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Simple Synthesis of Organo-soluble Chitosan Precursors and Maleic Chitosan-derived Biomaterial

Detailed Technology Description
The invention involves the simple synthesis of novel chitosan precursors that are organo-soluble and serve as core starting biomaterials for the development of maleic chitosan (MC), an anhydride chitosan derivative.
Others
  • Chih-chang Chu, Chao Zhong. “Organo-Soluble Chitosan Saltsand Chitosan-Derived Biomaterials Prepared Thereof” US Patent Number: 8,841,440
  • Chao Zhong, Jun Wu, C.A. Reinhart-King, C.C. Chu.“Synthesis, characterization and cytotoxicity of photo-crosslinked maleicchitosan-polyethylene glycol diacrylate hybrid hydrogels. Acta Biomaterialia, Volume 6, Issue 10, October 2010, Pages 3908-3918. DOI: 10.1016/j.actbio.2010.04.011
*Abstract

The present invention involves the synthesis of novel chitosan precursors that are organo-soluble and serve as core starting biomaterials for the development of maleic chitosan (MC), an anhydride chitosan derivative. The novel precursors are prepared in a simple one-step reaction in water and at room temperature. Their good solubility in common organic solvents enables a platform where many subsequent reactions can be carried out under mild homogeneous conditions that were previously not feasible or difficult to control.

 

MC has been designed based on the novel precursors, synthesized and characterized so that the resulting product could be fabricated into either viscous or solid gels from aqueous solution via photopolymerization means. These gels have controllable pore sizes and controllable amounts of anionic ligand sites to induce bone mineral formation. Preliminary biomineralization data using MC gels as organic scaffold hold great promise that the material is ideally suited to mimic the natural nucleation and growth of bone minerals within an organic matrix. In vitro cytotoxity data confirm the biocompatibility of the MC gels.

 

This figure contains images of maleic chitosan hydrogels. On the left is a digital image; on the right is a SEM image.

   

Potential Applications
  • Bone regeneration, dentistry (biomineralization templates)
  • Tissue engineering scaffolds
  • Drug, growth factor, and cell delivery
  • Contact lens solutions
  • Blood clotting bandages
  • Skin and hair care
  • Agricultural applications (fertilizer)
  • Antimicrobial textiles

   

Advantages
  • One-step reaction in water at room temperature in relatively short time
  • Involves no harsh heterogeneous reaction conditions
  • No expensive and complicated (multi-step) protection and deprotection protocols required
    • Increased yield of final product
    • Reduced susceptibility to backbone degradation (molecular weight loss)
  • Create new reaction sites of chitosan that would allow for a broader chemical modification
  • Allows higher degree of substitution and increased control of substitution position
  • Can be biofunctionalized via attaching bioactive agents
  • Biocompatible and biodegradable
  • Abundant natural raw materials (chitosan)
*Licensing
Martin Teschlmt439@cornell.edu(607) 254-4454
Country/Region
USA

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