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, problems of low yield during synthesis and rapid decomposition have impeded its use. This study concerns the synthesis and purification of cholestatrien-3 beta-ol by reverse phase high performance liquid chromatography (HPLC). Unlike cholestatrien-3 beta-ol recrystallized from solvents, the fluorescent sterol purified by HPLC was stable over several months at -70 degrees C either as a white, crystalline powder or in ethanolic solution. In model membranes the fluorescence of cholestatrien-3 beta-ol was stable to ultraviolet (UV) light. A simple spectroscopic assay for purity is presented. Included are detailed absorbance, fluorescence, mass, 1H-NMR, and 13C-NMR spectral analyses. The data confirm the structure of cholestatrien-3 beta-ol proposed, but not proven, over 50 years ago, delta 5,7,9(11)-cholestatrien-3 beta-ol.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Fischer RT,Stephenson FA,Shafiee A,Schroeder Fdoi
10.1016/0009-3084(84)90086-0subject
Has Abstractpub_date
1984-11-01 00:00:00pages
1-14issue
1eissn
0009-3084issn
1873-2941pii
0009-3084(84)90086-0journal_volume
36pub_type
杂志文章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：: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...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2015.03.002
更新日期：2015-05-01 00:00:00
abstract：:A simplified procedure for lipid digestion, well suited for handling a large number of samples, was used to analyze a variety of common phospholipids. This procedure involves digestion of phospholipids in perchloric acid at 130 degrees C with minimal sample manipulation. For all lipids tested, complete destruction, ne...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(86)90111-8
更新日期：1986-01-01 00:00:00
abstract：:For the design of new synthetic substrates for the assay of pancreatic lipases activity, acyl dialkylglycerols of variable chain length were prepared. Titrimetric assay of these substrates showed the highest lipolytic activity of porcine pancreas lipase (pPL) with butanoyl dibutylglycerol. The activity is lower but co...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(01)00143-8
更新日期：2001-06-01 00:00:00
abstract：:The gel-like liquid phase transition of dimyristoylphosphatidylcholine (DMPC) large unilamellar vesicles prepared by reverse phase evaporation has been investigated in buffers containing ethanol by quasi-elastic light scattering (QLS) and vibrational (infrared and Raman) spectroscopy. With the QLS technique, the relat...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90001-1
更新日期：1988-12-01 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：:We consider the situation of integral membrane proteins in a lipid bilayer matrix where the size of the polar group of the protein is important in determining the lateral packing of the proteins. We represent the cross-section of the protein hydrophobic core as a hexagon moving on a lattice, and represent the projecti...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90041-2
更新日期：1988-04-01 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：: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：:The apparent Mn2+ binding constant for L-alpha-dipalmitoylphosphatidylcholine (DPPC) bilayers dispersed in monovalent salt and MnCl2 dispersions was determined as a function temperature using electron paramagnetic resonance (ERP). Reproducibility in the data sets requires the use of a standard salt solution and dual c...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(88)90023-0
更新日期：1988-03-01 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：:In liotropic lipid systems phase transitions can be induced isothermally by changing the solvent concentration or composition; alternatively, lipid composition can be modified by (bio)chemical means. The probability for isothermal phase transitions increases with the decreasing transition entropy; it is proportional t...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/0009-3084(91)90082-m
更新日期：1991-03-01 00:00:00
abstract：:We investigated the effect of pegylation on the physical stability, morphology and membrane integrity of arsonoliposomes. Arsonoliposomes composed of distearoylglycerophosphocholine (DSPC), cholesterol (Chol) and the palmitoyl side chain arsonolipid (with concentrations ranging from 0 mol% [DSPC/Chol vesicles] to 53 m...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2005.11.003
更新日期：2006-02-01 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：:Inverted cubic and isotropic phases have been observed in phospholipid and glycolipid systems. These phases exhibit characteristic morphologies in freeze-fracture electron micrographs, isotropic 31P-NMR resonances and (in some cases) cubic X-ray diffraction patterns. It is proposed here that these phases may form from...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(86)90087-3
更新日期：1986-12-31 00:00:00
abstract：:The interaction of protoporphyrin IX (3,7,12,15-tetramethyl-8, 13-divinyl-2,18-porphyrine-dipropionic acid) (PPIX) with unilamellar dimyristoyl-L-alpha-phosphatidylcholine (DMPC) phospholipid vesicles has been studied by means of steady-state fluorescence quenching spectroscopy. The method of fluorescence-quenching-re...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(96)02605-9
更新日期：1996-09-30 00:00:00
abstract：:The application of fluorescence methodologies to obtain information about the extent, dynamics and topology of peptide interaction with binary phospholipid (mainly zwitterionic/anionic) mixtures is reviewed. First, general approaches based on peptide (tryptophan residues) fluorescence properties that give information ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(02)00180-9
更新日期：2003-01-01 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：:A study of the vibrational behavior of five saturated monoacid triacylglycerides is performed by Raman spectroscopy at room temperature in the 3100-500 cm(-1) spectral range. The splitting of the CO stretching mode leads to conclude on the existence of two or three geometries of CO in the "knot" group OCO. The CO stre...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2004.12.009
更新日期：2005-04-01 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：:DNA interactions with the bilayers of cationic liposomes were studied using a novel model experiment: DNAs were locally injected by a micropipette to a part of a giant unilamellar vesicle. The resulting phenomena were directly observed in optical microscope. Giant unilamellar vesicles (GUVs), about 100 microm in diame...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(99)00060-2
更新日期：1999-08-01 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：: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：:The effect of several synthetic peptides based on the sequence of human pulmonary surfactant-associated protein B (SPB) on the molecular packing of model membrane lipids (7:1 dipalmitoyl phosphatidylcholine (DPPC)/dipalmitoyl phosphatidylglycerol (DPPG)) was studied using fluorescence anisotropy. This information was ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(91)90039-e
更新日期：1991-12-01 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：: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：: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：: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：: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：:The indolic plant hormone, indole-3-acetic acid (IAA), mediated the transport of Mn2+ and other ions into small unilamellar vesicles prepared from soybean phosphatidylinositol (PI) and this process has been studied using 31P nuclear magnetic resonance spectroscopy (NMR). The rate of Mn2+ movement into PI vesicles is d...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(92)90010-m
更新日期：1992-04-01 00:00:00
