Xiangdong Xue, Yuanyuan Zhao, Xu Zhang, Chunqiu Zhang, Anil Kumar, Xiaoning Zhang, Guozhang Zou, Paul C. Wang, Jinchao Zhang, Xing-Jie Liang. Phenylboronic acid-functionalized magnetic nanoparticles for one-step saccharides enrichment and mass spectrometry analysis. Biophysics Reports, 2015, 1(2): 61-70. doi: 10.1007/s41048-015-0002-3
Citation: Xiangdong Xue, Yuanyuan Zhao, Xu Zhang, Chunqiu Zhang, Anil Kumar, Xiaoning Zhang, Guozhang Zou, Paul C. Wang, Jinchao Zhang, Xing-Jie Liang. Phenylboronic acid-functionalized magnetic nanoparticles for one-step saccharides enrichment and mass spectrometry analysis. Biophysics Reports, 2015, 1(2): 61-70. doi: 10.1007/s41048-015-0002-3

Phenylboronic acid-functionalized magnetic nanoparticles for one-step saccharides enrichment and mass spectrometry analysis

doi: 10.1007/s41048-015-0002-3
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  • Corresponding author: Guozhang Zou, Xing-Jie Liang
  • Received Date: 18 January 2015
  • Rev Recd Date: 01 April 2015
  • Publish Date: 03 October 2015
  • In this work, 2-(2-aminoethoxy) ethanolblocked phenylboronic acid-functionalized magnetic nanoparticles (blocked PMNPs) were fabricated for selective enrichment of different types of saccharides. The phenylboronic acid was designed for capturing the cis-diols moieties on saccharides molecules, and the 2-(2-aminoethoxy) ethanol can deplete the nonspecific absorption of peptides and proteins which always coexisted with saccharides. For mass spectrometry analysis, the PMNPs bound saccharides can be directly applied onto the MALDI plate with matrix without removing the PMNPs. By PMNPs, the simple saccharide (glucose) could be detected in pmol level. The complex saccharides can also be reliably purified and analyzed; 16 different Nglycans were successfully identified fromovalbumin, and the high-abundance N-glycans can be detected even when the ovalbumin was in very low concentration (2 μg). In human milk, ten different oligosaccharides were identified, and the lactose can still be detected when the human milk concentration was low to 0.01 μL.
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  • 参考文献
    Arnold JN, Saldova R, Hamid UM, Rudd PM (2008) Evaluation of the serum N-linked glycome for the diagnosis of cancer and chronic inflammation. Proteomics 8:3284-3293
    Bao J, Chen W, Liu T, Zhu Y, Jin P, Wang L, Liu J, Wei Y, Li Y (2007) Bifunctional Au-Fe3O4 Nanoparticles for Protein Separation. ACS Nano 1:293-298
    Caprioli RM, Farmer TB, Gile J (1997) Molecular imaging of biological samples: localization of peptides and proteins using MALDI-TOF MS. Anal Chem 69:4751-4760
    Chen C-T, Chen Y-C (2005) Fe3O4/TiO2 core/shell nanoparticles as affinity probes for the analysis of phosphopeptides using TiO2 surface-assisted laser desorption/ionization mass spectrometry. Anal Chem 77:5912-5919
    Dousseau F, Pezolet M (1990) Determination of the secondary structure content of proteins in aqueous solutions from their amide I and amide II infrared bands. Comparison between classical and partial least-squares methods. Biochemistry 29:8771-8779
    Dowlut M, Hall DG (2006) An improved class of sugar-binding boronic acids, soluble and capable of complexing glycosides in neutral water. J Am Chem Soc 128:4226-4227
    Fang H, Kaur G, Wang B (2004) Progress in boronic acid-based fluorescent glucose sensors. J Fluoresc 14:481-489
    Franc V, Šebela M, ?ehulka P, Kon?itíková R, Lenobel R, Madzak C, Kope?ný D (2012) Analysis of N-glycosylation in maize cytokinin oxidase/dehydrogenase 1 using a manual microgradient chromatographic separation coupled offline to MALDITOF/TOF mass spectrometry. J Proteomics 75:4027-4037
    Goetz J, Mechref Y, Kang P, Jeng M-H, Novotny M (2009) Glycomic profiling of invasive and non-invasive breast cancer cells. Glycoconj J 26:117-131
    Hamm P, Lim M, Hochstrasser RM (1998) Structure of the amide I band of peptides measured by femtosecond nonlinearinfrared spectroscopy. J Phys Chem B 102:6123-6138
    Hu J, Zhao B, Xu W, Li B, Fan Y (2002) Surface-enhanced Raman spectroscopy study on the structure changes of 4-mercaptopyridine adsorbed on silver substrates and silver colloids. Spectrochim Acta A 58:2827-2834
    Jeong H-J, Kim Y-G, Yang Y-H, Kim B-G (2012) High-throughput quantitative analysis of total N-glycans by matrix-assisted laser desorption/ionization time-of-flight mass spectrometry. Anal Chem 84:3453-3460
    Kaur G, Fang H, Gao X, Li H, Wang B (2006) Substituent effect on anthracene-based bisboronic acid glucose sensors. Tetrahedron 62:2583-2589
    Kim DK, Mikhaylova M, Zhang Y, Muhammed M (2003) Protective coating of superparamagnetic iron oxide nanoparticles. Chem Mater 15:1617-1627
    Lin P-C, Chou P-H, Chen S-H, Liao H-K, Wang K-Y, Chen Y-J, Lin C-C (2006) Ethylene glycol-protected magnetic nanoparticles for a multiplexed immunoassay in human plasma. Small 2:485-489
    Lin Z-A, Zheng J-N, Lin F, Zhang L, Cai Z, Chen G-N (2011) Synthesis of magnetic nanoparticles with immobilized aminophenylboronic acid for selective capture of glycoproteins. J Mater Chem 21:518-524
    Marth JD, Grewal PK (2008) Mammalian glycosylation in immunity. Nat Rev Immunol 8:874-887
    Medley CD, Bamrungsap S, Tan W, Smith JE (2011) Aptamerconjugated nanoparticles for cancer cell detection. Anal Chem 83:727-734
    Nash MA, Waitumbi JN, Hoffman AS, Yager P, Stayton PS (2012) Multiplexed enrichment and detection of malarial biomarkers using a stimuli-responsive iron oxide and gold nanoparticle reagent system. ACS Nano 6:6776-6785
    Ohtsubo K, Marth JD (2006) Glycosylation in cellular mechanisms of health and disease. Cell 126:855-867
    Selman MHJ, Hoffmann M, Zauner G, McDonnell LA, Balog CIA, Rapp E, Deelder AM, Wuhrer M (2012) MALDI-TOF-MS analysis of sialylated glycans and glycopeptides using 4-chloro-acyanocinnamic acid matrix. Proteomics 12:1337-1348
    Shimizu Y, Nakata M, Kuroda Y, Tsutsumi F, Kojima N, Mizuochi T (2001) Rapid and simple preparation of N-linked oligosaccharides by cellulose-column chromatography. Carbohydr Res 332:381-388
    Springsteen G, Wang B (2002) A detailed examination of boronic acid-diol complexation. Tetrahedron 58:5291-5300
    Sun L, Eklund EA, Chung WK, Wang C, Cohen J, Freeze HH (2005) Congenital disorder of glycosylation id presenting with hyperinsulinemic hypoglycemia and islet cell hyperplasia. J Clin Endocrinol Metab 90:4371-4375
    Tiwari A, Terada D, Yoshikawa C, Kobayashi H (2010) An enzymefree highly glucose-specific assay using self-assembled aminobenzene boronic acid upon polyelectrolytes electrospun nanofibers-mat. Talanta 82:1725-1732
    Wang Y, Wu S-L, Hancock WS (2006) Approaches to the study of N-linked glycoproteins in human plasma using lectin affinity chromatography and nano-HPLC coupled to electrospray linear ion trap—Fourier transform mass spectrometry. Glycobiology 16:514-523
    Wang C, Liu D, Wang Z (2012) Gold nanoparticle based dot-blot immunoassay for sensitively detecting Alzheimer’s disease related [small beta]-amyloid peptide. Chem Commun 48:8392-8394
    Xu Y,Wu Z, Zhang L, Lu H, Yang P, Webley PA, Zhao D (2008) Highly specific enrichment of glycopeptides using boronic acidfunctionalized mesoporous silica. Anal Chem 81:503-508
    Magnetic nanoparticles for saccharides enrichment and analysis METHODS  The Author(s) 2015. This article is published with open access at Springerlink.com Yan J, Springsteen G, Deeter S, Wang B (2004) The relationship among pKa, pH, and binding constants in the interactions between boronic acids and diols—it is not as simple as it appears. Tetrahedron 60:11205-11209
    Zhang L, Xu Y, Yao H, Xie L, Yao J, Lu H, Yang P (2009) Boronic acid functionalized core-satellite composite nanoparticles for advanced enrichment of glycopeptides and glycoproteins. Chem-Eur J 15:10158-10166
    Zhang LY, Liang Z, Yang KG, Xia SM, Wu Q, Zhang LH, Zhang YK (2012a) Mesoporous TiO2 aerogel for selective enrichment of phosphopeptides in rat liver mitochondria. Anal Chim Acta 729:26-35
    Zhang X, He X, Chen L, Zhang Y (2012b) Boronic acid modified magnetic nanoparticles for enrichment of glycoproteins via azide and alkyne click chemistry. J Mater Chem 22:16520-16526
    Zhao Y, Li Y, Li W, Wu Y, Wu L (2010) Preparation, structure, and imaging of luminescent SiO2 nanoparticles by covalently grafting surfactant-encapsulated europium-substituted polyoxometalates. Langmuir 26:18430-18436
    Zhou W, Yao N, Yao G, Deng C, Zhang X, Yang P (2008) Facile synthesis of aminophenylboronic acid-functionalized magnetic nanoparticles for selective separation of glycopeptides and glycoproteins. Chem Commun 43:5577-5579
    Zivkovic AM, German JB, Lebrilla CB, Mills DA (2011) Human milk glycobiome and its impact on the infant gastrointestinal microbiota. Proc Natl Acad Sci USA 108:4653-4658
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