A modular approach towards drug delivery vehicles using oxanorbornane-based non-ionic amphiphiles

Abstract

The self-assembly of non-ionic amphiphiles with hydroxylated oxanorbornane head-group was controlled using amino acid units as spacers between hydrophilic and lipophilic domains to get spherical supramolecular aggregates suitable for drug delivery applications.

Self-assembly of amphiphilic amino acid derivatives for biomedical applications

“…The self-assembly mechanism was not clear, but it was certainly facilitated by the hydrophilic head groups generating a H-bond network and by alkyl chain clustering. 87 Further investigations for phenylalanine and valine spacers with C-7 tails showed that both molecules formed ''vesicle-liked'' structure in acetone with B20 nm membrane thickness, which were supposed to be solid nanoparticles with heterogeneous periphery causing by drying or staining. The relationship between the HLB of the molecules and the morphology of the aggregates was studied, indicating that a higher HLB (8.0-10.0) tended to lead to the formation of spherical structures.…”

“…Reproduced with permission. 87 Copyright 2016, the Royal Society of Chemistry. Reproduced with permission.…”

“…The relationship between the HLB of the molecules and the morphology of the aggregates was studied, indicating that a higher HLB (8.0-10.0) tended to lead to the formation of spherical structures. 87 The molecules with C-7 chains were exploited as carriers of the anti-inflammatory drug ibuprofen. For this purpose, a thin film was formed between the C-7 tailed molecules and ibuprofen, and the film was then hydrated in PBS.…”

1‐Hydroxymethyl‐7‐oxabicyclo[2.2.1]hept‐2‐ene skeleton in enantiopure form through enzymatic kinetic resolution

“…[48][49][50][51][52][53][54][55][56][57][58][59] Several strategies have been attempted to overcome this, such as the use of chiral or sterically demanding acyl donors, 56,60 optimization of solvation conditions, 61 or through sequential resolutions. [62][63][64][65] Since access to this skeleton in enantio-pure form would allow us to make comparative assessment of properties, we set out to investigate the lipase catalysed enantioselective acylation of 6 as shown in Scheme 1. Our group has been working on new functional mimics of glycolipids based on hydroxylated oxanorbornane head group, for use in drug delivery.…”

“…Our group has been working on new functional mimics of glycolipids based on hydroxylated oxanorbornane head group, for use in drug delivery. [62][63][64][65] Since access to this skeleton in enantio-pure form would allow us to make comparative assessment of properties, we set out to investigate the lipase catalysed enantioselective acylation of 6 as shown in Scheme 1.…”