Stable histone adduction by 4-oxo-2-nonenal: A potential link between oxidative stress and epigenetics

James J. Galligan; Kristie L. Rose; William N. Beavers; Salisha Hill; Keri A. Tallman; William P. Tansey; Lawrence J. Marnett

doi:10.1021/ja503604t

Stable histone adduction by 4-oxo-2-nonenal: A potential link between oxidative stress and epigenetics

James J. Galligan
, Kristie L. Rose
, William N. Beavers
, Salisha Hill
, Keri A. Tallman
, William P. Tansey
, Lawrence J. Marnett

Research output: Contribution to journal › Article › peer-review

112 Scopus citations

Abstract

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.

Original language	English (US)
Pages (from-to)	11864-11866
Number of pages	3
Journal	Journal of the American Chemical Society
Volume	136
Issue number	34
DOIs	https://doi.org/10.1021/ja503604t
State	Published - Aug 27 2014
Externally published	Yes

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja503604t

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title = "Stable histone adduction by 4-oxo-2-nonenal: A potential link between oxidative stress and epigenetics",

abstract = "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.",

author = "Galligan, \{James J.\} and Rose, \{Kristie L.\} and Beavers, \{William N.\} and Salisha Hill and Tallman, \{Keri A.\} and Tansey, \{William P.\} and Marnett, \{Lawrence J.\}",

year = "2014",

month = aug,

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doi = "10.1021/ja503604t",

language = "English (US)",

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journal = "Journal of the American Chemical Society",

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TY - JOUR

T1 - Stable histone adduction by 4-oxo-2-nonenal

T2 - A potential link between oxidative stress and epigenetics

AU - Galligan, James J.

AU - Rose, Kristie L.

AU - Beavers, William N.

AU - Hill, Salisha

AU - Tallman, Keri A.

AU - Tansey, William P.

AU - Marnett, Lawrence J.

PY - 2014/8/27

Y1 - 2014/8/27

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84906748628

UR - https://www.scopus.com/pages/publications/84906748628#tab=citedBy

U2 - 10.1021/ja503604t

DO - 10.1021/ja503604t

M3 - Article

C2 - 25099620

AN - SCOPUS:84906748628

SN - 0002-7863

VL - 136

SP - 11864

EP - 11866

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 34

ER -

Stable histone adduction by 4-oxo-2-nonenal: A potential link between oxidative stress and epigenetics

Abstract

ASJC Scopus subject areas

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