Hydrocarbon chain packing and molecular motion in phospholipid bilayers formed from unsaturated lecithins. Synthesis and properties of sixteen positional isomers of 1,2-dioctadecenoyl-sn-glycero-3-phosphorylcholine.

Barton, Peter G.; Gunstone, Frank D.

doi:10.1016/s0021-9258(19)41327-6

Cited by 221 publications

(60 citation statements)

References 36 publications

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“…We prepared small unilamellar vesicles in two compositions: one consisting of solely 1,2-dioleoyl-sn-glycero-3-phosphocholine (DOPC, 850375C, Avanti Polar Lipids) and another consisting of DOPC with additional plant-derived cholesterol (Chol, 700100P, Avanti Polar Lipids) and sphingomyelin from chicken egg yolk (SM, S0756, Sigma-Aldrich), as previously described. 15 The gel-to-liquid crystalline phase-transition temperatures for DOPC and 16:0 SM (the bulk component of the egg yolk SM) are −21 40 and 41 °C, 41 respectively. In brief, stock solutions of Chol and SM were dissolved in chloroform (1 mg/mL) and sonicated for 30 min.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

Quaternary Amine-Terminated Quantum Dots Induce Structural Changes to Supported Lipid Bilayers

et al. 2018

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The cytoplasmic membrane represents an essential barrier between the cytoplasm and the environment external to cells. Interaction with nanomaterials can alter the integrity of the cytoplasmic membrane through the formation of holes and membrane thinning, which can ultimately lead to adverse biological impacts. Here we use supported lipid bilayers as experimental models for the cytoplasmic membrane to investigate the impact of quantum dots functionalized with the cationic polymer poly(diallyldimethylammonium chloride) (PDDA) on membrane structure. Using a quartz crystal microbalance with dissipation monitoring we show that the positively charged quantum dots attach to and induce structural rearrangement to zwitterionic bilayers in solely the liquid-disordered phase and in those containing phase-segregated liquid-ordered domains. Real-time atomic force microscopy imaging revealed that PDDA-coated quantum dots and, to a lesser extent, PDDA itself induced the disappearance of liquid-ordered domains. We hypothesize this effect is due to an increase in energy per unit area caused by collisions between PDDA-coated quantum dots at the membrane surface. This increase in free energy per area exceeds the approximate free-energy change associated with membrane mixing between the liquid-ordered and liquid-disordered phases and results in the destabilization of membrane domains.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Quaternary Amine-Terminated Quantum Dots Induce Structural Changes to Supported Lipid Bilayers

et al. 2018

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“…• ncti « n-ncii-1 * n-ncvs figure 2: Effect of the position of cis-double bonds, ncit, on the chain-melting phase-transition temperature of symmetric monounsaturated dioctadecenoylphosphatidylcholines. The filled circles show the transition-temperatures values reported by Barton and Gunstone (1975) for * < 0.5n; original data (bullets), supplemented with the corresponding Tm(nt¡) data of the saturated phosphatidylcholines (crosses) are shown in the insert to the main figure body. Dots in the main figure pertain to the corresponding ^> 0.5n data mirrored around the = 10 point.…”

Section: Hydrocarbon Effectsmentioning

confidence: 99%

“…It has been hardly attempted to date, however, to calculate the gel-to-fluid phase-transition temperature, even of most common phospholipids, as a function of the chain unsaturation or asymmetry. One of the few successful attempts was the approach of Berde et al (1980), who have theoretically reproduced the experimental data of Barton and Gunstone (1975) with a somewhat better than 7% accuracy.…”

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confidence: 99%

How membrane chain-melting phase-transition temperature is affected by the lipid chain asymmetry and degree of unsaturation: an effective chain-length model

Cevc¹

1991

Biochemistry

144

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Hydrocarbon effects on the lipid chain-melting phase-transition temperature are analyzed. The membrane fluidization temperature is shown to increase with the effective chain length, which is proportional to the thickness of the well-packed hydrocarbon region. The latter, as a rule, increases with the length of the longest ordered and aligned segment on each chain. This conclusion is independent of the cause for the reduced chain packing in membrane interior: chain unsaturation (which effectively decouples the two hydrocarbon segments disjoined by a double bond) or chain asymmetry (which causes the terminal hydrocarbon segments to lose close contact) both affect the bilayer chain-melting phase-transition temperature comparably on the effective chain-length scale. Thermodynamic consequences of the trans unsaturation are approximately 50% smaller than the effects of the double bonds in the cis conformation, owing to the smaller membrane perturbation by the former double bonds. A simple quantitative model is introduced for the analysis of the phospholipid chain-melting phase behavior. This new model permits quantitative predictions of the chain-melting transition temperature solely on the basis of the known lipid chemical composition. It also explains lipid sensitivity to the hydrocarbon type and attachment. The model agreement with the experimental data is usually better than to within 99% and thus comparable to experimental scatter, even when only a few or no adjustable parameters are used. The membrane fluidization temperature is calculated for a number of potentially interesting, also as yet unexplored, phospholipids, and the biological significance of the effective chain-length concept is discussed.

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“…Matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) imaging has been used to determine the co-localization of hypoxia-driven lipids and proteins in a breast tumor model . However, it would be useful to extend the use of MSI to differentiate between isomers because unsaturated lipids usually contain several isomers, which often have considerable differences in biological functionality. − Additionally, the ratios of the isomers of unsaturated lipids in diseased tissues are considerably altered from those in normal tissues …”

Section: Introductionmentioning

confidence: 99%

Rapid Imaging of Unsaturated Lipids at an Isomeric Level Achieved by Controllable Oxidation

et al. 2021

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Lipid imaging plays an important role in the research of some diseases, such as cancers. Unsaturated lipids are often present as isomers that can have different functions; however, traditional tandem mass spectrometry imaging (MSI) cannot differentiate between different isomers, which presents difficulties for the pathological study of lipids. Herein, we propose a method for the MSI of the CC double-bond isomers of unsaturated lipids based on oxidative reactions coupled with air flow-assisted desorption electrospray ionization, which can conveniently achieve rapid MSI of unsaturated lipids at an isomeric level. Using this method, tissue sections can be scanned directly with MSI after only 10 min of accelerated oxidation. This method was used for the imaging of mouse lung cancer tissues, revealing a distributional difference in the unsaturated lipid isomers of normal and pathological regions. Through the MSI of unsaturated lipids at an isomeric level in tissues infected with cancer cells, the regions where the isomers were enriched were exhibited, indicating that these regions were the most concentrated regions of cancer cells. This method provides a convenient platform for studying the functional effects of the isomers of unsaturated lipids in pathological tissues.

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Hydrocarbon chain packing and molecular motion in phospholipid bilayers formed from unsaturated lecithins. Synthesis and properties of sixteen positional isomers of 1,2-dioctadecenoyl-sn-glycero-3-phosphorylcholine.

Cited by 221 publications

References 36 publications

Quaternary Amine-Terminated Quantum Dots Induce Structural Changes to Supported Lipid Bilayers

Quaternary Amine-Terminated Quantum Dots Induce Structural Changes to Supported Lipid Bilayers

How membrane chain-melting phase-transition temperature is affected by the lipid chain asymmetry and degree of unsaturation: an effective chain-length model

Rapid Imaging of Unsaturated Lipids at an Isomeric Level Achieved by Controllable Oxidation

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