Thiol-modified chitosan sulfate nanoparticles for protection and release of basic fibroblast growth factor

Yi Cheng Ho, Shao Jung Wu, Fwu Long Mi, Ya Lin Chiu, Shu Huei Yu, Nilendu Panda, Hsing Wen Sung

Research output: Contribution to journalArticle

31 Citations (Scopus)

Abstract

A series of chitosan (CS) derivatives, the 6-O-carboxymethylchitosan (6-O-CC), 2-N sulfated 6-O-carboxymethylchitosan (N-SOCC) and the 2-N and 3,6-O sulfated 6-O-carboxymethyl chitosan (N,O-SOCC) were synthesized in this study. The chemical structures and the degrees of substituted carboxymethyl and sulfate groups of the synthesized compounds were respectively determined by FT-IR spectra and elemental analysis. N,O-SOCC displayed the highest protective efficiency for basic fibroblast growth factor (bFGF) as examined by the L929 fibroblast culture test and docking simulation. N,O-SOCC-4-thio-butylamidine (TBA) conjugates prepared by modification of N,O-SOCC with 2-iminothiolane were in situ cross-linkable. The degrees of thiol substitution of the 2-iminothiolane modified N,O-SOCC polymers were determined to be in the ranges of 45.9 ± 3.7 and 415.6 ± 12.5 μmol SH/g SOCC by quantifying the amount of thiol groups on the thiolated polymers with Ellman's reagent. The 2-iminothiolane modified N,O-SOCC and CS complex could be used for preparing nanoparticles by a polyelectrolyte self-assembly method, and the release of bFGF from the nanoparticles was successfully controlled. L929 fibroblast culture tests showed that the thiol modified N,O-SOCC/CS nanoparticles could effectively protect bFGF from inactivation over a 120 h period. The results of this study suggest that the thiol modified N,O-SOCC/CS nanoparticles may be useful as novel materials for specific delivery of bFGF with mitogenic activity.

Original languageEnglish
Pages (from-to)28-38
Number of pages11
JournalBioconjugate Chemistry
Volume21
Issue number1
DOIs
Publication statusPublished - Jan 20 2010
Externally publishedYes

Fingerprint

Fibroblast Growth Factor 2
Fibroblasts
Chitosan
Sulfhydryl Compounds
Nanoparticles
Cell culture
Polymers
chitosan sulfate
O-carboxymethylchitosan
Intercellular Signaling Peptides and Proteins
Sulfates
Dithionitrobenzoic Acid
Polyelectrolytes
Spectrum analysis
Self assembly
Spectrum Analysis
Substitution reactions
Derivatives

ASJC Scopus subject areas

  • Biotechnology
  • Bioengineering
  • Organic Chemistry
  • Pharmaceutical Science
  • Biomedical Engineering
  • Pharmacology

Cite this

Thiol-modified chitosan sulfate nanoparticles for protection and release of basic fibroblast growth factor. / Ho, Yi Cheng; Wu, Shao Jung; Mi, Fwu Long; Chiu, Ya Lin; Yu, Shu Huei; Panda, Nilendu; Sung, Hsing Wen.

In: Bioconjugate Chemistry, Vol. 21, No. 1, 20.01.2010, p. 28-38.

Research output: Contribution to journalArticle

Ho, Yi Cheng ; Wu, Shao Jung ; Mi, Fwu Long ; Chiu, Ya Lin ; Yu, Shu Huei ; Panda, Nilendu ; Sung, Hsing Wen. / Thiol-modified chitosan sulfate nanoparticles for protection and release of basic fibroblast growth factor. In: Bioconjugate Chemistry. 2010 ; Vol. 21, No. 1. pp. 28-38.
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AB - A series of chitosan (CS) derivatives, the 6-O-carboxymethylchitosan (6-O-CC), 2-N sulfated 6-O-carboxymethylchitosan (N-SOCC) and the 2-N and 3,6-O sulfated 6-O-carboxymethyl chitosan (N,O-SOCC) were synthesized in this study. The chemical structures and the degrees of substituted carboxymethyl and sulfate groups of the synthesized compounds were respectively determined by FT-IR spectra and elemental analysis. N,O-SOCC displayed the highest protective efficiency for basic fibroblast growth factor (bFGF) as examined by the L929 fibroblast culture test and docking simulation. N,O-SOCC-4-thio-butylamidine (TBA) conjugates prepared by modification of N,O-SOCC with 2-iminothiolane were in situ cross-linkable. The degrees of thiol substitution of the 2-iminothiolane modified N,O-SOCC polymers were determined to be in the ranges of 45.9 ± 3.7 and 415.6 ± 12.5 μmol SH/g SOCC by quantifying the amount of thiol groups on the thiolated polymers with Ellman's reagent. The 2-iminothiolane modified N,O-SOCC and CS complex could be used for preparing nanoparticles by a polyelectrolyte self-assembly method, and the release of bFGF from the nanoparticles was successfully controlled. L929 fibroblast culture tests showed that the thiol modified N,O-SOCC/CS nanoparticles could effectively protect bFGF from inactivation over a 120 h period. The results of this study suggest that the thiol modified N,O-SOCC/CS nanoparticles may be useful as novel materials for specific delivery of bFGF with mitogenic activity.

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