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 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 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 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.

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.

Changes in phospholipid polar head group turnover in SV40-transformed hamster fibroblasts

FEBS Letters ◽  
1982 ◽  
Vol 139 (2) ◽  
pp. 217-220 ◽  
Author(s):  
Cécile Maziére ◽  
Jean-Claude Maziére ◽  
Liliana Mora ◽  
Jacques Polonovski
Keyword(s):  
Head Group ◽  
Polar Head Group ◽  
Polar Head
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