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Regioselective succinylation and gelation behavior of glycol chitosan

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Abstract

Chitosan is normally acylated and subsequently conjugated with drugs for biomedical applications. This study examined the relationship between the succinylation and gelation behaviors of glycol chitosan. Glycol chitosan was acylated with succinic anhydride under a wide variety of reaction conditions, such as different molar ratios of succinic anhydride to glucosamine, different methanol content in the reaction media, and different reaction temperatures. Among these reaction parameters, the methanol content in the solvent played an important role in determining the regioseletive succinylating site. N-succinylation and N-N cross-linking occurred regardless of the reaction conditions. However, O-succinylation was observed under specific conditions, i.e. a methanol content > 0.6 (v/v) and a reaction temperature > 25 °C. O-succinylation accelerated the N-O cross-linking of glycol chitosan, and led to gelation. The N-succinylated glycol chitosans were water-soluble, whereas the N- and O-succinylated glycol chitosans formed a gel. These physico-chemical structural differences in the succinylated glycol chitosans would definitely influence subsequent drug-conjugation reactions and consequently the drug loading and release kinetics.

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Authors and Affiliations

  1. Carbon Nanomaterials Design Laboratory, Hyperstructured Organic Materials Research Center (HOMRC), Department of Materials Science and Engineering, Seoul National University, 151-744, Seoul, Korea

    Keunsoo Jeong, Wonbum Lee, Jueun Cha & Chong Rae Park

  2. Department of Chemical Engineering, Hanyang University, 426-791, Ansan, Korea

    Yong Woo Cho

  3. Biomedical Research Center, Korea Institute of Science and Technology, 126-791, Seoul, Korea

    Ick Chan Kwon

Authors
  1. Keunsoo Jeong
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  2. Wonbum Lee
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  3. Jueun Cha
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  4. Chong Rae Park
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  5. Yong Woo Cho
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  6. Ick Chan Kwon
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Corresponding author

Correspondence to Chong Rae Park.

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Jeong, K., Lee, W., Cha, J. et al. Regioselective succinylation and gelation behavior of glycol chitosan. Macromol. Res. 16, 57–61 (2008). https://doi.org/10.1007/BF03218961

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  • DOI: https://doi.org/10.1007/BF03218961

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