Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

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Chemical Compound Review:

CHEMBL329415 (5Z,8Z,12R,14Z)-12- hydroxyicosa-5,8,14...

Synonyms: CHEBI:247208, LMFA03050012, AC1NR1MT, 12R-HETrE, 12(R)DH-Hete, ...

Wainwright, S. et al., Du, L. et al., Nishimura, M. et al., Powell, W.S. et al.

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High impact information on 12R-HETrE

12R-HETrE was about 20 times less potent than its 12S isomer in stimulating cytosolic calcium in neutrophils and was also less active as a chemotactic agent [1].
Derivatization of 12-hydroxy-5,8,14-eicosatrienoic acid with (R)-(+)-alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid, followed by chromatography on a silicic acid column, enabled the resolution of 12R and 12S stereoisomers, which were identified by cochromatography with synthetic standards [2].
12(S)-HETE was metabolized to two products that were identified by gas chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy as 12-hydroxy-5,8,14-eicosatrienoic acid (10,11-dihydro-12-HETE) and 12-oxo-5,8,14-eicosatrienoic acid (10,11-dihydro-12-oxo-ETE) [2].
A biosynthetic pathway generating 12-hydroxy-5,8,14-eicosatrienoic acid from arachidonic acid is active in mouse skin microsomes [3].
Structures of the NADPH-dependent products were confirmed to be 12-oxo-5,8,14-eicosatrienoic acid (I) and 12-hydroxy-5,8,14-eicosatrienoic acid (II) [3].

Anatomical context of 12R-HETrE

The major metabolite of 12(R)-HETE in subcellular fractions of bovine corneal epithelial cells was a dihydro compound, 12-hydroxy-5,8,14-eicosatrienoic acid (12-HETrE) [4].

References

Effects of oxo and dihydro metabolites of 12-hydroxy-5,8,10,14-eicosatetraenoic acid on chemotaxis and cytosolic calcium levels in human neutrophils. Powell, W.S., Hashefi, M., Falck, J.R., Chauhan, K., Rokach, J., Wang, S.S., Mills, E., MacLeod, R.J. J. Leukoc. Biol. (1995) [Pubmed]
Metabolism of 12(S)-hydroxy-5,8,10,14-eicosatetraenoic acid and other hydroxylated fatty acids by the reductase pathway in porcine polymorphonuclear leukocytes. Wainwright, S., Falck, J.R., Yadagiri, P., Powell, W.S. Biochemistry (1990) [Pubmed]
A biosynthetic pathway generating 12-hydroxy-5,8,14-eicosatrienoic acid from arachidonic acid is active in mouse skin microsomes. Du, L., Yermalitsky, V., Hachey, D.L., Jagadeesh, S.G., Falck, J.R., Keeney, D.S. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
Metabolism of 12(R)-hydroxy-5,8,10,14-eicosatetraenoic acid (12(R)-HETE) in corneal tissues: formation of novel metabolites. Nishimura, M., Schwartzman, M.L., Falck, J.R., Lumin, S., Zirrolli, J.A., Murphy, R.C. Arch. Biochem. Biophys. (1991) [Pubmed]

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