RU2351606C1 - Uniformly tritiated triterpene glycosides of holothurians cucumaria - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: invention refers to production of new tritiated analogues of physiologically active compounds - triterpene glycosides of holothurians Cucumaria of formula:

.

EFFECT: there are produced new tritiated analogues of physiologically active compounds.

2 cl, 2 ex

Description

The invention relates to the field of organic chemistry and can find application in analytical chemistry, bioorganic chemistry, biochemistry and applied medicine.

When studying physiologically active compounds, their labeled analogues may be necessary.

Known triterpene glycosides of holothurium Cucumaria of the formula:

These triterpene glycosides have a pronounced immunomodulatory effect (Sedov AM; Apollonin, AV; Sevastyanova E.K. Stimulation of mice non specific antibacterial resistance to conditionally pathogenic gram-negative microorganisms. Antibiot. Khimioter. 1990, 35 (1), 23-26 ) [I].

However, these tritium-labeled triterpene glycosides are not described.

The technical result achieved by the present invention is to expand the range of labeled analogues of physiologically active compounds.

This technical result is achieved by obtaining highly tritiated triterpene glycosides of the formula:

It is known that replacing the atoms of compounds with their labeled analogues does not lead to a change in any properties of the starting compound (Evans E.A. - Tritium and its compounds London Butterworths, 1974, p. 48).

The following are examples of the implementation of the invention.

Example 1

70 mg of 5% Pd / C was placed in an ampoule, and a solution of 10 mg of unsaturated triterpene glycoside in 0.1 ml of dimethyl sulfoxide was added to it. The contents of the ampoule were frozen with liquid nitrogen, evacuated to a pressure of 0.1 Pa, filled with gaseous tritium to a pressure of 400 hPa and kept at 25 ° C for 6 h. Then, the contents of the ampoule were again frozen with liquid nitrogen and evacuated to a pressure of 0.1 Pa to remove tritium gas. 4 ml of water was added to the ampoule and the contents of the ampoule were stirred on a magnetic stirrer for 10 minutes. The aqueous solution was filtered, the substance from the catalyst was extracted with methanol (5 × 2 ml). The filtrates were combined and evaporated on a rotary evaporator. After isolation of the unsaturated triterpene glycoside by HPLC (Kromasil 100C18 column, 7 μm, 10 × 8 mm, system: methanol mixture with 5 mM H ₃ PO ₄ 3: 1, eluent flow rate - 2 ml / min, retention time - 3.70 min) the yield of the labeled drug was 26%, the molar radioactivity was 22 Ci / mmol, and the radiochemical purity was 96-98%.

Example 2

1 mg of tritium-labeled unsaturated triterpene glycoside (22 Ci / mmol), 40 mg of 5% Pd / C and 2 ml of water were placed in the ampoule. The contents of the ampoule were frozen with liquid nitrogen, evacuated to a pressure of 0.1 Pa, filled with gaseous tritium to a pressure of 400 hPa, heated to 25 ° C and stirred on a magnetic stirrer for 15 hours. Then, the contents of the ampoule were again frozen with liquid nitrogen and vacuum to a pressure of 0.1 Pa to remove gaseous tritium. The aqueous solution was filtered, the substance from the catalyst was extracted with methanol (5 × 2 ml). The filtrates were combined and evaporated on a rotary evaporator. Saturated triterpene glycoside was isolated by HPLC as described in Example 1 (retention time 5.23 min).

The yield of labeled saturated triterpene glycoside reached 12%, molar radioactivity - 71 Ci / mmol. After the first purification, 6.5 mCi of the labeled preparation with a radiochemical purity of 93-95% was isolated; after the second purification, 4.5 mCi of saturated triterpene glycoside with a radiochemical purity of 96-98% was obtained.

Thus, new physiologically active compounds highly labeled with tritium were obtained.

Claims (1)

High tritium-labeled triterpene glycosides of holothurium Cucumaria formula