Antitumor activities of D-glucosamine and its derivatives

The growth inhibitory effects of D-glucosamine hydrochloride （GlcNH2-HCl）, D-glucosamine （GlcNH2） and N-acetyl glucosamine （NAG） on human hepatoma SMMC-7721 cells in vitro were investigated. The results showed that GlcNH2.HCl and GlcNH2 resulted in a concentration-dependent reduction in hepatoma cell growth as measured by MTT （3-（4,5-dimethylthiazol- 2-yl）-2,5-diphenyltetrazolium bromide） assay. This effect was accompanied by a marked increase in the proportion of S cells as analyzed by flow cytometry. In addition, human hepatoma SMMC-7721 cells treated with GlcNH2-HCl resulted in the induction of apoptosis as assayed qualitatively by agarose gel electrophoresis. NAG could not inhibit the proliferation of SMMC-7721 cells. GlcNH2-HCl exhibited antitumor activity against Sarcoma 180 in Kunming mice at dosage of 125-500 mg/kg, dose of 250 mg/kg being the best. GlcNH2-HCl at dose of 250 mg/kg could enhance significantly the thymus index, and spleen index and could promote T lymphocyte proliferation induced by ConA. The antitumor effect of GlcNH2-HCl is probably host-mediated and cytocidal.

Synthesis of Indomethacin Conjugates with D-Glucosamine

Two series of indomethacin conjugates with D-glucosamine were prepared with theobjectives of reducing ulcerogenic potency, increasing the bioavailability of indomethacin andexerting the coordinative effects on osteoarthritis. The structures of the conjugates were identifiedby H NMR and C NMR. The ester conjugates inhibited edema as potent as indomethacin. 1 13

Ternary deep eutectic solvents catalyzed D-glucosamine self-condensation to deoxyfructosazine: NMR study

Ternary deep eutectic solvents(TDESs) comprising choline chloride(Ch Cl), glycerol and L-arginine were synthesized as catalysts and solvents for the conversion of D-glucosamine(GlcNH_(2)) into deoxyfructosazine(DOF). The interactions between these three components in the prepared TDESs were studied by ^(1)H-,^(35)Cl-NMR spectra and ^(1)H diffusion-ordered spectroscopy(DOSY) measurements. The chemical shift changes of active hydrogen in the ^(1)H-NMR spectra of TDES system and widening of signals in the^(35)Cl-NMR spectra confirmed the hydrogen bonding interaction between the components, which was further supported by the decrease of diffusion coefficients(D) of the TDES components according to ^(1)H DOSY measurements. The influences of reaction temperature and L-arginine content in the TDESs on the yield of DOF were also studied. The experimental results have shown that when the molar ratio of Ch Cl, glycerol, and L-arginine was 1:2:0.1, DOF was the major product with a yield of 22.6% at 90℃ for 120 min. The chemical shift titration indicated that the carboxyl group of L-arginine in the TDES is the catalytical active site, so the mechanism of the catalytic reaction between Glc NH_(2) and the TDES was proposed. Moreover, a reaction intermediate, dihydrofructosazine, was identified in the self-condensation reaction of Glc NH_(2) by an in situ ^(1)H NMR technique.

Synthesis and anti-HIV-1 activity of the conjugates of gossypol with oligopeptides and D-glucosamine

A series of novel gossypol derivatives were synthesized and screened for their in vitro anti-HIV- 1I activity. The results showed that replacing the aldehyde groups of gossypol with certain oligopeptides and Dglucosamine not only reduced the cytotoxicity of gossypol derivatives but also enhanced their antiviral activity against HIV-1. Interestingly, D-glucosamine derivative of gossypol that lacked the COONa group also exhibited the same potent anti-HIV-1 activity as oligopeptide derivatives with the COONa group. These compounds blocked the entry of HIV-1ⅢB into target cell. which was similar to T20. Furthermore, the molecular docking analysis rationalized their anti-HIV-1 activity. The results also implied that certain oligopeptides and D-glucosamine were important moities to prepare gossypol derivatives as HIV- 1 entry inhibitors besides certain amino acids.

Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction

A convenient and efficient protocol for the synthesis of unnatural N-glycosyl cz-amino acids was developed. Condensation of 1,3,4,6-tetra-O-actyl-/%D-glucosamine hydrochloride, alkenyl boronic acid, and glyoxylic acid was achieved in CH2C12 to give the derivatives of 2-（N-glycosyl）aminobut-3-enoic acid which may find applications in glycobiology research and medicinal chemistry.