PMID: 9434139Jan 20, 1998Paper

Thia fatty acids as substrates and inhibitors of stearoyl-CoA desaturase

Biochimica Et Biophysica Acta
K HøvikJ Bremer

Abstract

Thia fatty acids are fatty acid analogues, where sulfur atoms substitute methylene groups in the carbon chain. In 7800 C1 Morris hepatoma cells and in hepatocytes 9-thia and 10-thia stearic acid are strong inhibitors of stearoyl-Co desaturase, while 3,9-dithia stearic acid and 3,10-dithia stearic acid are much weaker inhibitors. No effect on the stearoyl-CoA desaturase can be observed with 3-thia stearic acid. In microsomes, an equimolar concentration of 9-thia stearoyl-CoA inhibits the delta9 desaturation of [1-14C]stearoyl-CoA approximately 75%, while 3,9-dithia stearoyl-CoA and 3,10-dithia stearoyl-CoA again are weak inhibitors. 3-Thia stearoyl-CoA has no effect on the desaturation of [1-14C]stearoyl-CoA. [2-14C]3-Thia stearoyl-CoA is delta9 desaturated to [2-14C]thia oleic acid. This desaturation is inhibited by unlabelled stearoyl-CoA, which therefore is the preferred substrate. These results show that a sulfur atom in the 3 position reduces the affinity of the CoA ester for the enzyme, but permits desaturation. A sulfur in the 9 or 10 position does not affect binding to the enzyme. The 9-thia and 10-thia stearoyl-CoA, which cannot be desaturated, therefore are strong inhibitors.

References

Feb 26, 1991·Biochimica Et Biophysica Acta·E N ChristiansenA C Rustan
Feb 1, 1981·Journal of Biochemistry·A KawaguchiS Okuda
Dec 7, 1995·Biochimica Et Biophysica Acta·U DiczfalusyS E Alexson

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Citations

Jan 23, 2003·Prostaglandins, Leukotrienes, and Essential Fatty Acids·Makoto Miyazaki, James M Ntambi
Feb 27, 2001·Insect Biochemistry and Molecular Biology·A PinillaG Fabriàs
Mar 3, 2009·International Journal for Parasitology·Andrés AlloattiAntonio D Uttaro
Feb 20, 2002·The Journal of Investigative Dermatology·Apostolos PappasJoel S Gordon
Feb 1, 2008·ChemMedChem·Jose M Munoz-OlayaGemma Fabriàs
Apr 22, 2016·Nutritional Neuroscience·Jimena Verónica LavanderaMarcela Aída González
Jun 9, 2001·Biochemical and Biophysical Research Communications·Y ChoiJ M Ntambi
Dec 31, 2002·Biochemical and Biophysical Research Communications·F Enrique GomezBrian G Fox
Jan 5, 2021·Journal of Medicinal Chemistry·Jan SkácelTakashi Tsukamoto

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