Tritium uniformly labeled [3h]-trans-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenic acid

FIELD: organic chemistry, radiolabeled compounds.

SUBSTANCE: invention relates to tritium uniformly labeled [3H]-trans-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenic acid of the formula: . This compound is analog of physiologically active compound that can be used in organic chemistry, biology and medicine.

EFFECT: valuable properties of compound.

1 ex

 

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 are necessary for their labeled counterparts.

It is known that replacement of hydrogen atoms in organic compounds on their isotopes does not change any properties of the original compound (E.A. Evans - Tritium and its compounds. London, Butterworths, 1974, p.48) [1].

A well-known TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen acid of the formula:

This compound is formed from vitamin a and is a strong mutagenic drug (R.P.Warrell, Jr. et al. // Leukemia. 1994. Vol.8. 929) [2].

However, the tritium-labeled analogue not described.

The technical result achieved by the present invention, is expanding the range labeled analogs of the physiologically active substances.

Achieved the specified technical result obtaining a new labeled physiologically active compounds - ravnomernoto tritium-TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenovoy acid of the formula:

The following is an example implementation of the invention.

Example I.

In the first chamber of the reaction chamber ampoule was placed to the telesfor - 25 mg of palladium oxide and 25 mg of 5% PdO/BaSO4in another solution of 5 mg of TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenovoy acid and 15 μl of triethylamine in 150 μl of dioxane. The second camera was frozen with liquid nitrogen, the vial was evacuated to a pressure of 0.1 PA and filled with gaseous tritium to pressure 333 hPa, then the first chamber was heated to 70°C. In the reaction, the palladium oxide was recovered tritium water (10 S) was peremarazhival the second chamber. The reaction vial, without stopping the cooling of the second chamber with liquid nitrogen, was evacuated to a pressure of 0.1 PA and filled with argon. Then the contents of the second chamber is transferred into the first chamber, which was then sealed.

Thus, the reaction mixture consisted of paradiesvogel catalyst, tritium water, triethylamine and a solution of TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenovoy acid in dioxane. The contents of the ampoules were heated for 30 min at 125°C. Then, the ampoule was opened, the reaction mixture was diluted with 0.5 ml of methanol, the catalyst was separated by filtration, washed with methanol (5×1 ml). Tritium water and triethylamine drove on the rotor. Labile tritium was removed, repeatedly dissolving the substance in methanol (5×2 ml) and pariva last (total radioactivity of the residue 180 MCI).

So how in addition to products on the decomposition in the reaction mixture containing the isomers of TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenovoy acid, purification of the desired preparation was carried out in two stages.

First separated degradation products on column Kromasil 100C18, 8*150 mm, in the system of 70% methanol-3 mm H3PO4v - 2 ml/min

The fraction containing the isomers of TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenovoy acid, had the radioactivity 16,8 MkI, of which 8 MCI had on the TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen acid. Analysis was performed by HPLC on Kromasil column C18, 4,0×150 mm 7.0 µm, the rate of eluent - 1.0 ml/min, the system 70% methanol-3 mm H3PO4the retention time of the desired labeled drug - 9,77 minutes

The isomers were separated by the method of preparative HPLC on a Kromasil column 100C18, 8,0×150 mm 7.0 µm, the rate of eluent - 2.0 ml/min, the system (60% methanol-3 mm H3PO4) and b (50% methanol), gradient from 0%to 50%In 30 minutes

The output labeled TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenovoy acid, after chromatography was 7 MCI (25%), molar radioactivity of 1.8 CI/mmol.

Thus, the resulting new ravnomernoto tritium physiologically active compound.

Ravnomernaya tritium [3H]TRANS-3,7-dimethyl-9-(2,6,6-trimethyl-3-oxo-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen acid formula



 

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