ArticleBiophysical journal2004
The 4,5-double bond of ceramide regulates its dipole potential, elastic properties, and packing behavior.
Article in Biophysical journal, 2004. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Who cites it
40 citing papers in PubMed, 98 citations in OpenAlex.
- Detergents without a drain: the evolutionary logic (and liability) of sphingolipids.Journal of lipid research · 2026Review
- Alteration of Lipid Bilayer Electrical Potential by Phytochemicals and Synthetic Analogs: Implications for Cellular Function.Biomolecules · 2026Review
- Role of Canonical and Non-Canonical Sphingolipids and their Metabolic Enzymes in Bone Health.Current osteoporosis reports · 2025Review
- Ceramide microdomains: the major influencers of the sphingolipid media platform.Biochemical Society transactions · 2024Review
- Adiponectin overexpression improves metabolic abnormalities caused by acid ceramidase deficiency but does not prolong lifespan in a mouse model of Farber Disease.Molecular genetics and metabolism reports · 2024Article
- The effect of long-term cigarette smoking on selected skin barrier proteins and lipids.Scientific reports · 2023Article
- Ganglioside GM1 and the Central Nervous System.International journal of molecular sciences · 2023Review
- Review
- Thermotropic Behavior and Structural Organization of C24:1 Sulfatide Dispersions and Its Mixtures with Cationic Bilayers.ACS omega · 2023Article
- Suppression of de novo sphingolipid biosynthesis mitigates sarcopenia.Nature aging · 2022Article
- Influence of ceramide on lipid domain stability studied with small-angle neutron scattering: The role of acyl chain length and unsaturation.Chemistry and physics of lipids · 2022Article
- A set of gene knockouts as a resource for global lipidomic changes.Scientific reports · 2022Article
- Characterization of a Bacterial Kinase That Phosphorylates Dihydrosphingosine to Form dhS1P.Microbiology spectrum · 2022Article
- Circulating Ceramides- Are Origins Important for Sphingolipid Biomarkers and Treatments?Frontiers in endocrinology · 2021Review
- Targeting a ceramide double bond improves insulin resistance and hepatic steatosis.Science (New York, N.Y.) · 2019Article
- Structural basis of phosphatidylcholine recognition by the C2-domain of cytosolic phospholipase AeLife · 2019Article
- Structural and barrier properties of the skin ceramide lipid bilayer: a molecular dynamics simulation study.Journal of molecular modeling · 2019Article
- Monitoring the SphingolipidFrontiers in cell and developmental biology · 2019Article
- A Coarse-Grained Model of Stratum Corneum Lipids: Free Fatty Acids and Ceramide NS.The journal of physical chemistry. B · 2016Article
- Effects of Dipole Potential Modifiers on Heterogenic Lipid Bilayers.The Journal of membrane biology · 2016Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
The biological activities of ceramides show a large variation with small changes in molecular structure. To help understand how the structure regulates the activity of this important lipid second messenger, we investigated the interfacial features of a series of synthetic ceramide analogs in monomolecular films at the argon-buffer interface. To minimize differences arising from the N-acyl moiety, each analog had either a N-hexadecanoyl or a N-cis-4-hexadecenoyl moiety amide linked to the nitrogen of the sphingosine backbone. We found that the trans 4,5-unsaturation in the sphingosine backbone promoted closer packing and lower compressibilities of ceramide analogs in interfaces relative to comparable saturated species. Moreover, structures with this feature exhibited dipole potentials as much as 150-250 mV higher than comparable compounds lacking 4,5-unsaturation. The results support the hypothesis by M.C. Yappert and co-workers that trans unsaturation in the vicinity of C4 of the sphingoid backbone augments intramolecular hydration/hydrogen bonding in the polar region. This intramolecular hydration may allow the close packing of the ceramide molecules and engender their high dipole potentials. These properties of ceramides and their analogs may be important determinants of biological function.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.