Abstract
A binary magnetic metal-organic framework (MOF)-functionalized material (magG@PDA@Ni-MOF@Fe-MOF) was prepared through grafting Ni-MOF and Fe-MOF on magnetic (Fe3O4) graphene with polydopamine (PDA) as a middle layer. Compared with single MOFs functionalized materials (magG@PDA@Ni-MOF and magG@PDA@Fe-MOF) under the same conditions, magG@PDA@Ni-MOF@Fe-MOF not only displays lower detection limits (4 fmol) and selectivity (1:1000), but also has better enrichment efficiency for both multi- and monophosphopeptides. Other than this, magG@PDA@Ni-MOF@Fe-MOF exhibits fine reusability (five cycles) and rapid enrichment property (1 min), and 24 phosphopeptides were detected when it was applied to the analysis of human saliva.
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Peng JX, Niu H, Zhang HY, Yao YT, Zhao XY, Zhou XY, Wan LH, Kang XH, Wu RA (2018) Highly specific enrichment of multi-phosphopeptides by the diphosphorylated fructose-modified dual-metal-centered zirconium-organic framework. ACS Appl Mater Interfaces 10(38):32613–32621
Zhao M, Xie YQ, Deng CH, Zhang XM (2014) Recent advances in the application of core-shell structured magnetic materials for the separation and enrichment of proteins and peptides. J Chromatogr A 1357:182–193
Zhou JQ, Liang YL, He XM, Chen LX, Zhang YK (2017) Dual-functionalized magnetic metal-organic framework for highly specific enrichment of phosphopeptides. ACS Sustain Chem Eng 5(12):11413–11421
Lundby A, Secher A, Lage K, Nordsborg NB, Dmytriyev A, Lundby C, Olsen JV (2012) Quantitative maps of protein phosphorylation sites across 14 different rat organs and tissues. Nat Commun 3:876
Xu HM, Liu M, Huang XD, Min QH, Zhu JJ (2018) Multiplexed quantitative MALDI MS approach for assessing activity and inhibition of protein kinases based on postenrichment dephosphorylation of phosphopeptides by metal-organic framework-templated porous CeO2. Anal Chem 90(16):9859–9867
Chen YJ, Xiong ZC, Peng L, Gan YY, Zhao YM, Shen J, Qian JH, Zhang LY, Zhang WB (2015) Facile preparation of core-shell magnetic metal-organic framework nanoparticles for the selective capture of phosphopeptides. ACS Appl Mater Interfaces 7(30):16338–16347
Yang SS, Chang YJ, Zhang H, Yu XZ, Shang WB, Chen GQ, Chen DDY, Gu ZY (2018) Enrichment of phosphorylated peptides with metal-organic framework nanosheets for serum profiling of diabetes and phosphoproteomics analysis. Anal Chem 90(22):13796–13805
Steen H, Jebanathirajah JA, Rush J, Morrice N, Kirschner MW (2006) Phosphorylation analysis by mass spectrometry: myths, facts, and the consequences for qualitative and quantitative measurements. Mol Cell Proteomics 5(1):172–181
Gao CH, Lin G, Lei ZX, Zheng Q, Lin JS, Lin Z (2017) Facile synthesis of core-shell structured magnetic covalent organic framework composite nanospheres for selective enrichment of peptides with simultaneous exclusion of proteins. J Mater Chem B 5(36):7496–7503
Yao JZ, Sun NR, Wang JW, Xie YQ, Deng CH, Zhang XM (2017) Rapid synthesis of titanium(IV)-immobilized magnetic mesoporous silica nanoparticles for endogenous phosphopeptides enrichment. Proteomics 17(8):1600320
Chen Y, Li DJ, Bie ZJ, He XP, Liu Z (2016) Coupling of phosphate-imprinted mesoporous silica nanoparticles-based selective enrichment with matrix-assisted laser desorption ionization-time-of-flight mass spectrometry for highly efficient analysis of protein phosphorylation. Anal Chem 88(2):1447–1454
Chen CT, Wang LY, Ho YP (2011) Use of polyethylenimine-modified magnetic nanoparticles for highly specific enrichment of phosphopeptides for mass spectrometric analysis. Anal Bioanal Chem 399(8):2795–2806
Luo B, Yang MG, Jiang PP, Lan F, Wu Y (2016) Multi-affinity sites of magnetic guanidyl-functionalized metal-organic framework nanospheres for efficient enrichment of global phosphopeptide. Nanoscale 10(18):8391–8396
Yan YH, Zhang XG, Deng CH (2014) Designed synthesis of titania nanoparticles coated hierarchially ordered macro/mesoporous silica for selective enrichment of phosphopeptides. ACS Appl Mater Interfaces 6(8):5467–5471
Su J, He XW, Chen LX, Zhan YK (2017) Adenosine phosphate functionalized magnetic mesoporous graphene oxide nanocomposite for highly selective enrichment of phosphopeptides. ACS Sustain Chem Eng 6(2):2188–2196
Salimi K, Kip C, Celikbicak O, Usta DD, Pinar A, Salih B, Tuncel A (2019) Ti(IV) attached-phosphonic acid functionalized capillary monolith as a stationary phase for in-syringe-type fast and robust enrichment of phosphopeptides. Biomed Chromatogr 33(6):e4488
Sun NR, Wang JW, Yao JZ, Chen HM, Deng CH (2019) Magnetite nanoparticles coated with mercaptosuccinic acid-modified mesoporous titania as a hydrophilic sorbent for glycopeptides and phosphopeptides prior to their quantitation by LC-MS/MS. Microchim Acta 186(3)
Zhang KN, Hu DH, Deng SM, Han M, Wang XF, Liu HL, Liu Y, Xie MX (2019) Phytic acid functionalized Fe3O4 nanoparticles loaded with Ti(IV) ions for phosphopeptide enrichment in mass spectrometric analysis. Microchim Acta 186(2):68
Wang JW, Wang ZD, Sun NR, Deng CH (2019) Immobilization of titanium dioxide/ions on magnetic microspheres for enhanced recognition and extraction of mono- and multi-phosphopeptides. Microchim Acta 186(4)
Peng JX, Zhang HY, Li X, Liu SJ, Zha XY, Wu J, Kang XH, Qin HQ, Pan ZF, Wu RA (2016) Dual-metal centered zirconium-organic framework: a metal-affinity probe for highly specific interaction with phosphopeptides. ACS Appl Mater Interfaces 8(51):35012–35020
Xiao J, Yang SS, Wu JX, Wang H, Yu XZ, Shang WB, Chen GQ, Gu ZY (2019) Highly selective capture of monophosphopeptides by two-dimensional metal-organic framework nanosheets. Anal Chem 91(14):9093–9101
Maka VK, Mukhopadhyay A, Savitha G, Moorthy JN (2018) Fluorescent 2D metal-organic framework nanosheets (MONs): design, synthesis and sensing of explosive nitroaromatic compounds (NACs). Nanoscale 10(47):22389–22399
Van de Voorde B, Ameloot R, Stassen I, Everaert M, De Vos D, Tan JC (2013) Mechanical properties of electrochemically synthesised metal-organic framework thin films. J Mater Chem C 1(46):7716–7724
Jiang M, Li J, Cai XF, Zhao Y, Pan LJ, Cao QQ, Wang DH, Du YW (2018) Ultrafine bimetallic phosphide nanoparticles embedded in carbon nanosheets: two-dimensional metal-organic framework-derived non-noble electrocatalysts for the highly efficient oxygen evolution reaction. Nanoscale 10(42):19774–19780
Wen LL, Zhou L, Zhang BG, Meng XG, Qu H, Li DF (2012) Multifunctional amino-decorated metal-organic frameworks: nonlinear-optic, ferroelectric, fluorescence sensing and photocatalytic properties. J Mater Chem 22(42):22603–22609
Dmello ME, Sundaram NG, Singh A, Singh AK, Kalidindi SB (2019) An amine functionalized zirconium metal-organic framework as an effective chemiresistive sensor for acidic gases. Chem Commun 55(3):349–352
Huan WW, Xing MY, Cheng C, Li J (2018) Facile fabrication of magnetic metal-organic framework nanofibers for specific capture of phosphorylated peptides. ACS Sustain Chem Eng 7(2):2245–2254
Jiang JB, Sun XN, She XJ, Li JJ, Li Y, Deng CH, Duan GL (2018) Magnetic microspheres modified with Ti(IV) and Nb(V) for enrichment of phosphopeptides. Microchim Acta 185(6):309
Liu QJ, Sun NR, Gao MX, Deng CH (2018) Magnetic binary metal-organic framework as a novel affinity probe for highly selective capture of endogenous phosphopeptides. ACS Sustain Chem Eng 6(3):4382–4389
Rui K, Zhao GQ, Chen YP, Lin Y, Zhou Q, Chen JY, Zhu JX, Sun WP, Huang W, Dou SX (2018) Hybrid 2D dual-metal-organic frameworks for enhanced water oxidation catalysis. Adv Funct Mater 28(26):1801554
Zeng J, Ji XX, Ma YH, Zhang ZX, Wang SG, Ren ZH, Zhi CY, Yu J (2018) 3D graphene fibers grown by thermal chemical vapor deposition. Adv Mater 30(12):1705380
Fei HL, Dong JC, Wan CZ, Zhao ZP, Xu X, Lin ZY, Wang YL, Liu HT, Zang KT, Luo J, Zhao SL, Hu W, Yan WS, Shakir I, Huang Y, Duan XF (2018) Microwave-assisted rapid synthesis of graphene-supported single atomic metals. Adv Mater 30(35):1802146
Wang YX, Wang SH, Niu HY, Ma YR, Zeng T, Cai YQ, Meng ZF (2013) Preparation of polydopamine coated Fe3O4 nanoparticles and their application for enrichment of polycyclic aromatic hydrocarbons from environmental water samples. J Chromatogr A 1283:20–26
Liu YL, Ai KL, Lu LH (2014) Polydopamine and its derivative materials: synthesis and promising applications in energy, environmental, and biomedical fields. Chem Rev 114(9):5057–5115
Sun NR, Deng CH, Li Y, Zhang XM (2014) Size-exclusive magnetic graphene/mesoporous silica composites with titanium(IV)-immobilized pore walls for selective enrichment of endogenous phosphorylated peptides. ACS Appl Mater Interfaces 6(14):11799–11804
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This work is supported by Zhejiang Natural Science Foundation (LQ19C050002), Ningbo Natural Science Foundation (2018A610279), and the K. C. Wong Magna Fund in Ningbo University.
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Wang, B., Liu, B., Yan, Y. et al. Binary magnetic metal-organic frameworks composites: a promising affinity probe for highly selective and rapid enrichment of mono- and multi-phosphopeptides. Microchim Acta 186, 832 (2019). https://doi.org/10.1007/s00604-019-3916-5
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DOI: https://doi.org/10.1007/s00604-019-3916-5