Aravindan, Deepalakshmi and Alagan, Addison Alvin and Heidelberg, Thorsten and Cheng, Sit Foon and Hussen, Rusnah Syahila Duali (2024) Enhanced assembly stability for amine-based cationic glycolipid. Carbohydrate Research, 543. p. 109224. ISSN 0008-6215, DOI https://doi.org/10.1016/j.carres.2024.109224.
Full text not available from this repository.Abstract
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 pHsensitive 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.
| Item Type: | Article |
|---|---|
| Funders: | Petronas RD D Sdn (PV050-2018) |
| Uncontrolled Keywords: | Guerbet glycoside; Vesicular drug delivery; Acid-induced hydrogen bonding; Vesicle formulation; Particle size modulation; Oswald ripening |
| Subjects: | Q Science > QD Chemistry |
| Divisions: | Faculty of Science > Department of Chemistry |
| Depositing User: | Ms. Juhaida Abd Rahim |
| Date Deposited: | 07 Apr 2025 03:17 |
| Last Modified: | 07 Apr 2025 03:17 |
| URI: | http://eprints.um.edu.my/id/eprint/46763 |
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