Singlet Oxygen: Applications in Biosciences and Nanosciences
Chapter 21: Reactions of Singlet Oxygen with Membrane Lipids: Lipid Hydroperoxide Generation, Translocation, Reductive Turnover, and Signaling Activity
Published:27 Jan 2016
Special Collection: 2016 ebook collection
A. W. Girotti and W. Korytowski, in Singlet Oxygen: Applications in Biosciences and Nanosciences, ed. S. Nonell, C. Flors, S. Nonell, and C. Flors, The Royal Society of Chemistry, 2016, ch. 21, pp. 409-430.
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Singlet molecular oxygen (1O2) is a reactive oxygen species that is typically generated by photodynamic action, but may also arise via disproportionation of lipid peroxyl radicals or as a low-yield product of certain enzymatic reactions, e.g. eosinophil peroxidases. This chapter provides a broad review of (i) how 1O2 reacts with unsaturated lipids in biomembranes, leading to membrane-damaging lipid peroxidation that can be exacerbated by iron and reductants; (ii) types of lipid hydroperoxides (LOOHs) generated by 1O2 attack and how some cholesterol-derived species (ChOOHs) qualify as reliable and convenient mechanistic reporters for distinguishing between 1O2 and free-radical attack; (iii) cutting-edge analytical approaches for 1O2-generated LOOHs; (iv) possible fates of these LOOHs, including one-electron vs. two-electron reduction, and spontaneous vs. protein-facilitated intermembrane translocation; and (v) unique features of LOOHs as potential redox-signaling molecules. Finally, some prospects for future developments in this area will be discussed.