Stable Histone Adduction by 4-Oxo-2-nonenal: A Potential Link between Oxidative Stress and Epigenetics

被引:102
作者
Galligan, James J. [1 ,5 ]
Rose, Kristie L. [4 ]
Beavers, William N. [2 ]
Hill, Salisha [4 ]
Tallman, Keri A. [2 ]
Tansey, William P. [6 ]
Marnett, Lawrence J. [1 ,2 ,3 ,5 ]
机构
[1] Vanderbilt Univ, Sch Med, AB Hancock Jr Mem Lab Canc Res, Dept Biochem, Nashville, TN 37232 USA
[2] Vanderbilt Univ, Sch Med, AB Hancock Jr Mem Lab Canc Res, Dept Chem, Nashville, TN 37232 USA
[3] Vanderbilt Univ, Sch Med, AB Hancock Jr Mem Lab Canc Res, Dept Pharmacol, Nashville, TN 37232 USA
[4] Vanderbilt Univ, Sch Med, AB Hancock Jr Mem Lab Canc Res, Mass Spectrometry Res Ctr, Nashville, TN 37232 USA
[5] Vanderbilt Univ, Sch Med, AB Hancock Jr Mem Lab Canc Res, Ctr Mol Toxicol, Nashville, TN 37232 USA
[6] Vanderbilt Univ, Sch Med, AB Hancock Jr Mem Lab Canc Res, Vanderbilt Inst Chem Biol, Nashville, TN 37232 USA
关键词
LIPID-PEROXIDATION; ACETYLATION; PRODUCT; DNA; H4;
D O I
10.1021/ja503604t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Lipid electrophiles modify cellular targets, altering their function. Here, we describe histones as major targets for modification by 4-oxo-2-nonenal, resulting in a stable Lys modification structurally analogous to other histone Lys acylations. Seven adducts were identified in chromatin isolated from intact cells: four 4-ketoamides to Lys and three Michael adducts to His. A 4-ketoamide adduct residing at H3K27 was identified in stimulated macrophages. Modification of histones H3 and H4 prevented nucleosome assembly.
引用
收藏
页码:11864 / 11866
页数:3
相关论文
共 22 条
[1]   Oxidative stress in neurodegeneration: cause or consequence? [J].
Andersen, JK .
NATURE MEDICINE, 2004, 10 (07) :S18-S25
[2]   Levuglandin Forms Adducts with Histone H4 in a Cyclooxygenase-2-Dependent Manner, Altering Its Interaction with DNA [J].
Carrier, Erica J. ;
Zagol-Ikapitte, Irene ;
Amarnath, Venkataraman ;
Boutaud, Olivier ;
Oates, John A. .
BIOCHEMISTRY, 2014, 53 (15) :2436-2441
[3]   Cigarette Smoke Component Acrolein Modulates Chromatin Assembly by Inhibiting Histone Acetylation [J].
Chen, Danqi ;
Fang, Lei ;
Li, Hongjie ;
Tang, Moon-shong ;
Jin, Chunyuan .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2013, 288 (30) :21678-21687
[4]   CHEMISTRY AND BIOCHEMISTRY OF 4-HYDROXYNONENAL, MALONALDEHYDE AND RELATED ALDEHYDES [J].
ESTERBAUER, H ;
SCHAUR, RJ ;
ZOLLNER, H .
FREE RADICAL BIOLOGY AND MEDICINE, 1991, 11 (01) :81-128
[5]   Chemical derivatization of histones for facilitated analysis by mass spectrometry [J].
Garcia, Benjamin A. ;
Mollah, Sahana ;
Ueberheide, Beatrix M. ;
Busby, Scott A. ;
Muratore, Tara L. ;
Shabanowitz, Jeffrey ;
Hunt, Donald F. .
NATURE PROTOCOLS, 2007, 2 (04) :933-938
[6]   Histone acetylation in chromatin structure and transcription [J].
Grunstein, M .
NATURE, 1997, 389 (6649) :349-352
[7]   Insights into the role of histone H3 and histone H4 core modifiable residues in Saccharomyces cerevisiae [J].
Hyland, EA ;
Cosgrove, MS ;
Molina, H ;
Wang, DX ;
Pandey, A ;
Cottee, RJ ;
Boeke, JD .
MOLECULAR AND CELLULAR BIOLOGY, 2005, 25 (22) :10060-10070
[8]   Crystal structure of the nucleosome core particle at 2.8 angstrom resolution [J].
Luger, K ;
Mader, AW ;
Richmond, RK ;
Sargent, DF ;
Richmond, TJ .
NATURE, 1997, 389 (6648) :251-260
[9]   EZH2 inhibition as a therapeutic strategy for lymphoma with EZH2-activating mutations [J].
McCabe, Michael T. ;
Ott, Heidi M. ;
Ganji, Gopinath ;
Korenchuk, Susan ;
Thompson, Christine ;
Van Aller, Glenn S. ;
Liu, Yan ;
Graves, Alan P. ;
Della Pietra, Anthony, III ;
Diaz, Elsie ;
LaFrance, Louis V. ;
Mellinger, Mark ;
Duquenne, Celine ;
Tian, Xinrong ;
Kruger, Ryan G. ;
McHugh, Charles F. ;
Brandt, Martin ;
Miller, William H. ;
Dhanak, Dashyant ;
Verma, Sharad K. ;
Tummino, Peter J. ;
Creasy, Caretha L. .
NATURE, 2012, 492 (7427) :108-+
[10]   A novel lipid hydroperoxide-derived cyclic covalent modification to histone H4 [J].
Oe, T ;
Arora, JS ;
Lee, SH ;
Blair, IA .
JOURNAL OF BIOLOGICAL CHEMISTRY, 2003, 278 (43) :42098-42105