Agent for antiplatelet, anti-inflammatory and cytoprotective therapy

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to medicine, and concerns an agent for prevention and treatment of cardiovascular diseases. The peptide 3-mercaptopropionyl-Phe-Ile-lle-Arg-Lys-Pro-Asp-Lys-NH2 is synthetised which has greater availability and lower price than known analogues; it possesses the antiplatelet, anti-inflammatory and cytoprotective properties.

EFFECT: invention provides reduced spontaneous thrombocyte aggregation, inflammation inhibition by reducing histamine secretion, cell protection against neurotoxic actions of thrombin.

1 cl, 4 ex

 

The present invention relates to medicine, in particular to the means for prevention and treatment of diseases of the cardiovascular system.

One of the causes of mortality in patients with various cardiovascular diseases and acute cerebrovascular disease (cerebral vascular accident) are thrombotic complications. The most important participants in the development of such complications are platelet activation, which plays a key role in the launch of the mechanisms of thrombus formation. It is known that platelets in pathology acquire the ability to spontaneously aggregate to form aggregates of small size, which can circulate in the blood of patients and to be the centers that in areas of damaged endothelium formed clots. The formation of such units depends on a number of reasons, the most important of which are inflammation and the initiation of the formation of thrombin, which leads to increased expression of cells of the cardiovascular, immune and nervous system receptors, thrombin and other proteases, called receptors, activated proteases (PAIRS).

There are four subtypes PAR: PAR-1, PAR-2, PAR-3 and PAR-4. According to the latest data, the blockade by antagonists of PAIRS of functions of these receptors inhibits platelet activation induced by thrombin and block the processes of inflammation and killed the Lee of cells (apoptosis), including neurons. In humans is mediated by thrombin activation of platelets occurs through PAR-1 and PAR-4, therefore, the search and selection of antagonists PAIRS directed to the development of drugs capable of inhibiting these receptors. The most important PAR-1 is the major thrombin receptor, mediating events associated with inflammation and activation of blood coagulation. The specificity of binding of PAR-1 by thrombin almost 2 orders of magnitude higher than that of PAR-3 and PAR-4, so PAIRS of 4 persons is activated by thrombin in higher concentrations than PAR-1.

Inflammation and the initiation of the formation of thrombin is one of the reasons for the development of atherogenesis and its complications - atherothrombosis, cerebral vascular accident (stroke), etc. Should be noted that the use of known drugs aspirin combined with clopidogrel or the combination of aspirin with dipyridamole - to reduce blood clots and exclusion of recurrent stroke in patients with ischaemic stroke of arterial origin leads to side effects (bleeding and disorders of the digestive system).

Development of new and highly effective antiaggregatory, anti-inflammatory and cytoprotective therapy at the present time is very important.

In the international application WO/2004/098628, C07K 5/09 serves to suppress activation of the aggregation process, trombi is tov to use synthetic analogs of the peptide Arg-Pro-Pro-Gly-Phe, which contain one or more amino acid substitutions. A disadvantage of the proposed peptide analogues is that they are direct inhibitors of a molecule of thrombin. They block proteolytic cleavage by thrombin all its substrates (including amide and protein) and thus, slows platelet aggregation, while significantly prolong the clotting time of blood, which is a negative side effect.

In [Andrade-Gordon P. A. O. PNAS. 1999; v.96(22): R-12262 and Derian S.K., etc. Biochemistry 2002, t, p.66-76] was synthesized and tested as antagonist PAR-1 peptidomimetic RWJ-56110 the following structure:

RWJ-56110 - [(S)-N-[(1S)-3-amino-1-[[(phenylmethyl)amino)carbonyl]-[[[[1-(2,6-dichlorophenyl)methyl]-3-(1-pyrrolidinyl)-1H-indol-6-yl]amino]carbonyl]amino]-3,4-diftorbenzofenonom.

However, RWJ-56110 inhibits aggregation induced only very low concentrations of thrombin, and when they increase insolvent, which limits its applicability. In addition, the synthesis of these compounds is complex.

[Morley D. S.A. Pharm. Rev. 2002, v.54: p.203] was synthesized peptide 3-mercaptopropionyl-Phe-Cha-Cha-Arg-Lys-Pro-Asp-Lys-NH2that exhibits activity as an inhibitor of PAR-1. As can be seen from the above structure, the sequence of this peptide contains the it two residue β-cyclohexylamine (Cha). It should be noted that the derivative of this amino acid is expensive: the cost required for the synthesis of a derivative of this amino acid in 18 times higher than the cost of similar bifunctional derivatives of natural amino acids. Thus the disadvantage of peptide is its high cost and low availability.

Object of the present invention to provide an effective means antiaggregatory, anti-inflammatory and cytoprotective therapy in the form of a peptide antagonist PAIRS 1, wherein a lower cost and affordability in comparison with the known analogues.

The goal was solved by the synthesis of a peptide of the following structure: S-mercaptopropionyl-Phe-Ile-Ile-Arg-Lys-Pro-Asp-Lys-NHz (IPAR-1-I).

It was unexpectedly found that the inclusion in the structure of the peptide instead of two residues of β-cyclohexylamine, residues isoleucine allows you to get a connection with antiaggregatory, anti-inflammatory and cytoprotective activity and at the same time much cheaper than the peptide-analogue. Tests IPAR-1-I ex vivo showed that the use of IPAR-1-I allows you 3 times to reduce the degree of spontaneous platelet aggregation (SPA) patients with coronary heart disease (CHD). IPAR-1-I also has anti-inflammatory and cytoprotective activity.

The following examples illustrate comprises the acts invention.

Example 1.

Obtaining peptide 3-mercaptopropionyl-Phe-Ile-Ile-Arg-Lys-Pro-Asp-Lys-NH2(IPAR-I).

For solid-phase peptide synthesis (TPS) used a derivative of the amino acid L-series. The peptide was synthesized using Fmoc methodology, i.e. in combination with the Nα-Fmoc-protected to block the side chains of the amino acids used kislotolabilen protective groups: BOC - ε-amino groups of lysine, But-β-carboxyl function aspartic acid, Trt - for carboxamide function of asparagine and SH-groups mercaptopropionic acid, as well as Pmc for guanidino function of arginine. The synthesis was carried out on an insoluble polymer carrier is a copolymer of styrene with 1% divinylbenzene with anchor group, designed to obtain amides of the peptide - Rink polymer containing amino groups 0.64 mmol/g Synthesis of the peptide was performed on the basis of 0.2 g (0.125 mmol) of the polymer, since the C-end and increasing peptide chain by one amino acid. For removal of Nα-Fmoc-protection was used a 25% solution of 4-methylpiperidine to create amide bond used TBTU/HOBt in the presence of diisopropylethylamine. For completeness of the reactions in the process of TFS used test Kaiser. At the end of the TFS of the target product was tsalala from polymer with simultaneous removal of all protective groups of the side chains of amino acids, trifluoroacetic acid is you. The obtained crude peptide IPAR-1 was purified using preparative HPLC. The peptide is characterized by the data of NMR spectroscopy and mass spectrometry. In the mass spectrum of this substance was present molecular ion corresponding to the correct molecular weight of the target product (M=1217,53). Range1H-NMR confirms the structure of the synthesized peptide.

Example 2.

Test antiaggregative actions peptide IPAR-I.

The test of the obtained peptide was performed using the blood of patients with coronary heart disease CHD, verified using coronary angiography. The blood of patients with coronary artery disease received by gravity from the cubital vein into the tube from 0.13 M solution of sodium citrate (pH of 7.3). After 15 min after sampling and transportation at room temperature, the blood was centrifuged to obtain platelet-rich plasma (OTP). Evaluation of the aggregation capacity of platelets in the OTP was carried out on a laser aggregometry NPF "Biola" (Russia), allowing to estimate the spontaneous formation of aggregates (which corresponds to the curve on the testimony of the average size of the aggregates, expressed in relative units), and formation of aggregates in response to high concentrations of inducers (curves, the registration process of transmittance, expressed in %). Platelet-rich plasma to write the aggregation process Incubus is listed for 5 min at room temperature with the appropriate IPAR. As a selective agonist of PAR-1 (to start the mechanism of spontaneous aggregation) used the peptide agonist PAIRS-1 - SFLLRN.

The study antiaggregative actions IPAR - 1-I showed that IPAR - 1-I reduces spontaneous platelet aggregation CHD patient with a high value of this indicator almost to normal values. Spontaneous platelet aggregation was decreased in 3 times.

Example 3.

Test anti-inflammatory actions of peptide IPAR-I.

Among the cells involved in the inflammatory responses of the body, an important role belongs to the fat cells. Mast cells Express a variety of receptors, including the receptors of the family of PAIRS. The presence of fat cells receptor PAIRS is responsible for their reactivity against thrombin. Activated mast cells release a wide range of proinflammatory mediators, including histamine. Methods of evaluation of anti-inflammatory actions IPAR-I was based on measuring the secretion of mast cell histamine in the presence of IPAR-1-I.

Fat cells are taken from white male outbred rats weighing 250-350 g Acute inflammation in rats caused by intraperitoneal injection of thioglycolate Na. Fat cells were separated by centrifugation peritoneal fluid, suspended in HEPES-NaCl and purified in the gradient ficoll. Histamine secreted by fat cells, was determined with POM is by its condensation with ortho-phthalaldehyde, resulting in a fluorescent complex. Fluorescence was measured on the spot an Thermo Fluoroscan Ascent at 460 nm by exciting at 355 nm.

Study of anti-inflammatory actions IPAR-I, respectively, inhibiting them from secreting mast cells histamine showed that IPAR-I could inhibit inflammation, significantly reducing the secretion of histamine.

Example 4.

Test cytoprotective effect of peptide IPAR-I.

Studies were performed on primary cultures of hippocampal neurons (9-10 days) brain one to three-day rat Wistar rats. The obtained cell suspension was transferred on cover glasses coated with poly-D-lysine. Then deleted neprecejusies cell was added in the culture medium. 3-4 day arabinoside was added on day to inhibit the growth of glial cells. The cells were left for 7-10 days in the incubator. Replace 1/3 of the environment in the cells was carried out every 3 days. The obtained culture contained no more than 5% of glial cells.

Death/survival of neurons in culture was determined 24 hours after the 45-minute action of thrombin or after co-incubation IPAR-I with thrombin. Peptide IPAR-I (in concentrations from 0.4 to 100 nm/l) was treated neurons for 10 min before the addition of thrombin. As a control, neurons were treated with HEPES-saline buffer (HBSS). Death/viive the ity of neurons was assessed by biochemical MTT (3-(4,5-Dimethyl-2-thiazolyl)-2,5-diphenyl-2H-tetrazolium bromide) method. An aqueous solution of MTT was added to the culture medium to a final concentration of 1 mg/ml, and incubated the cells for 1.5 hours at 37°C. Then the medium was collected and DMSO was added to dissolve formisano. The optical density was measured spectrophotometrically (590 nm) at universal microplate spectrophotometer Anthos Lucy 1. Estimated percentage compared to control.

It was found that thrombin at a concentration of 100 nm/l caused the death of more than 20% of neurons (reduced survival relative to the control). The incubation of cells with IPAR-I before adding thrombin protected them almost completely from the neurotoxic action of thrombin (level of living cells compared to the control values were 98%).

Thus synthesized peptide has antiagregatini, anti-inflammatory and cytoprotective activity in greater availability compared with the nearest equivalent.

Peptide 3-mercaptopropionyl-Phe-Ile-Ile-Arg-Lys-Pro-Asp-Lys-NH2as a means antiaggregatory, anti-inflammatory and cytoprotective therapy.



 

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