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 are not stereochemically selective. Various studies have produced conflicting results regarding whether interactions with lipid bilayers are or can be stereoselective. In the current work, stereoselective interactions between a pair of atropisomers, R-(+)/(S)-(-) 1,1'-Bi-2-naphthol, and sphingomyelin nanodisc bilayers, are demonstrated. This is accomplished using nanodisc electrokinetic chromatography, demonstrating that this approach is sensitive to subtle differences in affinity between small molecule probes and lipid bilayers. Using the same approach, no evidence of stereoselectivity was observed using enantiomer or diastereomer probes of varied chemistry and structure.
journal_name
Chem Phys Lipidsjournal_title
Chemistry and physics of lipidsauthors
Penny WM,Palmer CPdoi
10.1016/j.chemphyslip.2018.05.002subject
Has Abstractpub_date
2018-08-01 00:00:00pages
11-14eissn
0009-3084issn
1873-2941pii
S0009-3084(18)30044-6journal_volume
214pub_type
杂志文章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 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
更新日期：2003-12-01 00:00:00
abstract：:We found that extracellular addition of 2% bovine serum albumin (BSA) to a suspension of rabbit platelets after stimulation with platelet-activating factor resulted in a biphasic extraction of [3H]1-O-alkyl-2-O-methyl (or 2-O-methylcarbamyl)-sn-glycero-3-phosphocholine. A fast phase of extraction of the phospholipid p...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(97)02664-9
更新日期：1997-03-28 00:00:00
abstract：:The in vitro effect of apolipoprotein C-II (apo C-II) on the apolipoprotein C-III (apo C-III) induced activation of bovine milk lipoprotein lipase (LPL) was studied in vitro using a synthetic substrate. Apo C-III effectively inhibited, in a dose-dependent manner, the activation of lipoprotein lipase induced by apo C-I...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(87)90038-7
更新日期：1987-10-01 00:00:00
abstract：:The study on aggregation capacity of novel imidazolium-containing amphiphiles of 1-(2-hydroxyethyl)alkylimidazolium bromide series and their interaction with bio-objects (DNA decamer, bovine serum albumin, phospholipid) was performed. It was revealed that introduction of hydroxyethyl moiety into the surfactant molecul...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2019.104791
更新日期：2019-09-01 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：:Apolipoprotein B-100 (apoB-100) is the major protein in low-density lipoprotein (LDL) and contains the ligand for binding LDL to its cell surface receptor. Lipoprotein [a] (Lp[a]) is a lipoprotein that consists of LDL and apolipoprotein [a] (apo[a]). The primary structure of apoB-100 has been determined by a combinati...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(94)90128-7
更新日期：1994-01-01 00:00:00
abstract：:Several cardiovascular risk factors are characterized by the coexistence of low-grade inflammation, enhanced oxidative stress and lipid peroxidation. It has been hypothesized that F2-isoprostanes, a product of in vivo lipid peroxidation, may transduce the effects of metabolic and hemodynamic abnormalities into increas...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2003.10.001
更新日期：2004-03-01 00:00:00
abstract：:Electrostatic interaction is an important secondary force affecting the structure, stability, and function of lipid vesicles (liposomes). For this study, a negatively charged lipid with carboxylic acid was mixed with phospholipid to produce anionic vesicles. The electrostatics of the carboxylated anionic vesicle (ca. ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2011.01.002
更新日期：2011-03-01 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：:Bacteriophage M13 major coat protein is extensively used as a biophysical, biochemical, and molecular biology reference system for studying membrane proteins. The protein has several elements that control its position and orientation in a lipid bilayer. The N-terminus is dominated by the presence of negatively charged...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2006.02.023
更新日期：2006-06-01 00:00:00
abstract：:The lipidic cubic phase was prepared by mixing monoolein (monooleoyl-rac-glycerol, MO) with water in 64:36% ratio and applied to the solid support-glassy carbon or platinum electrodes. Highly viscous, homogeneous and transparent cubic phase film remained stable and firmly attached to the electrode surface. In order to...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/s0009-3084(03)00051-3
更新日期：2003-07-01 00:00:00
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
更新日期：2001-02-01 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：: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 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
更新日期：1975-09-01 00:00:00
abstract：:The 3-sulfates of the S-acyl glutathione (GSH) conjugates of five natural bile acids (cholic, chenodeoxycholic, deoxycholic, ursodeoxycholic, and lithocholic) were synthesized as reference standards in order to investigate their possible formation by a rat liver cytosolic fraction. Their structures were confirmed by p...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2012.02.001
更新日期：2012-04-01 00:00:00
abstract：:Surface plasmon resonance (SPR) has become one of the most important techniques for studying macromolecular interactions. The most obvious advantages of SPR over other techniques are: direct and rapid determination of association and dissociation rates of binding process, no need for labelling of protein or lipids, an...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2006.02.010
更新日期：2006-06-01 00:00:00
abstract：:Cardiolipin (CL) is a phospholipid with many unique characteristics. CL is synthesized in the mitochondria and resides almost exclusively within the mitochondrial inner membrane. Unlike most phospholipids that have two fatty acyl chains, CL possesses four fatty acyl chains resulting in unique biophysical characteristi...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2015.09.005
更新日期：2015-12-01 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：:Nitration of unsaturated fatty acids is a (patho)physiologically important pathway of lipid modification induced by nitric oxide-derived species. We report herein on the unexpected chain rearrangement undergone by (13S,9Z,11E)-13-hydroxyoctadeca-9,11-dienoic acid (1), a linoleic acid metabolite, when exposed to nitrat...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/j.chemphyslip.2007.09.007
更新日期：2008-01-01 00:00:00
abstract：:Reduction of 3beta-benzoyloxy-14alpha,15alpha-epoxy-5alpha-cholest-7-ene with either lithium triethylboro-hydride or lithium aluminum hydride (4 molar excess) gave 5-alpha-cholest-8(14)-en-3beta,15alpha-diol in high yield. Reduction of the epoxy ester with lithium triethylborodeuteride or lithium aluminum deuteride (4...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(77)90013-5
更新日期：1977-04-01 00:00:00
abstract：:The interactions of liposomes with cells have been extensively studied to determine their potential use as vehicles for the delivery of drugs in vivo. Since intravenously administered liposomes are, for the most part, cleared by cells of the reticuloendothelial system (RES), considerable effort has been made to take a...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(86)90080-0
更新日期：1986-06-01 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 interactions of iodine, iodide and triiodide with phosphatidylcholine multilayers have been investigated in order to find supporting data for conduction mechanisms of iodine-doped bimolecular lipid membranes. On the basis of order-disorder parameters it can be concluded that phospholipid multilayers interact with ...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章
doi：10.1016/0009-3084(77)90096-2
更新日期：1977-06-01 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：: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：:Isoprostanes (IsoPs) are a complex family of compounds produced, in vivo, from peroxidation of polyunsaturated fatty acids (AA, DHA, EPA, alpha-linolenic) via a free-radical-catalyzed mechanism. Carbocyclic annulations are extremely important reactions and the stereocontrolled intramolecular free-radical cyclization h...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2003.10.008
更新日期：2004-03-01 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
abstract：:Oxysterols are oxidized products of cholesterol that play several roles in various pathophysiological processes, including the control of lipid metabolism, immunological processes, and cytotoxicity. Mesenchymal stem cells are multipotent cells with properties of self-renewal and the ability to differentiate into other...
journal_title：Chemistry and physics of lipids
pub_type： 杂志文章,评审
doi：10.1016/j.chemphyslip.2017.06.009
更新日期：2017-10-01 00:00:00
