Visokomerniye tritium derivatives of sialic acid

 

(57) Abstract:

Describes visokomerniye tritium derivatives of sialic acid of General formula I

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where R is CH3or

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The technical result is the expansion of the range labeled analogs of the physiologically active compounds.

The invention relates to the field of organic chemistry and can find application in biology and medicine.

In the study of physiologically active compounds need to be labeled analogs.

Known derivatives of sialic acid of General formula I:

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where R is CH3or

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-methylglucoside N-acetyl-neuraminic acid and disagreggated N-acetyl-neuraminic acid, respectively.

These compounds are functional fragments of gangliosides and glycoproteins and used for the study of higher nervous activity. In addition, they are components of all types of mucoproteins, mucopolysaccharides and some mucolipidosis. Erythrocytes of animals contain sialic acid in the form of N-glycolylated groups (R. Schauer. Sialic Acids: Chemistry, Metabolism, And Function. Ed. Springer-Verlag, New York, 1983, 346 pp).

However, tritium-labeled analogues of data Izvestia getting wisokomernix tritium compounds of General formula I.

Below are examples of implementation of the invention.

Example 1. The reaction vial was placed 2 mg-methylglucoside N-acetyl-neuraminic acid, put on 50 mg of 5% Pd/caso3then the ampoule was evacuated to a pressure of 0.1 PA, filled with gaseous tritium to pressure 333 hPa and kept at a temperature of 200oWith 5 minutes of Excess tritium was removed by vacuum. After cooling the reaction products were dissolved in water (6x1 ml), the catalyst was filtered, and the filtrate was evaporated several times to remove the labile tritium. The residue was chromatographically first by TLC on silicagel records in the system methanol-acetonitrile-water (3:3:2). The zone containing the desired substance, cut and labeled drug was suirable with a mixture of water with methanol (9:1) (5x1 ml). Eluate was evaporated, dissolved in 1 ml of a mixture of methanol-water (9:1) and filtered. Final purification was performed by HPLC. The output labeled drug 20-25%, and the molar radioactivity of 12.5 CI/mmol.

Analysis and purification of labeled preparation was carried out thin-layer (TLC) and high performance liquid (HPLC) chromatography.

Sodium salt of methylglucoside N-acetyl-neuraminic acid:

TLC (Sorbfil) - isopropanol-atlacatl acetonitrile-water-triperoxonane acid (70:30:0.05) retention time 13,00 min; in the system acetonitrile-water-triperoxonane acid (70:30:0.1) retention time of 6.96 min

-Disagreggated N-acetyl-neuraminic acid:

TCX(Sorbfil) -isopropanol-ethyl acetate-water (4:3:2), Rf of 0.15; methanol-acetonitrile-water (3:3:2), Rf of 0.65;

HPLC - Separon NH2, 7 μm, 3150 mm, v - 0.5 ml/min, acetonitrile-water-triperoxonane acid (80:20:0,08) retention time 5,32 minutes

For receiving and processing the chromatographic data were used hardware-software complex "Multichrom 1.5" (LLC "ampersand character", Russia) based on IBM PC/AT. Radioactivity was measured by scintillation counter with an efficiency of registration of tritium 30% in dioxane scintillator.

Example 2. The reaction vial was placed 4 mg-disagreggated N-acetyl-neuraminic acid, printed on 100 mg of 5% Pd/caso3then it was evacuated to a pressure of 0.1 PA, filled with gaseous tritium to pressure 333 hPa and kept at a temperature of 160oWith 20 minutes of Excess tritium was removed by vacuum. After cooling the reaction products were dissolved in water (61 ml), the catalyst was filtered, and the filtrate was evaporated several times to remove the labile tritium. The residue was chromatographically first by TLC on silicagel the drug was suirable with a mixture of water with methanol (9:1) (51 ml). Eluate was evaporated, dissolved in 1 ml of a mixture of methanol-water (9:1) and filtered. Final purification was performed by HPLC. The output labeled drug 10-15%, and the molar radioactivity 8,0-9,0 CI/mmol.

Thus, the resulting new visokomerniye tritium derivatives of sialic acid-methylglucoside N-acetyl-neuraminic acid and disagreggated N-acetyl-neuraminic acid.

Visokomerniye tritium derivatives of sialic acid of General formula I

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where R= CH3or



 

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