Journal
BIOCHEMISTRY
Volume 47, Issue 12, Pages 3917-3925Publisher
AMER CHEMICAL SOC
DOI: 10.1021/bi702530z
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Funding
- NCI NIH HHS [R01 CA089450-01, R01 CA089450, CA89450] Funding Source: Medline
- NIDA NIH HHS [DA02014] Funding Source: Medline
- NIEHS NIH HHS [T32 ES007028, ES07028] Funding Source: Medline
- NIGMS NIH HHS [T32 GM065086] Funding Source: Medline
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A novel class of lipids, N-acyltaurines, was recently discovered in fatty acid amide hydrolase knockout mice. In some peripheral tissues, such as liver and kidney, N-acyltaurines with long, polyunsaturated acyl chains are most prevalent. Polyunsaturated fatty acids are converted to a variety of signaling molecules by cyclooxygenases (COXs) and lipoxygenases (LOXs). The ability of COXs and LOXs to oxygenate arachidonoyltaurine was evaluated to gain insight into the potential metabolic fate of N-acyltaurines. Although arachidonoyltaurine was a poor substrate for COXs, mammalian 12S- and 15S-LOXs oxygenated arachidonoyltaurine with similar or better efficiency than arachidonic acid. Products of arachidonoyltaurine oxygenation were characterized by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The positional specificity of single oxygenation was retained for 15S-LOXs. However, platelet-type 12S-LOX produced 12- and 15-hydroxyeicosatetraenoyltaurines (HETE-Ts). Furthermore, LOXs generated dihydroxyeicosatetraenoyltaurines (diHETE-Ts). Metabolism of arachidonoyltaurine by murine resident peritoneal macrophages (RPMs) was also profiled. Arachidonoyltaurine was rapidly taken up and converted primarily to 12-HETE-T. Over prolonged incubations, RPMs also generated small amounts of diHETE-T. Oxidative metabolism of polyunsaturated N-acyltaurines may represent a pathway for the generation or termination of novel signaling molecules.
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