Abstract：
:Thio analogs of platelet activating factor (PAF) are of great interest because they exhibit antineoplastic properties both in vitro and in vivo. In contrast to most known anticancer agents, these lipids appear not to act through the synthesis and function of DNA and, therefore, offer a new avenue of approaching cancer chemotherapy. We have examined the conformational properties of 1-thiohexadecyl-2-O-methyl-S-glycero-3-phosphocholine (ET-S-16-OCH3) in organic solvents and in micelles. The conformational analysis was based on a combination of 1D, 2D NMR spectroscopy and molecular graphics. 1H and 13C spin lattice relaxation time (T1) experiments were also performed to study the dynamic properties of this molecule. The picture emerging from these studies is as follows. The alkyl chain of ET-S-16-OCH3 is the most mobile part of the molecule both in CDCl3/CD3OD and in micelles and exists as a mixture of interconverting conformers including an extended all trans and several low energy conformers with one or more gauche segments. This creates a twisting of the chain and facilitates a spatial communication between the alkyl chain and the glycerol backbone as well as between the alkyl chain and the headgroup. The methylene groups of the thioglycerol backbone and the headgroup are the least mobile while the methine group of the thioglycerol backbone appears to have an intermediate mobility. The conformation of the thioether lipid in the two media may be of relevance during its interaction with its site of action, the cellular membrane. Such a conformation may also play an important role in determining the selectivity of this interaction with different cell membranes.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Mavromoustakos T,Theodoropoulou E,Yang DP,Lin SY,Koufaki M,Makriyannis Adoi
10.1016/s0009-3084(96)02615-1subject
Has Abstractpub_date
1996-11-01 00:00:00pages
21-34issue
1eissn
0009-3084issn
1873-2941pii
S0009308496026151journal_volume
84pub_type
杂志文章abstract：:Low density lipoprotein (LDL) cholesterol is known to be oxidized both in vitro and in vivo giving rise to oxygenated sterols. Conflicting results, however, have been reported concerning both the nature and the relative concentrations of these compounds in oxidized human LDL. We examined the extracts obtained from Cu(...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(92)90057-v
更新日期：1992-10-01 00:00:00
abstract：:The proteolytic activity of an aspartyl protease of Mucor miehei was correlated with the adsorption of the protease to lipid vesicles. It was observed that the presence of phosphatidylethanolamines (PE's) in the membrane increased the enzyme activity in a 20% in the gel phase and 10% in the fluid phase. The effects of...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(02)00188-3
更新日期：2003-01-01 00:00:00
abstract：:Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(03)00087-2
更新日期：2003-10-01 00:00:00
abstract：:A new acoustical method for the investigation of lipid phase transition is introduced based on the measurement of the thermal acoustic radiation (TAR) inherent in lipids. The TAR of multilamellar vesicles from dipalmitoylphosphatidylcholine (DPPC) and dimyristoylphosphatidylcholine (DMPC) was measured in the megahertz...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2008.03.001
更新日期：2008-06-01 00:00:00
abstract：:Pulmonary surfactant is a lipid-protein complex, synthesized and secreted by the respiratory epithelium of lungs to the alveolar spaces, whose main function is to reduce the surface tension at the air-liquid interface to minimize the work of breathing. The activity of surfactant at the alveoli involves three main proc...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2006.02.017
更新日期：2006-06-01 00:00:00
abstract：:The aggregative properties of highly pure GM3 ganglioside in aqueous solution have been studied by static and dynamic laser light scattering measurements and fluorescence spectroscopy experiments performed by the use of a GM3 derivative containing the pyrene group at the end of the fatty acid moiety. GM3 ganglioside s...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(90)90119-c
更新日期：1990-02-01 00:00:00
abstract：:Determining the particle size and number of lipoprotein components found in blood plasma (HDL, LDL and VLDL) has become an important clinical tool in diagnosing risk of cardiovascular disease. Proton (1H) NMR spectroscopy methods to quantify lipoprotein particle subclasses have been advancing since NMR lineshape analy...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2020.104874
更新日期：2020-05-01 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：:The objective of this work was to examine the interaction of cholesterol with both phosphatidylcholines, 1-palmitoyl-2-oleoyl-sn-glycero-3-phosphocholine (POPC) or 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC), and sphingomyelins, N-oleoyl-D-sphingomyelin (O-SPM) or N-palmitoyl-D-sphingomyelin (P-SPM), in monolay...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(96)02535-2
更新日期：1996-06-17 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：:In cell biology (and in many biophysical) studies there is a natural tendency to consider ceramide as a highly condensed, solid-type lipid conferring rigidity and close packing to biomembranes. In the present work we advanced the understanding of the phase behavior of palmitoyl-ceramide restricted to a planar interfac...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2010.04.008
更新日期：2010-06-01 00:00:00
abstract：:New 1,20-substituted eicosanes carrying phosphate headgroups and readily derivatizable thiol, maleimido, and activated carboxylic ester moieties were prepared. The C20-backbone of these molecules was assembled by a halopolycarbon homologation from 1,8-dichlorooctane and 1,6-dibromohexane. 20-Mercapto- and 20-maleimido...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2004.09.016
更新日期：2005-01-01 00:00:00
abstract：:A binding protein is described for certain oxygenated derivatives of cholesterol which suppress 3-hydroxy-3-methylglutaryl coenzyme A reductase and cholesterol synthesis in cultured mammalian cells. This protein is found in the cytosolic fraction of many cell types and is distinct from cytosolic proteins which bind ch...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(85)90066-0
更新日期：1985-08-30 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：:Age-related fluorescent and cross-linked proteins increase with lipid oxidation of tissues. The fluorophores and cross-links have been considered to be conjugated Schiff bases between amino groups of proteins and malonaldehyde. Our recent studies showed that the fluorophores produced in the in vitro reaction of protei...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(87)90054-5
更新日期：1987-07-01 00:00:00
abstract：:Lipids play an important role in the maturation, viability and function of sperm cells. In this study, we examined the neutral and polar lipid composition of boar spermatozoa by thin-layer chromatography/mass spectrometry. Main representatives of the neutral lipid classes were diacylglycerols containing saturated (myr...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2013.11.001
更新日期：2014-01-01 00:00:00
abstract：:Monolactone (NeuAc1-9NeuAc linkage) formation of a ganglioside, GD1b, was observed at 20 degrees C on solutions ranging in concentration from 0.008 to 1.7 mM and in pH from 2 to 8.1, by following the change of ellipicity at 235 nm, where lactonized gangliosides showed a strong Cotton effect. The lactonization was foun...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(94)90051-5
更新日期：1994-03-31 00:00:00
abstract：:One of the contributions to the surface potential in charged phospholipid monolayers at air-water interfaces is the double layer potential. In this note several misconceptions found in the literature concerning the relationship between the double layer potential and the degree of dissociation of the lipid polar headgr...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(00)00123-7
更新日期：2000-04-01 00:00:00
abstract：:Binary membranes composed of dimyristoylphosphatidylcholine (DMPC) and natural ceramide (up to a mole fraction Xcer = 0.25) were investigated by measuring the excimer:monomer fluorescence emission intensity ratio IE:IM for the pyrene labeled phospholipid probe 1-palmitoyl-2[(pyren-1-yl)]decanoyl-sn-glycero-3-phosphoch...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(97)00040-6
更新日期：1997-08-08 00:00:00
abstract：:We examine the effects of cholesterol (Chol) on the mechanical properties of membranes consisting of 16:0/18:1 POPC lipid and of lipids with conjugated linoleic acid (CLA), cis-9/trans-11 CLA (C9T11) and trans-10/cis-12 CLA (T10C12). Atomistic molecular dynamics (MD) simulations of POPC-Chol and CLA-Chol mixtures at v...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2013.12.012
更新日期：2014-02-01 00:00:00
abstract：:Antioxidative effects of the principal polyphenolic components extracted from green tea leaves, i.e. (-)-epicatechin (EC), (-)-epicatechin gallate (ECG), (-)-epigallocatechin gallate (EGCG), (-)-epigallocatechin (EGC), and gallic acid (GA), against free radical initiated peroxidation of rat liver microsomes were studi...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(02)00110-x
更新日期：2002-12-01 00:00:00
abstract：:The work reported herein deals with the synthesis and the aggregation behavior studies of synthetic lipids bearing a non-ionic polar head made up of a tris(hydroxymethyl) aminomethane (tris) moiety linked with an aminoglycerol interface. The hydrophobic chains with variable lengths were grafted onto the hydroxyl funct...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2005.03.006
更新日期：2005-07-01 00:00:00
abstract：:Cardiolipins (CLs) are important biologically for their unique role in biomembranes that couple phosphorylation and electron transport like bacterial plasma membranes, chromatophores, chloroplasts and mitochondria. CLs are often tightly coupled to proteins involved in oxidative phosphorylation. The first step in under...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2013.12.010
更新日期：2014-02-01 00:00:00
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：: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
abstract：:The ionic transport properties, capacitance and breakdown voltage of bilayer macrovesicles made from lecithin, dodecaprenol and their mixtures have been studied. The electrical measurements showed that polyprenol in lipid bilayers increases membrane permeability and elasticity, and decreases membrane thickness. Some p...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(86)90116-7
更新日期：1986-03-01 00:00:00
abstract：:The fertilising ability of human spermatozoa may be impaired by inflammations of the genital tract, although details of these processes are still unknown. Hypochlorous acid (HOCl), an important product of myeloperoxidase released from stimulated neutrophils, induces a concentration-dependent increase in externalisatio...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2005.02.015
更新日期：2005-06-01 00:00:00
abstract：:Oxidation of low density lipoprotein (LDL) has been proposed to be involved in the pathogenesis of atherosclerosis. We have previously shown that LDL can be oxidised by iron in lysosomes. As the iron-storage protein ferritin might enter lysosomes by autophagy, we have investigated the ability of ferritin to catalyse L...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2018.09.016
更新日期：2018-12-01 00:00:00
abstract：:The activity of phytosterols on human organism includes the ability of these compounds to incorporate into membranes. In the consequence the plant sterols are able to increase total sterol concentration in membrane or/and to replace cholesterol molecules. The aim of this work was to compare the influence of both these...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2010.07.001
更新日期：2010-09-01 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
