In Vitro Investigation of Thiolated Chitosan Derivatives as Mucoadhesive Coating Materials for Solid Lipid Nanoparticles,Biomacromolecules

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In Vitro Investigation of Thiolated Chitosan Derivatives as Mucoadhesive Coating Materials for Solid Lipid Nanoparticles
Biomacromolecules ( IF 5.5 ) Pub Date : 2021-08-30 , DOI: 10.1021/acs.biomac.1c00776
Richard Wibel ₁ , Doris E Braun ₁ , Laurenz Hämmerle ₁ , Arne M Jörgensen ₁ , Patrick Knoll ₁ , Willi Salvenmoser ₂ , Christian Steinbring ₁ , Andreas Bernkop-Schnürch ₁

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In the present study, chitosan (CS) was thiolated by introducing l-cysteine via amide bond formation. Free thiol groups were protected with highly reactive 6-mercaptonicotinic acid (6-MNA) and less-reactive l-cysteine, respectively, via thiol/disulfide-exchange reactions. Unmodified CS, l-cysteine-modified thiolated CS (CS-Cys), 6-MNA-S-protected thiolated CS (CS-Cys-MNA), and l-cysteine-S-protected thiolated CS (CS-Cys-Cys) were applied as coating materials to solid lipid nanoparticles (SLN). The strength of mucus interaction followed the rank order plain < CS < CS-Cys-Cys < CS-Cys < CS-Cys-MNA, whereas mucus diffusion followed the rank order CS-Cys < CS-Cys-Cys < CS < CS-Cys-MNA < plain. In accordance with lower reactivity, CS-Cys-Cys-coated SLN were immobilized to a lower extent than CS-Cys-coated SLN, while CS-Cys-MNA-coated SLN dissociated from their coating material resulting in a similar diffusion behavior as plain SLN. Consequently, CS-Cys-Cys-coated SLN and CS-Cys-MNA-coated SLN showed the highest retention on porcine intestinal mucosa by enabling a synergism of efficient mucus diffusion and strong mucoadhesion.

中文翻译：

硫醇化壳聚糖衍生物作为固体脂质纳米颗粒粘膜粘附涂层材料的体外研究

在本研究中，壳聚糖 (CS)通过酰胺键形成引入l-半胱氨酸而被硫醇化。通过硫醇/二硫化物交换反应，游离硫醇基团分别用高反应性 6-巯基烟酸 (6-MNA) 和反应性较低的l-半胱氨酸保护。未修饰的 CS、l-半胱氨酸修饰的硫醇化 CS (CS-Cys)、6-MNA-S-保护的硫醇化 CS (CS-Cys-MNA) 和l-半胱氨酸-S-保护的硫醇化CS（CS-Cys-Cys）作为涂层材料应用于固体脂质纳米颗粒（SLN）。粘液相互作用的强度遵循普通 < CS < CS-Cys-Cys < CS-Cys < CS-Cys-MNA 的等级顺序，而粘液扩散遵循等级顺序 CS-Cys < CS-Cys-Cys < CS < CS- Cys-MNA < 平原。根据较低的反应性，CS-Cys-Cys 包覆的 SLN 的固定程度低于 CS-Cys 包覆的 SLN，而 CS-Cys-MNA 包覆的 SLN 与其包覆材料解离，导致与普通的扩散行为相似前哨淋巴结。因此，CS-Cys-Cys 包被的前哨淋巴结和 CS-Cys-MNA 包被的前哨淋巴结通过有效的粘液扩散和强黏膜粘附的协同作用在猪肠粘膜上显示出最高的保留。

更新日期：2021-09-13

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