Characterization of Bis(levuglandinyl) Urea Derivatives as Products of the Reaction between Prostaglandin H2 and Arginine

Biochemistry

Volumn 43, Issue 18, 2004, Pages 5503-5510

  Zagol Ikapitte, Irene ^a   Bernoud Hubac, Nathalie ^a   Amarnath, Venkataraman ^a   Roberts II, L Jackson ^a   Boutaud, Olivier ^a   Oates, John A ^a  

^a VANDERBILT UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; BIOMARKERS; DERIVATIVES; LIQUID CHROMATOGRAPHY; MOLECULAR STRUCTURE; REACTION KINETICS; SOLUTIONS; UREA;

POTENTIAL STRATEGY; UREA DERIVATIVES;

BIOCHEMISTRY;

ALDEHYDE; ALPHA N ACETYLARGININE; AMINE; ARGININE; ARGININE DERIVATIVE; BIS(LEVUGLANDINYL)UREA DERIVATIVE; LEVUGLANDIN E2; LYSINE; ORNITHINE; PEPTIDE; PROSTAGLANDIN H2; PROSTAGLANDIN SYNTHASE; PROTEIN; UNCLASSIFIED DRUG; UREA DERIVATIVE;

AQUEOUS SOLUTION; ARTICLE; COVALENT BOND; ENZYME ACTIVITY; HYDROLYSIS; LIPID PEROXIDATION; LIQUID CHROMATOGRAPHY; PRIORITY JOURNAL; PROTEIN MODIFICATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

ALDEHYDES; AMYLOID BETA-PROTEIN; ARGININE; GUANIDINE; HISTONES; HUMANS; LYSINE; ORNITHINE; PEPTIDE FRAGMENTS; PROSTAGLANDIN H2; PROSTAGLANDINS E; SCHIFF BASES; SERUM ALBUMIN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; UREA;

EID: 2442592927     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi049842r     Document Type: Article

References (17)

1. Salomon, R. G., Miller, D. B., Zagorski, M. G., and Coughlin, D. J. (1984) Solvent-Induced fragmentation of prostaglandin endoperoxides. New aldehyde products from PGH2 and a novel intramolecular 1,2-hydride shift during endoperoxide fragmentation in aqueous solution, J. Am. Chem. Soc. 106, 6049-6060.
2. Boutaud, O., Brame, C. J., Salomon, R. G., Roberts, L. J., II., and Oates, J. A. (1999) Characterization of the lysyl adducts formed from prostaglandin H2 via the levuglandin pathway, Biochemistry 38, 9389-9396.
3. Iyer, R. S., Ghosh, S., and Salomon, R. G. (1989) Levuglandin E2 cross-links proteins, Prostaglandins 37, 471-480,
4. Murthi, K. K., Friedman, L. R., Oleinick, N. L., and Salomon, R. G. (1993) Formation of DNA-protein cross-links in mammalian cells by levuglandin E2, Biochemistry 32, 4090-4097.
5. Brame, C. J., Salomon, R. G., Morrow, J. D., and Roberts, L. J., II. (1999) Identification of extremely reactive y-keto aldehydes (isolevuglandins) as products of the isoprostane pathway and characterization of their lysyl protein adducts, J. Biol. Chem. 274, 13139-13146.
6. Wilson, A. G., Kung, H. C., Anderson, M. W., and Eling, T. E. (1979) Covalent binding of intermediates formed during the metabolism of arachidonic acid by human platelet subcellular fractions, Prostaglandins 18, 409-422.
7. Boutaud, O., Brame, C. J., Chaurand, P., Li, J., Rowlinson, S. W., Crews, B. C., Ji, C., Marnett, L. J., Caprioli, R. M., Roberts, L. J., II., and Oates, J. A. (2001) Characterization of the lysyl adducts of prostaglandin H-synthases that are derived from oxygenation of arachidonic acid, Biochemistry 40, 6948-6955.
8. Boutaud, O., Li, J., Zagol, I., Shipp, E. A., Davies, S. S., Roberts, L. J., II, and Oates, J. A. (2003) Levuglandinyl adducts of proteins are formed via a prostaglandin H2 synthase-dependent pathway after platelet activation, J. Biol. Chem. 278, 16926-16928.
9. Boutaud, O., Aronoff, D. M., Richardson, J. H., Marnett, L. J., and Oates, J. A. (2002) Determinants of the cellular specificity of acetaminophen as an inhibitor of prostaglandin H2 synthases, Proc. Natl. Acad Sci. U.S.A. 99, 7130-7135.
10. Wang, N. C., and Anderson, H. J. (1977) Pyrrole chemistry. XVI. Acylation of the pyrrolyl ambident anion, Can. J. Chem. 55, 4103-4111.
11. Limatibul, S., and Watson, J. W. (1971). The mechanism of acid hydrolysis of guanidines, J. Org. Chem. 36, 3805-3807.
12. Kazmaier, U. (1995) in Stereoselective Synthesis (Helmchen, G., Hoffmann, R. W., Mulzer, J., and Schaumann, E., Eds.) pp 4248, Houben-Weyl, Stuttgart, Germany.
13. McMurry, J. (1984) in Organic Chemistry (Needham, M., Ed.) pp 172-174, Brook/Cole Publishing Company, Monterey, CA,
14. Perry, T. L. (1982) Cerebral amino acid pools, Vol. 1, 2nd ed, Plenum Press, New York.
15. Shih, V. E. (1978) in Urea cycle disorders and other congenital hyperammonemic syndromes (Stanbury, J. B., Wyngaarden, J. B., and Frederikson, D. S. Eds.) Plenum Press, McGraw-Hill, New York.
16. Wood, J. H. (1982) Physiological neurochemistry of cerebrospinal fluid, Vol. 1, 2nd ed., Plenum Press, New York.
17. Sadasivudu, B., and Rao, T. I. (1976) Studies on functional and metabolic role of urea cycle intermediates in brain, J. Neurochem. 27, 785-794.