Compound cis-diammineplatinum (ii) with a copolymer of na-salt of maleic acid and furan, with immunostimulatory and antitumor activity, with a wide interval of therapeutic doses of low nephrotoxicity

 

(57) Abstract:

The invention relates to the field of high-molecular chemical compounds with antitumor and immunostimulating activity. Usage: in medicine in the treatment of cancer. Compound CIS-diammineplatinum (P) with a copolymer of Na-salt of maleic acid and furan has immunostimulating and antitumor activity at low nephrotoxicity. 5 table.

The invention relates to the field of high-molecular chemical compounds with antitumor and immunostimulating activity.

Known to be similar in structure connection: copolymer salt of maleic acid with furan (SFMC) of the following formula:

HH (I) where m 10-60, 2300-13600, but unlike the claimed compounds do not contain complex-bound platinum. There is information about weak antitumor activity of the compounds of formula (I) [1] However, the effectiveness of antitumor activity of tested compounds of formula (1) is low and is not of interest for practical chemotherapy of tumors (see table.1). The connection is also weak immunostimulirutuyu activity [2]

Nearest in formula

(II)

Cisplatin is widely used in clinical practice for the treatment of cancer. Mechanism of action refers to the drugs, the overwhelming DNA synthesis of tumor cells.

However, during anticancer therapy cisplatin, as well as other drugs, in addition to the action on malignant neoplasms, have a significant toxic effect on the body. Cisplatin highly toxic substance (LD5012-14 mg/kg for mice and rats). The main factor which limits therapeutic course and forced to interrupt treatment the damage in varying degrees (depending on dose) the tortuous channel of the kidney [3]

One of the major drawbacks of applying currently anticancer drugs, including cisplatin, is their immunodepressant effect on the body (see tab.2).

The aim of the invention is the creation of new polymeric platinum complex having immunostimulating and antitumor activity with a wide interval of therapeutic doses at low nephrotoxicity.

The connection is an amorphous yellow powder, soluble in water and physiological CLASS="ptx2">

When heated this complex decomposes without melting at a temperature of 190aboutC.

Polymer complex obtained by interaction of the copolymer Na-salt of maleic acid and furan of formula II with Cys-his diaminedichloroplatinum (P) of the formula [Pt(NH3)2(OH)2] (NO3)2taken in a molar ratio of from 8:1 to 2:1 (excess polymer component) in aqueous solution.

The composition of the reaction products (the parameter x in the formula (III) is adjusted by changing the molar ratio platypodinae and polymeric reagents of the reaction mixture (see examples).

The structure of the obtained polymer complexes confirm methods of elemental analysis, atomic-absorption spectroscopy and IR spectroscopy.

The inventive compound of formula (III) is characterized by the following vibrational frequencies in the IR spectra (obtained on a Specord M-80), cm-1:

1590-1600 stretching vibrations of C=0 connection ionized COOH groups;

1070-1110 stretching vibrations ties WITH-0;

517-490 stretching vibrations due PT n

The above spectral data and elemental analysis and atomic adsorption spectroscopy (see examples) indicates, analysis and atomic adsorption spectroscopy), n 20-25, =5000-12000 (determined by the molecular weight used for the synthesis of compounds of the copolymer Na-salt of maleic acid and furan) and the content of PT in the sample.

For synthesis take as starting copolymer with =4500-5500 as at < 4500 biological activity of the compounds is markedly reduced, and when the > 5500 increases toxicity.

Obtaining complex is illustrated by the following examples.

P R I m e R 1. In distilled water (100 ml) dissolve 0.18 g (0,0006 mol) PT (NH3)2Cl2and add an aqueous solution 0,204 g (0,0012 mol AgNO3(reaction 1)

Pt(NH3)2Cl2+2AgNO3____ 2AgCl + (Pt(NH3)2(OH)(NO3)2(1)

Precipitated AgCl precipitate is filtered off and the filtrate is poured with stirring to a solution of the copolymer Na-salt of maleic acid and furan 0.28 to (0,0012 mol per comonomer link) dissolved in 100 ml of distilled water (reaction 2)

HH + Pt(NO3)2___

(2) ___ HH

To remove low molecular weight impurities (NaNO3, unreacted platinum complex) aqueous solution of complex compounds of platinum with a copolymer is subjected to ultrafiltration, are separated from the solution by lyophilic Duskwood molar ratio of 2:1 (excess polymer component). Output 0,230 g (73.5% of theory. ).

The elemental composition of the obtained product:

Calculated, 30,04, N 2,82, N Of 4.38, Pt 30,5, PA 7,2.

Found, C 31,02, H 2,95, N 4,87, Pt 26,07, Na 6,5.

The obtained compound of the following formula:

HH where x 0,46; r 25; 12000.

P R I m m e R 2. Conditions for obtaining complex compounds of platinum with a copolymer similar to that described in example 1. For the reaction to take 0,276 g (0,0012 mol) copolymer Na-salt of maleic acid and furan, and 0.09 g (0,0003 mol) PT (NH3)2CL2and 0,117 g (0,0006 mol AgNO3that corresponds to the ratio of SFMC:CPU=4:1 (excess of the copolymer). Output 0,233 g (71,2% of theoretical. ).

The elemental composition of the obtained product:

Calculated, 35,1; N 2,7; N 2,6; Pt 17,8; Na 12,6.

Found, C And 36.2; H 2,8; N 2,5; Pt 16,7; Na 11,5.

Received the following connection:

HH where x 0,23; 8100; n 20.

P R I m e R 3. Reaction conditions similar to those described in example 1. To obtain a polymer complex taking 0.28 g of copolymer Na-salt of maleic acid and furan, 0,045 (0,00015 mol) PT(NH3)2Cl2and 0,058 g (0,0003 mol AgNO3that corresponds to reagent ratio 8:1 (excess polymer component). Output 0,216 g (72.3% of theoretical.).

The elemental composition polucen is Holocene connection formulas

_ __ where x 0,11; 5000; n20.

Determination of acute toxicity of the compounds is carried out according to the method of C. B. Prozorovsky [2] found that LD50the tested substances ranged from 1500 to 1700 mg/kg depending on the percentage of platinum in the polymer complex. It should also be noted that even when using doses with a high content of platinum (in terms of metal) visible toxic effects not observed (example 13 of table.1).

The study of antitumor activity of polymeric complexes of platinum carried out in experiments on outbred mice (females weighing 20-25 g) inoculated intraperitoneally with Ehrlich adenocarcinoma. Ascitic carcinoma, Ehrlich tumor, relatively resistant to widely used currently in the clinic cisplatin formula II recommended Farmkomiteta the USSR as one of the models for testing new drugs.

Perepevku tumors carry intraperitoneally with the introduction of 0.5 ml of ascitic fluid. Drugs dissolved in saline and administered to the animals intraperitoneally once a day after tumor inoculation. The effectiveness of the treatment is evaluated on the basis of changes in the average long is presented in table.1.

Studied the antitumor activity SFMC-P model lymphocytic leukemia P-388, also recommended by Farmkomiteta the USSR for testing new drugs. Testing of anti-tumor activity in this model showed that the complex is significantly more active compared to the CPU at a much lower toxicity of effective doses. So, when administered to mice with experimental lymphocytic leukemia P-388 SFMC-P at a dose of 600 mg/kg there was an increase ALE by 128% compared to control, while the introduction of the CPU at the maximum tolerated dose of 7 mg/kg leads to an increase in mean life span of only 30%

The influence of polymeric complexes of platinum on some parameters of the immune response. Studies conducted on mice-female line of the IAS. In the experiment using five groups of animals, each of which is injected, respectively, cisplatin (similar biological activity), a copolymer of furan and Na-salt of maleic acid (similar structure), their mechanical mixture or complex compound of platinum.

The CPU is injected at the maximum tolerated dose of 7 mg/kg (containing 4.5 mg/kg of platinum). Mechanical mixture of the calculation 42 mg/kg SFMC and 7 mg/kg CPU (4.5 mg/kg of platinum). Drugs dissolved in physiological rocity sheep. In the course of the research study the following indicators: change in antibody productive activity of spleen cells (KLA) and the rosette activity of lymphoid cells of the spleen (AND ROCK). The results obtained are presented in table.2.

Studied the effect of polymer complex of platinum on the kidneys. Experiments carried out on white rats-female line Wister weighing 180-200 g of tested compound dissolved in saline injected animals intraperitoneally. The effect of the claimed compounds on renal function compared with the effect on them of cisplatin. Through 5 days after the administration of cisplatin at a dose of 5 mg/kg (3.5 kg in terms of pure metal) in rats revealed a typical picture of acute renal failure: a marked violation of the excretory function of the kidney drops sharply diuresis, more than 20 times reduced glomerular filtration, which is determined by the clearance of endogenous creatinine concentration of urea in serum is increased 15 times, as well as the content of creatinine (table. 3,5). Significant changes are observed in kidney tissue and the body weight increased almost in 2 times, develops massive edema renal tissue, increased content of Na, K, CA and Mg (see table.4).

From the data presented in table.3,4,5 shows that the proposed complex at a dose of 100 mg/kg for all indicators is considerably less toxic than cisplatin, despite the high (3 times higher than in the cisplatin) the content of platinum in terms of pure metal.

Compound CIS-diammineplatinum (II) with a copolymer of Na-salt of maleic acid and furan General formula

< / BR>
where X 0,11 0,46;

n 20 25,

with mol.m. 5000 12000,

possessing immunostimulatory and antitumor activity, with a wide interval of therapeutic doses at low nephrotoxicity.

 

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