Abstract:
:We present the results of a comparative differential calorimetric and Fourier transform infrared spectroscopic study of the effect of cholesterol and five analogues on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes. These sterols/steroids differ in both the nature and stereochemistry of the polar head group at C3 (β-OH, α-OH or CO) and in the presence or absence of a double bond in ring B and in the orientation of rings A and B. The Δ(5) sterols/steroid have a trans rather than a cis ring A/B junction, and the concentration of these compounds required to abolish the DPPC pretransition, inversely related to their relative ability to disorder gel state DPPC bilayers, decreases in the order β-OH > α-OH > CO. However, in the saturated ring junction-inverted (cis) series, these concentrations are much more similar, regardless of polar head group chemical structure. Similarly, the residual enthalpy of the DPPC main phase transition at 50 mol% sterol/steroid, which is inversely related to the miscibility of these compounds in fluid DPPC bilayers, also increases in the order β-OH > α-OH > CO, but this effect is attenuated in the saturated series with an inverted ring A/B orientation. Moreover, replacement of the double bond at C5-C6 with a saturated linkage and inversion of the ring A/B junction reduces both sterol/steroid solubility and the ability to order the hydrocarbon chains of fluid DPPC molecules all cases. Thus, the characteristic effects of sterols/steroids on fluid lipid bilayers are generally optimal when an OH group rather than CO group is present at C3, and when this OH group is in the equatorial (β) orientation, and when the orientation of the ring A/B fusion is trans rather than cis. Overall, these results demonstrate that variations in the saturation and stereochemistry of the steroid ring system influence the effect of variations in the nature and stereochemistry of the polar headgroup at C3 on the physical properties of phospholipid bilayers and vice versa. Moreover, the presence of a single double bond specifically at Δ(5) is required to maximize sterol solubility in fluid DPPC bilayers.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Benesch MG,Lewis RN,Mannock DA,McElhaney RNdoi
10.1016/j.chemphyslip.2015.03.002subject
Has Abstractpub_date
2015-05-01 00:00:00pages
10-26eissn
0009-3084issn
1873-2941pii
S0009-3084(15)00018-3journal_volume
188pub_type
杂志文章abstract::The activities of cytochrome P450-derived epoxide metabolites of omega-6 polyunsaturated fatty acids (PUFAs) in cellular homeostasis have generated considerable topical interest, but there is less information on the effects of omega-3 PUFA epoxides. Mass spectroscopic data on the epoxides of the omega-3 PUFA eicosapen...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2009.02.005
更新日期:2009-05-01 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::The transformation between a gel and a fluid phase in dipalmitoyl-phosphatidylcholine (DPPC) bilayers has been simulated using a coarse grained (CG) model by cooling bilayer patches composed of up to 8000 lipids. The critical step in the transformation process is the nucleation of a gel cluster consisting of 20-80 lip...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2005.03.001
更新日期:2005-06-01 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::Human serum amyloid A (SAA) is a precursor protein of AA amyloidosis and a component of high-density lipoproteins (HDLs), thus it is essential to investigate the amyloid fibril formation of SAA under a lipid environment. We used synthetic fragment peptides corresponding to the N-terminal (residues 1-27) and central (r...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2016.11.004
更新日期:2017-01-01 00:00:00
abstract::2',7'-Dichlorodihydrofluorescein diacetate (DCFH-DA) is commonly used to detect the generation of reactive oxygen intermediates and for assessing the overall oxidative stress in toxicological phenomenon. It has been suggested that DCFH-DA crosses the cell membrane, subsequently undergoing deacetylation by intracellula...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2004.04.006
更新日期:2004-08-01 00:00:00
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...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(96)02615-1
更新日期:1996-11-01 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::To exploit the potential of Didodecyldimethylammonium bromide (D12DAB) as a core lipidic constituent, an attempt was made to fabricate and optimize cationic nanostructured lipid carriers (cNLCs) using a cost-effective microemulsification methodology. Designed composition was optimized by studying the effect of differe...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2016.02.006
更新日期:2016-03-01 00:00:00
abstract::Lamellar structures of intercellular lipids in stratum corneum of hairless mouse were studied at various water contents by small-angle X-ray diffraction. At room temperature there are at least two lamellar structures, long and short lamellar structures, with repeat distances of 13.6 and around 6 nm, respectively. The ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(02)00126-3
更新日期:2003-03-01 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::The development of "molecular rulers" would allow one to quantitatively locate the penetration depth of intercalants within lipid bilayers. To this end, an attempt was made to correlate the (13)C NMR chemical shift of polarizable "reporter" carbons (e.g., carbonyls) of intercalants within DMPC liposomal bilayers - wit...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2014.07.007
更新日期:2014-12-01 00:00:00
abstract::The properties of dipalmitoylphosphatidylcholine (DPPC):6-ketocholestanol bilayer at 50 mol% sterol were studied using the molecular dynamics simulation technique. Our simulations were performed at constant pressure and temperature on a nanosecond time scale. Data from this simulation were compared to the results of o...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(01)00160-8
更新日期:2001-07-01 00:00:00
abstract::Chain-ordering/melting transition in a series of saturated diacylphosphatidylcholines (PCs) in aqueous dispersions have been studied experimentally (calorimetric and ultrasonic techniques) and theoretically (an Ising-like lattice model). The shape of the calorimetric curves was compared with the theoretical data and i...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2007.08.004
更新日期:2007-12-01 00:00:00
abstract::The aim of these works present in this paper consisted in the development and evaluation of quantitative structure property models (QSPR) for the prediction of the melting points of a series constituted by 62 fatty acids. The best multilinear regressions method (MLR) is used to develop models for the prediction of the...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2011.10.001
更新日期:2012-01-01 00:00:00
abstract::The concentration of TL in Penaeus kerathurus muscle and cephalothorax was 1.03+/-0.04 (75.9+/-0.8% of which was PhL) and 2.36+/-0.07% (45.5+/-0.8% of which was PhL) of the wet tissue, respectively. The phosphatidylethanolamine represented 26.4+/-0.6% (85.6% diacyl- and 14.4% alkyl-acyl- or alkenyl-acyl-analogues) of ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2008.01.003
更新日期:2008-04-01 00:00:00
abstract::Cholesterol has limited solubility in phospholipid bilayers. The solubility limit is strongly dependent on the nature of the lipid with which the cholesterol is mixed while properties of the crystals formed can be modified by phospholipid-cholesterol interactions. In this review we summarize the various methods that h...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章,评审
doi:10.1016/j.chemphyslip.2016.06.006
更新日期:2016-09-01 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::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::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::We constructed a chronic oxidative stress model in which Se-deficient diet was fed to male Wister rats for 8 weeks. As expected, effects of oxidative damage, including Fe accumulation and increase in peroxidized lipids, were identified in the liver owing to the lack of glutathione peroxidase. Although the oxidative st...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2007.04.005
更新日期:2007-08-01 00:00:00
abstract::Isomeric diacylglycerophosphocholines containing various octadecynoic acids (4-, 6-, 9-, 12-, 14- and 17-octadecynoic acid) were synthesized and purified to homogeneity. Their behaviour in monolayers, when studied by the Langmuir-Blodgett film balance technique, revealed systematic relationships between structure and ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(94)90086-8
更新日期:1994-04-19 00:00:00
abstract::Parkinson's disease is caused due to free radical generation in dopamine neurons leading to oxidative stress induced damage. The aim of this work was to ameliorate the free radical induced oxidative stress in rats by using TPGS (Tocopheryl polyethylene glycol 1000 succinate) loaded rutin nanoemulsion after oral admini...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2020.104890
更新日期:2020-05-01 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::The permeability of liposomes to water, glucose, Ca2+ and alkaline cations was monitored by recording the change in absorbance at 450 nm using a rapid reaction stopped-flow spectrophotometer. Liposomes were prepared with egg phosphatidylcholine and concentrations of dolichol ranging from 0.1% to 9% (w/w). Net permeabi...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/0009-3084(85)90028-3
更新日期:1985-11-01 00:00:00
abstract::20-hydroxycholesterol is a signaling oxysterol with immunomodulating functions and, thus, structural analogues with reporter capabilities could be useful for studying and modulating the cellular processes concerned. We have synthesized three new 20-hydroxycholesterol-like pregn-5-en-3β-ol derivatives with fluorescent ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2019.104850
更新日期:2020-03-01 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::Accumulation of excess non-esterified free cholesterol (FC) in macrophages is a key factor in macrophage death during late stages of atheroslerosis. Raising FC content in macrophages has been shown to trigger Rac activation and actin polymerisation and to inhibit cell migration. Here, the plasma membrane distribution ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2008.04.009
更新日期:2008-08-01 00:00:00
abstract::The interaction of the amphoteric surfactant N-dodecyl-N,N-dimethylbetaine (C12-Bet) with phosphatidylcholine (PC) liposomes was investigated. Permeability alterations were detected as a change in 5(6)-carboxyfluorescein (CF) released from the interior of vesicles and bilayer solubilization as a decrease in the static...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/s0009-3084(98)00045-0
更新日期:1998-07-01 00:00:00
abstract::The hydration behaviour of equimolar mixtures of phospholipids and nonionic surfactants with different chain length was investigated by gravimetric sorption, NMR spectroscopy and X-ray diffraction. At the most hydration degrees investigated, the incorporation of nonionic surfactants in a phospholipid bilayer leads to ...
journal_title:Chemistry and physics of lipids
pub_type: 杂志文章
doi:10.1016/j.chemphyslip.2009.12.005
更新日期:2010-03-01 00:00:00