Abstract:
:The dicyclohexylborane-mediated addition of allene 1 to (E)-2-tridecenal affords a quaternary protected 2-amino-2-vinyl-1,3-diol in good yield as a single diastereomer. This compound is readily transformed into the four stereoisomers of the quaternary (E)-2-vinyl analogs of sphingosine. The metabolic fate and the effect of these compounds on the basal sphingolipid metabolism in human A549 lung adenocarcinoma cells has been studied, together with the ceramide analog of the most relevant vinylsphingosine derivative.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Calderón R,Mercadal N,Abad JL,Ariza X,Delgado A,Garcia J,Rodríguez A,Fabriàs Gdoi
10.1016/j.chemphyslip.2017.04.008subject
Has Abstractpub_date
2017-06-01 00:00:00pages
34-41eissn
0009-3084issn
1873-2941pii
S0009-3084(17)30014-2journal_volume
205pub_type
杂志文章abstract::A new polymerizable surfactant, 12-methacryloyl dodecylphosphocholine (MDPC), has been synthesized using a three-step procedure in moderate yield. Phase transitions were characterized by DSC and phase behavior in water was determined by surface tension and polarizing microscopy. MDPC showed typical surfactant behavior...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2010.03.001
更新日期:2010-05-01 00:00:00
abstract::In this work we studied a binary lipid matrix of 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphoethanolamine (POPE) and 1-palmitoyl-2-oleoyl-sn-glycero-3-phospho-(1'-rac-glycerol) (POPG), a composition that mimics the inner membrane of Escherichia coli. More specifically, liposomes with varying fractions of POPG were analys...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2014.07.009
更新日期:2014-10-01 00:00:00
abstract::The melting behavior of members of newly synthesized series of rac-1,2-diglycerides with substituted phenyl groups or a benzyl group on the 3-position was investigated with differential scanning calorimetry (DSC). Solution crystallized samples had single melting temperatures, higher than those of the quenched or annea...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(78)90030-0
更新日期:1978-10-01 00:00:00
abstract::Alpha-tocopherol was reacted with 1-palmitoyl-2-[(9Z,11E)-(S)-13-hydroperoxy-9,11-octadecadienoyl]-3-sn-phosphatidylcholine (13-PLPC-OOH) in the presence of a lipid-soluble iron chelate, Fe(III) acetylacetonate, in methanol at 37 degrees C. The reaction product was isolated and identified as a mixture of 1-palmitoyl-2...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(02)00004-x
更新日期:2002-02-01 00:00:00
abstract::Even though lysophospholipids have attracted much interest in recent years on account of their unique bioactivity, research related to lysophospholipids is usually hampered by problems associated with standard sample preparation and discrimination of regioisomers. Herein, we demonstrate a quick tin-chemistry-based syn...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2016.09.003
更新日期:2016-10-01 00:00:00
abstract::Among the structurally diverse collection of lipids that comprise the membrane lipidome, polyunsaturated phospholipids are particularly vulnerable to oxidation. The role of α-tocopherol (vitamin E) is to protect this influential class of membrane phospholipid from oxidative damage. Whether lipid-lipid interactions pla...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2020.104910
更新日期:2020-09-01 00:00:00
abstract::Fluorescence measurements of 1,6-diphenyl-1,3,5-hexatriene (DPH) in large unilamellar phospholipid vesicles were performed to characterize the influence of the membrane physical properties on the short-lived lifetime component of the fluorescence decay. We have found that the short-lived component of DPH significantly...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2004.02.005
更新日期:2004-07-01 00:00:00
abstract::Structural analysis, a purification scheme and stability information on a fluorescent cholesterol analogue, which has been used as a probe in several model and biological systems, are presented. The proposed structure for the fluorophore, cholestatrien-3 beta-ol, closely resembles that of cholesterol. However, problem...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(84)90086-0
更新日期:1984-11-01 00:00:00
abstract::2-O-Arachidonoyl-1-O-stearoyl-sn-glycero-3-phosphocholine was synthesized with carbon-13 enrichment of the three glycerol carbons and the carbonyl of the stearoyl group. Phospholipase A(2) was utilized to give optically pure lyso-PC, and only 3% acyl migration occurred during reacylation with arachidonic acid anhydrid...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2009.08.001
更新日期:2010-01-01 00:00:00
abstract::Some thermodynamic and structural aspects of propranolol-DPPC liposomes interaction were investigated by DSC and X-ray diffraction: the lamellar arrangement of the lipid matrix remains intact even at high concentrations of the drug (until 1:1 drug/lipid molar ratio). However, the bilayer thickness increases significan...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(90)90171-m
更新日期:1990-09-01 00:00:00
abstract::Cannabinoid receptor agonists diminish responses to painful stimuli. Extensive evidence demonstrates that CB(1) cannabinoid receptor activation inhibits pain responses. Recently, the synthesis of CB(2) cannabinoid receptor-selective agonists has allowed testing whether CB(2) receptor activation inhibits pain. CB(2) re...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/s0009-3084(02)00155-x
更新日期:2002-12-31 00:00:00
abstract::The polymorphic behavior of three series of tris-homoacyl (C14:0, C16:0 and C18:0) cyclopentane-1,2,3-triol analogs of the natural saturated triglycerides has been studied using differential thermal analysis, Fourier transform infrared spectroscopy, and X-ray diffraction. It was found that the triglyceride analogs der...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(77)90003-2
更新日期:1977-03-01 00:00:00
abstract::In the first part of this article, chemical and physical stability of aqueous liposome dispersions have been addressed. Chemical stability of phospholipids has been considered in two parts: oxidation and hydrolysis. Major attention has been paid to hydrolysis kinetics of phospholipids as a function of pH, temperature,...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/0009-3084(93)90053-6
更新日期:1993-09-01 00:00:00
abstract::We found that extracellular addition of 2% bovine serum albumin (BSA) to a suspension of rabbit platelets after stimulation with platelet-activating factor resulted in a biphasic extraction of [3H]1-O-alkyl-2-O-methyl (or 2-O-methylcarbamyl)-sn-glycero-3-phosphocholine. A fast phase of extraction of the phospholipid p...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(97)02664-9
更新日期:1997-03-28 00:00:00
abstract::Phospholipid vesicles like erythrocyte ghosts [1] have been shown to display trends in freeze-thaw injury with Group I ions which are non-monotonic in nature. That is to say, the relative extent of injury with such ions, measured as calcein release, does not follow a lyotropic series related solely to the hydrated ion...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(91)90006-w
更新日期:1991-09-01 00:00:00
abstract::This minireview describes the use of fluorescence polarization to characterize the dynamics and organization of biological membranes, lipoproteins, liposomes and other lipid-based assemblies. The advantages, disadvantages and limitations of this method are discussed. There is special emphasis on the multiprobe approac...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/0009-3084(93)90061-7
更新日期:1993-09-01 00:00:00
abstract::Low density lipoprotein (LDL) particles exhibit extremely complex three-dimensional structural organization which is still not understood at the molecular level. The aim of this study was to provide the experimental evidence of a direct non-covalent interaction of the protein part with the lipid matrix. The approach w...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2006.02.014
更新日期:2006-06-01 00:00:00
abstract::The effect of peptides on bilayer----non-bilayer phase transitions can be used as a tool to investigate the molecular aspects of peptide-lipid interactions. In this contribution the action on membranes of the peptide antibiotic gramicidin A and the bee venom component melittin are compared. Although the known structur...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/0009-3084(91)90084-o
更新日期:1991-03-01 00:00:00
abstract::Bile acids directly related to liver and intestinal function are used as indicators of hepatobiliary and intestinal diseases. Here, we have designed and realized a capillary sensory platform for the detection of bile acids using liquid crystals (LCs). LC droplets confined in micro-capillaries are homeotropically align...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2017.02.003
更新日期:2017-04-01 00:00:00
abstract::Interaction of a cationic phenazinium dye, phenosafranin (PSF), with the anionic liposomal vesicle/bilayer of dimyristoyl-L-alpha-phosphatidylglycerol (DMPG) has been demonstrated using steady state and time resolved fluorescence and fluorescence anisotropy techniques. The charge transfer emission spectrum of PSF show...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2009.10.003
更新日期:2010-01-01 00:00:00
abstract::A known intermediate, (3 R, S; 5 R,S)-3,5-dimethyl-6-triphenylmethyloxyhexanal gave, in a Wittig reaction with 1-octyltriphenylphosphonium bromide and n-butyl lithium in anhydrous tetrahydrofuran, a mixture of olefininic compounds. Trityl deprotection and hydrogenation of the double bond afforded the (2 R, S; 4 R,S)-2...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(96)02570-4
更新日期:1996-08-19 00:00:00
abstract::This work is focused on the study of the dynamic surface properties of spread monolayers of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), which is the main component of the pulmonary surfactant (PS), in the region of high surface pressures and at different temperatures. The increase of temperature from 25 to 35 ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2019.104812
更新日期:2019-12-01 00:00:00
abstract::Based on size and compositional data, models for the two major density subclasses of human serum high density lipoproteins have been developed. Descriptions of both the surface structure of the high density lipoproteins and the structure of their apolar core regions are integral parts of these models. The surface is d...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(75)90054-7
更新日期:1975-04-01 00:00:00
abstract::The role of membrane cholesterol as a crucial regulator in the structure and function of membrane proteins and receptors is well documented. However, there is a lack of consensus on the mechanism for such regulation. We have previously shown that the function of an important neuronal receptor, the serotonin1A receptor...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2016.02.004
更新日期:2016-03-01 00:00:00
abstract::The 13C- and 31P-NMR spectra and DSC thermograms of unsonicated dispersions consisting of phospholipids of varying methylation stages of the propanolamine head group were investigated. Methylation of the head group was accompanied by a corresponding reduction in the phase transition temperatures. In the liquid crystal...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(77)90069-x
更新日期:1977-12-01 00:00:00
abstract::Oxysterols are oxidized products of cholesterol that play several roles in various pathophysiological processes, including the control of lipid metabolism, immunological processes, and cytotoxicity. Mesenchymal stem cells are multipotent cells with properties of self-renewal and the ability to differentiate into other...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/j.chemphyslip.2017.06.009
更新日期:2017-10-01 00:00:00
abstract::Plasmalogens (1-O-1'-alkenyl-2-acylglycerophospholipids) and to a lesser extent the 1-O-alkyl analogs are ubiquitous and in some cases major constituents of mammalian cellular membranes and of anaerobic bacteria. In archaebacteria polar lipids of the cell envelope are either diphytanylglycerolipids or bipolar macrocyc...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/0009-3084(94)90054-x
更新日期:1994-12-01 00:00:00
abstract::Lipoic acid-substituted phospholipids were synthesized from phosphatidyl cholines by exchanging the choline residue with a glycol group using phospholipase D, forming phosphatidylglycols, and coupling of lipoic acid (1,2-dithiolane-3-pentanoic acid) to the residual glycol hydroxyl group by esterification. The thermotr...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(93)90032-x
更新日期:1993-11-01 00:00:00
abstract::Divalent cation (Ca2+ and Mg2+) and hydrogen ion-induced fusions of small unilamellar phosphatidic acid vesicles were studied by the use of fluorescence fusion assay. These fusogenic ions also increased interfacial tension and reduced the surface dielectric constant of phosphatidic acid membranes as the ion concentrat...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(93)90017-w
更新日期:1993-10-01 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