Cation-stimulated drug delivery via lipid assembly comprising macrocyclized disaccharides - A DFT study.
Cation templated macrocycle synthesis
Coordination-induced conformation change
Glycolipid crown ether
Packing theory
Journal
Carbohydrate research
ISSN: 1873-426X
Titre abrégé: Carbohydr Res
Pays: Netherlands
ID NLM: 0043535
Informations de publication
Date de publication:
Oct 2023
Oct 2023
Historique:
received:
11
06
2023
revised:
07
08
2023
accepted:
09
08
2023
medline:
28
8
2023
pubmed:
21
8
2023
entrez:
20
8
2023
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 37598565
pii: S0008-6215(23)00185-4
doi: 10.1016/j.carres.2023.108923
pii:
doi:
Substances chimiques
Disaccharides
0
Lactose
J2B2A4N98G
Alkalies
0
Cations
0
Glycolipids
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
108923Informations de copyright
Copyright © 2023 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Thorsten Heidelberg has received industrial research funding from Petronas R&D Sdn. Bhd., Malaysia.