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 micromol 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.
Pregnane glycosides constitute a class of compounds widely distributed in the plant kingdom. Many of them have shown either anticarcinogenic or cancer inhibitory properties, besides other useful biological activities. New chromatographic techniques and advances in spectroscopic and spectrometric methods have accelerated the purification and structure determination of novel glycosides of this series. A compilation of the pregnane glycosides isolated from 1995 until the middle of 2005, along with their physical data, structures and occurrence are presented in this review, which also summarizes, with suitable examples, recent developments in isolation and purification techniques, and structural elucidation using modern spectrometric methods like ESIMS and tandem mass spectrometry, and 2D NMR spectroscopic strategies. The reported anticancer and other biological activities of pregnane glycosides are also discussed.
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