Stable isotope gas chromatography-tandem mass spectrometry determination of aminoethylcysteine ketimine decarboxylated dimer in biological samples

Analytical Biochemistry

Volumn 430, Issue 1, 2012, Pages 4-15

  Tsikas, Dimitrios ^a   Evans, Christopher E ^b,f   Denton, Travis T ^b   Mitschke, Anja ^a   Gutzki, Frank Mathias ^a   Pinto, John T ^c   Khomenko, Tetyana ^d,e   Szabo, Sandor ^d,e   Cooper, Arthur J L ^c  

^a HANNOVER MEDICAL SCHOOL   (Germany)

^b EASTERN WASHINGTON UNIVERSITY   (United States)

^c NEW YORK MEDICAL COLLEGE   (United States)

^d UNIVERSITY OF CALIFORNIA   (United States)

^e VA LONG BEACH HEALTHCARE SYSTEM   (United States)

^f MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

Author keywords

AECK DD; Brain; Cysteamine; GC MS MS; Organic cation transporters; Validation; Vegetables

Indexed keywords

BRAIN; DIMERS; IONIZATION OF GASES; ISOTOPES; MAMMALS; MASS SPECTROMETRY; METABOLITES; NEGATIVE IONS; PLASMA (HUMAN); VEGETABLES;

AECK-DD; CYSTEAMINE; GC-MS/MS; ORGANIC CATION TRANSPORTERS; VALIDATION;

GAS CHROMATOGRAPHY;

ACETONITRILE; AMINOETHYLCYSTEINE KETIMINE DECARBOXYLATED DIMER; BENZYL BROMIDE; CYSTEAMINE DERIVATIVE; STABLE ISOTOPE; UNCLASSIFIED DRUG;

AMINO ACID BRAIN LEVEL; ANIMAL TISSUE; ARTICLE; BENZYLATION; BLOOD SAMPLING; CHEMICAL ANALYSIS; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; DECARBOXYLATION; DERIVATIZATION; GAS CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; MOUSE; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE ANALYSIS; SENSITIVITY AND SPECIFICITY; SHALLOT; STANDARD; TANDEM MASS SPECTROMETRY; URINALYSIS;

MAMMALIA; RATTUS;

EID: 84865512701     PISSN: 00032697     EISSN: 10960309     Source Type: Journal    
DOI: 10.1016/j.ab.2012.07.022     Document Type: Article

References (44)

1. R.M. Coloso, L.L. Hirschberger, J.E. Dominy, J.I. Lee, and M.H. Stipanuk Cysteamine dioxygenase: evidence for the physiological conversion of cysteamine to hypotaurine in rat and mouse tissues Adv. Exp. Med. Biol. 583 2006 25 36
2. J.E. Dominy Jr., C.R. Simmons, L.L. Hirschberger, J. Hwang, R.M. Coloso, and M.H. Stipanuk Discovery and characterization of a second mammalian thiol dioxygenase, cysteamine dioxygenase J. Biol. Chem. 282 2007 25189 25198
3. G. Ricci, M. Nardini, G. Federici, and D. Cavallini The transamination of l-cystathionine, l-cystine, and related compounds by a bovine kidney transaminase Eur. J. Biochem. 157 1986 57 63
4. R. Coccia, C. Foppoli, C. Blarzino, C. De Marco, and B. Pensa Transamination of some sulphur- or selenium-containing amino acids by bovine liver glutamine transaminase Physiol. Chem. Phys. Med. NMR 24 1992 313 321
5. M. Nardini, R.M. Matarese, L. Pecci, A. Antonucci, G. Ricci, and D. Cavallini Detection of 2H-1,4-thiazine-5,6-dihydro-3-carboxylic acid (aminoethylcysteine ketimine) in the bovine brain Biochem. Biophys. Res. Commun. 166 1990 1251 1256
6. M. Nardini, G. Ricci, L. Vesci, L. Pecci, and D. Cavallini Bovine brain ketimine reductase Biochim. Biophys. Acta 957 1988 286 292
7. R.M. Matarese, A. Macone, A. Maggio, and D. Cavallini Aminoethylcysteine ketimine decarboxylated dimer detected in normal human urine by gas-liquid chromatography, selected-ion monitoring, and mass spectrometry J. Chromatogr. B 683 1996 269 272
8. R.M. Matarese, A. Macone, R. Antonini, A. Maggio, and A. Antonucci Identification of aminoethylcysteine ketimine decarboxylated dimer in human plasma J. Chromatogr. B 732 1999 137 144
9. M. Nardini, A. Macone, and R.M. Matarese Determination of aminoethylcysteine ketimine decarboxylated dimer in human plasma and cultured cells by high-performance liquid chromatography with electrochemical detection J. Chromatogr. B 795 2003 319 327
10. R.M. Matarese, A. Macone, G. Crescentini, S. Duprè, and D. Cavallini Detection of a decarboxylated dimer of aminoethylcysteine ketimine in bovine cerebellum Neurochem. Int. 32 1998 365 368
11. A. Macone, M. Nardini, A. Antonucci, A. Maggio, and R.M. Matarese Identification of aminoethylcysteine ketimine decarboxylated dimer, a natural antioxidant, in dietary vegetables J. Agric. Food Chem. 50 2002 2169 2172
12. L. Pecci, G. Montefoschi, A. Antonucci, and D. Cavallini Antioxidant properties of the decarboxylated dimer of aminoethylcysteine ketimine Physiol. Chem. Phys. Med. NMR 27 1995 223 229
13. R.M. Matarese, A. Macone, M. Fontana, S. Duprè, and D. Cavallini Antioxidant activity of aminoethylcysteine ketimine decarboxylated dimer on copper-induced LDL oxidation Biochem. Mol. Biol. Int. 46 1998 829 837
14. M. Fontana, L. Pecci, A. Macone, and D. Cavallini Antioxidant properties of the decarboxylated dimer of aminoethylcysteine ketimine: assessment of its ability to scavenge peroxynitrite Free Radic. Res. 29 1998 435 440
15. A. Macone, R.M. Matarese, V. Gentili, A. Antonucci, S. Duprè, and M. Nardini Effect of aminoethylcysteine ketimine decarboxylated dimer, a natural sulfur compound present in human plasma, on tert-butyl hydroperoxide-induced oxidative stress in human monocytic U937 cells Free Radic. Res. 38 2004 705 714
16. A. Macone, M. Fontana, M. Barba, B. Botta, M. Nardini, F. Ghirga, A. Calcaterra, L. Pecci, and R.M. Matarese Antioxidant properties of aminoethylcysteine ketimine decarboxylated dimer: a review Int. J. Mol. Sci. 12 2011 3072 3084
17. A. Antonucci, L. Pecci, R. Coccia, M. Fontana, and D. Cavallini The oxidation of aminoethylcysteine ketimine dimer by oxygen reactive species Amino Acids 7 1994 83 88
18. W. Shen, M.K. McGath, R. Evande, and D.B. Berkowitz A continuous spectrophotometric assay for human cystathionine β-synthase Anal. Biochem. 342 2005 103 110
19. J.T. Pinto, T. Khomenko, S. Szabo, G.D. McLaren, T.T. Denton, B.F. Krasnikov, T.M. Jeitner, and A.J.L. Cooper Measurement of sulfur-containing compounds involved in the metabolism and transport of cysteamine and cystamine: regional differences in cerebral metabolism J. Chromatogr. B 877 2009 3434 3441
20. T. Khomenko, J.T. Pinto, L. Chen, X. Deng, G. Tolstanova, A.J.L. Cooper, and S. Szabo Role of organic cation transporters (Oct1, Oct2, and Oct3) in the uptake of the duodenal ulcerogen cysteamine in rat duodenal mucosa and in rat small intestinal epithelial cell line IEC-6: use of siRNA technology Gastroenterology 134 2008 A-405
21. T. Khomenko, B. Paunovic, X.M. Deng, L. Chen, and S. Szabo Inhibition of cysteamine-induced duodenal ulcers in Oct1/2 knockout mice Gastroenterology 140 Suppl 1 2011 S-317
22. T. Khomenko, J. Kolodney, J.T. Pinto, G.D. McLaren, X. Deng, L. Chen, G. Tolstanova, B. Paunovic, B.F. Krasnikov, N. Hoa, A.J. Cooper, and S. Szabo New mechanistic explanation for the localization of ulcers in the rat duodenum: role of iron and selective uptake of cysteamine Arch. Biochem. Biophys. 525 2012 60 70
23. D. Tsikas, B. Beckmann, F.-M. Gutzki, and J. Jordan Simultaneous gas chromatography-tandem mass spectrometry quantification of symmetric and asymmetric dimethylarginine in human urine Anal. Biochem. 413 2011 60 62
24. R.D. Velásquez, G. Brunner, M. Varrentrapp, D. Tsikas, and J.C. Frölich Helicobacter pylori produces histamine and spermidine Z. Gastroenterol. 34 1996 116 122
25. A.A. Zoerner, K. Heusser, F.M. Gutzki, A. Mitschke, J. Tank, D.O. Stichtenoth, J. Jordan, and D. Tsikas Unique pentafluorobenzylation and collision-induced dissociation for specific and accurate GC-MS/MS quantification of the catecholamine metabolite 3,4-dihydroxyphenylglycol (DHPG) in human urine J. Chromatogr. B 879 2011 1444 1456
26. D. Tsikas De novo synthesis of trideuteromethyl esters of amino acids for use in GC-MS and GC-tandem MS exemplified for ADMA in human plasma and urine: standardization, validation, comparison, and proof of evidence for their aptitude as internal standards J. Chromatogr. B 877 2009 2308 2320
27. T.M. Jeitner, J.T. Pinto, B.F. Krasnikov, M. Horswill, and A.J.L. Cooper Transglutaminases and neurodegeneration J. Neurochem. 109 Suppl. 1 2009 160 166
28. R. Kleta, and W.A. Gahl Pharmacological treatment of nephropathic cystinosis with cysteamine Expert Opin. Pharmacother. 5 2004 2255 2262
29. Z. Zhang, J.D. Butler, S.W. Levin, K.E. Wisniewski, S.S. Brooks, and A.B. Mukherjee Lysosomal ceroid depletion by drugs: therapeutic implications for a hereditary neurodegenerative disease of childhood Nat. Med. 7 2001 478 484
30. J.Y. Lu, and S.L. Hofmann Inefficient cleavage of palmitoyl-protein thioesterase (PPT) substrates by aminothiols: implications for treatment of infantile neuronal ceroid lipofuscinosis J. Inherit. Metab. Dis. 29 2006 119 126
31. J.R. Kouvaris, V.E. Kouloulias, and L.J. Vlahos Amifostine: the first selective-target and broad-spectrum radioprotector Oncologist 12 2007 738 747
32. T. Khomenko, S. Szabo, X. Deng, H. Ishikawa, G.J. Anderson, and G.D. McLaren Role of iron in the pathogenesis of cysteamine-induced duodenal ulceration in rats Am. J. Physiol. Gastrointest. Liver Physiol. 296 2009 G1277 G1286
33. G. Pitari, G. Maurizi, V. Flati, C.L. Ursini, L. Spera, S. Duprè, and D. Cavallini Enzymatic synthesis of S-aminoethyl-l-cysteine from pantetheine Biochim. Biophys. Acta 1116 1992 27 33
34. G. Pitari, F. Malergue, F. Martin, J.M. Philippe, M.T. Massucci, C. Chabret, B. Maras, S. Duprè, P. Naquet, and F. Galland Pantetheinase activity of membrane-bound vanin-1: lack of free cysteamine in tissues of vanin-1 deficient mice FEBS Lett. 483 2000 149 154
35. -/- mice exhibit a glutathione-mediated tissue resistance to oxidative stress Mol. Cell Biol. 24 2004 7214 7224
36. C. Berruyer, L. Pouyet, V. Millet, F.M. Martin, A. LeGoffic, A. Canonici, S. Garcia, C. Bagnis, P. Naquet, and F. Galland Vanin-1 licenses inflammatory mediator production by gut epithelial cells and controls colitis by antagonizing peroxisome proliferator-activated receptor γ activity J. Exp. Med. 203 2006 2817 2827
37. S. Meghari, C. Berruyer, H. Lepidi, F. Galland, P. Naquet, and J.L. Mege Vanin-1 controls granuloma formation and macrophage polarization in Coxiella burnetii infection Eur. J. Immunol. 37 2007 24 32
38. M.W. Duffel, D.L. Logan, and D.M. Ziegler Cysteamine and cystamine Methods Enzymol. 143 1987 149 154
39. J. Ogony, S. Mare, W. Wu, and N. Ercal High performance liquid chromatography analysis of 2-mercaptoethylamine (cysteamine) in biological samples by derivatization with N-(1-pyrenyl) maleimide (NPM) using fluorescence detection J. Chromatogr. B 843 2006 57 62
40. M. Bousquet, C. Gibrat, M. Ouellet, C. Rouillard, F. Calon, and F. Cicchetti Cystamine metabolism and brain transport properties: clinical implications for neurodegenerative diseases J. Neurochem. 114 2010 1651 1658
41. D.K. Rassin, and G.E. Gaull Subcellular distribution of enzymes of transmethylation and transsulphuration in rat brain J. Neurochem. 24 1975 969 978
42. V. Régnier, J.M. Billard, S. Gupta, B. Potier, S. Woerner, E. Paly, A. Ledru, S. David, S. Luilier, J.C. Bizot, G. Vacano, J.P. Kraus, D. Patterson, W.D. Kruger, J.M. Delabar, and J. London Brain phenotype of transgenic mice overexpressing cystathionine β-synthase PLoS One 7 2012 e29056
43. S. Yu, K. Sugahara, J. Zhang, T. Ageta, H. Kodama, M. Fontana, and S. Duprè Simultaneous determination of urinary cystathionine, lanthionine, S-(2-aminoethyl)-l-cysteine, and their cyclic compounds using liquid chromatography-mass spectrometry with atmospheric pressure chemical ionization J. Chromatogr. B 698 1997 301 307
44. S. Kalra, E.V. Knatko, Y. Zhang, T. Honda, M. Yamamoto, and A.T. Dinkova-Kostova Highly potent activation of Nrf2 by topical tricyclic bis(cyano enone): implications for protection against UV radiation during thiopurine therapy Cancer Prev. Res. 5 2012 973 981