Chitosan is a hydrophilic polymer with prominent mucoadhesive properties. However, it forms weak hydrogen bonds with mucin thus limiting its mucoadhesion and exhibit reduced bioavailability due to its short retention time in the body. The aim of the present study was to synthesize and characterize novel thiolated chitosan with improved functional property. A unique approach of using molecular docking to select ligand to chemically modify chitosan has been employed in the present research. A set of ligands were screened virtually using docking analysis and 2‐mercapto benzoic acid showed the lowest glide score of −4.31 Kcal/Mol thus displayed better binding interaction with chitosan. Based on the docking results, the best‐fit ligand was selected for wet lab synthesis. 2‐Mercapto benzoic acid was covalently attached to chitosan via formation of an amide bond and the reaction was mediated by carbodiimide and N‐hydroxysuccinimide. The synthesized polymer was in turn evaluated for zeta potential, Fourier transformed infrared, differential scanning calorimetry, molecular weight that confirmed conjugation of chitosan with the thiol ligand. The prepared thiomer was further subjected to mucoadhesion studies and displayed better mucoadhesion properties as compared to unmodified chitosan. Thus, the potential of the novel thiomer can be further explored as an excipient for drug delivery system with an emphasis on mucoadhesion.

中文翻译：

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壳聚糖-接枝-2-巯基苯甲酸衍生物作为潜在药物载体的分子对接，合成和表征

壳聚糖是具有突出的粘膜粘附特性​​的亲水性聚合物。但是，它与粘蛋白形成弱的氢键，从而限制了其粘膜粘附并由于其在体内的保留时间短而显示出降低的生物利用度。本研究的目的是合成和表征具有改进功能特性的新型硫醇化壳聚糖。在本研究中已采用了一种独特的方法，该方法使用分子对接来选择配体以化学修饰壳聚糖。使用对接分析实际上筛选了一组配体，2-巯基苯甲酸的滑移分数最低，为−4.31 Kcal / Mol，因此与壳聚糖的结合相互作用更好。根据对接结果，选择最适合的配体进行湿法实验室合成。N-羟基琥珀酰亚胺。依次评估合成的聚合物的ζ电位，傅立叶变换红外光谱，差示扫描量热法，分子量，证实了壳聚糖与硫醇配体的结合。与未改性的壳聚糖相比，所制备的硫醇聚合物进一步经受粘膜粘附性研究并显示出更好的粘膜粘附性。因此，可以进一步探索新型硫代聚合物作为药物递送系统的赋形剂的潜力，重点是粘膜粘附。