Hypochlorite-induced oxidation of amino acids, peptides and proteins

被引：498

作者：

Hawkins, CL ^{[1
]}

Pattison, DI ^{[1
]}

Davies, MJ ^{[1
]}

机构：

[1] Heart Res Inst, Free Rad Grp, Sydney, NSW 2050, Australia

来源：

AMINO ACIDS | 2003年 / 25卷 / 3-4期

关键词：

hypochlorite; myeloperoxidase; protein oxidation; chloramines; chloramides; radicals; oxidative stress; fragmentation; HUMAN NEUTROPHILS EMPLOY; LOW-DENSITY-LIPOPROTEIN; HYDROGEN-PEROXIDE-CHLORIDE; ABSOLUTE RATE CONSTANTS; L-TYROSINE OXIDATION; REACTIVE ALDEHYDES; ENDOTHELIAL-CELLS; INDUCED DAMAGE; MAJOR PRODUCT; P-HYDROXYPHENYLACETALDEHYDE;

D O I：

10.1007/s00726-003-0016-x

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Activated phagocytes generate the potent oxidant hypochlorite (HOCl) via the release of the enzyme myeloperoxidase and hydrogen peroxide. HOCl is known to react with a number of biological targets including proteins, DNA, lipids and cholesterol. Proteins are likely to be major targets for reaction with HOCl within a cell due to their abundance and high reactivity with HOCl. This review summarizes information on the rate of reaction of HOCl with proteins, the nature of the intermediates formed, the mechanisms involved in protein oxidation and the products of these reactions. The predicted targets for reaction with HOCl from kinetic modeling studies and the consequences of HOCl-induced protein oxidation are also discussed.

引用

页码：259 / 274

页数：16

共 115 条

[41] Degradation of hyaluronic acid, poly- and monosaccharides and model compounds by hypochlorite: Evidence for radical intermediates and fragmentation [J].

Hawkins, CL ;

Davies, MJ .

FREE RADICAL BIOLOGY AND MEDICINE, 1998, 24 (09) :1396-1410

[42] Generation and propagation of radical reactions on proteins [J].

Hawkins, CL ;

Davies, MJ .

BIOCHIMICA ET BIOPHYSICA ACTA-BIOENERGETICS, 2001, 1504 (2-3) :196-219

[43]

HAYATSU H, 1971, CHEM PHARM BULL, V19, P2189

[44] Secondary radicals derived from chloramines of apolipoprotein B-100 contribute to HOCl-induced lipid peroxidation of low-density lipoproteins [J].

Hazell, LJ ;

Davies, MJ ;

Stocker, R .

BIOCHEMICAL JOURNAL, 1999, 339 :489-495

[45] OXIDATION OF LOW-DENSITY-LIPOPROTEIN BY HYPOCHLORITE CAUSES AGGREGATION THAT IS MEDIATED BY MODIFICATION OF LYSINE RESIDUES RATHER THAN LIPID OXIDATION [J].

HAZELL, LJ ;

VANDENBERG, JJM ;

STOCKER, R .

BIOCHEMICAL JOURNAL, 1994, 302 :297-304

[46] Human neutrophils employ myeloperoxidase to convert α-amino acids to a battery of reactive aldehydes:: A pathway for aldehyde generation at sites of inflammation [J].

Hazen, SL ;

Hsu, FF ;

d'Avignon, A ;

Heinecke, JW .

BIOCHEMISTRY, 1998, 37 (19) :6864-6873

[47] p-hydroxyphenylacetaldehyde, the major product of L-tyrosine oxidation by the myeloperoxidase-H2O2-chloride system of phagocytes, covalently modifies epsilon-amino groups of protein lysine residues [J].

Hazen, SL ;

Gaut, JP ;

Hsu, FF ;

Crowley, JR ;

dAvignon, A ;

Heinecke, JW .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1997, 272 (27) :16990-16998

[48] Mass spectrometric quantification of 3-chlorotyrosine in human tissues with attomole sensitivity: A sensitive and specific marker for myeloperoxidase-catalyzed chlorination at sites of inflammation [J].

Hazen, SL ;

Crowley, JR ;

Mueller, DM ;

Heinecke, JW .

FREE RADICAL BIOLOGY AND MEDICINE, 1997, 23 (06) :909-916

[49] Human neutrophils employ the myeloperoxidase hydrogen peroxide chloride system to oxidize α-amino acids to a family of reactive aldehydes -: Mechanistic studies identifying labile intermediates along the reaction pathway [J].

Hazen, SL ;

d'Avignon, A ;

Anderson, MM ;

Hsu, FF ;

Heinecke, JW .

JOURNAL OF BIOLOGICAL CHEMISTRY, 1998, 273 (09) :4997-5005

[50] 3-chlorotyrosine, a specific marker of myeloperoxidase-catalyzed oxidation, is markedly elevated in low density lipoprotein isolated from human atherosclerotic intima [J].

Hazen, SL ;

Heinecke, JW .

JOURNAL OF CLINICAL INVESTIGATION, 1997, 99 (09) :2075-2081

← 1 2 3 4 5 6 7 8 9 10 →