ArticleJournal of lipid research2013
Probing lipid-protein adduction with alkynyl surrogates: application to Smith-Lemli-Opitz syndrome.
Article in Journal of lipid research, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed, 38 citations in OpenAlex.
- Lipid Metabolism and Immune Function: Chemical Tools for Insights into T-Cell Biology.Chembiochem : a European journal of chemical biology · 2025Review
- The drug release of PLGA-based nanoparticles and their application in treatment of gastrointestinal cancers.Heliyon · 2024Review
- GAPDH inhibition mediated by thiol oxidation in human airway epithelial cells exposed to an environmental peroxide.Redox biology · 2024Article
- Synthesis of a Side Chain Alkyne Analogue of Sitosterol as a Chemical Probe for Imaging in Plant Cells.Biomolecules · 2024Article
- Evaluation of ω-alkynyl-labeled linoleic and arachidonic acids as substrates for recombinant lipoxygenase pathway enzymes.Biochimica et biophysica acta. Molecular and cell biology of lipids · 2023Article
- 7-Dehydrocholesterol Encapsulated Polymeric Nanoparticles As a Radiation-Responsive Sensitizer for Enhancing Radiation Therapy.Small (Weinheim an der Bergstrasse, Germany) · 2022Article
- Protein Lipidation Types: Current Strategies for Enrichment and Characterization.International journal of molecular sciences · 2022Review
- A Not-So-Ancient Grease History: Click Chemistry and Protein Lipid Modifications.Chemical reviews · 2021Review
- Maternal cariprazine exposure inhibits embryonic and postnatal brain cholesterol biosynthesis.Molecular psychiatry · 2020Article
- Ozone-derived oxysterols impair lung macrophage phagocytosis via adduction of some phagocytosis receptors.The Journal of biological chemistry · 2020Article
- Reactive Sterol Electrophiles: Mechanisms of Formation and Reactions with Proteins and Amino Acid Nucleophiles.Chemistry (Basel, Switzerland) · 2020Article
- Oxysterols and Retinal Degeneration in a Rat Model of Smith-Lemli-Opitz Syndrome: Implications for an Improved Therapeutic Intervention.Molecules (Basel, Switzerland) · 2018Review
- Cilia-Associated Oxysterols Activate Smoothened.Molecular cell · 2018Article
- Dichlorophenyl piperazines, including a recently-approved atypical antipsychotic, are potent inhibitors of DHCR7, the last enzyme in cholesterol biosynthesis.Toxicology and applied pharmacology · 2018Article
- Prevention of Retinal Degeneration in a Rat Model of Smith-Lemli-Opitz Syndrome.Scientific reports · 2018Article
- Probes for protein adduction in cholesterol biosynthesis disorders: Alkynyl lanosterol as a viable sterol precursor.Redox biology · 2017Article
- Ozone-derived Oxysterols Affect Liver X Receptor (LXR) Signaling: A POTENTIAL ROLE FOR LIPID-PROTEIN ADDUCTS.The Journal of biological chemistry · 2016Article
- On the cellular metabolism of the click chemistry probe 19-alkyne arachidonic acid.Journal of lipid research · 2016Article
- A highly sensitive protocol for microscopy of alkyne lipids and fluorescently tagged or immunostained proteins.Journal of lipid research · 2016Article
- Lipid peroxidation causes endosomal antigen release for cross-presentation.Scientific reports · 2016Article
Corrections and comments
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Authors and funding
8 authors at 2 institutions in 2 countries.
Funding
Abstract
Lipid modifications aid in regulating (and misregulating) protein function and localization. However, efficient methods to screen for a lipid's ability to modify proteins are not readily available. We present a strategy to identify protein-reactive lipids and apply it to a neurodevelopmental disorder, Smith-Lemli-Opitz syndrome (SLOS). Alkynyl surrogates were synthesized for polyunsaturated fatty acids, phospholipids, cholesterol, 7-dehydrocholesterol (7-DHC), and a 7-DHC-derived oxysterol. To probe for protein-reactive lipids, we used click chemistry to biotinylate the alkynyl tag and detected the lipid-adducted proteins with streptavidin Western blotting. In Neuro2a cells, the trend in amount of protein adduction followed known rates of lipid peroxidation (7-DHC >> arachidonic acid > linoleic acid >> cholesterol), with alkynyl-7-DHC producing the most adduction among alkynyl lipids. 7-DHC reductase-deficient cells, which cannot properly metabolize 7-DHC, exhibited significantly more alkynyl-7-DHC-protein adduction than control cells. Model studies demonstrated that a 7-DHC peroxidation product covalently modifies proteins. We hypothesize that 7-DHC generates electrophiles that can modify the proteome, contributing to SLOS's complex pathology. These probes and methods would allow for analysis of lipid-modified proteomes in SLOS and other disorders exhibiting 7-DHC accumulation. More broadly, the alkynyl lipid library would facilitate exploration of lipid peroxidation's role in specific biological processes in numerous diseases.
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