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Reactive Sterol Electrophiles: Mechanisms of Formation and Reactions with Proteins and Amino Acid Nucleophiles

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Department of Chemistry and Vanderbilt Institute of Chemical Biology, Vanderbilt University, Nashville, TN 37235, USA
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Department of Medicinal Chemistry, University of Washington, Seattle, WA 98195, USA
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Department of Chemistry and Biomolecular Sciences, University of Ottawa, 10 Marie Curie Pvt., Ottawa, ON K1N 6N5, Ontario, Canada
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Author to whom correspondence should be addressed.
Dedicated to Prof. Bernd Giese in Recognition of His Contributions to the Understanding of Selectivity and Reactivity in Free Radical Chemistry, on the Occasion of His 80th Birthday.
Chemistry 2020, 2(2), 390-417; https://doi.org/10.3390/chemistry2020025
Received: 6 April 2020 / Revised: 27 April 2020 / Accepted: 30 April 2020 / Published: 6 May 2020
Radical-mediated lipid oxidation and the formation of lipid hydroperoxides has been a focal point in the investigation of a number of human pathologies. Lipid peroxidation has long been linked to the inflammatory response and more recently, has been identified as the central tenet of the oxidative cell death mechanism known as ferroptosis. The formation of lipid electrophile-protein adducts has been associated with many of the disorders that involve perturbations of the cellular redox status, but the identities of adducted proteins and the effects of adduction on protein function are mostly unknown. Both cholesterol and 7-dehydrocholesterol (7-DHC), which is the immediate biosynthetic precursor to cholesterol, are oxidizable by species such as ozone and oxygen-centered free radicals. Product mixtures from radical chain processes are particularly complex, with recent studies having expanded the sets of electrophilic compounds formed. Here, we describe recent developments related to the formation of sterol-derived electrophiles and the adduction of these electrophiles to proteins. A framework for understanding sterol peroxidation mechanisms, which has significantly advanced in recent years, as well as the methods for the study of sterol electrophile-protein adduction, are presented in this review. View Full-Text
Keywords: peroxidation; free radical; sterol; cholesterol; lipid electrophiles peroxidation; free radical; sterol; cholesterol; lipid electrophiles
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Porter, N.A.; Xu, L.; Pratt, D.A. Reactive Sterol Electrophiles: Mechanisms of Formation and Reactions with Proteins and Amino Acid Nucleophiles. Chemistry 2020, 2, 390-417.

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