title: 15-Deoxy-Δ¹²,¹⁴-prostaglandin J₂ as an electrophilic mediator.
abstract: Lipid-derived electrophilic molecules are endogenously generated and are causally involved in many pathophysiological effects. Prostaglandin D2, a major cyclooxygenase product in a variety of tissues and cells, readily undergoes dehydration to yield the J-series PGs such as 15-deoxy-Δ(12,14)-PGJ2 (15d-PGJ2). Because of the electrophilic α,β-unsaturated ketone moiety present in its cyclopentenone ring, 15d-PGJ2 acts as an endogenous electrophile. 15d-PGJ2 can covalently react via the Michael addition reaction with critical cellular nucleophiles, such as the free cysteine residues of proteins that play a key role in the regulation of the intracellular signaling pathways. Covalent modification of cellular proteins by 15d-PGJ2 may be one of the most important mechanisms by which 15d-PGJ2 induces many biological responses involved in the pathophysiological effects associated with inflammation. This current review is intended to provide a comprehensive summary of 15d-PGJ2 as an endogenous electrophilic mediator of biological activities.
authors.affiliation: a Laboratory of Food and Biodynamics, Graduate School of Bioagricultural Sciences , Nagoya University , Nagoya , Japan.
authors.forename: Takahiro
authors.initials: T
authors.lastname: Shibata
mesh_terms: D000818:Animals; D000975:Antioxidants / Q000378:metabolism; D017209:Apoptosis / Q000502:physiology*; D006801:Humans; D007249:Inflammation / Q000276:immunology / Q000378:metabolism*; D010084:Oxidation-Reduction; D018384:Oxidative Stress; D015230:Prostaglandin D2 / Q000031:analogs & derivatives* / Q000737:chemistry / Q000276:immunology / Q000378:metabolism; D011506:Proteins / Q000378:metabolism; D015398:Signal Transduction
chemical_list: C097240:15-deoxy-delta(12,14)-prostaglandin J2; D000975:Antioxidants; D011506:Proteins; D015230:Prostaglandin D2
keywords: electrophile; lipid mediator; prostaglandin; protein modification