Cation-stimulated drug delivery via lipid assembly comprising macrocyclized disaccharides: A DFT study
Document Type
Article
Publication Date
10-1-2023
Abstract
In the attempt to create a delivery system for an alkali-cation stimulated drug release, a computational study was conducted, aiming for the evaluation of synthetic access towards glycolipid crown ethers analogs and their potential for coordination-induced changes of packing constraints for molecular assemblies. The results disfavor amide-linkages for the creation of macrocycles around the inter-glycosidic bond of a disaccharide. Conformational changes upon cation coordination of the macrocycle decrease the intersection area for easily accessible macrocycles based on lactose. This leads to shrinking intersection areas upon alkali complexation. Maltose-based analogs, on the other hand, exhibited the targeted increase of the glycolipid intersection area and, hence, may be considered as a promising resource.
Keywords
Glycolipid crown ether, Cation templated macrocycle synthesis, Packing theory, Coordination-induced conformation change
Divisions
CHEMISTRY
Funders
Petronas R&D Sdn [Grant no. PV050-2018],Ministry of Higher Education, Malaysia [Grant no. FRGS/1/2019/STG01/UM/02/21],Universiti Malaya
Publication Title
Carbohydrate Research
Volume
532
Publisher
Elsevier
Publisher Location
125 London Wall, London, ENGLAND