scholarly journals Interactions of gangliosides with phospholipids and glycosphingolipids in mixed monolayers

1978 ◽  
Vol 175 (3) ◽  
pp. 1113-1118 ◽  
Author(s):  
B Maggio ◽  
F A Cumar ◽  
R Caputto
Keyword(s):  
Surface Potential ◽  
High Surface ◽  
Head Group ◽  
Polar Head Group ◽  
Molecular Area ◽  
Mixed Monolayers ◽  
Polar Head ◽  
Head Groups ◽  
Electrostatic Repulsions ◽  
The Ideal

1. The interactions among five different gangliosides and three chemically related glycosphingolipids and their behaviour in mixed monolayers with six different phospholipids were investigated at the air/145 mM-NaCl interface at pH 5.6. 2. The mixed monolayers of any of the different gangliosides showed an immiscible behaviour at high surface pressures, with absence of interactions among them revealed by an ideal behaviour for mean molecular area and surface potential per molecule. 3. This behaviour was probably the consequence of steric hindrance and electrostatic repulsions between their polar head groups. 4. Di- and tri-sialogangliosides could be differentiated from neutral sphingolipids and monosialogangliosides on the basis of their interactions with phospholipids, which were correlated to the perpendicular electric field at the interface contributed by the carbohydrate residues. 5. The presence of the phosphocholine polar head group in phosphatidylcholine was important to establish interactions with di- and tri-sialogangliosides revealed by negative deviations from the ideal behaviour for mean molecular areas and mean surface potential per molecule. 6. The possible significance of these observations is discussed in relation to the participation of gangliosides in the organization of membranes and to their capability of inducing membrane fusion.

scholarly journals Surface behaviour of gangliosides and related glycosphingolipids

1978 ◽  
Vol 171 (3) ◽  
pp. 559-565 ◽  
Author(s):  
B Maggio ◽  
F A Cumar ◽  
R Caputto
Keyword(s):  
Dipole Moment ◽  
Surface Potential ◽  
Progressive Increase ◽  
Head Group ◽  
Polar Head Group ◽  
Water Interface ◽  
Collapse Pressure ◽  
Polar Head ◽  
Air Water Interface ◽  
Electrostatic Repulsions

1. The surface behaviour of six different gangliosides and eight chemically related glycosphingolipids was investigated in monolayers at the air-water interface. 2. Mono-, di-, tri and tetra-hexosylceramides had force-area isotherms showing similar limiting molecular areas on 145 mM-NaCl, pH 5.6. The increasing number of negatively charged sialosyl residues in mono-, di- and tri-sialogangliosides induced a progressive increase in the liquid-expanded character of the films and in the limiting area occupied per molecule, owing to electrostatic repulsions. When the ganglioside monolayers were spread on subphases at pH 1.2, the limiting area per molecule was similar to that found for neutral glycosphingolipids. 3. The monolayer collapse pressure at pH 5.6 increased with the number of uncharged carbohydrate units up to when the polar head group contained 3-4 residues. For gangliosides the collapse pressures were lower and decreased from mono- to tri-sialogangliosides. Ganglioside monolayers on subphases at pH 1.2 showed increases in their collapse pressure. 4. The glycosphingolipid monolayers studied had various surface in their collapse pressure. 4. The glycosphingolipid monolayers studied had various surface potentials according to the complexity of the polar head group of the lipid. Attempts to calculate the dipolar contributions to the surface potential from each carbohydrate residue suggest that the second and third sialosyl residues in di- and tri-sialogangliosides contributed with a vertical dipole moment opposite to that of the first sialosyl residue.

scholarly journals Biosynthesis of Ether-Type Polar Lipids in Archaea and Evolutionary Considerations

2007 ◽  
Vol 71 (1) ◽  
pp. 97-120 ◽  
Author(s):  
Yosuke Koga ◽  
Hiroyuki Morii
Keyword(s):  
Mevalonate Pathway ◽  
Polar Lipids ◽  
In Vivo Studies ◽  
Head Group ◽  
Polar Head Group ◽  
Phospholipid Synthesis ◽  
Polar Head ◽  
Head Groups

SUMMARY This review deals with the in vitro biosynthesis of the characteristics of polar lipids in archaea along with preceding in vivo studies. Isoprenoid chains are synthesized through the classical mevalonate pathway, as in eucarya, with minor modifications in some archaeal species. Most enzymes involved in the pathway have been identified enzymatically and/or genomically. Three of the relevant enzymes are found in enzyme families different from the known enzymes. The order of reactions in the phospholipid synthesis pathway (glycerophosphate backbone formation, linking of glycerophosphate with two radyl chains, activation by CDP, and attachment of common polar head groups) is analogous to that of bacteria. sn-Glycerol-1-phosphate dehydrogenase is responsible for the formation of the sn-glycerol-1-phosphate backbone of phospholipids in all archaea. After the formation of two ether bonds, CDP-archaeol acts as a common precursor of various archaeal phospholipid syntheses. Various phospholipid-synthesizing enzymes from archaea and bacteria belong to the same large CDP-alcohol phosphatidyltransferase family. In short, the first halves of the phospholipid synthesis pathways play a role in synthesis of the characteristic structures of archaeal and bacterial phospholipids, respectively. In the second halves of the pathways, the polar head group-attaching reactions and enzymes are homologous in both domains. These are regarded as revealing the hybrid nature of phospholipid biosynthesis. Precells proposed by Wächtershäuser are differentiated into archaea and bacteria by spontaneous segregation of enantiomeric phospholipid membranes (with sn-glycerol-1-phosphate and sn-glycerol-3-phosphate backbones) and the fusion and fission of precells. Considering the nature of the phospholipid synthesis pathways, we here propose that common phospholipid polar head groups were present in precells before the differentiation into archaea and bacteria.

scholarly journals Phosphonodithioester–Amine Coupling as a Key Reaction Step for the Design of Cationic Amphiphiles Used for Gene Delivery

Molecules ◽  
2021 ◽  
Vol 26 (24) ◽  
pp. 7507
Author(s):  
Montassar Khalil ◽  
Alexis Hocquigny ◽  
Mathieu Berchel ◽  
Tristan Montier ◽  
Paul-Alain Jaffrès
Keyword(s):  
Cell Lines ◽  
Head Group ◽  
Polar Head Group ◽  
Polar Head ◽  
Cationic Amphiphiles ◽  
Head Groups ◽  
New Synthesis ◽  
Lipid Moiety ◽  
Low Charge ◽  
Amine Coupling

A convergent synthesis of cationic amphiphilic compounds is reported here with the use of the phosphonodithioester–amine coupling (PAC) reaction. This versatile reaction occurs at room temperature without any catalyst, allowing binding of the lipid moiety to a polar head group. This strategy is illustrated with the use of two lipid units featuring either two oleyl chains or two-branched saturated lipid chains. The final cationic amphiphiles were evaluated as carriers for plasmid DNA delivery in four cell lines (A549, Calu3, CFBE and 16HBE) and were compared to standards (BSV36 and KLN47). These new amphiphilic derivatives, which were formulated with DOPE or DOPE-cholesterol as helper lipids, feature high transfection efficacies when associated with DOPE. The highest transfection efficacies were observed in the four cell lines at low charge ratios (CR = 0.7, 1 or 2). At these CRs, no toxic effects were detected. Altogether, this new synthesis scheme using the PAC reaction opens up new possibilities for investigating the effects of lipid or polar head groups on transfection efficacies.

scholarly journals Niosomes based on synthetic cationic lipids for gene delivery: the influence of polar head-groups on the transfection efficiency in HEK-293, ARPE-19 and MSC-D1 cells

2015 ◽  
Vol 13 (4) ◽  
pp. 1068-1081 ◽  
Author(s):  
E. Ojeda ◽  
G. Puras ◽  
M. Agirre ◽  
J. Zárate ◽  
S. Grijalvo ◽  
...  
Keyword(s):  
Gene Delivery ◽  
Transfection Efficiency ◽  
Cationic Lipids ◽  
Head Group ◽  
Polar Head Group ◽  
Hek 293 ◽  
Polar Head ◽  
Head Groups

We designed niosomes based on three lipids that differed only in the polar-head group to analyze their influence on the transfection efficiency.

scholarly journals Configuration and interactions of the polar head group in gangliosides

1980 ◽  
Vol 189 (3) ◽  
pp. 435-440 ◽  
Author(s):  
Bruno Maggio ◽  
Federico A. Cumar ◽  
Ranwel Caputto
Keyword(s):  
Surface Potential ◽  
Head Group ◽  
Polar Head Group ◽  
Molecular Models ◽  
Molecular Plane ◽  
Polar Head ◽  
Moment Vector ◽  
Oligosaccharide Chain ◽  
Terminal Galactose ◽  
Surface Potential Measurements

1. The interactions of gangliosides with Ca2+ and some polar-head-group requirements for establishment of particular interactions with phosphatidylcholine were studied in monolayers at the air/145mm-NaCl interface. 2. Ganglioside–Ca2+ interactions, as revealed by surface-potential measurements, depended on the position occupied by sialosyl residues in the oligosaccharide chain. The interactions with Ca2+ of the single sialosyl residue of monosialogangliosides occurred above 0.1mm-CaCl2, whereas the interaction of the cation with additional sialosyl groups in di- or tri-sialogangliosides depended on the carbohydrate residue to which the sialosyl moiety was attached. The sialosyl residue bound in sialosyl–sialosyl linkage interacted very little with Ca2+. The sialosyl residue attached to the terminal galactose of the neutral tetrasaccharide chain interacted with Ca2+ above 1μm-CaCl2. 3. Experiments with mixed monolayers containing dihexadecyl phosphate and hexadecyltrimethylammonium indicated that for the occurrence of interactions of polysialogangliosides with phosphatidylcholine characterized by reductions in molecular packing and surface potential both charged groups of the phospholipid and sialosyl residues with particular dipolar properties in the ganglioside are participating. 4. Possible configurations that can explain the behaviour in monolayers were inspected with space-filling molecular models. The position of the carboxylate group of sialosyl residues with respect to the interface and to the sialosyl molecular plane can explain the different orientation of the dipole-moment vector of this residue, which depends on the position to which it is linked in the oligosaccharide chain. Favoured interactions of polysialogangliosides with phosphatidylcholine may result from a configuration allowing a partial matching of two oppositely oriented electrical vectors contributed by the zwitterionic phosphocholine group and particular sialosyl groups.

The effect of polar head group of dodecyl surfactants on the growth of wheat and cucumber

Chemosphere ◽  
2020 ◽  
Vol 254 ◽  
pp. 126918
Author(s):  
Aleksandar Tot ◽  
Ivana Maksimović ◽  
Marina Putnik-Delić ◽  
Milena Daničić ◽  
Slobodan Gadžurić ◽  
...  
Keyword(s):  
Head Group ◽  
Polar Head Group ◽  
Polar Head

Glycosylinositol phosphoceramide-specific phospholipase D activity catalyzes transphosphatidylation

2019 ◽  
Vol 166 (5) ◽  
pp. 441-448 ◽  
Author(s):  
Rumana Yesmin Hasi ◽  
Makoto Miyagi ◽  
Katsuya Morito ◽  
Toshiki Ishikawa ◽  
Maki Kawai-Yamada ◽  
...  
Keyword(s):  
Chain Length ◽  
Phospholipase D ◽  
Secondary Alcohol ◽  
Primary Alcohol ◽  
Tertiary Alcohol ◽  
Head Group ◽  
Polar Head Group ◽  
Polar Head ◽  
A Chain ◽  
Sugar Chains

Abstract Glycosylinositol phosphoceramide (GIPC) is the most abundant sphingolipid in plants and fungi. Recently, we detected GIPC-specific phospholipase D (GIPC-PLD) activity in plants. Here, we found that GIPC-PLD activity in young cabbage leaves catalyzes transphosphatidylation. The available alcohol for this reaction is a primary alcohol with a chain length below C4. Neither secondary alcohol, tertiary alcohol, choline, serine nor glycerol serves as an acceptor for transphosphatidylation of GIPC-PLD. We also found that cabbage GIPC-PLD prefers GIPC containing two sugars. Neither inositol phosphoceramide, mannosylinositol phosphoceramide nor GIPC with three sugar chains served as substrate. GIPC-PLD will become a useful catalyst for modification of polar head group of sphingophospholipid.

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