10.1007/s40204-022-00201-x

Tailoring the properties of chitosan by grafting with 2-mercaptobenzoic acid to improve mucoadhesion: in silico studies, synthesis and characterization

  • Tejinder K. Marwaha*1,
  • Ashwini Madgulkar1,
  • Mangesh Bhalekar1,
  • Kalyani Asgaonkar2,
  • Rajesh Gachche3,
  • Pallavi Shewale3,
  1. Department of Pharmaceutics, AISSMS College of Pharmacy, RB Motilal Kennedy Rd, Near RTO, Pune, Maharashtra, 411001, IN
  2. Department of Chemistry, AISSMS College of Pharmacy, Pune, IN
  3. Department of Biotechnology, Savitribaiphule Pune University, Pune, IN

Published in Issue 2022-10-07

How to Cite

Marwaha, T. K., Madgulkar, A., Bhalekar, M., Asgaonkar, K., Gachche, R., & Shewale, P. (2022). Tailoring the properties of chitosan by grafting with 2-mercaptobenzoic acid to improve mucoadhesion: in silico studies, synthesis and characterization. Progress in Biomaterials, 11(4 (December 2022). https://doi.org/10.1007/s40204-022-00201-x
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Abstract

Abstract Mucoadhesive polymers improve oral bioavailability of drugs by prolonging the duration of adhesion of drugs with mucosa. Various methods could be employed to address the problems of mucoadhesive polymers like weak adhesion forces. Chemical modification of polymers, such as the addition of a thiol group or thiolation, is another way for improving the polymers’ mucoadhesive properties that is studied in present research work. A novel thiomer of chitosan was prepared by attaching 2-mercaptobenzoic acid, a hydrophobic ligand onto it. The docking of thiomer and chitosan with mucin structure showed higher binding energy for former. The prepared thiomer was subjected to X-ray diffraction and DSC which established reduction in crystallinity and formation of a new compound through changes in glass transition, melting point and change in diffraction pattern. The NMR studies established conjugation of 2-mercapto benzoic acid to chitosan. The increased mucoadhesion in thiomer behaviour (2–3 fold) was confirmed through mucus glycoprotein assay as well as through texture analysis. The permeation enhancing the property of thiomer was established by demonstrating the permeation of phenol red across thiomer treated intestinal membrane. An in vitro cell toxicity assay was done to establish toxicity of chitosan and thiolated chitosan. Finally, the reduced water uptake of thiomer over chitosan proved that the increase in mucoadhesion is not contributed by swelling. Thus, a thiomer with improved mucoadhesion and enhanced permeation properties was prepared and characterized. Hence, all these properties render the newly synthesized polymer a better alternative to chitosan as an excipient for mucoadhesive drug delivery systems.

Keywords

  • Chitosan,
  • Thiomer,
  • Mucin,
  • Mucoadhesion,
  • Docking

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