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Updated: Dec 6, 2025
Fabrication of Size-Controlled and Emulsion-Free Chitosan-Genipin Microgels for Tissue Engineering Applications
Published on: April 13, 2022
An applied quantum-chemical model for genipin-crosslinked chitosan (GCS) nanocarrier
Marjan Nasrabadi1, Ali Morsali1, S Ali Beyramabadi1
1Department of Chemistry, Mashhad Branch, Islamic Azad University, Mashhad, Iran; Research Center for Animal Development Applied Biology, Mashhad Branch, Islamic Azad University, Mashhad 917568, Iran.
Abstract:
The genipin-crosslinked chitosan (GCS) nanocarrier has received a lot of attention due to its unique biological and chemical properties as an effective drug delivery system. GCS was modeled by considering two chitosan (CS) polymer sequences with six monomer units that are crosslinked by genipin. To investigate the characteristics of this model, we considered it as a nanocarrier of the anti-cancer drug cladribine (2CdA). Seven configurations of GCS and 2CdA (GCS/2CdA1-7) were optimized at M06-2X/6-31G(d,p) in aqueous solution. The average binding energy above 100 kJ mol-1 indicates a high drug loading amount. The high adsorption of the drug on GCS is due to the hydrogen bonds that were investigated by AIM analysis. Hydrogen bonds also allow the drug to be released more slowly. These results were confirmed by experimental evidence and the comparison of this model with the simple model of one polymer chain. Also, the mechanism of GCS formation was investigated by calculating the activation parameters, which indicates that solvent (H2O) molecules are explicitly involved in the formation of GCS.
