RU2309929C2 - Chlorohexidine highly labeled with tritium - Google Patents

Abstract

FIELD: organic chemistry, radiolabeled compounds.

SUBSTANCE: invention relates to a novel chlorohexidine highly labeled with tritium of the formula:

with molar radioactivity 17 Cu/mole. The compound possesses the strong disinfecting and antibacterial effect and can be used in analytical chemistry in investigation of effect of this compound.

EFFECT: valuable properties of compound.

Description

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

In the study of physiologically active compounds, their labeled analogues are necessary.

Known chlorhexidine formula

This compound is a potent antibacterial and disinfectant (D. M. Foulkes, J. Peri odont. Res. 8, Suppl. 12, 55-60 (1973) [1].

It is known that replacing the atoms of compounds with their isotopes does not lead to a change in any properties of the parent compound, including biological activity (Evans EA - Tritium and its compounds London Butterworths, 1974, p. 48) [2].

However, its tritium-labeled analogue is known (Journal of Labelled Compounds and Radiopharmaceuticals, 1978. V. 14. 559, 570, 573-574 [3].

However, the molar radioactivity of this known labeled analog is low and amounts to 0.15 Ci / mmol.

The technical result achieved by the present invention is to expand the assortment of labeled analogues of physiologically active compounds, increasing the molar radioactivity of tritium-labeled chlorohexidine.

This technical result is achieved by obtaining highly labeled with tritium chlorohexidine of the formula

with molar radioactivity of 17 Ci / mmol.

The following is an example implementation of the invention.

Example.

A solution of 50 mg of chlorhexidine and 0.5 ml of acetic acid was placed in the flask. 50 μl of bromine was added to this flask; the bromination reaction was carried out for 120 minutes with stirring. Then the reaction mixture was evaporated, the residue was dissolved in 3 ml of methanol and the solution was again evaporated. The residue was dissolved in 3 ml of a mixture of methanol with triethylamine (29: 1) and the solution was evaporated, the residue was dissolved in 3 ml of methanol, the solution was again evaporated, the residue was dissolved in 5 ml of methanol. The resulting solution of the brominated chlorhexidine derivative was used without preliminary purification. 1 ml of this solution was added to the ampoule, evaporated, the residue was dissolved in 0.4 ml of dimethylformamide. 30 mg of 5% Pd / CaCO ₃ were placed in the same vial. Then, the ampoule was frozen with liquid nitrogen, evacuated to a pressure of 0.1 Pa and filled with gaseous tritium to a pressure of 333 hPa. The reaction was carried out at room temperature for 120 minutes with stirring.

HPLC analysis: on a Reprosil-pur C ₁₈ AQ column, 4.6 × 150 mm, 5 μm, eluent speed 1.0 ml / min, methanol system: 50 mM buffer, pH 2.8, 60:40, time retention 9.38 min.

The yield of the labeled preparation after chromatography was 35%, molar radioactivity 17 Ci / mmol, radiochemical purity 98%.

Thus, a new physiologically active compound highly labeled with tritium was obtained.

Claims (1)

High Tritium Chlorohexidine Formula

with a molar radioactivity of 17 Ci / mmol.