Enhanced assembly stability for amine-based cationic glycolipid.

Autor: Aravindan D; Chemistry Department, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia., Alagan AA; Chemistry Department, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia., Heidelberg T; Chemistry Department, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia. Electronic address: heidelberg@um.edu.my., Cheng SF; Chemistry Department, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia., Duali Hussen RS; Chemistry Department, Faculty of Science, University of Malaya, 50603, Kuala Lumpur, Malaysia.
Jazyk: angličtina
Zdroj: Carbohydrate research [Carbohydr Res] 2024 Sep; Vol. 543, pp. 109224. Date of Electronic Publication: 2024 Jul 29.
DOI: 10.1016/j.carres.2024.109224
Abstrakt: Glycolipids incorporating positive charges, mediated by an imidazolium cation, have shown potential for effective formulation of vesicular drug carriers, reflecting repulsive electrostatic forces, promoting the formation of nanosized assemblies and preventing unwanted Oswald ripening (Goh et al. (2019), ACS Omega 4, 17,039). Our continuous development of an assembly-based drug delivery system prompted us to investigate a pH-sensitive analogue, leading to the synthesis of a 6-amino-Guerbet glycoside. However, in contrast to the imidazolium counterpart, the amine-mediated charge increased the intermolecular cohesions, furnishing bigger assemblies instead, which further increased upon introduction of acid. Moreover, assemblies exhibited a significantly reduced positive charge density. It is concluded that strong proton-initiated hydrogen bonding between amino groups provide cohesive head group interactions overcompensating possible repulsive charge interactions. While this behavior invalidates the application of the amino-glucoside as dispersing agent for the formulation of small vesicles, it potentially paves a route towards enhanced vesicle stability.
Competing Interests: Declaration of competing interest The authors declare the following financial interests/personal relationships which may be considered as potential competing interests: Thorsten Heidelberg reports financial support was provided by PETRONAS Research Sdn Bhd. Thorsten Heidelberg has patent A FUNCTIONALIZED GLYCOLIPID AND AN APPLICATION THEREOF pending to Universiti Malaya. If there are other authors, they declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.
(Copyright © 2024 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
Externí odkaz: