12(S)-HETE is a product of arachidonic acid metabolism through the 12-lipoxygenase pathway. It is primarily found in platelets, leukocytes, and to a lesser extent in smooth muscle cells.¹ It enhances tumor cell adhesion to endothelial cells, fibronectin, and the subendothelial matrix.² tetranor-12(S)-HETE is the major β-oxidation product resulting from peroxisomal metabolism of 12(S)-HETE in numerous tissues, and Lewis lung carcinoma cells.^3,4 No biological function has yet been determined for tetranor-12(S)-HETE. Some data indicate it may play a role in controlling the inflammatory response in injured corneas.⁴ In some diseases (e.g., Zellweger’s Syndrome) peroxisomal abnormalities result in the inability of cells to metabolize 12(S)-HETE, which may be responsible for symptoms of the disease. The tetranor derivative of 12(S)-HETE is available as a research tool for the elucidation of the metabolic fate of its parent compound.

1 Evans, J.F., Leblanc, Y., Fitzsimmons, B.J., et al. Activation of leukocyte movement and displacement of [³H]leukotriene B₄ from leukocyte membrane preparations by (12R)- and (12S)-hydroxyeicosatetraenoic acid. Biochim Biophys Acta 917 406-410 (1987).

2 Grossi, I.M., Fitzgerald, L.A., Umbarger, L.A., et al. Bidirectional control of membrane expression and/or activation of the tumor cell IRGpIIb/IIIa receptor and tumor cell adhesion by lipoxygenase products of arachidonic acid and linoleic acid. Cancer Res 49 1029-1037 (1989).

3 Wigren, J., Herbertsson, H., Tollbom Ö, et al. Metabolism of 12(S)-hydroxy-5,8,10,14-eicosatetraenoic acid by kidney and liver peroxisomes. J Lipid Res 34 625-631 (1993).

4 Hurst, J.S., Bazan, H.P., and Balazy, M. The incorporation and release of 12(S)-hydroxyeicosatetraenoic acid and its major metabolite, 8(S)-hydroxyhexadecatrienoic acid, from rabbit corneal lipids. Exp Eye Res 59 97-106 (1994).

Evans, J.F., Leblanc, Y., Fitzsimmons, B.J., et al. Activation of leukocyte movement and displacement of [³H]leukotriene B₄ from leukocyte membrane preparations by (12R)- and (12S)-hydroxyeicosatetraenoic acid. Biochim Biophys Acta 917 406-410 (1987).

Grossi, I.M., Fitzgerald, L.A., Umbarger, L.A., et al. Bidirectional control of membrane expression and/or activation of the tumor cell IRGpIIb/IIIa receptor and tumor cell adhesion by lipoxygenase products of arachidonic acid and linoleic acid. Cancer Res 49 1029-1037 (1989).

Hurst, J.S., Bazan, H.P., and Balazy, M. The incorporation and release of 12(S)-hydroxyeicosatetraenoic acid and its major metabolite, 8(S)-hydroxyhexadecatrienoic acid, from rabbit corneal lipids. Exp Eye Res 59 97-106 (1994).

Wigren, J., Herbertsson, H., Tollbom Ö, et al. Metabolism of 12(S)-hydroxy-5,8,10,14-eicosatetraenoic acid by kidney and liver peroxisomes. J Lipid Res 34 625-631 (1993).

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tetranor-12(S)-HETE is available in the following screening library:

• Bio-active Lipid II Screening Library (96-Well)