Chemical Communications · 2016 · 21 citations · 16 references
Life SciencesBiochemistryBioisosterismLipid BiochemistryMembrane BiochemistryBiological MembranesLipid Bilayer StructureLipid BilayersLipid ChemistryLipid StructureMembrane Lipid CompositionLarge Unilamellar VesiclesLipid Bilayer MembranesLipid VesiclesLiposomesPhase Transition TemperaturePhospholipid BilayersPhysicochemical PropertiesPolar Lipids
We describe a novel class of amphiphiles with squaramide moiety as a phosphate bioisostere. Most synthesized squaramide-based amphiphiles have the favorable physicochemical properties of lipids, such as: formation of stable liposomes or giant unilamellar vesicles in aqueous solution, high phase-transition temperature, low vesicle leakage and phospholipase resistance properties.
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The use of phosphate bioisosteres in medicinal chemistry and chemical biology
Thomas Elliott, Aine Slowey, Yulin Ye et al. · MedChemComm · 2012 · 184 citations