Carnosine is a quencher of 4-hydroxy-nonenal: Through what mechanism of reaction?

Biochemical and Biophysical Research Communications

Volumn 298, Issue 5, 2002, Pages 699-706

  Aldini, Giancarlo ^a   Carini, Marina ^a   Beretta, Giangiacomo ^a   Bradamante, Silvia ^a   Facino, Roberto Maffei ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

4 Hydroxy trans 2,3 nonenal; Carnosine; ESI MS; Michael and imine adducts; NMR; Rat skeletal muscle

Indexed keywords

4 HYDROXYNONENAL; ACETAL; ALDEHYDE; AMINO ACID; BETA ALANINE; BUFFER; CARNOSINE; DIPEPTIDE; HISTIDINE; HISTIDINE DERIVATIVE; IMINE; MACROCYCLIC COMPOUND; N ACETYLCARNOSINE; PHOSPHATE; UNCLASSIFIED DRUG;

ADDITION REACTION; ANIMAL TISSUE; ARTICLE; CATALYSIS; CONTROLLED STUDY; CYTOTOXICITY; MALE; MICHAEL ADDITION; NONHUMAN; OXIDATION; PH; PRIORITY JOURNAL; PROTEIN ANALYSIS; PROTEIN DETERMINATION; RAT; REACTION ANALYSIS; SKELETAL MUSCLE;

ALDEHYDES; ANIMALS; CARNOSINE; LIPID PEROXIDATION; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MASS SPECTROMETRY; MODELS, BIOLOGICAL; MUSCLE, SKELETAL; OXIDATION-REDUCTION; RATS; RATS, WISTAR; THIOBARBITURIC ACID REACTIVE SUBSTANCES;

EID: 0036435601     PISSN: 0006291X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-291X(02)02545-7     Document Type: Article

References (19)

1. P.J. Quinn, A.A. Boldyrev, V.E. Formazuyk, Carnosine: Its properties, functions, and potential therapeutic applications, Mol. Aspects Med. 13 (1992) 379-444.
2. W. Gulewitsch, S. Amiradzibi, Ueber das carnosin, eine neue organische base des fleischextractes, Ber. Dtsch. Chem. Ges. 33 (1900) 1902-1903.
3. A.A. Boldyrev, Problems and perspectives in studying the biological role of carnosine, Biochemisty - Moscow 65 (2000) 751-756.
4. A.R. Hipkiss, J.E. Preston, D.T. Himsworth, V.C. Worthington, M. Keown, J. Michaelis, J. Lawrence, A. Mateen, L. Allende, P.A. Eagles, N.J. Abbot, Pluripotent protective effects of carnosine, a naturally occurring dipeptide, Ann. N. Y. Acad. Sci. 854 (1998) 37-53.
5. A.R. Hipkiss, Carnosine and protein carbonyl groups: A possible relationship, Biochemistry - Moscow 65 (2000) 771-778.
6. A.R. Hipkiss, J.E. Preston, D.T. Himswoth, V.C. Worthington, N.J. Abbot, Protective effects of carnosine against malondialdehyde-induced toxicity towards cultured rat brain endothelial cells, Neurosci. Lett. 238 (1997) 135-138.
7. A.R. Hipkiss, Could carnosine be a naturally occurring scavenger for acrolein and other reactive aldehydes in the brain? Neurobiol. Aging 23 (2002) 645-646.
8. G. Poli, R.J. Schaur, 4-Hydroxynonenal in the pathomechanisms of oxidative stress, IUBMB Life 50 (2000) 315-321.
9. F.J. Romero, F. Bosch-Morell, M.J. Romero, E.J. Jareno, B. Romero, N. Marin, J. Roma, Lipid peroxidation products and antioxidants in human disease, Environ. Health Perspect. 106 (1998) 1229-1234.
10. G. Poli, M.U. Dianzani, K.H. Cheeseman, T.F. Slater, J. Lang, H. Esterbauer, Separation and characterization of the aldehydic products of lipid peroxidation stimulated by carbon tetrachloride or ADP-iron in isolated rat hepatocytes and rat liver microsomal suspensions, Biochem. J. 227 (1985) 629-638.
11. H. Esterbauer, R.J. Schaur, H. Zollner, Chemistry and biochemistry of 4-hydroxynonenal, malonaldehyde, and related aldehydes, Free Radic. Biol. Med. 11 (1991) 81-128.
12. J. Pan, F.L. Chung, Formation of Cyclic deoxyguanosine adducts from ω-3 and ω-6 polyunsaturated fatty acids under oxidative conditions, Chem. Res. Toxicol. 15 (2002) 367-372.
13. S. Zhou, E.A. Decker, Ability of carnosine and other skeletal muscle components to quench unsaturated aldehydic lipid oxidation products, J. Agric. Food Chem. 47 (1999) 51-55.
14. G. Aldini, P. Granata, M. Carini, Detoxification of cytotoxic α,β-unsaturated aldehydes by carnosine: Characterization of conjugated adducts by ESI-MS/MS and detection by LC-MS in rat skeletal muscle, J. Mass Spectrom. 37 (12), December 2002, in press.
15. M.A. Markwell, S.M. Haas, N.E. Tolbert, L.L. Bieber, Protein determination in membrane and lipoprotein samples: Manual and automated procedures, Method Enzymol. 72 (1981) 296-303.
16. M. Carini, G. Aldini, E. Bombardelli, P. Morazzoni, R. Maffei Facino, UVB-induced hemolysis of rat erythrocytes: Protective effect of procyanidins from grape seeds, Life Sci. 67 (2000) 1799-1814.
17. L. Tsai, E.A. Sokoloski, The reaction of 4-hydroxy-2-nonenal with N-α-acetyl-L-histidine, Free Radic. Biol. Med. 19 (1995) 39-44.
18. K. Uchida, E.R. Stadtman, Modification of histidine residues in proteins by reaction with 4-hydroxynonenal, Proc. Natl. Acad. Sci. USA 89 (1992) 4544-4548.
19. D.V. Nadkarni, L.M. Sayre, Structural definition of early lysine and histidine adduction chemistry of 4-hydroxynonenal, Chem. Res. Toxicol. 8 (1995) 284-291.