Hyaluronic acid L-cysteine conjugate exhibits controlled-release potential for mucoadhesive drug delivery

Pharmazie. 2012 Mar;67(3):224-8.

Abstract

Hyaluronic acid-L-cysteine conjugate, a novel thiolated polymer, was synthesized and characterized for mucoadhensive drug delivery. L-Cysteine was covalently attached to hyaluronic acid via the formation of an amide bond. Adhesion studies on the mucosa indicated a 4.82-fold increase in the adhesion force of the obtained conjugate (containing 210.58 micromol thiol groups per gram polymer) versus unmodified hyaluronic acid. The results of a peptidase inhibition study revealed that the inhibitory effect of hyaluronic acid toward trypsin and chymotrypsin was significantly improved compared to hyaluronic acid. Permeation studies utilizing a MDCK cell monolayer system demonstrated a sustained drug release. Based on these features the novel thiolated polymer might represent a promising multifunctional excipient for various drug delivery systems.

MeSH terms

  • Animals
  • Cell Line
  • Cell Membrane Permeability / drug effects
  • Cell Survival / drug effects
  • Chymotrypsin / antagonists & inhibitors
  • Coloring Agents
  • Cysteine / chemical synthesis
  • Cysteine / chemistry*
  • Cysteine / pharmacology
  • Delayed-Action Preparations
  • Dogs
  • Drug Delivery Systems
  • Excipients
  • Hyaluronic Acid / chemical synthesis
  • Hyaluronic Acid / chemistry*
  • Hyaluronic Acid / pharmacology
  • Intestines / enzymology
  • Mucous Membrane
  • Protease Inhibitors / pharmacology
  • Sulfhydryl Compounds / chemistry
  • Tetrazolium Salts
  • Thiazoles
  • Tissue Adhesives*
  • Trypsin Inhibitors / pharmacology

Substances

  • Coloring Agents
  • Delayed-Action Preparations
  • Excipients
  • Protease Inhibitors
  • Sulfhydryl Compounds
  • Tetrazolium Salts
  • Thiazoles
  • Tissue Adhesives
  • Trypsin Inhibitors
  • Hyaluronic Acid
  • Chymotrypsin
  • thiazolyl blue
  • Cysteine