An on-column derivatization method for the determination of homocysteine-thiolactone and protein N-linked homocysteine

Amino Acids

Volumn 41, Issue 1, 2011, Pages 187-194

  Głowacki, Rafał ^a   Bald, Edward ^a   Jakubowski, Hieronim ^b,c,d  

^a UNIVERSITY OF LODZ   (Poland)

^b RUTGERS NEW JERSEY MEDICAL SCHOOL   (United States)

^c INSTITUTE OF BIOORGANIC CHEMISTRY   (Poland)

^d POZNA UNIVERSITY OF LIFE SCIENCES   (Poland)

Author keywords

Homocysteine thiolactone; HPLC; Human plasma; O Phthaldialdehyde; Protein N linked homocysteine; Urine

Indexed keywords

HOMOCYSTEINE; HOMOCYSTEINE THIOLACTONE; PHTHALALDEHYDE; PROTEIN N LINKED HOMOCYSTEINE; UNCLASSIFIED DRUG;

AMINO ACID ANALYSIS; ARTICLE; BLOOD ANALYSIS; CONTROLLED STUDY; FLUORESCENCE ANALYSIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; NORMAL HUMAN; PRIORITY JOURNAL; PROTEIN DETERMINATION; PROTEIN HYDROLYSIS; PROTEIN STRUCTURE; REACTION TIME; URINALYSIS;

BLOOD PROTEINS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; HOMOCYSTEINE; HUMANS; REFERENCE VALUES;

EID: 79960396482     PISSN: 09394451     EISSN: 14382199     Source Type: Journal    
DOI: 10.1007/s00726-010-0521-7     Document Type: Article

References (36)

1. Bald E, Głowacki R (2001) 2-Chloro-1-methylquinolinium tetrafluo-roborate as effective and thiol specific UV-tagging reagent for liquid chromatography. J Liq Chromatogr Rel Techn 24:1323-1339 (Pubitemid 32539038)
2. Bald E, Głowacki R (2005) Analysis of saliva for glutathione and metabolically related thiols by liquid chromatography with ultraviolet detection. Amino Acids 28:431-433 (Pubitemid 40884736)
3. Bald E, Chwatko G, Głowacki R, Kusmierek K (2004) Analysis of plasma thiols by high-performance liquid chromatography with ultraviolet detection. J Chromatogr A 1032:109-115 (Pubitemid 38270350)
4. Chwatko G, Jakubowski H (2005a) Urinary excretion of homocys-teine- thiolactone in humans. Clin Chem 51:408-415
5. Chwatko G, Jakubowski H (2005b) The determination of homocys-teine- thiolactone in human plasma. Anal Biochem 337:271-277
6. Chwatko G, Boers GH, Strauss KA, Shih DM, Jakubowski H (2007) Mutations in methylenetetrahydrofolate reductase or cystathio-nine beta-synthase gene, or a high-methionine diet, increase homocysteine thiolactone levels in humans and mice. Faseb J 21:1707-1713 (Pubitemid 46855616)
7. Daneshvar P, Yazdanpanah M, Cuthbert C, Cole DE (2003) Quantitative assay of plasma homocysteine thiolactone by gas chromatography/mass spectrometry. Rapid Commun Mass Spec-trom 17:358-362 (Pubitemid 36193676)
8. Głowacki R, Bald E (2009) Determination of N-acetylcysteine and main endogenous thiols in human plasma by HPLC with ultraviolet detection in the form of their S-quinolinium derivatives. J Liq Chromatogr Rel Techn 32:2530-2544
9. Głowacki R, Jakubowski H (2004) Cross-talk between Cys34 and lysine residues in human serum albumin revealed by N-homocysteinylation. J Biol Chem 279:10864-10871 (Pubitemid 38401576)
10. Głowacki R, Borowczyk K, Bald E, Jakubowski H (2010) On-column derivatization with o-phthaldialdehyde for fast determination of homocysteine in human urine. Anal Bioanal Chem (in press). doi:10.1007/s00216-010-3456-7
11. Gu W, Lu J, Yang G, Dou J, Mu Y, Meng J, Pan C (2008) Plasma homocysteine thiolactone associated with risk of macrovascul-opathy in Chinese patients with type 2 diabetes mellitus. Adv Ther 25:914-924
12. Jakubowski H (1990) Proofreading in vivo: editing of homocysteine by methionyl-tRNA synthetase in Escherichia coli. Proc Natl Acad Sci USA 87:4504-4508
13. Jakubowski H (1997) Metabolism of homocysteine thiolactone in human cell cultures: possible mechanism for pathological consequences of elevated homocysteine levels. J Biol Chem 272:1935-1942 (Pubitemid 27043288)
14. Jakubowski H (1999) Protein homocysteinylation: possible mechanism underlying pathological consequences of elevated homo-cysteine levels. Faseb J 13:2277-2283
15. Jakubowski H (2000) Homocysteine thiolactone: metabolic origin and protein homocysteinylation in humans. J Nutr 130:377S-381S (Pubitemid 30073754)
16. Jakubowski H (2001a) Translational accuracy of aminoacyl-tRNA synthetases: implications for atherosclerosis. J Nutr 131:2983S-2987S
17. Jakubowski H (2001b) Protein N-homocysteinylation: implications for atherosclerosis. Biomed Pharmacother 55:443-447 (Pubitemid 32913568)
18. Jakubowski H (2002a) Homocysteine is a protein amino acid in humans. Implications for homocysteine-linked disease. J Biol Chem 277:30425-30428 (Pubitemid 34970732)
19. Jakubowski H (2002b) The determination of homocysteine-thiolac-tone in biological samples. Anal Biochem 308:112-119
20. Jakubowski H (2004) Molecular basis of homocysteine toxicity in humans. Cell Mol Life Sci 61:470-487 (Pubitemid 38316582)
21. Jakubowski H (2005) Anti-N-homocysteinylated protein autoantibod-ies and cardiovascular disease. Clin Chem Lab Med 43:1011-1014 (Pubitemid 41581953)
22. Jakubowski H (2006a) Pathophysiological consequences of homo-cysteine excess. J Nutr 136:1741S-1749S
23. Jakubowski H (2006b) Mechanism of the condensation of homocys-teine thiolactone with aldehydes. Chem Eur J 12:8039-8043 (Pubitemid 44672724)
24. Jakubowski H (2007) The molecular basis of homocysteine thiolac-tone-mediated vascular disease. Clin Chem Lab Med 45:1704-1716 (Pubitemid 350232966)
25. Jakubowski H (2008a) The pathophysiological hypothesis of homo-cysteine thiolactone-mediated vascular disease. J Physiol Pharmacol 59(suppl 9):155-167
26. Jakubowski H (2008b) New method for the determination of protein N-linked homocysteine. Anal Biochem 380:257-261
27. Jakubowski H, Goldman E (1993) Synthesis of homocysteine thiolactone by methionyl-tRNA synthetase in cultured mammalian cells. FEBS Lett 317:237-240 (Pubitemid 23045796)
28. Jakubowski H, Boers GH, Strauss KA (2008) Mutations in cystathi-onine {beta}-synthase or ethylenetetrahydrofolate reductase gene increase N-homocysteinylated protein levels in humans. FASEB J 22:4071-4076
29. Jakubowski H, Perla-Kajan J, Finnell RH, Cabrera RM, Wang H, Gupta S, Kruger WD, Kraus JP, Shih DM (2009) Genetic or nutritional disorders in homocysteine or folate metabolism increase protein N-homocysteinylation in mice. FASEB J 23:1721-1727
30. Lentz SR (2005) Mechanisms of homocysteine-induced atherothrom-bosis. J Thromb Haemost 3:1646-1654
31. Mukai Y, Togawa T, Suzuki T, Ohata K, Tanabe S (2002) Determination of homocysteine thiolactone and homocysteine in cell cultures using high-performance liquid chromatography with fluorescence detection. J Chromatogr B Analyt Technol Biomed Life Sci 767:263-268 (Pubitemid 34142317)
32. Perla-Kajan J, Twardowski T, Jakubowski H (2007) Mechanisms of homocysteine toxicity in humans. Amino Acids 32:561-572 (Pubitemid 46790938)
33. Perla-Kajan J, Stanger O, Luczak M, Ziolkowska A, Malendowicz LM, Twardowski T, Lhotak S, Austin RC, Jakubowski H (2008) Immunohistochemical detection of N-homocysteinylated proteins in humans and mice. Biomed Pharmacother 62:473-479
34. Perna AF, Satta E, Acanfora F, Lombardi C, Ingrosso D, De Santo NG (2006) Increased plasma protein homocysteinylation in hemodialysis patients. Kidney Int 69:869-876
35. Uji Y, Motomiya Y, Hanyu N, Ukaji F, Okabe H (2002) Protein-bound homocystamide measured in human plasma by HPLC. Clin Chem 48:941-944 (Pubitemid 34587598)
36. Yang X, Gao Y, Zhou J, Zhen Y, Yang Y, Wang J, Song L, Liu Y, Xu H, Chen Z, Hui R (2006) Plasma homocysteine thiolactone adducts associated with risk of coronary heart disease. Clin Chim Acta 364:230-234 (Pubitemid 43120647)