State Key Laboratory of Microbial Technology, Shandong University, Jinan, Shandong, 250100, China
2Department of Chemistry and Chemical Biology, Department of Chemical and Biological Engineering, Department of Biology, Department of Biomedical Engineering, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, NY 12180, USA
3Key Laboratory of Separation Science for Analytical Chemistry, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, Liaoning, 116023, China
4Jinan Center for Food and Drug Control, Jinan, Shandong 250102, China
5Department of Virology, School of Public Health, Shandong University, Jinan, Shandong 250100, China

Tài liệu tham khảo

Rabenstein, 2002, Heparin and heparan sulfate: structure and function, Nat. Prod. Rep., 19, 312, 10.1039/b100916h Quader, 1998, Low molecular weight heparins: current use and indications, J. Am. Coll. Surg., 187, 641, 10.1016/S1072-7515(98)00255-5 Higashi, 2012, Photochemical preparation of a novel low molecular weight heparin, Carbohydr. Polym., 87, 1737, 10.1016/j.carbpol.2011.09.087 Bisio, 2009, Structural features of low-molecular-weight heparins affecting their affinity to antithrombin, Thromb. Haemost., 102, 865, 10.1160/TH09-02-0081 Guerrini, 2007, Low molecular weight heparins: structural differentiation by bidimensional nuclear magnetic resonance spectroscopy, Semin. Thromb. Hemost., 33, 478, 10.1055/s-2007-982078 Dalteparin Sodium, British Pharmacopoeia, 2009. British Pharmacopoeia Volume I & II, Monographs: Medicinal and Pharmaceutical Substances. Nadroparin Calcium, European Pharmacopoeia, 5.0, 01/2005:1134. Verhave, 2015, Anticoagulation with dalteparin and nadroparin in nocturnal haemodialysis, Neth. J. Med., 73, 270 Lee, 2013, Scientific considerations in the review and approval of generic enoxaparin in the United States, Nat. Biotechnol., 31, 220, 10.1038/nbt.2528 Linhardt, 1999, Production and chemical processing of low molecular weight heparins, Semin. Thromb. Hemost., 25, 5 Linhardt, 2012, Synthetic heparin, Curr. Opin. Pharmacol., 12, 217, 10.1016/j.coph.2011.12.002 Mouriera, 2015, Analytical and statistical comparability of generic enoxaparins from the US market with the originator product, J. Pharm. Biomed. Anal., 115, 431, 10.1016/j.jpba.2015.07.038 Zhang, 2012, Structural analysis of low molecular weight heparin by ultraperformance size exclusion chromatography/time of flight mass spectrometry and capillary zone electrophoresis, Anal. Chem., 85, 1819, 10.1021/ac303185w Bo, 2012, Characterization of currently marketed heparin products: analysis of heparin digests by RPIP-UHPLC-QTOF-MS, J. Pharm. Biomed. Anal., 67–68, 42 Galeotti, 2013, Novel reverse-phase ion pair-high performance liquid chromatography separation of heparin, heparan sulfate and low molecular weight-heparins disaccharides and oligosaccharides, J. Chromatogr. A, 1284, 141, 10.1016/j.chroma.2013.02.013 Ouyang, 2016, Development of hydrophilic interaction chromatography with quadruple time-of-flight mass spectrometry for heparin and low molecular weight heparin disaccharide analysis, Rapid Commun. Mass Spectrom., 30, 277, 10.1002/rcm.7437 Volpi, 2014, Analysis of glycosaminoglycan-derived precolumn, 2-aminoacridone-labeled disaccharides with LC-fluorescence and LC–MS detection, Nat. Protoc., 9, 541, 10.1038/nprot.2014.026 Galeotti, 2011, Anal. Chem., 83, 6770, 10.1021/ac201426e Wang, 2014, Liquid chromatography-diode array detection–mass spectrometry for compositional analysis of low molecular weight heparins, Anal. Biochem., 451, 35, 10.1016/j.ab.2014.02.005 Sun, 2016, Comprehensive identification and quantitation of basic building blocks for low-molecular weight heparin, Anal. Chem., 88, 7738, 10.1021/acs.analchem.6b01709 Li, 2014, Bottom-up low molecular weight heparin analysis using liquid chromatography-fourier transform mass spectrometry for extensive characterization, Anal. Chem., 86, 6626, 10.1021/ac501301v Li, 2012, Top-down approach for the direct characterization of low molecular weight heparins using LC-FT-MS, Anal. Chem., 84, 8822, 10.1021/ac302232c Fu, 2013, Separation of carbohydrates using hydrophilic interaction liquid chromatography, Carbohydr. Res., 379, 13, 10.1016/j.carres.2013.06.006 Guo, 2014, Hydrophilic interaction chromatography for selective separation of isomeric saponins, J. Chromatogr. A, 1325, 121, 10.1016/j.chroma.2013.12.006 Sheng, 2016, Synthesis and evaluation of a maltose-bonded silica gel stationary phase for hydrophilic interaction chromatography and its application in Ginkgo Biloba extract separation in two-dimensional systems, J. Sep. Sci., 39, 3339, 10.1002/jssc.201600430 Domon, 1988, A systematic nomenclature for carbohydrate fragmentations in FAB-MS/MS spectra of glycoconjugates, Glycoconj. J., 5, 397, 10.1007/BF01049915 Beccati, 2012, Identification of a novel structure in heparin generated by sequential oxidative-reductive treatment, Anal. Chem., 84, 5091, 10.1021/ac3007494