Electrophilic oxysterols: generation, measurement and protein modification

Miyamoto, Sayuri; Lima, Rodrigo S.; Inague, Alex; Viviani, Lucas G.

doi:10.1080/10715762.2021.1879387

Cited by 9 publications

(15 citation statements)

References 181 publications

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“…437 Formation of Schiff bases between cholesterol aldehydes and proteins leads to changes in protein folding that are potentially important in the development of disease. 453,463 Ketosterols are generally unreactive toward Schiff base formation.…”

Section: Cholesterolmentioning

confidence: 99%

“…Their levels are usually low in vivo , but as they are metabolic precursors to cholesterol and vitamin D 3 they can accumulate in some circumstances. Incorporation of a second alkene into the sterol core, particularly when conjugated or homoconjugated to the C5–C6 alkene, significantly increases reactivity toward autoxidation . For example, the propagation rate constant for 7-dehydrocholesterol (DHC, 95 ) is 2260 M –1 .…”

Section: Oxidationmentioning

confidence: 99%

“…Oxidized lipids and sterols are particularly associated with a number of diseases, including cardiovascular diseases, most notably atherosclerosis, ,,,,− nonalcoholic fatty liver disease, lysosomal storage disorders, and Alzheimer’s disease. ,− In general, the presence of oxidized lipids can lead to biological consequences either through changes to the material properties of the membrane or through a direct biological activity of the oxidized lipids as enzyme substrates or receptor ligands. Examples of the effects of oxidized lipids on membrane structure include the release of cytochrome c from mitochondrial membranes following oxidative damage by CYP activity and the loss of membrane integrity seen during ferroptosis.…”

Section: Oxidationmentioning

confidence: 99%

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The Chemical Reactivity of Membrane Lipids

Duché,

Sanderson

2024

Chem. Rev.

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It is well-known that aqueous dispersions of phospholipids spontaneously assemble into bilayer structures. These structures have numerous applications across chemistry and materials science and form the fundamental structural unit of the biological membrane. The particular environment of the lipid bilayer, with a water-poor low dielectric core surrounded by a more polar and better hydrated interfacial region, gives the membrane particular biophysical and physicochemical properties and presents a unique environment for chemical reactions to occur. Many different types of molecule spanning a range of sizes, from dissolved gases through small organics to proteins, are able to interact with membranes and promote chemical changes to lipids that subsequently affect the physicochemical properties of the bilayer. This Review describes the chemical reactivity exhibited by lipids in their membrane form, with an emphasis on conditions where the lipids are well hydrated in the form of bilayers. Key topics include the following: lytic reactions of glyceryl esters, including hydrolysis, aminolysis, and transesterification; oxidation reactions of alkenes in unsaturated fatty acids and sterols, including autoxidation and oxidation by singlet oxygen; reactivity of headgroups, particularly with reactive carbonyl species; and E/Z isomerization of alkenes. The consequences of reactivity for biological activity and biophysical properties are also discussed. CONTENTS

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Section: Cholesterolmentioning

confidence: 99%

Section: Oxidationmentioning

confidence: 99%

Section: Oxidationmentioning

confidence: 99%

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The Chemical Reactivity of Membrane Lipids

Duché,

Sanderson

2024

Chem. Rev.

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“…136 Because of their high electrophilicity, aldehydic cholesterols and ketocholesterols can exert potential biological activity by irreversible covalent modification of proteins. 137 Therefore, cholesterol may function as a target molecule in 1 O 2 -dependent lipid peroxidation occurring in biological systems.…”

Section: Reactions Of 1 O 2 With Biomolecules and Their Consequencesmentioning

confidence: 99%

Revisiting carotenoids as dietary antioxidants for human health and disease prevention

寺尾¹

2023

Food Funct.

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“…Cholesterol is oxidized by enzymes and non-enzymatic oxidants to give diverse products termed oxysterols including hydroxides, hydroperoxides, epoxides, and carbonyl compounds. Miyamoto et al [7] reviewed the generation and measurement of reactive sterol oxidation products with emphasis on electrophilic oxysterols which modify a variety of proteins, changing their structures and eliciting a broad range of cellular effects. They also showed that secosterol aldehydes were formed as secondary products derived from cholesterol hydroperoxide decomposition.…”

Section: Special Issue On "Recent Topics Of Redox Chemistry and Biology"mentioning

confidence: 99%