N,o-(2,3-dihydroxypropyl)chitosanyl-borate, having antibacterial, immunomodulating and antitoxic effect

FIELD: chemistry.

SUBSTANCE: invention relates to a novel compound - N,O-(2,3-dihydroxypropyl)chitosanyl-borate, having formula , where m=500-3000.

EFFECT: compound has antibacterial, immunomodulating and antitoxic effect.

1 tbl, 6 ex


The invention relates to the field of biologically active compounds and relates to a borate complex of the N,O-(2,3-dihydroxypropyl)chitosan, antibacterial, immunomodulatory and anti-toxic effect, intended for the prevention and treatment of severe forms of dyspepsia in animals is complicated by pathogenic forms of enterobacteria and cocci. The invention can be used in veterinary institutions, research laboratories, as well as in livestock and poultry.

Boric acid and its salts are widely used as components of external antiseptic drugs: pasta Teymurova, liniment "boron-zinc" ointment "Borno", solution "fukortsin", alcohol and glycerine solution of boric acid and sodium tetraborate in the compositions of creams, ointments for treating burns (Mashkovsky M. D. Medicines, Moscow, New wave, 2000). In addition, it is often used as a mild antiseptic in solutions for storing eye contact lenses. Known antibacterial agents based on boron compounds (WO 2013104897, WO 2013093615, WO 2013033461, WO 2011060196), borates (WO 2011056168, SU 201404) and boric acid (F. Haesebrouck, M. Baele, H. De Keyser. Antimicrobial activity of an acetic and boric acid solution against Staphylococcuspseudointermedius // Vlaams Diergeneeskundig Tijdschrin, 78 (2009). P. 89-90).

The drawback of such dosage forms is the presence�their free of boric acid and its molecular complexes with trivalent alcohols, aromatic hydroxycarboxylic acids and phenols and boron compounds, which provide a rapid supply of a therapeutic dose of boron ions (III) in the body, which, firstly, leads to rapid excretion of the drug, and secondly, may cause toxic effects if decompensation excretory capacity of the kidneys.

The closest analogue of the invention is a borate complex on the basis of the block copolymer carboxymethylchitin and polyglycerol (A. A. Alencar de Queiroz et all. Physicochemical and antimicrobial properties of boron-complexed polyglycerolchitosan of // J. Biomater. Sci Polymer Edn. 17 (2006). P. 689-707). To obtain it initially synthesize the polyglycerol by polymerization of glycidol in the presence of NaOH at 260°C and then at 120°C in vacuum for 24 hours. Next spend getting carboxymethylchitin by treating the chitosan with Chloroacetic acid in an aqueous solution of NaOH at 30°C for 12 hours, and then carry out the esterification carboxymethylchitin the polyglycerol when heated to reflux and the use of dimethyl sulfate as a catalyst. Next, the obtained blockcopolymer polyglycerol and carboxymethylchitin treated with boric acid at 160°C for 3 hours. The obtained polyglycerol-carboxymethylchitin-Borat has an antibacterial effect.

The disadvantages of this are complex with�agnosti its synthesis, consisting of four stages, using a long heating at high temperature. This explains its low commercial availability. In addition, the high viscosity of low-concentrated solutions causes inconvenience in their use and requires no additional fixing materials.

Object of the invention is obtaining a new connection - N,O-(2,3-dihydroxypropyl)chitosan-borate, antibacterial, immunomodulatory and anti-toxic effect simple and effective way using readily available substances.

The task is solved by obtaining the N,O-(2,3-dihydroxypropyl)chitosan-borate of the formula

by first obtaining N,O-(2,3-dihydroxypropyl)chitosan with a degree of substitution of 2.0 to 3.0 by the interaction of chitosan with an aqueous solution of glycidol in the presence of hydrochloric acid at 55-65°C for 12-14 hours (EN 2496793), then the interaction of N,O-(2,3-dihydroxypropyl)of chitosan with an aqueous solution of boric acid at pH 9 at a temperature of 20-30°C for 24 hours, followed by separation of the formed gel from the solution. The composition and structure of the obtained N,O-(2,3-dihydroxypropyl)chitosan-Borat characterize the data of elemental analysis, ft-IR spectroscopy.

Preparation of aqueous solution of N,O-(2,3-dihydroxypropyl)chitosan-Borat� is carried out by dilution of the gel to the desired concentration with distilled water.

Toxicological studies of N,O-(2,3-dihydroxypropyl)chitosan-Borat conducted on laboratory animals (white mice). The aqueous solution is administered to white mice (weighing 25-30 g) in the stomach with a syringe with an elastic probe. The animals are monitored for 2 weeks after the administration, given the General condition of the animals, the preservation of motor function, appetite, condition of coat, breathing, reaction to external stimuli.

Conducted study of the morphological composition of blood cells and biochemical indices of blood serum in the experimental group did not differ from those in control. Histological examination of internal organs from mice treated with the complex for 20 days, no changes were detected that characterizes the lack of toxic effect of the drug on the body. The maximum tolerated dose of N,O-(2,3-dihydroxypropyl)chitosan-Borat is 1600 mg/kg, preventive - 70 mg/kg, and therapeutic index (the ratio of these doses) is 22.8, which indicates a sufficient limit the safe use of N,O-(2,3-dihydroxypropyl)chitosan-Borat in veterinary medicine.

For bacteriostatic studies using bacterial cultures: Escherichia coli, Staphylococcus aureus, Klebsiella pneumonias, Staphylococcus epidermidis isolates from clinically ill animals with severe dyspepsia. Mi�Kalou inhibitory concentration (MIC) is determined, using serial solutions of N,O-(2,3-dihydroxypropyl)chitosan-Borat on mesopatamia broth. In each test tube add 50 µl of saline containing a suspension of bacteria at a concentration of 6*107CFU/ml Control serves as a vial containing pure culture medium. The effect of the concentration N,O-(2,3-dihydroxypropyl)chitosan-borate on growth dynamics of culture in a liquid medium, are examined by the modified method. To do this, 50 μl of cell suspension 18-hour culture of bacteria that contains 6*107CFU/ml was added to 100 μl mycopathologia agar containing N,O-(2,3-dihydroxypropyl)chitosan-borate at different concentrations and pH 6.0. In the control variant N,O-(2,3-dihydroxypropyl)chitosan-Borat is not added. The mixture was incubated at 37°C on a rocker at 180 rpm.

To assess the immunomodulatory, antimicrobial and antitoxic properties of the N,O-(2,3-dihydroxypropyl)chitosan-Borat conduct experiments concerning animals suffering from colibacillosis in cattle farming and dysfunctional in this disease. Experiments carried out on calves of the Holstein (black and white suit) rocks ranging in age from birth to one month. This forms two groups of newborn calves by 10 goals each.

Animals first experimental group at day old once � day asking N,O-(2,3-dihydroxypropyl)chitosan-borate in aqueous solution, dissolved in milk, and fed to calves within 15 days. Control calves left intact. Blood samples for biochemical studies take at the age of 1 day and 20 days. Observation of clinical status, growth and development of calves within 2 months with manifestations of diarrhea show that the calves of the control group significantly lag behind their peers. The intensity of the biomass growth of calves of the experimental group is higher than control, respectively, 13.8% at 30 days and 21.7% on the 60th day after the start of treatment. Thus, the calves fed for the treatment of N,O-(2,3-dihydroxypropyl)chitosan-Borat, have the greatest rate of growth in comparison with the control group. In Hematology the study of blood of the calves of the control group revealed significant changes, indicating the presence of acute inflammation in animals. In particular, the marked increase in the total number of cells by 69%, reduced number of red blood cells by 29.5%, and the number of hemoglobin by 36%, reduced levels of carotene by 27% calcium 34%, phosphorus by 21%, increased reserve alkalinity and total protein content in serum, exceeded the value of the ESR in 4 times. Such changes indicate a profound metabolic disorders and the occurrence of infectious-inflammatory processes in to�trolley group of animals. The effectiveness of the treatment of animals in the experimental group was 100% recovery of calves. In the control group died 2 calf out of 10.

Disinfectant properties of the N,O-(2,3-dihydroxypropyl)chitosan-Borat determined on contaminated test cultures (Escherichia coli, Staphylococcus aureus) objects. As test objects, using a wooden surface with porous structure. Contaminated test object is dried for one hour at room temperature, and then treated with an aqueous solution of N,O-(2,3-dihydroxypropyl)chitosan-Borat from the sprayer. The temperature of the working solution of the drug and the air during the experiments is 18-20°C, relative humidity 65-75%.

Obtaining N,O-(2,3-dihydroxypropyl)chitosan-Borat illustrated by the following examples.

Example 1.

10 g of powdered N,O-(2,3-dihydroxypropyl)chitosan with a molecular weight of 930 kDa (corresponding to the value of m=3000) with a degree of substitution of 2.0 is dissolved in 300 ml of water with pH=9 containing 2.25 g of boric acid, with stirring for 1 hour and allowed to stand for 23 hours at room temperature. The formed gel was separated from the solution. Found, %: 3,70; N 0,36; At 0.53. IR spectrum (cm-1): 3381 (N-H), (O-H), 2922 (C-H), 1660 (C=O amide I), 1568 (N-H amide II), 1435 (C-H), 1372 (C-N amide III), 1150 (C-O), (C-C), 1067 (C-O), (P-C).

Example 2.

10 g of powdered N,O-(2,3-dihydroxypropyl)hit�Zan with a molecular weight of 193 kDa (corresponding to the value of m=500) with a degree of substitution of 3.0 is dissolved in 200 ml of water with pH=9, containing 1.5 g of boric acid, with stirring for 1 hour, then add 100 ml of water with pH=9 containing 0.75 g of boric acid, stirred for 1 hour and incubated for 22 hours at room temperature. The formed gel was separated from the solution. Found, %: 4,63; N 0,45; 0,93. IR spectrum (cm-1): 3381 (N-H), (O-H), 2922 (C-H), 1660 (C=O amide I), 1568 (N-H amide II), 1435 (C-H), 1372 (C-N amide III), 1150 (C-O), (C-C), 1067 (C-O), (P-C).

The use of N,O-(2,3-dihydroxypropyl)chitosan-borate in the form of a solution

Example 3.

0.9 g N,O-(2,3-dihydroxypropyl)chitosan-borate obtained in example 2, was dissolved at 29.1 ml of water, the resulting solution is diluted with the required amount of milk and fed the newborn animal at day old. The procedure was repeated 1 times a day for 15 days.

Example 4.

1.8 g of N,O-(2,3-dihydroxypropyl)chitosan-borate obtained in example 1, was dissolved at 58.2 ml of water, the resulting solution is diluted with the necessary quantity of milk or added to dry food, animal feed, at the age of 1 year. The procedure was repeated 1 times a day for 15 days.

Example 5.

1.8 g of N,O-(2,3-dihydroxypropyl)chitosan-borate obtained in example 2, was dissolved at 58.2 ml of water, the resulting solution is impregnated gauze swabs and fill their wounds. Drainage is to retain the appearance of granulation tissue on the affected surface.

Used�a lo g N,O-(2,3-dihydroxypropyl)chitosan-borate in the form of a gel

Example 6.

Surgical instruments made of alloys and polymers immersed in an aqueous gel obtained in example 2 for 3 hours. After bactericidal treatment items washed in water with surface-active substance.

A method of producing N,O-(2,3-dihydroxypropyl)chitosan-Borat simple in design, requires the use of commercially available compounds, can significantly reduce the amount of used organic solvents as in the modification process, and in the process of selection of the product, consists of two stages and does not require prolonged heating at a high temperature.

An aqueous solution of N,O-(2,3-dihydroxypropyl)chitosan-Borat has the consistency of a gel that provides the ease of use. Advantages of the claimed compounds is the use of biosecurity and biocompatible polymers, which ensures, first, the lack of toxicity to the living body - all components are substances 4 hazard class and, secondly, their degradation by digestive enzymes and nonspecific enzyme lysozyme. The latter property provides a natural removal of polymers from the oral cavity and gastrointestinal tract.

The use of high molecular weight complexes of boric acid reduces the side fiziologicheskii boron ions, and also enhance therapeutic effect with the gradual release of boric acid from the complex and the manifestation of a bacteriostatic effect. High mucoadhesives connection due to N,O-(2,3-dihydroxypropyl)chitosan provides high diffusion of the drug in the intercellular substance of damaged tissues and mucous membranes of the gastro-intestinal tract. Thus, the use of N,O-(2,3-dihydroxypropyl)chitosan-Borat can significantly reduce exposure of the main active substances (boric acid) and, therefore, to avoid adverse physiological reactions, providing a prolonged release of boron ions.

N,O-(2,3-dihydroxypropyl)chitosan-borate can be used as the main active component of the disinfectant, and as a Supplement to other antiseptic preparations, increasing their bactericidal effect. N,O-(2,3-dihydroxypropyl)chitosan-Borat not contain strong oxidizing agents, bases, aldehydes, aromatic alcohols, which provides him since it is hypoallergenic and no toxic reactions when administered orally. Does not cause allergic reactions and damaging effect on the skin, has no smell, has a long-lasting antimicrobial activity to the surface of things, can't cause different corrosion of materials. The presence of N,O-(2,3-dihydroxypropyl)of chitosan in the composition of the compounds provides a film formation on the treated subjects, which hampers the subsequent washout of N,O-(2,3-dihydroxypropyl)chitosan-borate, increases its bactericidal properties and duration of bactericidal activity of the drug on the treated surface.

N,O-(2,3-dihydroxypropyl)chitosan-borate, having the structural formula
where m=500-3000.


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