Abstract：
:Ceramide-1-phosphate (C1P) is an important signaling sphingolipid and a metabolite of ceramide. C1P contains an anionic phosphomonoester head group and has been shown to regulate physiological and pathophysiological processes such as cell proliferation, inflammation, apoptosis, phagocytosis, and macrophage chemotaxis. Despite this mechanistic information on its role in intra- and intercellular communication, little information is available on the biophysical properties of C1P in biological membranes and how it interacts with effector proteins. Fluorescently labeled lipids have been a useful tool to understand the membrane behavior properties of lipids such as phosphatidylserine, cholesterol, and some phosphoinositides. However, to the best of our knowledge, fluorescently labeled C1P hasn't been implemented to investigate its ability to serve as a mimetic of endogenous C1P in cells or untagged C1P in in vitro experiments. Cellular and in vitro assays demonstrate TopFluor-C1P harbors a fluorescent group that is fully buried in the hydrocarbon core and fluoresces across the spectrum of physiological pH values. Moreover, TopFluor-C1P didn't affect cellular toxicity at concentrations employed, was as effective as unlabeled C1P in recruiting an established protein effector to intracellular membranes, and its subcellular localization recapitulated what is known for endogenous C1P. Notably, the diffusion coefficient of TopFluor-C1P was slower than that of TopFluor-phosphatidylserine or TopFluor-cholesterol in the plasma membrane and similar to that of other fluorescently labeled sphingolipids including ceramide and sphingomyelin. These studies demonstrate that TopFluor-C1P should be a reliable mimetic of C1P to study C1P membrane biophysical properties and C1P interactions with proteins.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Shirey CM,Ward KE,Stahelin RVdoi
10.1016/j.chemphyslip.2016.06.004subject
Has Abstractpub_date
2016-10-01 00:00:00pages
32-41eissn
0009-3084issn
1873-2941pii
S0009-3084(16)30063-9journal_volume
200pub_type
杂志文章abstract：:A fluorescent assay for Clostridium perfringens phospholipase C is described using 1-palmitoyl-2-[6(pyren-1-yl)hexanoyl]-sn-glycero-3- phospho-N-(trinitrophenyl)aminoethanol (PPHTE) as the substrate. This method is based on the decrease of the quenching of pyrene monomer fluorescence when phospholipase C hydrolyzes PP...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(91)90064-i
更新日期：1991-08-01 00:00:00
abstract：:Enveloped viruses, which include many medically important viruses such as human immunodeficiency virus, influenza virus and hepatitis C virus, are intracellular parasites that acquire lipid envelopes from their host cells. Success of replication is intimately linked to their ability to hijack host cell mechanisms, par...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2010.03.002
更新日期：2010-06-01 00:00:00
abstract：:The stereochemistry of fat digestion and absorption was studied by feeding a triacylglycerol analogue to rats with a thoracic duct cannula. The analogue, rac-1,2-dioleoyl-3-S-tetradecyl-3-thioglycerol-S-oxide was chosen since its enantiomers exhibited high rotation in optical rotary dispersion (ORD) and circular dichr...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(81)90067-0
更新日期：1981-12-01 00:00:00
abstract：:Bacteriophage M13 major coat protein is extensively used as a biophysical, biochemical, and molecular biology reference system for studying membrane proteins. The protein has several elements that control its position and orientation in a lipid bilayer. The N-terminus is dominated by the presence of negatively charged...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2006.02.023
更新日期：2006-06-01 00:00:00
abstract：:The reasons for lipid diversity in membranes are not understood. Here we review evidence supporting the proposal that factors related to the polymorphic capabilities of lipids provide a rationale for lipid diversity. In particular, the ability of lipids to adopt different polymorphic phases appears to be related to a ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(86)90067-8
更新日期：1986-06-01 00:00:00
abstract：:The stratum corneum (SC), the outermost layer of the mammalian skin, is the main skin barrier. Ceramides (CERs) as the major constituent of the SC lipid matrix are of particular interest. At the moment, 11 classes of CERs are identified, but the effect of each single ceramide species is still not known. Therefore in t...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2009.10.007
更新日期：2010-01-01 00:00:00
abstract：:An investigation into the effect of alpha-tocopherol on phospholipid model membranes has been carried out by electron spin resonance (ESR) and saturation transfer ESR. The use of stearic acid and of perdeutero -di-t-butyl nitroxide spin probes has allowed us to monitor, in particular, the effect of alpha-tocopherol on...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(90)90129-f
更新日期：1990-03-01 00:00:00
abstract：:The MARTINI coarse-grained model is used to gain insight into the association of WALP23 helices in three different lipid membranes: DMPC, DPPC and DOPC. Potentials of mean force describing the association of two WALP23 helices embedded in different lipid bilayers indicate no barrier of association and a stabilization ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2013.02.001
更新日期：2013-04-01 00:00:00
abstract：:Melatonin and its structural analogues display antioxidant activity in vivo but their activity in model membranes is not very well known. In this study, we have investigated the antioxidant capacity of melatonin and structural analogues on Fe(2+)-initiated peroxidation of sonicated liposomes made of retinal lipids. Th...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2011.07.004
更新日期：2011-10-01 00:00:00
abstract：:Various hydrophobic benzenediacetic esters, the corresponding benzenedipropionic esters, and branched alkyl esters were intercalated into DMPC liposomes, where the molar ratio (n/n) of ester:DMPC was 1:5. In the case of the very long-chain derivatives, double carbonyl peaks were observed in the 13C NMR spectrum. This ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2008.07.005
更新日期：2008-10-01 00:00:00
abstract：:Understanding how stereochemistry affects interactions with cell membranes is important for effective drug development. Chirality has been shown to greatly effect pharmaceutical distribution and metabolism within the cell. However it has been thought that interactions with, and passive diffusion through, the membrane ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2018.05.002
更新日期：2018-08-01 00:00:00
abstract：:We have investigated monomolecular fluid-like films of palmitoyl oleoylphosphatidyl lipids with choline, glycerol and serine head groups, respectively. Conventional Langmuir trough experiments have been evaluated towards a thermodynamic analysis applying a novel approach that was recently developed in this laboratory....
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(99)00129-2
更新日期：2000-03-01 00:00:00
abstract：:The mass spectra of a number of C-4alpha- and C-4beta-alkylated cholestan-3beta, 5alpha-diols have been found to contain an intense ion at m/e 332. the corresponding 6beta-alkylated (R) cholestan-3beta, 5alpha-diols exhibit an abundant ion at m/e 331 + R. The mass spectra of cholestan-5alpha-ol and cholestan-3beta, 5a...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(76)90013-x
更新日期：1976-02-01 00:00:00
abstract：:Eugenol and its related compounds are major active constituents of essential oils and have been extensively used as food flavoring agents with significant lipid peroxidation inhibition activity, highlighting the importance of understanding detailed molecular mechanisms behind their interactions with lipid bilayer. For...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2018.03.008
更新日期：2018-07-01 00:00:00
abstract：:Bovine serum albumin (BSA) undergoes a number of deteriorative changes when exposed to E-2-octenal. Reaction of BSA with E-2-octenal produced fluorescent BSA with an excitation maximum at 350 nm and emission maximum at 440 nm and promoted polymerization. Amino acid analysis of the modified BSA showed that the E-2-octe...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(95)02470-4
更新日期：1995-08-25 00:00:00
abstract：:Small unilamellar vesicles (SUV) formed by egg yolk phosphatidylcholine (PC) and free oleic acid (OA) undergo aggregation induced by Ca2+ at pH greater than 7.0. The rate of the process, as monitored by turbidity changes, presents a linear dependence on phospholipid concentration and a hyperbolic dependence on Ca2+ co...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90040-0
更新日期：1988-04-01 00:00:00
abstract：:In the last 30 years, ceramides have been found to mediate a myriad of biological processes. Ceramides have been recognized as bioactive molecules and their metabolizing enzymes are attractive targets in cancer therapy and other diseases. The molecular mechanism of action of cellular ceramides are still not fully esta...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2018.09.013
更新日期：2018-11-01 00:00:00
abstract：:A brief review is given on the principles and methods used to investigate structural phase transitions in phospholipid supramolecular structures. The conceptual differences of approaches close to and far from equilibrium are addressed, and the consequences in terms of the limits of interpretation for different types o...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(91)90072-j
更新日期：1991-03-01 00:00:00
abstract：:In X-ray diffraction studies of hydrated (greater than 60%) cholesterol/dioleoylphosphatidylcholine mixtures the lipid packing band showed an abrupt transition from liquid crystal-type to gel-type position and definition at a temperature which decreased progressively to almost -50 degrees C as the proportion of choles...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90115-6
更新日期：1988-01-01 00:00:00
abstract：:Ceramides with chemically modified polar headgroups were prepared and examined for their ability to form complex high axial ratio microstructures (CHARMS), potential drug delivery vehicles. In general, if the modified ceramide had either a hydrogen bond donor or acceptor at C-1 and C-3, including hydrophobic or hydrop...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(00)00204-8
更新日期：2001-01-01 00:00:00
abstract：:Reported herein is the synthesis of (+)- and (-)-(1,3/2)-1-O-(phosphocholine)-2,3-O-dihexanoylcyclopentane-1,2, 3-triol. These are the enantiomers of a contrained analogue of dihexanoylphosphatidylcholine in which the glycerol backbone is replaced by all-trans cyclopentane-1,2,3-triol. Evidence is presented to demonst...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90017-5
更新日期：1988-03-01 00:00:00
abstract：:A comparative study of the polymorphism exhibited by the polymerizable, tubule-forming phospholipid 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3- phosphocholine (DC23PC) and its saturated analog 1,2-ditricosanoyl-sn-glycero-3-phosphocholine (DTPC) in aqueous suspension is reported. Differential scanning calorimetry (DSC...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90092-8
更新日期：1988-10-01 00:00:00
abstract：:The oligosaccharide chain of glycosphingolipids (GSLs) has a marked influence on their thermotropic behavior, intermolecular packing and surface electrical potential. The transition temperature and enthalpy of GSLs decrease proportionally to the complexity of the polar head group and show a linear dependence with the ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(86)90042-3
更新日期：1986-12-15 00:00:00
abstract：:A polymorphic variation of sialic acid species of sialosyllactosylceramide was found in dog erythrocytes. The analysis of the glycolipids in the erythrocytes of the individual dogs in a family of a Japanese breed of dog, Shiba-Inu, showed that the expression of sialosyllactosylceramide containing N-glycolylneuraminic ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(86)90044-7
更新日期：1986-12-15 00:00:00
abstract：:Surface plasmon resonance (SPR) has become one of the most important techniques for studying macromolecular interactions. The most obvious advantages of SPR over other techniques are: direct and rapid determination of association and dissociation rates of binding process, no need for labelling of protein or lipids, an...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2006.02.010
更新日期：2006-06-01 00:00:00
abstract：:Lipid-based carriers represent the most widely used alternative to viral vectors for gene expression and gene silencing purposes. This class of non-viral vectors is particularly attractive for their ease of synthesis and chemical modifications to endow them with desirable properties. Despite combinatorial approaches h...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2020.105032
更新日期：2021-01-08 00:00:00
abstract：:Phosphoinositide 3-kinase (PI 3-kinase) is a key signaling enzyme implicated in a variety of receptor-stimulated cell responses. Stimulation of receptors possessing (or coupling to) protein-tyrosine kinase activates heterodimeric PI 3-kinases, which consist of an 85-kDa regulatory subunit (p85) containing Src-homology...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/s0009-3084(99)00020-1
更新日期：1999-04-01 00:00:00
abstract：:Iron is required for the initiation of lipid peroxidation. Evidence is presented that lipid peroxidation requires both Fe3+ and Fe2+, perhaps with oxygen to form a Fe3+-dioxygen-Fe2+ complex. Other mechanisms of initiation, mostly involving the iron-catalyzed formation of hydroxyl radical, are described and discussed ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(87)90050-8
更新日期：1987-07-01 00:00:00
abstract：:Temperature and pH effects were studied for stability, structural organization, fluidity and permeability of vesicles from a polar lipid methanol fraction isolated from the Aeropyrum pernix. We determined the permeability of C(25,25) liposomes using fluorescence intensity of released calcein. At pH 7.0 and 9.0, and fr...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2011.01.005
更新日期：2011-03-01 00:00:00
abstract：:EmrE is a bacterial transporter protein that forms an anti-parallel homodimer with four transmembrane helices in each monomer. EmrE transports positively charged aromatic compounds, such as TPP+ and its derivatives. We performed molecular dynamics (MD) simulations of EmrE in complex with TPP+, MeTPP+, and MBTPP+ embed...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2017.12.004
更新日期：2018-05-01 00:00:00
