El-Qarra Lamisse H, Cosottini Niccolò, Tangsombun Chayanan, Smith David K
Department of Chemistry, University of York, Heslington, York, YO10 5DD, UK.
Chemistry. 2024 Dec 23;30(72):e202402530. doi: 10.1002/chem.202402530. Epub 2024 Nov 13.
A two-component low-molecular-weight gelator (LMWG) formed from a modified amino acid and an aldehyde was formulated with active pharmaceutical ingredients (APIs). Basic APIs (propranolol, atropine) can be mixed with the LMWG prior to gel assembly while acidic APIs (naproxen, rosuvastatin) inhibit assembly by disrupting the LMWG imine bond and were loaded by diffusion after gel assembly. For diffusion-loaded gels, the API in the liquid-like phase was rapidly released, with the remainder, interacting with gel fibres, retained in the gel. Rosuvastatin release was particularly low with Saturation Transfer Difference (STD) NMR indicating interactions between the aromatic ring and the self-assembled gel network. Propranolol also interacted with the gel via its aromatic unit, and its release led to gel erosion. Using agarose as a polymer gelator additive reinforced the gel, restricting erosion. In contrast, atropine was readily released over a period of hours - it is primarily in the liquid-like phase with STD NMR indicating no interactions with the gel network. The atropine-loaded gel retained its thixotropic properties. Overall, APIs must be carefully chosen to optimise formulation/release. Of the APIs investigated, atropine has most potential for further development. Atropine has applications in treating myopia, and our results suggest potential ophthalmic applications of supramolecular gels.
由一种改性氨基酸和一种醛形成的双组分低分子量凝胶剂(LMWG)与活性药物成分(API)一起被配制。碱性API(普萘洛尔、阿托品)可在凝胶组装前与LMWG混合,而酸性API(萘普生、瑞舒伐他汀)会破坏LMWG亚胺键从而抑制组装,并在凝胶组装后通过扩散进行负载。对于扩散负载的凝胶,处于类液相的API会迅速释放,其余与凝胶纤维相互作用的API则保留在凝胶中。瑞舒伐他汀的释放特别低,饱和转移差(STD)核磁共振表明其芳香环与自组装凝胶网络之间存在相互作用。普萘洛尔也通过其芳香单元与凝胶相互作用,其释放导致凝胶侵蚀。使用琼脂糖作为聚合物凝胶剂添加剂可增强凝胶,限制侵蚀。相比之下,阿托品在数小时内很容易释放——它主要处于类液相,STD核磁共振表明其与凝胶网络没有相互作用。负载阿托品的凝胶保留了其触变性。总体而言,必须谨慎选择API以优化制剂/释放。在所研究的API中,阿托品具有最大的进一步开发潜力。阿托品在治疗近视方面有应用,我们的结果表明超分子凝胶在眼科方面具有潜在应用。