Method for preparing boron-containing hyaluronic acid

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to a method for preparing sodium salt of hyaluronic acid modified by boron compounds with no fluid medium added. The method consists in the fact that powdered sodium salt of hyaluronic acid together with a modifying agent and mixed modifying agents is pre-homogenised in a mixer at temperature ranging within 20° to 50°C; thereafter the prepared homogenous powder mixture is simultaneously exposed to pressure and shearing deformation in a mechanochemical reactor at temperature ranging within 20° to 50°C and pressure 5-1000 MPa.

EFFECT: invention provides preparing boron-containing sodium salt of hyaluronic acid applied in boron neutron capture therapy in one-stage process parameters with no fluid medium added which requires low power, labour and water consumptions.

13 cl, 15 ex

 

The invention relates to synthetic polymer chemistry, and in particular to methods of modification of hyaluronic acid - a natural polymer from the class of polysaccharides. The modification is aimed at the introduction into the molecule of sodium salt of hyaluronic acid of boron isotopes with atomic mass 10. Thus modified sodium salt of hyaluronic acid can be used in various fields of medicine, for example, boron neutron capture therapy (BNCT), photodynamic therapy, boron neutron capture of synovectomy, radioimmuno-diagnosis and radioimmuno therapy. Method BNCT is promising in the treatment of cancers, especially malignant brain tumors [Ibetween, Weaze. Boron neutron capture therapy of cancer. The chemical aspect. Grew up with. chem. J., 2004, .XLVIII, No. 4, pp.109].

Unknown ways to obtain sodium salt of hyaluronic acid-modified compounds of boron. Here and hereinafter as compounds of boron are considered only compounds of boron isotope with an atomic mass of 10.

Modern strategy of identifying compounds suitable for BNCT, the synthesis of boron-containing biologically active compounds that are compatible with the diseased cells of the body (in particular, cancer cells, cells infected with rheumatoid arthritis, and others).

Known methods according to the teachings of some boron-containing biologically active compounds, boron-containing nucleotides and nucleosides [U.S. Pat. U.S. No. 7338669 (2008), U.S. Pat. U.S. No. 6583122 (2003)], boron-containing porphyrins [U.S. Pat. U.S. No. 6995260 (2006), U.S. Pat. U.S. No. 6566517 (2003)], boron amino acid [U.S. Pat. U.S. No. 6037490 (2000)]. The disadvantages of these methods are the multi-stage chemical processes, high toxicity of organic reagents and solvents, time-consuming purification of the final products.

Closest to the claimed invention is a method of producing polysaccharide dextran, modified boron compounds [L.Gedda, P.Olsson, J.Carlsson. Bioconjugate Chem., 1996, v.7, p.584]. This method has the following disadvantages: large material and labor costs, a multi-stage synthesis, the high toxicity of organic reagents and solvents, time-consuming cleaning and low yield of the final product.

The objective of the invention is the creation of a universal environmentally friendly way to obtain a sodium salt of hyaluronic acid-modified compounds of boron, in one technological mode in the absence of a liquid medium, without large energy labor and vadastra, with a target products with a quantitative yield.

The problem is solved in that a versatile, environmentally safe way to obtain in the absence of a liquid medium. How is that powdered sodium salt of hialuronovoy with the modifier or a mixture of two or more modifiers pre-homogenized in the mixer at a temperature of from 20° to 50°C, then the resulting homogeneous powder mixture is subjected to the simultaneous action of pressure and shear strain in mechanochemical reactor at a temperature of from 20° to 50°C, the pressure is in the range from 5 to 1000 MPa. As the use of boron boron isotope with an atomic mass of 10. As a modifier use of boron compounds from the series: boric anhydride, decahydrate of sodium tetraborate (borax), acid: boric, metaboric, tetraborate. The molar ratio of sodium salt of hyaluronic acid to the modifier or the amount of modifier is from 500:1 to 1:6.

The duration of the effects of pressure and shear strain is from 0.1 to 10 minutes. The mixer is a mill or a mixer, a screw type, for example, twin-screw extruder. As a mechanochemical reactor you can use the machine screw type: twin screw extruder with a unidirectional rotation of the screw, twin-screw extruder with oppositely directed rotation of the screw, twin-screw extruder with a set of Cams of different types, for example, transport, locking, peretiraya. As a mechanochemical reactor can also be used Bridgman anvils, while the shear deformation is carried out by changing the angle of rotation of the lower anvil in the range from 50 to 350 degrees.

The decision of the post is often a task made possible by the fact that that the process of interaction of initial reagents is carried out in contrast to the known method, not in solution, and by the interaction of initial reagents in solid powdered state with the simultaneous action of pressure and shear strain. This has led to a new technical result consists in the creation of a universal environmentally friendly way to obtain a sodium salt of hyaluronic acid-modified compounds of boron, in one technological mode in the absence of a liquid medium, to obtain the target product with a quantitative yield. The method does not require large energy, labor and vadastra.

Chemical substance reactions of sodium salt of hyaluronic acid with boron compounds lies in the interaction alcohol (-OH) groups of hyaluronic acid with boric acids (or their anhydrides or salts) with the formation of esters of boric acid, with the formation of boron-oxygen-carbon (B-O-C) bond. The formation of esters of boric acid proved using Fourier transform infrared spectral analysis of the initial reagents and reaction products. It is established that in the spectra of target products are characteristic bands boron-oxygen-carbon linkages in interval 1420-1470 cm-1. In addition, the method of fractional precipitation shows that the target produktionstorvet the original substance; and target products vary in solubility from the original substances.

The invention can be illustrated by the following examples:

Example 1. 400,0 g (1 mol) of powdery sodium salt of hyaluronic acid (ha) and 474,0 g (6 mol) of boric acid (Bq) homogenized in a twin-screw extruder with a unidirectional rotating augers at 50°C for 10 minutes the resulting powder mixture is subjected to the simultaneous action of pressure and shear strain at 50°C and a pressure of 15 MPa in a twin-screw extruder with a unidirectional rotation of the screw within 10 minutes Of the extruder obtained white powder, the output of which is 766,0 g (99.8 per cent). The IR spectrum of the product has an absorption band in the region of 1420 cm-1and 1460 cm-1that are characteristic of esters of boric acid.

Example 2. Performed analogously to example 1, but in contrast Bq take in the amount of 0.16 g (0,002 mol). From the extruder the obtained white powder, the output of which is 398 g (99.6 percent). The IR spectrum of the product has absorption bands in the region 1422 cm-1and 1463 cm-1that are characteristic of esters of boric acid.

Example 3. 400,0 g (1 mol) of powdery sodium salt SC and 378 g (1 mole) of decahydrate of sodium tetraborate (Borax) homogenized in a twin-screw extruder with AGNONA allonym rotation of the augers at 20°C for 10 minutes Next, the resulting powder mixture is subjected to the simultaneous action of pressure and shear strain at 40°C and a pressure of 10 MPa in a twin-screw extruder with a unidirectional rotation of the screw within 10 minutes Of the extruder obtained white powder, the output of which is 595 grams (99,5%). The IR spectrum of the product has absorption bands in the region 1426 cm-1and 1461 cm-1that are characteristic of esters of boric acid.

Example 4. Performed analogously to example 3, but in contrast borax take in quantity 0,76 g (0,002 mol). From the extruder the obtained white powder, the output of which is 399 g (99.8 per cent). The IR spectrum of the product has absorption bands in the region 1425 cm-1and 1460 cm-1that are characteristic of esters of boric acid.

Example 5. 400,0 g (1 mol) of powdery sodium salt of ha and 0.14 g (0,002 mol) of boric anhydride (BA) homogenized in a twin-screw extruder with a unidirectional rotating augers at 20°C for 10 minutes the resulting powder mixture is subjected to the simultaneous action of pressure and shear strain at 20°C and a pressure of 5 MPa in a twin-screw extruder with a unidirectional rotation of the screw within 10 minutes Of the extruder obtained white powder, the output of which is 399 g (99.8 per cent). The IR spectrum of the product contains bands of the absorption in the region 1424 cm -1and 1463 cm-1that are characteristic of esters of boric acid.

Example 6. Performed analogously to example 5, but in contrast, BA take in the amount of 68 g (1 mol). From the extruder the obtained white powder, the output of which is 367 g (99.8 per cent). The IR spectrum of the product has absorption bands in the region 1427 cm-1and 1465 cm-1that are characteristic of esters of boric acid.

Example 7. Performed analogously to example 1, but in contrast Bq take in the amount of 3.95 g (0.05 mole). From the extruder the obtained white powder, the output of which is 402 g (99.8 per cent). The IR spectrum of the product has absorption bands in the region 1428 cm-1and 1466 cm-1that are characteristic of esters of boric acid.

Example 8. Performed analogously to example 3, but in contrast borax take in the amount of 3.78 g (0,01 mol). From the extruder the obtained white powder, the output of which is 401 g (99.6 percent). The IR spectrum of the product has absorption bands in the region 1425 cm-1and 1460 cm-1that are characteristic of esters of boric acid.

Example 9. Performed analogously to example 5, but in contrast, BA take in the amount of 13.6 g (0.2 mol). From the extruder the obtained white powder, the output of which is 412,7 g (99.8 per cent). The IR spectrum of the product present on the wasps absorption in the region 1429 cm -1and 1460 cm-1that are characteristic of esters of boric acid.

Example 10. 400,0 g (1 mol) of powdery sodium salt of hyaluronic acid, 1.7 g (0,025 mol) of BA and of 9.45 g (0,025 mol) of borax homogenized in a twin-screw extruder with a unidirectional rotating augers at 20°C for 10 minutes the resulting powder mixture is subjected to the simultaneous action of pressure and shear strain at 30°C and a pressure of 10 MPa in a twin-screw extruder with a unidirectional rotation of the screw within 10 minutes Of the extruder obtained white powder, the output of which is 405 g (99.6 percent). The IR spectrum of the product has absorption bands in the region 1424 cm-1and 1459 cm-1that are characteristic of esters of boric acid.

Example 11. Performed analogously to example 10, however in contrast instead take BA BC in the number 1,975 g (0,025 mol). From the extruder the obtained white powder, the output of which is 406 g (99.4 per cent). The IR spectrum of the product has absorption bands in the region 1423 cm-1and 1458 cm-1that are characteristic of esters of boric acid.

Example 12. Performed analogously to example 10, however in contrast instead of borax take BC in the number 1,975 g (0,025 mol). From the extruder the obtained white powder, the output of which is 402 g (99.7 per cent). The IR spectrum of the product are present floor the si absorption in the region 1422 cm -1and 1463 cm-1that are characteristic of esters of boric acid.

Example 13. 400,0 g (1 mol) of powdery sodium salt of hyaluronic acid, 1.13 g (0,0167 mol) of BA, 6,30 g (0,0167 mole) of borax and of 1.32 g (0,0167 mole) Bq homogenized in a twin-screw extruder with a unidirectional rotating augers at 20°C for 10 minutes the resulting powder mixture is subjected to the simultaneous action of pressure and shear strain at 30°C and a pressure of 30 MPa in a twin-screw extruder with a unidirectional rotation of the screw within 10 minutes Of the extruder obtained white powder, the output of which is 404 (99,7%). The IR spectrum of the product has an absorption band in the region of 1420 cm-1and 1464 cm-1that are characteristic of esters of boric acid.

Example 14. 27.9 mg (6,8·10-5mole) of powdered sodium salt SC, and to 26.0 mg (6,8·10-5mole) of borax homogenized mill at 20°C for 10-15 minutes and Then the powder mixture is placed on the lower anvil Bridgman (the diameter of the working surface=3 cm), cover the top of the anvil, the anvil put under a press and subjected to pressure of 1000 MPa at 20°C, at an angle of rotation of the lower anvil 50° C for 0.1 min Then relieve pressure, remove the anvil from the press. The resulting white powder mass which makes up 40.7 mg (99.5%pure). The IR spectrum of the product presence is Tvout absorption bands in the region 1425 cm -1and 1460 cm-1that are characteristic of esters of boric acid.

Example 15. 29,5 mg (7,2·10-5mole) of powdered sodium salt of hyaluronic acid, and 5.8 mg (7,2·10-5mole) Bq homogenized mill at 20°C for 10-15 minutes and Then the powder mixture is placed on the lower anvil Bridgman (the diameter of the working surface = 3 cm), cover the top of the anvil, the anvil put under a press and subjected to pressure of 500 MPa at 20°C, at an angle of rotation of the lower anvil 350° for 1 minute Then take off the pressure, remove the anvil from the press. The resulting white powder, the weight of which amounts to 34.1 mg (99.5%pure). The IR spectrum of the product has absorption bands in the region 1423 cm-1and 1464 cm-1that are characteristic of esters of boric acid.

As examples, create a simple universal environmentally safe way to obtain a sodium salt of hyaluronic acid, a modified boron compounds, in one technological mode in the absence of a liquid medium, to obtain the target product with a quantitative yield. The method does not require large energy, labor and vadastra. The target products of the reaction are white powders, soluble in water, and can find application in BNCT.

1. The method of obtaining sodium salt hialuronowy the th acid, modified boron compounds in the absence of a liquid medium, which consists in the fact that powdered sodium salt of hyaluronic acid with the modifier or a mixture of two or more modifiers pre-homogenized in the mixer at a temperature of from 20° to 50°C, then the resulting homogeneous powder mixture is subjected to the simultaneous action of pressure and shear strain in mechanochemical reactor at a temperature of from 20° to 50°C, the pressure is in the range from 5 MPa to 1000 MPa.

2. The method according to claim 1, characterized in that as the use of boron boron isotope with an atomic mass of 10.

3. The method according to claim 2, characterized in that as a modifier use of boron compounds from the series: boric anhydride, decahydrate of sodium tetraborate (borax), acid: boric, metaboric, tetraborate.

4. The method according to claim 3, characterized in that as a modifier use boric anhydride, decahydrate of sodium tetraborate (borax), boric acid.

5. The method according to claim 4, characterized in that the molar ratio of sodium salt of hyaluronic acid to the modifier or the amount of modifier is from 500:1 to 1:6.

6. The method according to claim 5, characterized in that the duration of the effects of pressure and shear strain is from 0.1 min to 10 minutes

7. The method according to claim 1, characterized in that the mixer are the two who is the mill.

8. The method according to claim 1, characterized in that the mixer is a mixer, a screw type, for example a twin screw extruder.

9. The method according to claim 1, characterized in that the mechanochemical reactor device is a screw type or Bridgman anvils.

10. The method according to claim 9, characterized in that the reactor using the machine screw type.

11. The method according to claim 10, characterized in that the apparatus is selected from the set: twin screw extruder with a unidirectional rotation of the screw, twin-screw extruder with oppositely directed rotation of the screw, twin-screw extruder with a set of Cams of different types, such as transport, locking, peretiraya.

12. The method according to claim 8, characterized in that the reactor using the Bridgman anvils, while the shear deformation is carried out by changing the angle of rotation of the lower anvil.

13. The method according to item 12, characterized in that the rotation angle of the Bridgman anvil is in the range from 50° to 350°.



 

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8 cl, 9 ex

FIELD: chemistry.

SUBSTANCE: method involves feeding wastes to be treated into artificial containers, biotreatement, tapping the filtrate and removing the obtained biomass. Biotreatement is carried out by culturing hoverfly larvae from the freshly laid eggs phase to the pupation phase in the fermented wastes to be treated, placed in artificial meshed containers the bottom and walls of which are covered with filter cloth. The apparatus has artificial containers, devices for feeding the wastes to be treated, outputting the filtrate and collecting the biomass. The artificial containers have a meshed bottom and walls covered with filter cloth.

EFFECT: invention enables to combine biotreatment of methane wastes with production of chitin containing biomass.

8 cl, 1 dwg

FIELD: chemistry.

SUBSTANCE: method of producing nanoparticles of low-molecular chitosan involves preparing a solution of pre-purified low-molecular chitosan in filtered 1-2 wt % aqueous acetic acid, adding solutions of hydroxides of alkali metals or ammonia for 2 hours, dispersing the system using a mechanical mixer at a rate of 200-300 rpm at temperature 20°C to pH 6.9-7.0. Further, the dispersion is centrifuged at 10000 rpm. The obtained solid residue is redispersed in bidistillate while mechanically mixing at a rate of 200-300 rpm at temperature 20°C.

EFFECT: invention simplifies the method of producing nanoparticles of low-molecular chitosan and apparatus design without formation of undesirable harmful substances.

3 ex

FIELD: chemistry.

SUBSTANCE: starting high-molecular chitosan is dissolved in acid solution. The chitosan dissolved in the acid is then precipitated by adding alkali solution. The re-precipitated high-molecular chitosan is washed from the formed salt and excess alkali using a coarse-porous filter. The re-precipitated chitosan is dissolved in acid solution until achieving pH 5.5. An enzyme preparation is then added and hydrolysis is carried out. The reaction is stopped after formation of low-molecular chitosan.

EFFECT: method is characterised by avoiding the need to remove salts from the enzymatic mixture and the end product, as well as low level of loss of material.

2 dwg, 7 tbl, 6 ex

FIELD: medicine.

SUBSTANCE: method for the recovery of high-purity and completely soluble partially deacetylated chitin polymer of deacetylation degree (DD) 30-60 % involves the stages: neutralisation of partially deacetylated chitin; dissolution of partially deacetylated chitin in an acid; removal of undissolved particles by sequential filtration stages; pH reduction of the solution to 8 and more; precipitation of completely dissolved and purified partially deacetylated chitin by temperature rise and salt addition where the precipitate is removed and rinsed after precipitation by filtration or centrifugation and where rinsing water and deposit temperature is 40°C and higher. Also the invention refers to a neogenesis composition containing therapeutically active N-acetylglucosamine (A) and glucosamine (D) chitooligomers where the composition contains heterochitooligomers which shall meet the following criteria: said oligomers have a chain length in the range 5-20 monomer residues; each oligomer chain can have two residues of N-acetyl-D-glucosamine (AA) on any or both ends of the oligomer chain, the remained inside of the oligomer has a maximum number of the residues A; the sequence of said inside of the chain is such that the N-acetyl-D-glucosamine residue (A) does not adjoin to the other N-acetyl-D-glucosamine (A) residue (such as, e.g. AA).

EFFECT: biomaterial based on said compositions intensifies the bone repair and hemostasis in healing of a fractured or seriously injured bone.

21 cl, 32 dwg, 9 tbl, 9 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to field of medicine, cosmetology and to production of biologically active substances. In order to isolate glycosaminoglycans from skins, extraction, proteolysis and sedimentation are carried out. For extraction used is 0.9% NaCl solution, for fermentative proteolysis used is papain enzyme, for sedimentation used is 4% alcohol solution of potassium acetate.

EFFECT: method application makes it possible to obtain target product with the least expenditures for its production.

1 dwg, 1 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention refers to pharmaceutical industry, particularly using an aqueous extract of tobacco leaves for preparing an agent for treating tobacco dependence. Using an aqueous solution of the aqueous extract of tobacco leaves or a lyophilizate of the aqueous extract of tobacco leaves in sterile water for preparing the agent in the form of injections for treating tobacco dependence wherein said solution have the certain content of a dry substance. A kit for treating tobacco dependence comprising a syringe, a sterile water bottle and the lyophilizate of the aqueous extract of tobacco leaves.

EFFECT: aqueous extract of tobacco leaves and kit are effective for treating tobacco dependence.

8 cl, 2 ex

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