A methodology for simultaneous fluorogenic derivatization and boronate affinity enrichment of 3-nitrotyrosine-containing peptides

Analytical Biochemistry

Volumn 418, Issue 2, 2011, Pages 184-196

  Dremina, Elena S ^a   Li, Xiaobao ^a,b   Galeva, Nadezhda A ^a   Sharov, Victor S ^a   Stobaugh, John F ^a   Schöneich, Christian ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b Integrated Analytical Laboratories   (United States)

Author keywords

(3R,4S) 1 (4 (Aminomethyl)phenylsulfonyl)pyrrolidine 3,4 diol (APPD); 3 Nitrotyrosine; Boronate affinity chromatography; Fluorescence; Fluorogenic derivatization; Mass spectrometry; Proteomics

Indexed keywords

AFFINITY CHROMATOGRAPHY; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; KETONES; MASS SPECTROMETRY; PROTEOMICS; SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL); TRANSPORT PROPERTIES;

3-NITROTYROSINE; BACKBONE FRAGMENTATION; BORONATE; CHROMATOGRAPHIC CONDITIONS; DERIVATIZATIONS; FLUORESCENCE SPECTROMETRY; IDENTIFICATION OF PROTEINS; PYRROLIDINES;

PEPTIDES;

1 [4 (AMINOMETHYL)PHENYLSULFONYL]PYRROLIDINE 3,4 DIOL; 3 NITROTYROSINE; BENZENEBORONIC ACID; BORONIC ACID DERIVATIVE; PEROXYNITRITE; PROTEIN HYDROLYSATE; REAGENT; SULFONAMIDE; UNCLASSIFIED DRUG;

AFFINITY CHROMATOGRAPHY; ANIMAL CELL; ANIMAL CELL CULTURE; ARTICLE; BINDING AFFINITY; CHEMICAL STRUCTURE; CONTROLLED STUDY; DERIVATIZATION; FLUORESCENCE ANALYSIS; LIMIT OF DETECTION; NONHUMAN; PRIORITY JOURNAL; PROTEIN ANALYSIS; SPECTROFLUOROMETRY; SYNTHESIS; TANDEM MASS SPECTROMETRY;

EID: 80052732326     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2011.07.024     Document Type: Article

References (33)

1. I.V. Turko, and F. Murad Protein nitration in cardiovascular diseases Pharmacol. Rev. 54 2002 619 634 (Pubitemid 35351199)
2. M.R. Reynolds, R.W. Berry, and L. Binder Nitration in neurodegeneration: deciphering the "Hows" "nYs" Biochemistry 46 2007 7325 7336 (Pubitemid 46986359)
3. H. Ischiropoulos Biological selectivity and functional aspects of protein tyrosine nitration Biochem. Biophys. Res. Commun. 305 2002 776 783
4. R. Radi Nitric oxide, oxidants, and protein tyrosine nitration Proc. Natl. Acad. Sci. USA 101 2004 4003 4008 (Pubitemid 38405874)
5. P. Pacher, J.S. Beckman, and L. Liaudet Nitric oxide and peroxynitrite in health and disease Physiol. Rev. 87 2007 315 424 (Pubitemid 46217686)
6. K.S. Aulak, M. Miyagi, L. Yan, K.A. West, D. Massillon, J.W. Crabb, and D.J. Stuehr Proteomic method identifies proteins nitrated in vivo during inflammatory challenge Proc. Natl. Acad. Sci. USA 98 2001 12056 12061 (Pubitemid 32959825)
7. J. Kanski, S.-J. Hong, and C. Schöneich Proteomic analysis of protein nitration in aging skeletal muscle and identification of nitrotyrosine-containing sequences in vivo by nanoelectrospray ionization tandem mass spectrometry J. Biol. Chem. 280 2005 24261 24266 (Pubitemid 40884916)
8. J. Kanski, A. Behring, J. Pelling, and C. Schöneich Proteomic identification of 3-nitrotyrosine-containing rat cardiac proteins: effects of biological aging Am. J. Physiol. 288 2005 H371 H381 (Pubitemid 40023869)
9. J. Kanski, M.A. Alterman, and C. Schöneich Proteomic identification of age-dependent protein nitration in rat skeletal muscle Free Radic. Biol. Med. 35 2003 1229 1239 (Pubitemid 37357248)
10. C.A. Sacksteder, W.-J. Qian, T.V. Knyushko, H. Wang, M.H. Chin, G. Lacan, W.P. Melega, D.G. Camp, R.D. Smith, D.J. Smith, T.C. Squier, and D.J. Bigelow Endogenously nitrated proteins in mouse brain: links to neurodegenerative disease Biochemistry 45 2006 8009 8022 (Pubitemid 43993222)
11. B. Ghesquiere, N. Colaert, K. Hensens, L. Dejager, C. Vanhaute, K. Verleysen, K. Kas, E. Timmerman, M. Goethals, C. Libert, J. Vandekerckhove, and K. Gevaert In vitro and in vivo protein-bound tyrosine nitration characterized by diagonal chromatography Mol. Cell. Proteomics 8 2009 2642 2652
12. G. Nikov, V. Bhat, J.S. Wishnok, and S.R. Tannenbaum Analysis of nitrated proteins by nitrotyrosine-specific affinity probes and mass spectrometry Anal. Biochem. 320 2003 214 222 (Pubitemid 36962845)
13. Q. Zhang, W. Qian, T.V. Knyuschko, T.R.W. Clauss, S.O. Purvine, R.J. Moore, C.A. Sacksteder, M.H. Chin, D.J. Smith, D.G. Camp II, D.J. Bigelow, and R.D. Smith A method for selective enrichment and analysis of nitrotyrosine-containing peptides in complex proteome samples J. Proteome Res. 6 2007 2257 2268 (Pubitemid 46985113)
14. J. Pennington, C. Schöneich, and J.F. Stobaugh Selective fluorogenic derivatization with isotope coding of catechols and 2-aminophenol with benzylamine: a chemical basis for the relative determination of 3-hydroxytyrosine and 3-nitrotyrosine peptides Chromatograhia 66 2007 649 659 (Pubitemid 350059781)
15. V.S. Sharov, E.S. Dremina, J. Pennington, J. Killmer, C. Asmus, M. Thorson, S.J. Hong, X.-B. Li, J.F. Stobaugh, and C. Schöneich Selective fluorogenic derivatization of 3-nitrotyrosine and 3,4-dihydroxyphenylalanine (DOPA) in peptides: a method designed for quantitative proteomic analysis Methods Enzymol. 441 2008 19 32
16. A. Bergold, and W.H. Scouten Borate chromatography Chem. Anal. 66 1983 149 187
17. X.-C. Liu, and W.H. Scouten Miscellaneous methods in affinity chromatography: I. Boronic acids as selective ligands for affinity chromatography Biochromatography 2002 307 317
18. N.L. Wilson, N.G. Karlsson, and N.H. Packer Enrichment and analysis of glycoproteins in the proteome G.B. Smejkal, A. Lazarev, Separation Methods in Proteomics 2006 CRC Press Boca Raton, FL 345 362
19. D.S. Hage Clinical applications of high-performance affinity chromatography Adv. Chromatogr. 42 2003 377 420
20. R.P. Singhal, S. DeSilva, and M. Shyamali Boronate affinity chromatography Adv. Chromatogr. 31 1992 293 335
21. A. Foettinger, A. Leitner, W. Lindner, and D. Christian Solid-phase capture and release of arginine peptides by selective tagging and boronate affinity chromatography J. Chromatogr. A 1079 2005 187 196 (Pubitemid 40823008)
22. I.C. Smith, B.L. Carson, and T.L. Ferguson Osmium: an appraisal of environmental exposure Environ. Health Perspect. 8 1974 201 213
23. T. Najrana, Y. Saito, F. Uraki, K. Kubo, and K. Yamamoto Spontaneous and osmium tetroxide-induced mutagenesis in an Escherichia coli strain deficient in both endonuclease III and endonuclease VIII Mutagenesis 15 2000 121 125 (Pubitemid 30162869)
24. W.A. Pryor, R. Cueto, X. Jin, W.H. Koppenol, M. Ngu-Schwemlein, G.L. Squadrito, P.L. Uppu, and R.M. Uppu A practical method for preparing peroxynitrite solutions of low ionic strength and free of hydrogen peroxide Free Radic. Biol. Med. 18 1995 75 83
25. X.-B. Li, J. Pennington, J.F. Stobaugh, and C. Schöneich Synthesis of sulfonamide- and sulfonyl-phenylboronic acid modified silica phases for boronate affinity chromatography at physiological pH Anal. Biochem. 372 2008 227 236 (Pubitemid 350116769)
26. K. Ikehata, T.G. Duzhak, N.A. Galeva, T. Ji, Y.M. Koen, and R.P. Hanzlik Protein targets of reactive metabolites of thiobenzamide in rat liver in vivo Chem. Res. Toxicol. 21 2008 1432 1442
27. B.T. Hansen, S.W. Davey, A.J. Ham, and D.C. Liebler P-Mod: an algorithm and software to map modifications to peptide sequences using tandem MS data J. Proteome Res. 4 2005 358 368 (Pubitemid 40548140)
28. A. Keller, A.I. Nesvizhskii, E. Kolker, and R. Aebersold Empirical statistical model to estimate the accuracy of peptide identifications made by MS/MS and database search Anal. Chem. 74 2002 5383 5392 (Pubitemid 35215372)
29. A.I. Nesvizhskii, A. Keller, E. Kolker, and R. Aebersold A statistical model for identifying proteins by tandem mass spectrometry Anal. Chem. 75 2003 4646 4658 (Pubitemid 37082259)
30. J.C. Miller, and J.N. Miller Statistics for Analytical Chemistry 1992 Ellis Horwood London pp. 115-117
31. A. Mitsugu, and S. Kyozo Characterization of a model compound for the lysine tyrosylquinone cofactor of lysyl oxidase Biochem. Byophys. Res. Commun. 218 2001 193 199
32. V.S. Sharov, E.S. Dremina, N.A. Galeva, G.S. Gerstenecker, X.-B. Li, R.T. Dobrowsky, J.F. Stobaugh, and C. Schöneich Fluorogenic tagging of protein 3-nitrotyrosine with 4-(aminomethyl) benzenesulfonic acid for quantitative analysis of protein tyrosine nitration Chromatographia 71 2010 37 53
33. T. Nuriel, R.S. Deeb, D.P. Hajjar, and S.S. Gross Protein 3-nitrotyrosine in complex biological samples: quantitation by high-pressure liquid chromatography/electrochemical detection and emergence of proteomic approaches for unbiased identification of modification sites Methods Enzymol. 441 2008 1 17