Fatty acid chlorohydrins and bromohydrins are cytotoxic to human endothelial cells

Redox Report : Communications in Free Radical Research
M C VissersC C Winterbour

Abstract

Reaction of unsaturated lipids with the hypohalous acids (hypochlorous acid and hypobromous acid) results in the addition of the halide (X) across double bonds to form halohydrins (-CH2CH(OH)CH(X)CH2-). These modified lipids could be potentially destabilising to cell membranes due to their increased polarity. We have investigated the effect of pre-formed halohydrins on human umbilical vein endothelial cells (HUVEC) by incubating cultured cells with oleic acid micelles containing chlorohydrins or bromohydrins. Cell detachment and necrotic death were observed with increasing doses of halohydrins, whereas the cells were unaffected by equivalent doses of oleic acid. Bromohydrins caused more lysis than did chlorohydrins at equivalent doses. Complete lysis was seen with 200 microM fatty acid/chlorohydrin micelles and with 50 microM fatty acid/bromohydrin micelles. Chlorohydrin uptake was much less than the oleic acid control whereas bromohydrins were incorporated into the endothelial cells similarly to oleic acid. This difference or the bulkier nature of the bromohydrins could account for their increased toxicity. This study has demonstrated the potential toxicity of the halohydrins, and implications for their formation in inflammati...Continue Reading

References

Aug 1, 1992·Archives of Biochemistry and Biophysics·C C WinterbournF A Kuypers
Oct 10, 1986·Science·S J WeissS Regiani
Apr 1, 1995·The Biochemical Journal·M C Vissers, C C Winterbourn
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Dec 16, 1998·Redox Report : Communications in Free Radical Research·A C CarrC C Winterbourn
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Apr 3, 2001·Free Radical Biology & Medicine·X M YuanA Sevanian
Feb 1, 1997·Redox Report : Communications in Free Radical Research·A J Kettle, C C Winterbourn

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Citations

Nov 8, 2001·Archives of Biochemistry and Biophysics·C L HawkinsM J Davies
Mar 12, 2008·Antioxidants & Redox Signaling·Michael J DaviesMartin D Rees
Nov 15, 2011·Free Radical Biology & Medicine·Fiona H GreigCorinne M Spickett
Jun 2, 2010·Chemistry and Physics of Lipids·Agnieszka RobaszkiewiczMirosław Soszyński
Nov 17, 2007·Free Radical Biology & Medicine·Gary J DeverCorinne M Spickett
Jul 31, 2007·Pharmacology & Therapeutics·Corinne M Spickett
Sep 23, 2011·Biochemical Society Transactions·Corinne M Spickett, Norsyahida Mohd Fauzi
Mar 19, 2014·Free Radical Biology & Medicine·Benjamin S RaynerClare L Hawkins
May 16, 2006·Biochimica Et Biophysica Acta·Ernst MalleMichael J Davies
Mar 13, 2014·Archives of Biochemistry and Biophysics·Agnieszka RobaszkiewiczMirosław Soszyński
Apr 18, 2003·FEBS Letters·Gary DeverCorinne M Spickett
Jan 29, 2020·Antioxidants & Redox Signaling·Michael J Davies, Clare L Hawkins
Jan 17, 2017·Oxidative Medicine and Cellular Longevity·Jenny Schröter, Jürgen Schiller
Dec 1, 2007·Chemical Research in Toxicology·Ojia SkaffMichael J Davies
Sep 9, 2006·Cellular Signalling·Yann Wan YapNam Sang Cheung

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