Mass spectrometry for detection of 4-hydroxy-trans-2-nonenal (HNE) adducts with peptides and proteins

被引:147
作者
Carini, M [1 ]
Aldini, G [1 ]
Facino, RM [1 ]
机构
[1] Univ Milan, Ist Chim Farmaceut Tossicol, Fac Pharm, I-20131 Milan, Italy
关键词
4-hydroxy-trans-2-nonenal; peptide interaction; mass spectrometry; adduct characterization;
D O I
10.1002/mas.10076
中图分类号
O433 [光谱学];
学科分类号
0703 ; 070302 ;
摘要
Despite the great technical advancement of mass spectrometry, this technique has contributed in a limited way to the discovery and quantitation of specific/precocious markers linked to free radical-mediated diseases. Unsaturated aldehydes generated by free radical-induced lipid peroxidation of polyunsaturated fatty acids, and in particular 4-hydroxy-trans-2 nonenal (HNE), are involved in the onset and progression of many pathologies such as cardiovascular (atherosclerosis, long-term complications of diabetes) and neurodegenerative diseases (Alzheimer's disease, Parkinson's disease, and cerebral ischemia). Most of the biological effects of HNE are attributed to the capacity of HNE to react with the nucleophilic sites of proteins and peptides (other than nucleic acids), to form covalently modified biomolecules that can disrupt important cellular functions and induce mutations. By considering the emerging role of HNE in several human diseases, an unequivocal analytical approach as mass spectrometry to detect/elucidate the structure of protein-HNE adducts in biological matrices is strictly needed not only to understand the reaction mechanism of HNE, but also to gain a deeper insight into the pathological role of HNE. This with the aim to provide intermediate diagnostic biomarkers for human diseases. This review sheds focus on the. "state-of-the-art" of mass spectrometric applications in the field of HNE-protein adducts characterization, starting from the fundamental early studies and discussing the different MS-based approaches that can provide detailed information on the mechanistic aspects of HNE-protein interaction. In the last decade, the increases in the accessible mass ranges of modem instruments and advances in ionization methods have made possible a fundamental improvement in the analysis of protein-HNE adducts by mass spectrometry, and in particular by matrix-assisted laser desorption/ionization (MALDI) and electrospray ionization (ESI) tandem mass spectrometry. The recent developments and uses of combined analytical approaches to detect and characterize the type/site of interaction have been highlighted, and several other aspects, including sample preparation methodologies, structure elucidation, and data analysis have also been considered. (C) 2004 Wiley Periodicals, Inc.
引用
收藏
页码:281 / 305
页数:25
相关论文
共 87 条
[11]   MAXIMUM-ENTROPY DECONVOLUTION OF HETEROGENEITY IN PROTEIN MODIFICATION - PROTEIN ADDUCTS OF 4-HYDROXY-2-NONENAL [J].
BRUENNER, BA ;
JONES, AD ;
GERMAN, JB .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 1994, 8 (07) :509-512
[12]   DIRECT CHARACTERIZATION OF PROTEIN ADDUCTS OF THE LIPID-PEROXIDATION PRODUCT 4-HYDROXY-2-NONENAL USING ELECTROSPRAY MASS-SPECTROMETRY [J].
BRUENNER, BA ;
JONES, AD ;
GERMAN, JB .
CHEMICAL RESEARCH IN TOXICOLOGY, 1995, 8 (04) :552-559
[13]  
CARINI M, 2002, 22 IFSCC ED 23 26 SE, P129
[14]   Role of 4-hydroxynonenal in modification of cytochrome c oxidase in ischemia/reperfused rat heart [J].
Chen, JJ ;
Henderson, GI ;
Freeman, GL .
JOURNAL OF MOLECULAR AND CELLULAR CARDIOLOGY, 2001, 33 (11) :1919-1927
[15]   STUDIES ON EPITOPES ON LOW-DENSITY-LIPOPROTEIN MODIFIED BY 4-HYDROXYNONENAL - BIOCHEMICAL-CHARACTERIZATION AND DETERMINATION [J].
CHEN, Q ;
ESTERBAUER, H ;
JURGENS, G .
BIOCHEMICAL JOURNAL, 1992, 288 :249-254
[16]   Chemical characterization of a protein-4-hydroxy-2-nonenal cross-link: Immunochemical detection in mitochondria exposed to oxidative stress [J].
Cohn, JA ;
Tsai, L ;
Friguet, B ;
Szweda, LI .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1996, 328 (01) :158-164
[17]   Hydroxynonenal inactivates cathepsin B by forming Michael adducts with active site residues [J].
Crabb, JW ;
O'Neil, J ;
Miyagi, M ;
West, K ;
Hoff, HF .
PROTEIN SCIENCE, 2002, 11 (04) :831-840
[18]   4-hydroxynonenal inhibits interleukin-1 beta converting enzyme [J].
Davis, DW ;
Hamilton, RF ;
Holian, A .
JOURNAL OF INTERFERON AND CYTOKINE RESEARCH, 1997, 17 (04) :205-210
[19]  
Del Corso A, 1998, ARCH BIOCHEM BIOPHYS, V350, P245
[20]   Covalent adduction of nucleophilic amino acids by 4-hydroxynonenal and 4-oxononenal [J].
Doorn, JA ;
Petersen, DR .
CHEMICO-BIOLOGICAL INTERACTIONS, 2003, 143 :93-100