Search

A method for the synthesis of mixed-ligand gold glyconanoparticles with average particle size of 20–25 nm at widely variable ratio of the initial glycoligands on the basis of aldoses 6-mercaptohexanoyl hydrazones—condensation products of a series of natural aldoses (N-acetylamino-D-glucose, D-mannose, D-galactose, and L-fucose) with 6-mercaptohexanoic acid hydrazide—has been developed. It has been shown that the obtained gold glyconanoparticles exhibit low toxicity and are active against influenza A/Puerto Rico/8/34 (H1N1) virus at concentrations of 3 and 6 μg/mL.

The condensation products of natural monosaccharides L-fucose, L-rhamnose, N-acetylamino-D-glucose and N-acetylamino-D-mannose with thioglycolic acid hydrazide have a cyclic 1,3,4-thiadiazine structure or are presented in solution in DMSO-d6 by a tautomeric mixture of pyranose and 1,3,4-thiadiazine forms. It was shown that L-rhamnose and N-acetylamino-D-mannose mercaptoacetyl hydrazones exhibit high radioprotective activity, increasing the survival rate of mortally irradiated mice by 35–45%.

A method for the synthesis of gold glyconanoparticles with average particle size of 18–21 nm and low polydispersity index based on readily available thiolated compounds: 3-thiopropionylhydrazones of L-fucose, L-rhamnose, N-acetyl-D-glucosamine, and N-acetyl-D-mannosamine has been developed. It has been shown that some of the gold glyconanoparticles exhibit antitumor activity, and the initial thiolated glycoligands have shown strong radioprotective activity, increasing the survival rate of mortally irradiated mice by 50–70%.

The 1H and 13C NMR spectroscopy was used to study the structure of previously unknown aldose series condensation products (L-fucose, L-rhamnose, D-mannose, D-galactose, D-glucose, N-acetyl-D-glucosamine, N-acetyl-D-mannosamine, D-lactose and D-maltose) with 6-mercapto­hexanoic acid hydrazide—promising glycoligands of noble metal nanoparticles. It was shown that L-fucose, L-rhamnose, D-mannose, D-galactose and N-acetyl-D-mannosamine derivatives exist in solution in DMSO-d6 as a tautomeric mixture of open hydrazone and cyclic pyranose forms. The linear hydrazone form is represented by a set of Z′,E′-conformational isomers, which differ in the arrangement of substituents relative to the C–N amide bond in comparable amounts. The condensation products obtained on the basis of D-glucose, N-acetyl-D-glucosamine, D-lactose and D-maltose in the crystalline state and in solutions in DMSO-d6 have an exclusively cyclic pyranose structure represented by α,β-configurational isomers. A similar transition to the pyranose form is observed in solutions of all the studied compounds in D2O.

A procedure has been developed for the synthesis of gold glyconanoparticles with an average particle size of 15–30 nm and a low polydispersity index on the basis of natural hexose (d-glucose, d-galactose, d-mannose) sulfanylacetyl-, 3-sulfanylpropanoyl-, and 2-sulfanylbenzoylhydrazones and thiolated poly(2-deoxy-2-methacryloylamino-d-glucose).

A procedure has been developed for the synthesis of previously unknown aldose 4-[(ω-sulfanylalkyl) oxy]benzoylhydrazones (where alkyl is hexyl or decyl and aldoses are D-glucose, D-galactose, D-maltose, and D-lactose) that a repromising glycoligands for noble metal nanoparticles. According to the 1H and 13C NMR data, 4-[(ω-sulfanylalkyl)oxy]benzoylhydrazones derived from D-glucose, D-maltose, and D-lactose in crystal and in DMSO-d6 solution have exclusively the cyclic pyranose structure (α- and β-anomers). D-Galactose 4-[(ω-sulfanylalkyl)oxy]benzoylhydrazones in DMSO-d6 solution exist as tautomeric mixtures of cyclic pyranose and open-chain acylhydrazone structures.

A procedure has been developed for the synthesis of gold glyconanoparticles with an average particle size of 16–24 nm and low polydispersity index on the basis of accessible D-maltose and D-maltose 2-sulfanylacetyl-, 3-sulfanylpropanoyl-, and 2-sulfanylbenzoylhydrazones.

A method of synthesis of 3-thiopropinyl derivatives of 5-oxo-1,3,4-benzothiadiazepine-4-acetic acid, potential antihypertensive drugs, vasopeptidase inhibitors, starting from 2-thiobenzoic acid hydrazide has been elaborated.

A method of synthesis of silver glyconanoparticles with average particle size 15–40 nm and low polydispersity index based on available 3-thiopropionylhydrazones of mono- and disaccharides has been elaborated. The prepared compounds have exhibited high antifungal, antibacterial, and antiviral activity and are promising for further comprehensive study.

The accessible D-ribose mercaptoacetyl-, 3-mercaptopropionyl-, and 2-mercaprobenzoylhydrazones were used to develop a method of synthesis of gold glyconanoparticles with the average particle diameter of 10–40 nm and a low polydispersity index.