title: Interactions of sugar-based bolaamphiphiles with biomimetic systems of plasma membranes.
abstract: Glycolipids constitute a class of molecules with various biological activities. Among them, sugar-based bolaamphiphiles characterized by their biocompatibility, biodegradability and lower toxicity, became interesting for the development of efficient and low cost lipid-based drug delivery systems. Their activity seems to be closely related to their interactions with the lipid components of the plasma membrane of target cells. Despite many works devoted to the chemical synthesis and characterization of sugar-based bolaamphiphiles, their interactions with plasma membrane have not been completely elucidated. In this work, two sugar-based bolaamphiphiles differing only at the level of their sugar residues were chemically synthetized. Their interactions with membranes have been investigated using model membranes containing or not sterol and with in silico approaches. Our findings indicate that the nature of sugar residues has no significant influence for their membrane interacting properties, while the presence of sterol attenuates the interactions of both bolaamphiphiles with the membrane systems. The understanding of this distinct behavior of bolaamphiphiles towards sterol-containing membrane systems could be useful for their applications as drug delivery systems.
authors.affiliation: Laboratoire de Biophysique Moléculaire aux Interfaces, Gembloux Agro-Bio Tech, Université de Liège, 2, Passage des Déportés, B-5030 Gembloux, Belgium. Electronic address: mn.nasir@ulg.ac.be.
authors.forename: Mehmet Nail
authors.initials: MN
authors.lastname: Nasir
authors.affiliation: Laboratoire de Biophysique Moléculaire aux Interfaces, Gembloux Agro-Bio Tech, Université de Liège, 2, Passage des Déportés, B-5030 Gembloux, Belgium.
authors.forename: Jean-Marc
authors.initials: JM
authors.lastname: Crowet
authors.affiliation: Laboratoire de Biophysique Moléculaire aux Interfaces, Gembloux Agro-Bio Tech, Université de Liège, 2, Passage des Déportés, B-5030 Gembloux, Belgium.
authors.forename: Laurence
authors.initials: L
authors.lastname: Lins
authors.affiliation: Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, UFR Sciences, Boîte n° 44 BP 1039, F-51687 Reims Cedex 2, France.
authors.forename: Firmin
authors.initials: F
authors.lastname: Obounou Akong
authors.affiliation: Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, UFR Sciences, Boîte n° 44 BP 1039, F-51687 Reims Cedex 2, France.
authors.forename: Arnaud
authors.initials: A
authors.lastname: Haudrechy
authors.affiliation: Institut de Chimie Moléculaire de Reims, UMR CNRS 7312, UFR Sciences, Boîte n° 44 BP 1039, F-51687 Reims Cedex 2, France.
authors.forename: Sandrine
authors.initials: S
authors.lastname: Bouquillon
authors.affiliation: Laboratoire de Biophysique Moléculaire aux Interfaces, Gembloux Agro-Bio Tech, Université de Liège, 2, Passage des Déportés, B-5030 Gembloux, Belgium. Electronic address: magali.deleu@ulg.ac.be.
authors.forename: Magali
authors.initials: M
authors.lastname: Deleu
mesh_terms: D000327:Adsorption; D001665:Binding Sites; D001667:Binding, Competitive; D001672:Biocompatible Materials / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D032701:Biomimetics; D002462:Cell Membrane / Q000737:chemistry* / Q000378:metabolism; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D006017:Glycolipids / Q000737:chemistry / Q000378:metabolism; D057927:Hydrophobic and Hydrophilic Interactions; D008051:Lipid Bilayers / Q000737:chemistry / Q000378:metabolism; D008958:Models, Molecular; D011728:Pyridones / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D012210:Rhamnose / Q000737:chemistry* / Q000378:metabolism; D017550:Spectroscopy, Fourier Transform Infrared; D013261:Sterols / Q000737:chemistry / Q000378:metabolism; D014994:Xylose / Q000737:chemistry* / Q000378:metabolism
chemical_list: D001672:Biocompatible Materials; D005663:Furans; D006017:Glycolipids; D008051:Lipid Bilayers; D011728:Pyridones; D013261:Sterols; C543575:bolaamphiphile; D014994:Xylose; D012210:Rhamnose
keywords: Cholesterol influence; Glycolipid; IR spectroscopy; In silico analysis; Isothermal titration calorimetry; Langmuir monolayer; Membrane interaction