Method for production of modified arabinogalactan

FIELD: chemistry.

SUBSTANCE: invention relates to new derivants of arabinogalactan. The method for production of modified arabinogalactan by oxygenising its primary hydroxy groups with system of 2,2,6,6,-tetramethylpiperydine-1-oxyl radical NaBr-NaClO-H2O with pH 10.2 to carboxyl groups and further conjugation of carboxy groups of oxidised arabinogalactan with amino containing compounds in the presence of condensing agent 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide in aqueous medium at the ambient temperature and pH 4.7-4.8 is described. A number of pharmaceutically important amines are used as amino containing compounds: n- and o-aminophenols , 5- and 4-aminosalicylic, anthroic and n-aminobenzoic acids, ethyl ester of n-aminobenzoinc acid (benzocaine), (3-diethylaminoethyl ester of n-n-aminobenzoinc acid (ethocaine hydrochloride), 1-phenyl-2,3-dimethul-4-amonipyrazolon-5(4-aminoantipyrine), isonicotinic acid hydrazide (isoniaside), sulfanamides, such as n-sulphanilamide (streptocide), n-aminobenzolsulfacetamide-sodium (sulfacyl sodium), 2-aminoethanesulfonic acid (taurine), natural α-amino acids (amino acetic acid, diamino-hexanoic acod, etc), diamines (hydrazine, ethylene diamine) and dihydrazides (dehydrazide of hexandioic acid). The derivants of arabinogalactan which can be used in medicine and pharmacology are derived. Conversion of carboxygroups to amide groups of oxidised arabinogalactan achieves 90-95%.

EFFECT: invention can be applied in medicine, pharmacology

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The invention relates to the field of chemistry, in particular to a method for producing new substances derivatives of arabinogalactan, which can be used in medicine, pharmacology.

Arabinogalactan class of polysaccharides, the construction material of the cell wall of many trees and plants [Medvedev E.N., Babkin VA, Ostroukhova L.A. // Chemistry of plant raw materials. 2003. No. 1. P.27-37]. The Western larch (Larix occidentalis) and Siberian {Larix sibirica) are commercially important sources of arabinogalactan, which is used as an emulsifier or stabilizer in the manufacture of certain food products. High molecular weight arabinogalactan is recommended for use as an immunostimulating agent that activates macrophages [Application WO 2006082707], but in combination with the salts of iron in iron deficiency anemia [U.S. Pat. EN 2208440].

Molecules of arabinogalactan consist of a main chain of (1→3) - linked residues of D-galactose consisting of L-arabinose and D-galactose (1→6) - branches in almost all the rest of D-galactose in the main chain [Methods in carbohydrate chemistry. Edited by Kochetkov NK Moscow: 1967. 317 C.]. In larch arabinogalactan the ratio of galactose:arabinose is from 5:1 to 10:1. Like many polysaccharides of molecular weight arabinogalactan varies from 104up to 2·106 Yes.

Not so long ago established that members of the arabinogalactan of L-arabinose and D-galactose, unlike, for example, monosaccharides such as glucose or mannose, show affinity to asialoglycoprotein receptors of liver cells, especially important when it performs 4-Oh-group of the galactose [Groman E.V., Enriquez P.M., Jung S, Josephson L. // Bioconjug. Chem. 1994. V.5 (6). P.547-556]. This property has stimulated work on the synthesis and study of properties of modified arabinogalactan as drug-delivery systems to the liver cells. For example, in the presence of NaBH3CN with poly-L-lysine was obtained graft-copolymer of arabinogalactan by the reaction of reductive amination between residue of a reducing sugar at the end of the chain of arabinogalactan and the ε-amino group of poly-L-lysine. Dendrite copolymer as a DNA delivery to cells of the liver showed high specificity to asialoglycoprotein receptors that promising for the application of the copolymer in gene therapy [J.U. Park, Ishihara T., Kano, A., Akaike T., Maruyama A. // Prep. Biochem. Biotechnol. 1999. V.29 (4). P.353-370].

Other graft copolymers of arabinogalactan get grafted copolymerization with acrylamide and followed by treatment with dimethylamine and formaldehyde in the reaction of manniche. Such copolymers are used to improve dehydration and increase paper strength [AV is. St. No. 633965].

Known esters of arabinogalactan with cinnamic acid or its derivatives containing alkyl, allyl, CN, Hal, or NH2group; in many cases, were modified at least 50% of the hydroxy groups of arabinogalactan [Application JP 60219202]. On the hydroxyl groups of arabinogalactan obtained conjugates with thiophenecarbonitrile acids (they can be useful as carriers, adsorbents or resins [Application JP 60219201]) and some fatty acids (palmitic, stearic and decanoic) [Application US 2001036933]. Water-soluble biocompatible arabinogalactan with lipophilic substituents can be used as adjuvants, inhibitors of cell adhesion, infection or inflammation.

The number of derivatives of arabinogalactan, showing affinity to asialoglycoprotein receptors synthesized with the aim of obtaining compounds with antiviral, anti-inflammatory, radioprotective properties [U.S. Pat. WO 9325239]. Arabinogalactan was first modified with hydrazine or Ethylenediamine or anywhereman with poly-L-lysine. Received free amino groups using 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (CBI) were attached antiviral agents adenosine-5'-monophosphate and adenine arabinoside-5'-monophosphate, as well as anti-inflammatory agent pepstatin. Phosphate groups in phosphorylase nom the arabinogalactan were tarifitsirovana in the presence of the OED S-2-(3-aminopropylene)ethylthiophene acid, with radioprotective properties [U.S. Pat. WO 9325239].

In nature there are acidic form of arabinogalactans, contain a small percentage of uronic acids. Arabinogalactan with carboxypentyl receive and synthetically - esterification of the hydroxy groups of succinic or glutaric anhydride or processing of arabinogalactan-dianhydride diethylenetriaminepentaacetic (DTPA) acid. The content of carboxylate in hemisuccinate arabinogalactan was 1.96 Milli-equivalent/g of the product, in the ether of arabinogalactan with DTPA - 0.117 Milli-equivalent/g Carboxymethyl - and carboxymethylaminomethyl obtained by the reaction with bromoxynil and 2 bromopropionic acids contained 5.2 and 1.3 Milli-equivalents of carboxylate per gram of final product [U.S. Pat. WO 9325239].

Another way of introducing carboxylate molecule arabinogalactan is the oxidation of the primary alcohol group. The oxidation by hydrogen peroxide in aqueous medium at elevated temperature (90°C) with bubbling through the reaction mixture to air oxidation products contained up to 10-12% of uronic acids [Borisov IM, Shirokova E.N., Mudarisov A.D., etc. // Izvestiya an. The series of chem. 2004. No. 2. P.á305-311]. Also the degradation of macromolecules, accompanied by oxidation of the anomeric centre to the carboxyl group.

Selective oxidation method primary Hydra is syrupy in polysaccharides (hyaluronic acid, cellulose, chitin) is the oxidation system 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)-NaBr-NaClO-H2O (pH 10.2) [Jiang C., Drouet E., M. Milas, M. Rinaudo // Carbohydr. Res. 2000. V.327. P.455-461; Isogai, A., Kato Y. // Cellulose. 1998. V.5. P.153-164]. However, for the oxidation of arabinogalactan this method was not applied.

Closest to the proposed invention is a method of obtaining conjugates alginic acid containing the amino compounds in the presence of the OED at room temperature in aqueous medium (pH 4.7-4.8) [U.S. Pat. Of the Russian Federation No. 2283848]. According to this method are compared with the conversion of carboxylate in the amide to 100%.

Object of the present invention to provide a modified arabinogalactan.

This is achieved as follows. Primary hydroxy-group of arabinogalactan from larch selectively oxidized to carboxyl in the system 2,2,6,6-tetramethylpiperidine-1-oxyl radical (TEMPO)-NaBr-NaClO-H2O (pH 10.2). So get arabinogalactan containing carboxyl group (AG-COOH), which are then in the presence of a condensing reagent CBI involved in the reaction with compounds containing primary amino group (RNH2). The reaction is carried out in aqueous medium (pH 4.7-4.8) at room temperature for 20-30 min at a ratio of reagents AG-COOH:RNH2:CBI = 1:2:1.5 or AG-COOH:RNH2:CBI = 1:5:1.5, if RNH2IP is resultsa α-amino acids and their derivatives. As aminecontaining compounds used pharmacochimie n (1) and o-aminophenol (2), n-aminobenzoic (3) Anthranilic (4), 4- (5) and 5-aminosalicylic (6) acid, ethyl ester n-aminobenzoic acid (benzocaine) (7), β-diethylaminoethylamine ether n-aminobenzoic acid (novocaine) (8), isonicotinic acid hydrazide (isoniazid) (9), 2-aminoethanesulfonic acid (taurine) (10), 1-phenyl-2,3-dimethyl-4-aminopyrazole-5 (4-aminoantipyrine) (11), and sulfa drugs, containing a free amino group such as n-aminobenzenesulfonic (streptocid) (12), n-aminobenzenesulfonamide-sodium (sulfacetamide) (13). Can be used and other amines: α-amino acids (glycine (14), lysine (15) and others) or their esters, various diamines (hydrazine, Ethylenediamine, hexamethylenediamine were) and dihydrazide, for example dehydrated adipic acid.

It should be noted that according to the method proposed in the work of Jiang C. et al., hyaluronic acid was oxidized by primary hydroxyl groups is not more than ~80%. Arabinogalactan was oxidized primary hydroxy groups at 100%, which is 5.1 Milli-equivalents of carboxylate on 1 g of the product AG-COOH (as sodium salt). Other methods given in the description of the prior art, such a result is not obtained. The high content of uronic acids in the modified structure is on arabinogalactan can increase pharmacological stress on the macromolecule, that is, effective carbodiimide conjugation of carboxypropyl with amines.

The invention is illustrated by the following examples.

Example 1.

a) Arabinogalactan (AG) are oxidized by the method described in [Jiang C., Drouet E., M. Milas, M. Rinaudo Study on TEMPO-mediated selective oxidation of hyaluronan and the effects of salt on the reaction kinetics // Carbohydr. Res. 2000. V.327. P.455-461]. Reaction conditions for the oxidation of AG: pH 10.2, 0°C, TEMPO=0.027 mmol, NaBr=0.5 mmol, AH=2.5 mmol in 200 ml of water and 4 ml of a 13%aqueous sodium hypochlorite solution (NaClO), the reaction time is 1 hour. The oxidized product of an aqueous solution produce precipitation in methanol. The precipitate was separated by centrifugation, washed with methanol, diethyl ether and dried under reduced pressure and a temperature not exceeding 60°C. Receive water-soluble yellow powder. The selectivity of the oxidation of CH2IT groups to carboxyl confirmed by IR(on the appearance of an intense peak at 1600 cm-1for the carboxylate anion) and13With NMR spectroscopy. In13From the NMR spectrum of oxidized arabinogalactan (AG-COOH) in the field 176-178 ppm seeing the emergence of a group of signals corresponding to carbon atoms of carboxyl groups of the oxidized residue of arabinose and galactose (arabinofuranose and the galacturonic acid, respectively). The signals of the carbon atoms of CH2HE groups in the area 62-63 ppm lack the comfort, which also indicates complete transformation of the primary hydroxy groups of arabinogalactan in the carboxyl (Fig.1).

b) To a mixture of 60 mg (~0.3 mmol) AG-COOH and 66.5 mg (0.6 mmol) of n-aminophenol (1) in 10 ml of N2About add 0.1 N. NaOH (or, if you want, 0.1 N. HCl) to pH 4.7-4.8, then under vigorous stirring and the temperature of 20-22°C make 86.3 mg (0.45 mmol) carbodiimide (the ratio of reagents Ar-COOH:RNH2:CBI=1:2:1.5), maintaining the pH 4.7-4.8 titration with 0.1 N. model HC1. After 0.5 h to a cooled to 0°C. the reaction mixture successively added 0.1 N. NaOH (to pH 7-8), 2-3 ml of saturated NaCl solution and 30 ml of chilled methanol. Dropped the precipitate was separated by centrifugation, dissolved in 10 ml of 6% NaCl, add 30 ml of methanol. Again precipitated precipitate is centrifuged, washed with methanol (10×3 ml), then ether (10×3 ml) and dried at a temperature ≤60°C and reduced pressure. Get ~60 mg of conjugate in the form of a white powder. Conversion carboxypropyl in the amide in the conjugate n-aminophenol ~100%.

Conversion of the carboxyl groups of AG-COOH in the amide determined according to the1H-NMR spectroscopy using the integrated intensity of the characteristic signals of the protons of residues corresponding amines in relation to the internal standard intensity signals of all protons of a test specimen in the field 3.25-4.50 ppm

Range is 1H-NMR were recorded for solutions in D2O spectrometer Bruker AMX-300 (operating frequency for1H-NMR 300.13 MHz), as internal standard used the sodium salt of 3-(trimethylsilyl)-1-propanesulfonic acid. UV spectra were obtained on a spectrophotometer Specord M-40. Control the pH of the solutions was performed using a pH meter pH-340".

Examples 2-13. Oxidation of arabinogalactan and the reaction of the obtained AG-COOH with an appropriate amine (2-13) and cleaning products is carried out analogously to example 1. Conversion carboxypropyl in amide oxidized arabinogalactan reaches 90-95%.

Examples 14, 15. Oxidation of arabinogalactan and the reaction of AG-COOH with glycine (14), D,L-lysine (15) is carried out analogously to example 1, but with a ratio of reagents AG-COOH:RNH2:CBI=1:5:1.5; when this ratio conversion carboxypropyl in amide oxidized arabinogalactan reaches 90-95%. Cleaning target conjugates carried out analogously to example 1.

Some spectral characteristics of the conjugates (in comparison with amines) in the table.

A method of obtaining modified arabinogalactan, characterized in that the oxidized arabinogalactan in the system 2,2,6,6-tetramethylpiperidine-1-oxyl radical-NaBr-NaClO-N2Oh, R is 10.2, with the receipt containing the carboxyl group of arabinogalactan (AG-COOH), which is then in an aqueous environment at room temperature, pH 4.7-4.8, in the presence of a condensing agent, 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide (CBI) is subjected to interaction with containing a primary amino group in compounds of General formula RNH2where
RNH2- n - or o-aminophenol, n-aminobenzoic or Anthranilic acid, 4 - or 5-aminosalicylic acid, ethyl ester n-aminobenzoic acids, β-diethylaminoethylamine ether n-aminobenzoic acid, isonicotinic acid hydrazide, 1-phenyl-2,3-dimethyl-4-aminopyrazole-5, as well as sulfa drugs, containing a free amino group such as n-aminobenzenesulfonic, n-aminobenzenesulfonamide-sodium, at a molar ratio of reagents AG-COOH:RNH2:CBI = 1:2:1.5, with aminecontaining compounds of General formula RNH2where RNH2-2-aminoetansulfonovaya acid, glycine, lysine, in the molar ratio of AG-COOH:RNH2:CBI = 1:5:1,5.



 

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