Possibilities and pitfalls in quantifying the extent of cysteine sulfenic acid modification of specific proteins within complex biofluids

BMC Biochemistry

Volumn 11, Issue 1, 2010, Pages

  Rehder, Douglas S ^a   Borges, Chad R ^a  

^a ARIZONA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYSTEINE SULFENIC ACID; NITROBENZOIC ACID DERIVATIVE; PLASMA PROTEIN; SULFENIC ACID DERIVATIVE; THIONITROBENZOIC ACID; UNCLASSIFIED DRUG; 5,5 DIMETHYL 1,3 CYCLOHEXANEDIONE; CYCLOHEXANONE DERIVATIVE; CYSTEINE; CYSTEINESULFENIC ACID; DRUG DERIVATIVE; PREALBUMIN; SERUM ALBUMIN; THIOL DERIVATIVE;

ARTICLE; ELECTROSPRAY MASS SPECTROMETRY; FEMALE; HUMAN; NORMAL HUMAN; PLASMA; CHEMISTRY; METABOLISM; OXIDATION REDUCTION REACTION;

CYCLOHEXANONES; CYSTEINE; HUMANS; NITROBENZOATES; OXIDATION-REDUCTION; PREALBUMIN; SERUM ALBUMIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SULFENIC ACIDS; SULFHYDRYL COMPOUNDS;

EID: 77954072854     PISSN: None     EISSN: 14712091     Source Type: Journal    
DOI: 10.1186/1471-2091-11-25     Document Type: Article

References (51)

1. Protein sulfenic acids in redox signaling. LB Poole PA Karplus A Claiborne, Annu Rev Pharmacol Toxicol 2004 44 325 347 10.1146/annurev.pharmtox. 44.101802.121735 14744249
2. Dynamic redox control of NF-kappaB through glutaredoxin-regulated S-glutathionylation of inhibitory kappaB kinase beta. NL Reynaert A van der Vliet AS Guala T McGovern M Hristova C Pantano NH Heintz J Heim YS Ho DE Matthews,, et al. Proc Natl Acad Sci USA 2006 103 35 13086 13091 10.1073/pnas.0603290103 16916935
3. Discovering mechanisms of signaling-mediated cysteine oxidation. LB Poole KJ Nelson, Current opinion in chemical biology 2008 12 1 18 24 10.1016/j.cbpa.2008.01.021 18282483
4. OxyR: a molecular code for redox sensing? JD Helmann, Sci STKE 2002 2002 157 E46 10.1126/stke.2002.157.pe46 12419849
5. The requirement of reversible cysteine sulfenic acid formation for T cell activation and function. RD Michalek KJ Nelson BC Holbrook JS Yi D Stridiron LW Daniel JS Fetrow SB King LB Poole JM Grayson, J Immunol 2007 179 10 6456 6467 17982034
6. Formation and reactions of sulfenic acids in proteins. WS Allison, Accts of Chem Res 1976 9 293 299 10.1021/ar50104a003
7. The activation and inactivation of the acyl phosphatase activity of glyceraldehyde-3-phosphate dehydrogenase. WS Allison MJ Connors, Arch Biochem Biophys 1970 136 2 383 391 10.1016/0003-9861(70)90209-2 4314108
8. The conversion of glyceraldehyde-3-phosphate dehydrogenase to an acylphosphatase by trinitroglycerin and inactivation of this activity by azide and ascorbate. KS You LV Benitez WA McConachie WS Allison, Biochim Biophys Acta 1975 384 2 317 330 235996
9. Formation and repair of papain sulfenic acid. WS Lin DA Armstrong GM Gaucher, Canadian journal of biochemistry 1975 53 3 298 307 10.1139/o75-042 1125817
10. Protein-sulfenic acid stabilization and function in enzyme catalysis and gene regulation. A Claiborne H Miller D Parsonage RP Ross, Faseb J 1993 7 15 1483 1490 8262333
11. Protein-sulfenic acids: diverse roles for an unlikely player in enzyme catalysis and redox regulation. A Claiborne JI Yeh TC Mallett J Luba EJ Crane V Charrier D Parsonage, Biochemistry 1999 38 47 15407 15416 10.1021/bi992025k 10569923
12. How to flip the (redox) switch. G Georgiou, Cell 2002 111 5 607 610 10.1016/S0092-8674(02)01165-0 12464172
13. The OhrR repressor senses organic hydroperoxides by reversible formation of a cysteine-sulfenic acid derivative. M Fuangthong JD Helmann, Proc Natl Acad Sci USA 2002 99 10 6690 6695 10.1073/pnas.102483199 11983871
14. Sulfenic acid formation in human serum albumin by hydrogen peroxide and peroxynitrite. S Carballal R Radi MC Kirk S Barnes BA Freeman B Alvarez, Biochemistry 2003 42 33 9906 9914 10.1021/bi027434m 12924939
15. Sulfenic acid in human serum albumin. S Carballal B Alvarez L Turell H Botti BA Freeman R Radi, Amino Acids 2007 32 4 543 551 10.1007/s00726-006-0430-y 17061035
16. Structure of the native cysteine-sulfenic acid redox center of enterococcal NADH peroxidase refined at 2.8 A resolution. JI Yeh A Claiborne WG Hol, Biochemistry 1996 35 31 9951 9957 10.1021/bi961037s 8756456
17. Crystal structure of a novel human peroxidase enzyme at 2.0 A resolution. HJ Choi SW Kang CH Yang SG Rhee SE Ryu, Nat Struct Biol 1998 5 5 400 406 10.1038/nsb0598-400 9587003
18. Structure, mechanism and regulation of peroxiredoxins. ZA Wood E Schroder J Robin Harris LB Poole, Trends Biochem Sci 2003 28 1 32 40 10.1016/S0968-0004(02)00003-8 12517450
19. Redox regulation of MAP kinase phosphatase 3. D Seth J Rudolph, Biochemistry 2006 45 28 8476 8487 10.1021/bi060157p 16834321
20. Enzyme inactivation through sulfhydryl oxidation by physiologic NO-carriers. K Becker SN Savvides M Keese RH Schirmer PA Karplus, Nat Struct Biol 1998 5 4 267 271 10.1038/nsb0498-267 9546215
21. The inactivation of the acyl phosphatase activity catalyzed by the sulfenic acid form of glyceraldehyde 3-phosphate dehydrogenase by dimedone and olefins. LV Benitez WS Allison, J Biol Chem 1974 249 19 6234 6243 4371119
22. Expanding the functional diversity of proteins through cysteine oxidation. KG Reddie KS Carroll, Current opinion in chemical biology 2008 12 6 746 754 10.1016/j.cbpa.2008.07.028 18804173
23. Fluorescent and affinity-based tools to detect cysteine sulfenic acid formation in proteins. LB Poole C Klomsiri SA Knaggs CM Furdui KJ Nelson MJ Thomas JS Fetrow LW Daniel SB King, Bioconjug Chem 2007 18 6 2004 2017 10.1021/bc700257a 18030992
24. Reactivity of sulfenic acid in human serum albumin. L Turell H Botti S Carballal G Ferrer-Sueta JM Souza R Duran BA Freeman R Radi B Alvarez, Biochemistry 2008 47 1 358 367 10.1021/bi701520y 18078330
25. Widespread sulfenic acid formation in tissues in response to hydrogen peroxide. AT Saurin H Neubert JP Brennan P Eaton, Proc Natl Acad Sci USA 2004 101 52 17982 17987 10.1073/pnas.0404762101 15604151
26. Protein sulfenation as a redox sensor: proteomics studies using a novel biotinylated dimedone analogue. RL Charles E Schroder G May P Free PR Gaffney R Wait S Begum RJ Heads P Eaton, Mol Cell Proteomics 2007 6 9 1473 1484 10.1074/mcp.M700065-MCP200 17569890
27. A chemical approach for detecting sulfenic acid-modified proteins in living cells. KG Reddie YH Seo WB Muse Iii SE Leonard KS Carroll, Molecular bioSystems 2008 4 6 521 531 10.1039/b719986d 18493649
28. Profiling protein thiol oxidation in tumor cells using sulfenic acid-specific antibodies. YH Seo KS Carroll, Proc Natl Acad Sci USA 2009 106 38 16163 16168 10.1073/pnas.0903015106 19805274
29. Mass spectrometric immunoassay. RW Nelson JR Krone AL Bieber P Williams, Anal Chem 1995 67 7 1153 1158 10.1021/ac00103a003 15134097
30. High-throughput affinity mass spectrometry. UA Kiernan D Nedelkov EE Niederkofler KA Tubbs RW Nelson, Methods Mol Biol 2006 328 141 150 16785646
31. High-throughput protein characterization using mass spectrometric immunoassay. UA Kiernan KA Tubbs K Gruber D Nedelkov EE Niederkofler P Williams RW Nelson, Anal Biochem 2002 301 1 49 56 10.1006/abio.2001.5478 11811966
32. Investigating diversity in human plasma proteins. D Nedelkov UA Kiernan EE Niederkofler KA Tubbs RW Nelson, Proc Natl Acad Sci USA 2005 102 31 10852 10857 10.1073/pnas.0500426102 16043703
33. Investigation of human protein variants and their frequency in the general population. D Nedelkov DA Phillips KA Tubbs RW Nelson, Mol Cell Proteomics 2007 6 7 1183 1187 10.1074/mcp.M700023-MCP200 17468123
34. High-throughput comprehensive analysis of human plasma proteins: a step toward population proteomics. D Nedelkov KA Tubbs EE Niederkofler UA Kiernan RW Nelson, Anal Chem 2004 76 6 1733 1737 10.1021/ac035105+ 15018576
35. Population studies of vitamin d binding protein microheterogeneity by mass spectrometry lead to characterization of its genotype-dependent o-glycosylation patterns. CR Borges JW Jarvis PE Oran RW Nelson, J Proteome Res 2008 7 9 4143 4153 10.1021/pr8002936 18686987
36. Quantitative multiplexed C-reactive protein mass spectrometric immunoassay. UA Kiernan R Addobbati D Nedelkov RW Nelson, J Proteome Res 2006 5 7 1682 1687 10.1021/pr0601133 16823976
37. Multiplexed mass spectrometric immunoassay in biomarker research: a novel approach to the determination of a myocardial infarct. UA Kiernan D Nedelkov RW Nelson, J Proteome Res 2006 5 11 2928 2934 10.1021/pr060062+ 17081044
38. Mass spectrometry-based immunoassays for the next phase of clinical applications. D Nedelkov, Expert review of proteomics 2006 3 6 631 640 10.1586/14789450.3.6.631 17181477
39. Quantitative mass spectrometric immunoassay of insulin like growth factor 1. RW Nelson D Nedelkov KA Tubbs UA Kiernan, J Proteome Res 2004 3 4 851 855 10.1021/pr0499388 15359740
40. Detection of Endogenous B-Type Natriuretic Peptide at Very Low Concentrations in Patients with Heart Failure. EE Niederkofler UA Kiernan J O'Rear S Menon S Saghir AA Protter RW Nelson U Schellenberger, Circulation: Heart Failure 2008 1 258 264 10.1161/CIRCHEARTFAILURE.108.790774 19808300
41. Determination of beta-2 microglobulin levels in plasma using a high-throughput mass spectrometric immunoassay system. EE Niederkofler KA Tubbs K Gruber D Nedelkov UA Kiernan P Williams RW Nelson, Anal Chem 2001 73 14 3294 3299 10.1021/ac010143j 11476228
42. Development of recombinant-based mass spectrometric immunoassay with application to resistin expression profiling. KA Tubbs UA Kiernan EE Niederkofler D Nedelkov AL Bieber RW Nelson, Anal Chem 2006 78 10 3271 3276 10.1021/ac060013g 16689526
43. Sulfenic acid - a key intermediate in albumin thiol oxidation. L Turell H Botti S Carballal R Radi B Alvarez, J Chromatogr B Analyt Technol Biomed Life Sci 2009 877 28 3384 3392 10.1016/j.jchromb.2009.03.035 19386559
44. Oxidation of the albumin thiol to sulfenic acid and its implications in the intravascular compartment. L Turell S Carballal H Botti R Radi B Alvarez, Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas/Sociedade Brasileira de Biofisica [et al] 2009 42 4 305 311 19330257
45. Estimation of aqueous solubility of chemical compounds using E-state indices. IV Tetko VY Tanchuk TN Kasheva AE Villa, Journal of chemical information and computer sciences 2001 41 6 1488 1493 11749573
46. Personal Communication. LB Poole, 2009
47. Free cysteine is increased in plasma from hemodialysis patients. T Nakanishi Y Hasuike Y Otaki Y Hama M Nanami K Miyagawa R Moriguchi H Nishikage M Izumi Y Takamitsu, Kidney international 2003 63 3 1137 1140 10.1046/j.1523-1755.2003.00808.x 12631098
48. Rapid HPLC determination of total homocysteine and other thiols in serum and plasma: sex differences and correlation with cobalamin and folate concentrations in healthy subjects. DW Jacobsen VJ Gatautis R Green K Robinson SR Savon M Secic J Ji JM Otto LM Taylor Jr, Clin Chem 1994 40 6 873 881 8087981
49. Determination of cysteine in human plasma by high-performance liquid chromatography and ultraviolet detection after pre-column derivatization with 2-chloro-1-methylpyridinium iodide. G Chwatko E Bald, Talanta 2000 52 3 509 515 10.1016/S0039-9140(00)00394-5 18968010
50. Cysteine reactivity and thiol-disulfide interchange pathways in AhpF and AhpC of the bacterial alkyl hydroperoxide reductase system. TJ Jonsson HR Ellis LB Poole, Biochemistry 2007 46 19 5709 5721 10.1021/bi7001218 17441733
51. Quick measurement of protein sulfhyrdyls with Ellman's reagent and with 4,4'-dithiodipyridine. CK Reiner G Kada HJ Gruber, Anal Bioanal Chem 2002 373 266 276 10.1007/s00216-002-1347-2 12110978