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 demonstrate that the (-)-enantiomer is a substrate for phospholipase A2 (PLA2) (Crotalus atrox) while the (+)-enantiomer is not. This strict enantiomeric (and positional) specificity was exploited in conjunction with a novel application of DEAE-cellulose column chromatography, to achieve racemic resolution with an excellent yield. The constrained backbone geometry, and the experimentally accessible critical micellar concentration (CMC) of these analogues should render them useful probes for assessing the contribution of substrate conformation and flexibility to the catalytic efficiency of PLA2.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Barlow PN,Vidal JC,Lister MD,Hancock AJ,Sigler PBdoi
10.1016/0009-3084(88)90017-5subject
Has Abstractpub_date
1988-03-01 00:00:00pages
157-64issue
3eissn
0009-3084issn
1873-2941pii
0009-3084(88)90017-5journal_volume
46pub_type
杂志文章abstract：:A convenient universal and fast mass spectrometrical method designed for the molecular species analysis of natural lipids is described. In contrast to the commonly employed procedures the method does not require chemical or enzymatic treatment and does not include chromatographic steps. The method relies on the recogn...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(83)90027-0
更新日期：1983-11-01 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：:Dimer structure and liquid structure of fatty acids in the binary liquid mixture of dodecanoic (LA) and 3-phenylpropionic acids (PPA) were studied through the measurements of DSC, self-diffusion coefficient (D), density, viscosity, 13C NMR spin-lattice relaxation time, small-angle X-ray scattering (SAXS), and small-an...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2004.01.005
更新日期：2004-05-01 00:00:00
abstract：:Fungal infections are an important cause of morbidity and pose a serious health concern especially in immunocompromised patients. Luliconazole (LUL) is a topical imidazole antifungal drug with a broad spectrum of activity. To overcome the limitations of conventional dosage forms, LUL loaded lyotropic liquid crystallin...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2020.105028
更新日期：2021-01-01 00:00:00
abstract：:In the present work, we report the physico-chemical properties and structural characteristics of special polyhydroxy fatty acid nanoparticles after their fusion by means of attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR), X-ray diffraction (XRD), differential scanning calorimetry (DSC), ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2010.01.006
更新日期：2010-03-01 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：: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：:In this report we have investigated the differences in the uptake and metabolization of exogenous GM1 by human fibroblasts, as a function of its supramolecular organization in solution. For this we used a tritium labelled GM1, given alone or inserted in dispersions of phosphatidylcholine (PC) or sulphatide. The additi...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(90)90080-b
更新日期：1990-08-01 00:00:00
abstract：:The current-voltage steady-state characteristics, cyclic voltammograms and capacitance-voltage steady-state relationships of bilayer lipid membranes made from dioleoylphosphatidylcholine or its mixtures with dolichyl-12 phosphate have been studied. Sustained fluctuations of the capacitance of dolichyl phosphate modifi...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(90)90158-n
更新日期：1990-01-01 00:00:00
abstract：:Seven members of the methyl-6-O-(n-acyl)-α-D-glucopyranosides have been synthesised and their transitional properties determined. The undecanoyl and octadecanoyl members do not exhibit liquid crystallinity while the members having chain lengths between dodecanoyl and hexadecanoyl exhibit a monotropic smectic A phase. ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2010.11.007
更新日期：2011-02-01 00:00:00
abstract：:The addition of hydrophilic and hydrophobic molecules to the 1-monooleoyl glycerol (MO)/water (W) system has been investigated at a molecular level by 13C nuclear magnetic resonance (NMR) relaxation. Depending on the nature of the additive, the liquid crystalline phases of the MO/W binary system are modified. The 13C ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(00)00201-2
更新日期：2001-03-01 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：: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：: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：: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
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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：: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：:In the current study, we have focused on the design, development and in-vitro evaluation of d-α-tocopheryl polyethylene glycol 1000 succinate modified amphotericin B (AmB) and paromomycin (PM) loaded solid lipid nanoparticles (TPGS-SLNPs) by emulsion-solvent evaporation method. The optimized TPGS-SLNPs had a mean part...
journal_title：Chemistry and physics of lipids
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doi：10.1016/j.chemphyslip.2020.104946
更新日期：2020-09-01 00:00:00
abstract：:Cardiolipins (CLs) are ancient and unusual dimeric phospholipids localized in the plasma membrane of bacteria and in the inner mitochondrial membrane of eukaryotes. In mitochondria, two types of asymmetries--trans-membrane and molecular--are essential determinants of CL functions. In this review, we describe CL-based ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2013.11.010
更新日期：2014-04-01 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：:Fourier transform (FT) Raman spectroscopy and differential scanning calorimetry (DSC) were used to study the thermotropic phase behaviour of mixtures of ceramides type IV (CER) and stearic acid (SA). For comparison the melting behaviour of SA was re-examined. The Raman spectra of all mixtures in the solid state show s...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(97)00049-2
更新日期：1997-09-24 00:00:00
abstract：:N-acyltaurines (NATs) are amides of fatty acids that can be structurally related to endocannabinoids. They show interesting physiological and pharmacological properties. We have synthesized a homologous series of NATs with saturated acyl chains (n = 9-18) and investigated their supramolecular structure and thermotropi...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2020.104929
更新日期：2020-08-01 00:00:00
abstract：:The molecular mechanism underlying the action of local anesthetics is still elusive. Phenylethanol (PEtOH) is an ingredient of essential oils with a rose-like odor and has been used as a local anesthetic. In this work, we have explored the effect of PEtOH on thermotropic behavior and organization of dipalmitoylphospha...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2017.12.003
更新日期：2018-01-01 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：:Cholesterol has many functions, including those that affect biophysical properties of membranes, and is a precursor to hormone synthesis. These actions are governed by enzymatic pathways that modify the sterol nucleus or the isooctyl tail. The addition of oxygen to the cholesterol backbone produces its derivatives kno...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2011.06.006
更新日期：2011-09-01 00:00:00
abstract：:High density lipoprotein (HDL) is prone to modification by the oxidizing and chlorinating agent hypochlorite anion (OCl-). Oxidation of apolipoprotein (apo) A-I, the major protein in HDL, reduces ABCA-1 mediated cholesterol efflux and other protective responses to HDL. The apoA-I mimetic peptide 4F has been shown to u...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2019.01.009
更新日期：2019-03-01 00:00:00
abstract：:The Golgi complex constitutes a central way station of the eukaryotic endomembrane system, an intricate network of organelles engaged in control of membrane trafficking and the processing of various cellular components. Previous ideas of compartmental stability within this network are gradually being reshaped by conce...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2016.06.005
更新日期：2016-10-01 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：:X-ray diffraction data taken at high instrumental resolution were obtained for EPC and DMPC under various osmotic pressures, primarily at T = 30 degrees C. The headgroup thickness DHH was obtained from relative electron density profiles. By using volumetric results and by comparing to gel phase DPPC we obtain areas AE...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(98)00068-1
更新日期：1998-09-01 00:00:00
abstract：:The present study is aimed to characterize the electrostatic parameters of oil in water emulsion droplets composed of MCT (medium chain triglycerides), PL (phospholipids) and Poloxamer and containing increasing concentrations of the cationic lipid oleylamine (OA), in Hepes 20 mM pH 7.4. The initial zeta-potential data...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2004.04.003
更新日期：2004-08-01 00:00:00
