Packing and Electrostatic Behavior of sn-2-Docosahexaenoyl and -Arachidonoyl Phosphoglycerides

Brockman, Howard L.; Applegate, Kenneth R.; Momsen, Maureen M.; King, Weiling C.; Glomset, John A.

doi:10.1016/s0006-3495(03)74662-1

Cited by 29 publications

(40 citation statements)

References 74 publications

(92 reference statements)

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“…Hence, values of P coll , A coll , and A 35mN/m for SDPC monolayers span a range from 37.0 to 45.4 mN/m, from 50.2 to 57.5 Å 2 /lipid and from 56.0 to 70.6 Å 2 /lipid, respectively [14,35,36]. In addition, it seems that salmon PC, rich in LC-PUFA tough, does not follow the general trend of PUFA-enriched monolayers which show a shift to higher molecular areas of the compression isotherm when increasing unsaturation on sn-2 position [14,35]. Just as noticed for the mean area per lipid evaluated from the repeat distance, salmon PC monolayers have a peculiar behavior as they present smaller areas per lipid compared to either egg or soybean PC, whatever the surface pressure applied.…”

Section: Surface Pressure-molecular Area Isothermsmentioning

confidence: 96%

“…Most of the studies used PUFA in synthetic phosphatidylcholine (PC) membrane as model membranes to explain the physical mechanisms by which the unsaturation may impact on membrane properties. It has been pointed out that unsaturation of acyl chains affects important membrane properties such as the area per lipid and the membrane thickness [10], the gel-to-liquid crystalline phase transition temperature [11], the specific volume of the PL [12], the hydration [13], and the packing characteristics of the hydrocarbon chains [14].…”

Section: Introductionmentioning

confidence: 99%

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Structural, hydration, and phase transition properties of phosphatidylcholine from salmon heads

Sautot

Tarek²,

Stébé³

et al. 2011

Eur. J. Lipid Sci. Technol.

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Prior studies on membranes have reported that unsaturations affect important bilayers properties, but most of these studies have been based on single-component membranes. This report compares the properties of a phosphatidylcholine (PC) membrane enriched in long chain PUFA (LC-PUFA), extracted and purified from salmon heads (Salmo salar), with those of other multicomponent PC membranes from egg and soybean. Detailed description of the composition, the structural parameters, the thermal behavior, the hydration, and monolayer properties are given. Hydration properties of salmon PC showed greater adsorbance of water compared to egg and soybean PC. A greater adsorption of water was also observed for salmon PC multibilayers in bulk water before demixing compared to egg and soybean PC. An interesting feature concerns the evolution of area per lipid when increasing the water content where salmon PC showed a relative constant molecular area upon hydration. Another specific feature was the ability of salmon PC monolayer to occupy smaller molecular area upon compression than do egg and soybean PC. We hypothesize that specific hydration properties at the interface and enhanced packing properties of the LC-PUFA are responsible for this particular behavior of salmon PC membrane.

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Section: Surface Pressure-molecular Area Isothermsmentioning

confidence: 96%

Section: Introductionmentioning

confidence: 99%

Structural, hydration, and phase transition properties of phosphatidylcholine from salmon heads

Sautot

Tarek²,

Stébé³

et al. 2011

Eur. J. Lipid Sci. Technol.

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“…The intercept term, DV 0 , is lipid-specific and appears to arise from an epitaxial ordering of interfacial water molecules (30,33). DV versus 1/A plots of various liquid-expanded lipids are linear from ?1 mN/m up to surface pressures at which the second derivative of the p-A isotherms (d 2 p/dA 2 ) goes from positive to negative values (p d ) (33,34). The linearity indicates a lack of significant dipole reorientation over the range of surface pressures leading up to p d and typically encompasses 80-90% of the p 2 A data for liquid-expanded films.…”

Section: Analyses Of Monolayer Isothermsmentioning

confidence: 97%

“…Table 1 summarizes the values of m ± and DV 0 , obtained from plots of the dipole potential versus inverse crosssectional molecular area (V 2 A 21 ). DV 0 values for B7-PC were 551 mV, compared with 24 mV for PB-PC (26) and 110-140 mV for the fluid nonfluorescent phosphatidylcholines lacking docosahexenoyl acyl chains (30,33,34). However, the dipole moment, m ± , of B7-PC was found to be 2850 milliDebyes, compared with 874 milliDebyes for PB-PC (26) and 480-550 milliDebyes for phosphatidylcholines lacking docosahexenoyl acyl chains (30,33,34).…”

Section: Probe Lateral Packing and Spectral Properties In Monolayersmentioning

confidence: 99%

New BODIPY lipid probes for fluorescence studies of membranes

Болдырев

Zhai

Momsen

et al. 2007

Journal of Lipid Research

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Many fluorescent lipid probes tend to loop back to the membrane interface when attached to a lipid acyl chain rather than embedding deeply into the bilayer. To achieve maximum embedding of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) fluorophore into the bilayer apolar region, a series of sn-2 acyl-labeled phosphatidylcholines was synthesized bearing 4,4-difluoro-1,3,5,7-tetramethyl-4-bora-3a,4a-diaza-s-indacene-8-yl (Me 4 -BODIPY-8) at the end of C 3 -, C 5 -, C 7 -, or C 9 -acyl. A strategy was used of symmetrically dispersing the methyl groups at BODIPY ring positions 1, 3, 5, and 7 to decrease fluorophore polarity. Iodide quenching of the phosphatidylcholine probes in bilayer vesicles confirmed that the Me 4 -BODIPY-8 fluorophore was embedded in the bilayer. Parallax analysis of Me 4 -BODIPY-8 fluorescence quenching by phosphatidylcholines containing iodide at different positions along the sn-2 acyl chain indicated that the penetration depth of Me 4 -BODIPY-8 into the bilayer was determined by the length of the linking acyl chain. Evaluation using monolayers showed minimal perturbation of ,10 mol% probe in fluid-phase and cholesterol-enriched phosphatidylcholine. Spectral characterization in monolayers and bilayers confirmed the retention of many features of other BODIPY derivatives (i.e., absorption and emission wavelength maxima near 498 nm and ?506-515 nm) but also showed the absence of the 620-630 nm peak associated with BODIPY dimer fluorescence and the presence of a 570 nm emission shoulder at high Me 4 -BODIPY-8 surface concentrations. We conclude that the new probes should have versatile utility in membrane studies, especially when precise location of the reporter group is needed. Fluorescent lipid probes have proven to be valuable tools in membrane studies (see Ref. 1 for review). Because the determination of depth-dependent parameters of bilayers can benefit the understanding of membranous structures (2), sets of probes bearing the same fluorophore at different distances from the bilayer surface are potentially quite useful. Ideally, such fluorophores should be apolar enough to localize at the membrane depth that reflects the apolar nature of the surrounding acyl chain region without being strongly influenced by the transbilayer polarity gradient (3). The first probe set designed to achieve this goal was a series of n-(9-anthroyloxy) fatty acids synthesized by Thulborn and Sawyer (4), who showed that the fluorophore resided in the bilayer at a graded series of depths that coincided with the attachment point of the anthroyloxy fluorophore along the acyl chain. Other widely used fluorophores, such as N-dansyl (5) or N-NBD (6, 7), have been shown to have polar characteristics that interfere with localization deep inside the bilayer even when attached to the end of the acyl chain.During the past decade, BODIPY (4,4-difluoro-4-bora3a,4a-diaza-s-indacene) fluorophore probes have found a wide range of applications in cell biology and biophysics, even though this zwitterionic fluorophore wa...

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“…Surface pressures >36 mN/m were needed to block glycolipid removal from POPE which remains in a fl uid liquid-expanded state up to ‫ف‬ 40 mN/m. Above ‫ف‬ 40 mN/m, POPE undergoes a phase transition and both liquid-expanded and liquid-condensed phases coexist ( 46 ). Figure 5A shows that the initial removal rate of B15-GalCer is linear with respect to surface pressure regardless of whether the fl uid-phase monolayer matrix is POPE or POPC, but the removal rate is much faster from POPE than from POPC and persists at higher surface pressures for POPE compared with POPC .…”

Section: Glycolipid Removal By Gltp Is Mitigated By Pc But Induced By Pementioning

confidence: 99%

GLTP-fold interaction with planar phosphatidylcholine surfaces is synergistically stimulated by phosphatidic acid and phosphatidylethanolamine

Zhai

Momsen

Malakhov

et al. 2013

Journal of Lipid Research

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Proteins are considered to be amphitropic when translocation to/from biomembranes: i ) is required for function; ii ) occurs transiently and reversibly from the cytoplasm; and iii ) involves interaction with the lipid bilayer ( 1-3 ). Glycolipid transfer proteins (GLTPs) comprise a structurallyunique amphitropic protein superfamily defi ned by their ability to reversibly interact with membranes to achieve selective transport of glycosphingolipids ( 4 ). Human GLTP resides in the cytosol ( 5 ), but is capable of delivering glucosylceramide to the cytosolic face of the plasma membrane ( 6, 7 ) and contains a nonclassical diphenylalanine-in-anacidic-tract targeting sequence to the endoplasmic reticulum ( 8 ). GLTPs occur widely among eukaryotes ( 4, 9 ) and GLTP-like domains serve as key functional regions in larger human proteins, i.e., FAPP2 ( 10, 11 ). The GLTPfold is dominated by ␣ -helices, lacks intramolecular disulfi des, and uses a two-layer "sandwich" motif to form a single glycolipid binding site consisting of a surface-localized sugar headgroup recognition center and an expandable hydrophobic pocket for accommodation of the ceramide hydrocarbon chains of the glycolipid ( 12-17 ). During glycolipid transfer, GLTP interacts with membranes transiently and in a minimally perturbing manner ( 18, 19 ) via a membrane interaction domain formed by a cluster of Trp, Tyr, Lys, and nonpolar residues on the GLTP surface Abstract Among amphitropic proteins, human glycolipid transfer protein (GLTP) forms a structurally-unique fold that translocates on/off membranes to specifi cally transfer glycolipids. Phosphatidylcholine (PC) bilayers with curvature-induced packing stress stimulate much faster glycolipid intervesicular transfer than nonstressed PC bilayers raising questions about planar cytosol-facing biomembranes being viable sites for GLTP interaction. Herein, GLTP-mediated desorption kinetics of fl uorescent glycolipid (tetramethyl-boron dipyrromethene (BODIPY)-label) from lipid monolayers are assessed using a novel microfl uidics-based surface balance that monitors lipid lateral packing while simultaneously acquiring surface fl uorescence data. At biomembrane-like packing (30-35 mN/m), GLTP uptake of BODIPY-glycolipid from POPC monolayers was nearly nonexistent but could be induced by reducing surface pressure to mirror packing in cur vature-stressed bilayers. In contrast, 1-palmitoyl-2-oleoyl-phosphatidylethanolamine (POPE) matrices supported robust BODIPY-glycolipid uptake by GLTP at both high and low surface pressures. Unexpectedly, negativelycharged cytosol-facing lipids, i.e., phosphatidic acid and phosphatidylserine, also supported BODIPY-glycolipid uptake by GLTP at high surface pressure. Remarkably, including both 1-palmitoyl-2-oleoyl-sn -glycero-3-phosphate (5 mol%) and POPE (15 mol%) in POPC synergistically activated GLTP at high surface pressure. Our study shows that matrix lipid headgroup composition, rather than molecular packing per se, is a key regulator of GLTP-fold function while demonstrating th...

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Packing and Electrostatic Behavior of sn-2-Docosahexaenoyl and -Arachidonoyl Phosphoglycerides

Cited by 29 publications

References 74 publications

Structural, hydration, and phase transition properties of phosphatidylcholine from salmon heads

Structural, hydration, and phase transition properties of phosphatidylcholine from salmon heads

New BODIPY lipid probes for fluorescence studies of membranes

GLTP-fold interaction with planar phosphatidylcholine surfaces is synergistically stimulated by phosphatidic acid and phosphatidylethanolamine

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