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15-Deoxy-Δ 12,14 -prostaglandin J 2 : An Electrophilic Trigger of Cellular Responses

2007; American Chemical Society; Volume: 21; Issue: 1 Linguagem: Inglês

10.1021/tx700177j

1520-5010

Kôji Uchida, Takahiro Shibata,

Estrogen and related hormone effects

Electrophilic molecules are endogenously generated and are causally involved in many pathophysiological effects. Prostaglandin D2 (PGD2), a major cyclooxygenase product in a variety of tissues, readily undergoes dehydration to yield the cyclopentenone-type PGs of the J2-series such as 15-deoxy-Δ12,14-PGJ2 (15d-PGJ2). 15d-PGJ2 is an electrophile, which can covalently react via the Michael addition reaction with nucleophiles, such as the free sulfhydryls of glutathione and cysteine residues in cellular proteins that play an important role in the control of the redox cell-signaling pathways. Covalent binding of 15d-PGJ2 to cellular proteins may be one of the mechanisms by which 15d-PGJ2 induces a cellular response involved in most of the pathophysiological effects associated with inflammation. In the present perspective, we provide a comprehensive summary of 15d-PGJ2 as an electrophilic mediator of cellular responses.