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Preparation and characterization of PEGylated chitosan nanocapsules as a carrier for pharmaceutical application

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Abstract

A new method to conjugate methoxy polyethylene glycol (mPEG) to C6 position of chitosan under the mild condition is introduced that improves the biocompatibility and water solubility of chitosan. Harsh deprotecting step and several purification cycles are two major disadvantages of the current methods for preparing PEGylated chitosan. In this study, the amine groups at C2 position of chitosan are protected using SDS followed by grafting the PEG. The protecting group of chitosan is simply removed by dialyzing against Tris solution. The chemical structure of the prepared polymer is characterized by FTIR and 1H NMR spectroscopy. Fourier transformed-infrared (FT-IR) and 1H NMR spectra confirmed that the mPEG is successfully grafted to C6 position of chitosan. Prepared methoxy polyethylene glycol (mPEG) is then employed to prepare the nanocapsules for the encapsulation of poor water-soluble drug, propofol. The TEM, AFM, and DLS techniques are used to characterize the prepared nanocapsules size and morphology. The results show a size of about 80 nm with spherical shape for nanocapsules. In vitro drug release is carried out to evaluate the potential of nanocarriers for the intravenous delivery of drugs. The profile of release from formulated nanocapsules is similar to those of commercial lipid emulsion (CLE). In vivo animal sleep-recovery test on rats shows a close similarity between the time of unconsciousness and recovery of righting reflex between nanoparticles and CLE. This study provides an efficient, novel, and easy method for preparing a carrier system that requires less intensive reaction conditions, fewer reaction steps, and less purification steps. In addition, the nanocapsules introduced here could be a promising nano carrier for the delivery of poor water-soluble drugs.

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Acknowledgments

The authors wish to express their gratitude to Iran National Science Foundation (INSF) and Amirkabir University of Technology for their support in carrying out this project. We would also like to thank Prof. A. Khademhosseini (Hravard medical school), Ms. F. Khosravi, and Dr. Ramin Omidvar in nano lab of Amirkabir University of Technology for their help.

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Authors and Affiliations

  1. Department of Chemistry, Amirkabir University of Technology, Tehran, P.O. Box 1587-4413, Iran

    Alireza Hassani Najafabadi & Majid Abdouss

  2. Tissue Engineering and Biomaterials Division, National Institute of Genetic Engineering and Biotechnology, Tehran, 14965/161, Iran

    Shahab Faghihi

Authors
  1. Alireza Hassani Najafabadi
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  2. Majid Abdouss
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  3. Shahab Faghihi
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Correspondence to Majid Abdouss.

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Najafabadi, A.H., Abdouss, M. & Faghihi, S. Preparation and characterization of PEGylated chitosan nanocapsules as a carrier for pharmaceutical application. J Nanopart Res 16, 2312 (2014). https://doi.org/10.1007/s11051-014-2312-7

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