Vitamin E - phosphatidylethanolamine interactions in mixed membranes with sphingomyelin: Studies by 2H NMR.

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 play a role in supporting this function is an unanswered question. Here, we compare the molecular organization of polyunsaturated 1-[2H31]palmitoyl-2-docosahexaenoylphosphatidylethanolamine (PDPE-d31) and, as a control, monounsaturated 1-[2H31]palmitoyl-2-oleoylphosphatidylethanolamine (POPE-d31) mixed with sphingomyelin (SM) and α-tocopherol (α-toc) (2:2:1 mol) by solid-state 2H NMR spectroscopy. In both cases the effect of α-toc appears similar. Spectral moments reveal that the main chain melting transition of POPE-d31 and PDPE-d31 is broadened beyond detection. A spectral component attributed to the formation of inverted hexagonal HII phase in coexistence with lamellar Lα phase by POPE-d31 (20 %) and PDPE-d31 (18 %) is resolved following the addition of α-toc. Order parameters in the remaining Lα phase are increased slightly more for POPE-d31 (7%) than PDPE-d31 (4%). Preferential interaction with polyunsaturated phospholipid is not apparent in these results. The propensity for α-toc to form phase structure with negative curvature that is more tightly packed at the membrane surface, nevertheless, may restrict the contact of free radicals with lipid chains on phosphatidylethanolamine molecules that accumulate polyunsaturated fatty acids.

journal_name

Chem Phys Lipids

authors

Cavazos AT,Kinnun JJ,Williams JA,Wassall SR

doi

10.1016/j.chemphyslip.2020.104910

subject

Has Abstract

pub_date

2020-09-01 00:00:00

pages

104910

eissn

0009-3084

issn

1873-2941

pii

S0009-3084(20)30041-4

journal_volume

231

pub_type

杂志文章
  • Conformational requirements for endocannabinoid interaction with the cannabinoid receptors, the anandamide transporter and fatty acid amidohydrolase.

    abstract::Anandamide (N-arachidonoylethanolamine) has been identified as an endogenous ligand of the G-protein coupled cannabinoid CB(1) receptor. Recent studies have postulated the existence of carrier-mediated anandamide transport which is involved in the termination of the biological effects of anandamide. A membrane bound a...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章,评审

    doi:10.1016/s0009-3084(00)00185-7

    authors: Reggio PH,Traore H

    更新日期:2000-11-01 00:00:00

  • Cholestryl-phosphoryl-choline in lipid bilayers.

    abstract::Cholesteryl-phosphoryl-choline (CPC), a hybrid between cholesterol and lecithin, is incorporated into sonicated liposomes and erythrocyte membranes similarly to cholesterol. The effect of CPC on lipid microviscosity and degree of order is smaller, but not significantly than that of cholesterol. It is proposed that CPC...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(79)90094-x

    authors: Lyte M,Shinitzky M

    更新日期:1979-04-01 00:00:00

  • The phase transition behavior of 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) model membrane influenced by 2,4-dichlorophenol--an FT-Raman spectroscopy study.

    abstract::The effect of 2,4-dichlorophenol (DCP) on the structures and phase transitions of fully hydrated 1,2-dipalmitoyl-sn-glycero-3-phosphocholine (DPPC) liposomes was studied using FT-Raman spectroscopy. Whereas the Raman frequency shifts of the most frequently investigated bands of C-C and C-H stretching regions only indi...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2005.11.005

    authors: Csiszár A,Koglin E,Meier RJ,Klumpp E

    更新日期:2006-02-01 00:00:00

  • Indole-3-acetic acid-mediated transport of Mn2+ and other ions across phosphatidylinositol vesicular membranes as determined by 31P-NMR.

    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

    authors: Jones GP,Misso NL,Paleg LG

    更新日期:1992-04-01 00:00:00

  • Binding of a cationic phenazinium dye in anionic liposomal membrane: a spectacular modification in the photophysics.

    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

    authors: Bose D,Ghosh D,Das P,Girigoswami A,Sarkar D,Chattopadhyay N

    更新日期:2010-01-01 00:00:00

  • The conformational properties of the antineoplastic ether lipid 1-thiohexadecyl-2-O-methyl-S-glycero-3-phosphocholine.

    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

    authors: Mavromoustakos T,Theodoropoulou E,Yang DP,Lin SY,Koufaki M,Makriyannis A

    更新日期:1996-11-01 00:00:00

  • Aminoglycoside antibiotics prevent the formation of non-bilayer structures in negatively-charged membranes. Comparative studies using fusogenic (bis(beta-diethylaminoethylether)hexestrol) and aggregating (spermine) agents.

    abstract::Aminoglycoside antibiotics cause aggregation but not fusion of negatively-charged liposomes at an extent proportional to their capacity to interact with acidic phospholipids (Van Bambeke et al., 1995, Eur. J. Pharmacol., 289, 321-333). To understand why aggregation is not followed by fusion, we have examined here the ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(95)02520-0

    authors: van Bambeke F,Mingeot-Leclercq MP,Brasseur R,Tulkens PM,Schanck A

    更新日期:1996-03-29 00:00:00

  • Fluorescence depolarization study on non-bilayer phases of phosphatidylethanolamine and phosphatidylcholine lipid mixtures.

    abstract::The orientational order and rotational dynamics of 1-palmitoyl-2-[[2-[4-(6-phenyl-trans-1,3,5- hexatrienyl)phenyl]ethyl] carbon yl]-3-sn-phosphatidylcholine (DPH-PC) in dilinoleoylphosphatidylethanolamine (DLPE) and 1-palmitoyl-2-oleoylphosphatidylcholine (POPC) binary lipid mixtures were investigated. A previous stud...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(89)90047-9

    authors: Cheng KH

    更新日期:1989-10-01 00:00:00

  • Protein-lipid interactions and surface activity in the pulmonary surfactant system.

    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

    authors: Serrano AG,Pérez-Gil J

    更新日期:2006-06-01 00:00:00

  • Infrared and time-resolved fluorescence spectroscopic studies of the polymorphic phase behavior of phosphatidylethanolamine/diacylglycerol lipid mixtures.

    abstract::Fourier transform infrared (FTIR) and time-resolved fluorescence spectroscopy have been employed to examine the structural dynamics of lipid fatty acyl chains and lipid/water interfacial region of a binary lipid mixture containing unsaturated phosphatidylethanolamine (PE) and diacylglycerol (DG). Infrared vibrational ...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(90)90097-b

    authors: Chen SY,Cheng KH

    更新日期:1990-12-01 00:00:00

  • The PMR analysis of non-conjugated alkenoic and alkynoic acids and esters.

    abstract::The 220 MHz PMR spectra of 143 non-conjugated alkenoic and alkynoic acids and esters are correlated so as to provide a method for the structural analysis of such compounds in general. The spectral data are explained in terms of long-range deshielding of the double bonds, triple bonds, acid and ester groups in the mole...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(75)90032-8

    authors: Frost DJ,Gunstone FD

    更新日期:1975-09-01 00:00:00

  • Comprehensive analysis of the phospholipids and phytosterols in Schisandra chinensis oil by UPLC-Q/TOF- MSE.

    abstract::Characterization of phospholipids (PLs) and phytosterols were determined in Schisandra chinensis (S. chinensis) oil by UPLC-Q/TOF-MSE. The determination process was based on feature fragment information of components generated by the MSE detector. A total of 49 and 39 PLs were identified in S. chinensis oil under nega...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2019.03.003

    authors: Gao Y,Wu S

    更新日期:2019-07-01 00:00:00

  • Prediction of the melting points of fatty acids from computed molecular descriptors: a quantitative structure-property relationship study.

    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

    authors: Guendouzi A,Mekelleche SM

    更新日期:2012-01-01 00:00:00

  • Chemical stability of liposomes: implications for their physical stability.

    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

    authors: Grit M,Crommelin DJ

    更新日期:1993-09-01 00:00:00

  • The first total synthesis of the marine fatty acid (+/-)-2-methoxy-13-methyltetradecanoic acid: a cytotoxic fatty acid to leukemia cells.

    abstract::The recently discovered marine fatty acid (+/-)-2-methoxy-13-methyltetradecanoic acid was synthesized for the first time in six steps (26% overall yield) starting from commercially available methyl 12-methyltridecanoate. The synthetic approach provided enough material to corroborate the structure of the acid, which wa...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(03)00110-5

    authors: Carballeira NM,Cruz H,Orellano EA,González FA

    更新日期:2003-12-01 00:00:00

  • Translational diffusion measurements of a fluorescent phospholipid between MDCK-I cells support the lipid model of the tight junctions.

    abstract::The diffusion of a lipid fluorescent analogue across tight junctions in MDCK-I cells was studied by FRAP measurements. Cells were labelled with C6-NBD-PC at the apical cell membrane. Transepithelial resistance of MDCK-I cells was found to be higher than 3000 omega x cm2, which indicates the presence of a very tight ep...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(94)90066-3

    authors: Grebenkämper K,Galla HJ

    更新日期:1994-05-23 00:00:00

  • Combined force spectroscopy, AFM and calorimetric studies to reveal the nanostructural organization of biomimetic membranes.

    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

    authors: Suárez-Germà C,Morros A,Montero MT,Hernández-Borrell J,Domènech Ò

    更新日期:2014-10-01 00:00:00

  • Inhibition of pain responses by activation of CB(2) cannabinoid receptors.

    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

    authors: Malan TP Jr,Ibrahim MM,Vanderah TW,Makriyannis A,Porreca F

    更新日期:2002-12-31 00:00:00

  • Extensive surface studies help to analyse zeta potential data: the case of cationic emulsions.

    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

    authors: Rabinovich-Guilatt L,Couvreur P,Lambert G,Goldstein D,Benita S,Dubernet C

    更新日期:2004-08-01 00:00:00

  • Poly (vinyl pyrrolidone)-lipid based hybrid nanoparticles for anti viral drug delivery.

    abstract::Zidovudine (AZT) is an antiviral drug with moderate solubility in water. It has limited application due to its short half life in vivo and consequent requirement for frequent administrations. To solve this problem, zidovudine loaded polyvinylpyrrolidone (PVP)/stearic acid (SA)-polyethylene glycol (PEG) nanoparticles (...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2017.11.003

    authors: Joshy KS,Snigdha S,Anne G,Nandakumar K,Laly A P,Sabu T

    更新日期:2018-01-01 00:00:00

  • Thermodynamic and structural effects of propranolol on DPPC liposomes.

    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

    authors: Albertini G,Donati C,Phadke RS,Ponzi Bossi MG,Rustichelli F

    更新日期:1990-09-01 00:00:00

  • Differential scanning calorimetric study of the thermotropic phase behavior of a polymerizable, tubule-forming lipid.

    abstract::A comparative study of the polymorphism exhibited by the polymerizable, tubule-forming phospholipid 1,2-bis(10,12-tricosadiynoyl)-sn-glycero-3- phosphocholine (DC23PC) and its saturated analog 1,2-ditricosanoyl-sn-glycero-3-phosphocholine (DTPC) in aqueous suspension is reported. Differential scanning calorimetry (DSC...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(88)90092-8

    authors: Burke TG,Rudolph AS,Price RR,Sheridan JP,Dalziel AW,Singh A,Schoen PE

    更新日期:1988-10-01 00:00:00

  • Synthesis and NMR characterization of the methyl esters of eicosapentaenoic acid monoepoxides.

    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

    authors: Cui PH,Zhang WV,Hook J,Tattam BN,Duke CC,Murray M

    更新日期:2009-05-01 00:00:00

  • A DSC and FTIR spectroscopic study of the effects of the epimeric coprostan-3-ols and coprostan-3-one on the thermotropic phase behaviour and organization of dipalmitoylphosphatidylcholine bilayer membranes: Comparison with their 5-cholesten analogues.

    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

    authors: Benesch MG,Lewis RN,Mannock DA,McElhaney RN

    更新日期:2015-05-01 00:00:00

  • Isothermal lipid phase transitions.

    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

    authors: Cevc G

    更新日期:1991-03-01 00:00:00

  • Ceramide-epoxides.

    abstract::Previously unknown 4,5-epoxy-N-acetyl-sphingosine (1) was synthesized by epoxidation of N-acetyl-sphingosine with 1,1-dimethyldioxirane. A by-product generated by HPLC purification is the tetrahydrofuryl derivative of acetamide (2). Mainly allylic oxidation was observed when natural ceramides were reacted with dimethy...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/s0009-3084(00)00208-5

    authors: Möllenberg A,Spiteller G

    更新日期:2001-02-01 00:00:00

  • Isolation and purification of Lea blood-group active and related glycolipids from human plasma of blood-group A Lea individuals.

    abstract::From 81 of human plasma of blood-group A Lea nonsecretors three different Lea blood-group active ceramide pentasaccharides (a total of 4.65 mg) have been isolated, all revealing glucose, galactose, N-acetylglucosamine and fucose in molar ratios of 1 : 2 : 1 : 1 as determined by gas liquid chromatography. A fourth bloo...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/0009-3084(78)90040-3

    authors: Hanfland P,Kladetzky RG,Egli H

    更新日期:1978-09-01 00:00:00

  • Interaction of photosensitizers with liposomes containing unsaturated lipid.

    abstract::Small unilamellar liposomes were made of dipalmitoyl-phosphatidylcholine and dioleoyl-phosphatidylcholine, and photosensitized by a symmetrically or an asymmetrically substituted glycosilated tetraphenyl-porphyrin derivative. As differential scanning calorimetry and electron paramagnetic resonance spectroscopy (EPR) r...

    journal_title:Chemistry and physics of lipids

    pub_type: 杂志文章

    doi:10.1016/j.chemphyslip.2006.10.005

    authors: Voszka I,Budai M,Szabó Z,Maillard P,Csík G,Gróf P

    更新日期:2007-02-01 00:00:00

  • Active oxygen chemistry within the liposomal bilayer. Part IV: Locating 2',7'-dichlorofluorescein (DCF), 2',7'-dichlorodihydrofluorescein (DCFH) and 2',7'-dichlorodihydrofluorescein diacetate (DCFH-DA) in the lipid bilayer.

    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

    authors: Afri M,Frimer AA,Cohen Y

    更新日期:2004-08-01 00:00:00

  • Membrane specificity of non-monotonic trends in cation-mediated injury to rapidly frozen phospholipid vesicles.

    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

    authors: Brearley CA,Hodges NA,Oliff CJ

    更新日期:1991-09-01 00:00:00