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Related Concept Videos

Lipids as Anchors01:32

Lipids as Anchors

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In the plasma membrane, the lipids forming the bilayer can also act as an anchor to tether proteins to the membrane. The three main types of lipid anchors found in eukaryotes are – prenyl groups, fatty acyl groups, and glycosylphosphatidylinositol or GPI groups. Prenyl and fatty acyl groups act as anchors on the cytosolic surface of the membrane, whereas GPI anchors proteins on the extracellular side.
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Protein glycosylation starts in the ER lumen and continues in the Golgi apparatus. Glycosyltransferases catalyze the addition of sugar molecules or glycosylation of proteins. Usually, these enzymes add sugars to the hydroxyl groups of selected serine or threonine residues to form O-linked glycans or the amino groups of asparagine residues to form N-linked glycans. Different positions on the same polypeptide chain can contain differently linked glycans.
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Enhanced assembly stability for amine-based cationic glycolipid.

Deepalakshmi Aravindan1, Addison Alvin Alagan1, Thorsten Heidelberg1

  • 1Chemistry Department, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia.

Carbohydrate Research
|July 31, 2024
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Summary

Positively charged glycolipids can form small drug carrier vesicles. However, a new amino-glucoside analogue forms larger assemblies due to hydrogen bonding, suggesting potential for enhanced vesicle stability rather than small vesicle formulation.

Keywords:
Acid-induced hydrogen bondingGuerbet glycosideOswald ripeningParticle size modulationVesicle formulationVesicular drug delivery

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Area of Science:

  • Supramolecular Chemistry
  • Materials Science
  • Drug Delivery

Background:

  • Positively charged glycolipids, like imidazolium-based ones, are effective in forming nanosized vesicular drug carriers.
  • These carriers utilize repulsive electrostatic forces to prevent aggregation and Oswald ripening.
  • The development of assembly-based drug delivery systems necessitates exploring new charged glycolipids.

Purpose of the Study:

  • To synthesize and characterize a pH-sensitive analogue of charged glycolipids.
  • To investigate the self-assembly behavior of a novel 6-amino-Guerbet glycoside.
  • To compare the assembly properties of the amino-glucoside with imidazolium-based glycolipids for drug delivery applications.

Main Methods:

  • Synthesis of a novel 6-amino-Guerbet glycoside.
  • Characterization of self-assembly behavior using techniques sensitive to size and charge.
  • Analysis of intermolecular interactions, including hydrogen bonding and electrostatic forces.

Main Results:

  • The 6-amino-Guerbet glycoside formed larger assemblies compared to imidazolium-based glycolipids.
  • Assembly size increased significantly upon acidification.
  • Assemblies exhibited reduced positive charge density due to strong hydrogen bonding between amino groups.
  • Intermolecular cohesion from hydrogen bonding overcompensated electrostatic repulsion.

Conclusions:

  • The strong proton-initiated hydrogen bonding in the amino-glucoside hinders its use as a dispersing agent for small vesicles.
  • The observed cohesive interactions suggest potential for developing more stable vesicular structures.
  • This finding opens new avenues for designing robust vesicle formulations with enhanced stability.