CS273084B1 - Method of carboxymethyl-(1-6)-beta-d-gluco-(1-3)-beta-d-glucan's sodium salt's defined fractions preparation - Google Patents
Method of carboxymethyl-(1-6)-beta-d-gluco-(1-3)-beta-d-glucan's sodium salt's defined fractions preparation Download PDFInfo
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- CS273084B1 CS273084B1 CS655988A CS655988A CS273084B1 CS 273084 B1 CS273084 B1 CS 273084B1 CS 655988 A CS655988 A CS 655988A CS 655988 A CS655988 A CS 655988A CS 273084 B1 CS273084 B1 CS 273084B1
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- 229920002498 Beta-glucan Polymers 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims abstract description 6
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- 159000000000 sodium salts Chemical class 0.000 title abstract 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims abstract description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 4
- 239000011707 mineral Substances 0.000 claims abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000000243 solution Substances 0.000 claims abstract 3
- 239000007864 aqueous solution Substances 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 31
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 8
- 229910052708 sodium Inorganic materials 0.000 claims description 7
- 239000011734 sodium Substances 0.000 claims description 7
- 239000011780 sodium chloride Substances 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 4
- 235000010755 mineral Nutrition 0.000 claims description 3
- 150000001447 alkali salts Chemical class 0.000 claims 1
- 230000001376 precipitating effect Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 239000002904 solvent Substances 0.000 abstract 1
- 239000013049 sediment Substances 0.000 description 9
- 239000006228 supernatant Substances 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- 238000001816 cooling Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 238000005119 centrifugation Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000233866 Fungi Species 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 241000235070 Saccharomyces Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- 241000222480 Schizophyllum Species 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000002519 immonomodulatory effect Effects 0.000 description 1
- 239000000411 inducer Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 108010001062 polysaccharide-K Proteins 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 229960005486 vaccine Drugs 0.000 description 1
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- Polysaccharides And Polysaccharide Derivatives (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Vynález sa týká sposobu přípravy definovaných frakoií sodnej soli karboxymetyl-(1*6)-beta-D-gluko-(1+3)-beta-D-glukánu.The invention relates to a process for the preparation of defined fractions of sodium carboxymethyl- (1 * 6) -beta-D-gluco- (1 + 3) -beta-D-glucan.
Stěnový (1-*6)-beta-D-gluko-(l*3)-beta-D-glukán izolovaný z kvasiniek, húb a lišajníkov zvyšuje rezistenoiu organizmov voči infekčným a malígnyra ochoreniam. Je doležitou adjuvantnou složkou vakcín a významným induktorom krvitvorby živočichov [n.R. Diluzio, Springer Semin. Iramunopathol., 8, 387, 1985]· Biologické efekty tohto polysacharidu (imunomodulačný, antibakteriálny, antivirový a antituraorový) úzko súvisia s jeho-molekulovými parametrami. Napr. u sohizofylanu, extracelulámeho polysacharidu produkovaného hubami Schizophyllum oommune, sa zistilo, že podmlenkou antitumorovej aktivity na sarkom 180 je molekulová hmotnost nad 5x10^ Da, optimálně výše 2x103 Da [t. Kojima,Wall (1- * 6) -beta-D-gluco- (1,3 *) -beta-D-glucan isolated from yeast, fungi and lichens increases the resistance of organisms to infectious and malignant diseases. It is an important adjuvant component of vaccines and a significant inducer of animal haematopoiesis [nR Diluzio, Springer Semin. Iramunopathol., 8, 387, 1985] The biological effects of this polysaccharide (immunomodulatory, antibacterial, antiviral and antituraor) are closely related to its molecular parameters. E.g. for sohizophylan, an extracellular polysaccharide produced by Schizophyllum oommune fungi, it has been found that the precondition for antitumor activity on sarcoma 180 is a molecular weight above 5x10 6 Da, optimally above 2x10 3 Da [t. Kojima,
K. Tabata, W. Itoh, T. Yanaki, Agric. Biol. Chem., 50 (1), 231-232, 1986]. Tiež bol sledovaný protinádorový účinok a protistafylokoková aktivita rozpustného glukánu, připraveného z partikulárneho glukánu z buniek kvasiniek Saooharorayces oerevisiae jjr. R. Di Luzio, D. Ir. Williams, R. B. McNamee, B. P. Edwarda, A. Kitahama, Int. J. Canoer, 24, 773-779, 1979]. Sodná soí karboxymetyl-(l*6)-beta-D-gluko-(l-*3)-beta-D-glukánu, ktorá sa dá připravil chemickou modifikáciou (l->ó)-beta-D-gluko-(1->3)-beta-D-glukánu, izolovaného zo Saccharomyces oerevisiae (AO 261819, PV 1789-87; 270103 , PV 3944-86), je látkou s poměrně širokou di3tribúoiou molekulovej hmotnosti.Tabata K., Itoh W., Yanaki T., Agric. Biol. Chem., 1986, 50 (1), 231-232]. The anti-tumor effect and anti-staphylococcal activity of soluble glucan prepared from particulate glucan from yeast cells of Saooharorayces oerevisiae jjr was also studied. R. Di Luzio, D.I. Williams, R. B. McNamee, B. P. Edward, A. Kitahama, Int. J. Canoer, 24, 773-779 (1979)]. Sodium salt of carboxymethyl- (1 * 6) -beta-D-gluco- (1- * 3) -beta-D-glucan, which can be prepared by chemical modification of (1-> 6) -beta-D-gluco- (1). -> 3) -beta-D-glucan, isolated from Saccharomyces oerevisiae (AO 261819, PV 1789-87; 270103, PV 3944-86), is a substance with a relatively broad molecular weight distribution.
Tieto nedostatky je možné odstrániť přípravou jej definovaných frakcii spásobom podía vynálezu. Podstata vynálezu spočívá v tom, že 0,1 až 0,5 %-ný roztok sodnej soli karboxymetyl-(1-^6)-beta-D-gluko-(1-»3)-beta-D-glukánu v 0,3 až 1 %-nom roztoku alkaliokej soli minerálnej kyseliny s výhodou v chloride sodnom alebo draselnom, sa prezráža organickým rozpúšťadlom rozpúšťajúoim sa vo vodě, krotým može byť aceton, n-propylalkohol, izopropylalkohol, etylalkohol, dioxán apod. Oddělí sa hrubá predfrakeia a získaný roztok sa postupné opakované zráža organickým rozpúšťadlom, aké sa použilo na prezrážanie. Získané frakcie sa oddelia (napr. odoentrifugovaním) a vysušia z éteru. Před vysušením sa mázu ešte přečistit prezrážaním rovnakým organickým rozpúšťadlom.These drawbacks can be overcome by preparing its defined fractions according to the invention. The invention is characterized in that a 0.1 to 0.5% solution of sodium carboxymethyl- (1- [beta]) -beta-D-gluco- (1- > 3) -beta-D-glucan in 0, 2, 3, A 3 to 1% solution of an alkali metal salt of a mineral acid, preferably in sodium or potassium chloride, is precipitated with an organic solvent dissolved in water, but may be acetone, n-propyl alcohol, isopropyl alcohol, ethyl alcohol, dioxane and the like. The coarse pre-fraction is separated and the solution obtained is repeatedly precipitated repeatedly with the organic solvent used for precipitation. The fractions obtained are separated (e.g., by centrifugation) and dried from ether. Before drying, they can be further purified by reprecipitation with the same organic solvent.
Riešenie podía vynálezu umožňuje pripraviť definované frakoie sodnej soli karboxyraetyl-(l-i6)-beta-D-gluko-(1->3)-beta-D-glukánu s definovaným a opakovateíným zložením.The solution according to the invention makes it possible to prepare defined fractions of sodium carboxyraethyl- (1-6) -beta-D-gluco- (1-> 3) -beta-D-glucan with a defined and repeatable composition.
Uvedené příklady ilustrujú, ale neobmedzujú predmet vynálezu.These examples illustrate but do not limit the scope of the invention.
Příklad 1 g sodnej soli karboxymetyl-(1*6)-beta-D-gluko-(l*3)-beta-D-glukánu sa rozpustí v 250 ml 0,5 % hmot. vodného roztoku NaCl. Nerozpustný podiel sa oddělí odstředěním.Example 1 g of sodium carboxymethyl- (1 * 6) -beta-D-gluco- (1 * 3) -beta-D-glucan is dissolved in 250 ml of 0.5 wt. aqueous NaCl solution. The insoluble matter is separated by centrifugation.
K čirému roztoku sa přidá 220 ml acetonu, až vznikne jemná suspenzia. Táto sa ochladí na teplotu 10 °C a potom sa odstředí. Sediment (10 %) sa oddělí ako hrubá predfrakeia s nejednotnou molekulovou hmotnosťou (dokaž gélovou chroraatografiou). K čirému roztoku sa Sálej přidá 60 ml acetonu a vzniknutá suspenzia sa ochladí na 10 °C a odstředí. Sediment sa rozpustí v 10 ml 0,5 % hmot. vodného roztoku NaCl, prezráža acetónom (60 ml) a dekantuje s 2x60 ml acetonu a s 2x40 ml dietyléteru. Nakoniee sa vysuší pri laboratórnej teplote. Výťažok takto pripravenej širokej frakcie sodnej soli karboxymetyl-(1-6)-beta-D-gluko-(1-3)-beta-D-glukán je 72,3 %· Jej limitné-viskozitné Číslo stanovené v 0,1 M vodnom roztoku NaCl při 25 °C je-0,966 dl.g1. Molekulová hmotnosť vrcholu ehromatografického záznamu vztiahnuté na kalibraoné Standardy dextránu je 1,02 x 10^ Da. Příklad 2220 ml of acetone are added to the clear solution until a fine suspension is formed. This was cooled to 10 ° C and then centrifuged. The sediment (10%) is separated as a crude pre-fraction with a non-uniform molecular weight (evidenced by gel chromatography). 60 ml of acetone was added to the clear solution and the resulting suspension was cooled to 10 ° C and centrifuged. The sediment is dissolved in 10 ml of 0.5 wt. aqueous NaCl solution, precipitated with acetone (60 mL) and decanted with 2x60 mL of acetone and 2x40 mL of diethyl ether. Dry the Nakoniee at room temperature. The yield of the thus prepared wide fraction of sodium carboxymethyl- (1-6) -beta-D-gluco- (1-3) -beta-D-glucan is 72.3%. · Its limit - viscosity Number determined in 0.1 M aqueous The NaCl solution at 25 ° C is 0,90.966 dl.g 1 . The molecular weight of the peak of the ehromatographic record relative to the calibraone dextran standards is 1.02 x 10 6 Da. Example 2
Prakcia z příkladu 1 v množstve 1,2 g sa rozpustí v 300 ml 0,5 % hmot. vodného roztoku NaCl. Potom sa zráža 296 ml acetonu a vzniknutá suspenzia sa ochladí na 10 °C a odstředí. Sediment sa oddělí (9,3 %) ako frakcia s nejednotnou molekulovou hmotnosťou (gélovou chromatografiou sa získá trojvrcholový záznam frakoie). Supernatant sa zráža Sálej s 20 ml acetónom a po oohladení na 10 °C sa suspenzia odstr.edí. SedimentThe work of Example 1 in an amount of 1.2 g was dissolved in 300 ml of 0.5 wt. aqueous NaCl solution. 296 ml of acetone are then precipitated and the resulting suspension is cooled to 10 ° C and centrifuged. The sediment was collected (9.3%) as a non-uniform molecular weight fraction (gel chromatography gave a three-peak fraction record). The supernatant is precipitated with 20 ml of acetone and, after cooling to 10 ° C, the suspension is centrifuged. sediment
CS 273 084 B1 aa prezráža a vysuší ako v příklade 1. Výťažok frakcie je 45,9 %. Supernatant sa použije v příklade 3. 0,55 S vysušeného sedimentu sa rozpustí v 138 ml 0,5 % hmot. vodného roztoku NaCl. Roztok sa zráža s 123 ml acetonu a vzniknutá suapenzia sa po ochladení na 10 °C odstředí. Získaný sediment sa prezráža a vysuší ako v příklade 1. Takto sa získá frakcia I, ktorej výťažok je 11 %. Chromatogram tejto frakcie má 2 píky, a to 1,5x10^ Da a 1,6x10^ Da. Získaný supernatant sa dalej zráža s 20 ml acetonu. Vypadne zrazenina, ktorá sa oddělí po ochladení na 10 °C odstředěním. Po prezrážaní a vysušení ako v příklade 1 sa získá frakcia II (výťažok 20,5 %). Jej J^] stanovené ako v příklade 1 je 1,193 dl.g^ a molekulová hmotnost' z chromatografického záznamu je 2,3x10^ Da. Supernatant po oddělení frakcie II sa áalej zráža s prehytkom acetonu (40 ml) a po ochladení na 10 °C sa zrazenina odstředí. Po prezrážaní a vysušení ako v příklade 1 sa získá frakcia III (výtažok 9,7 %)· Jej limitné viskozitné číslo a molekulová hmotnost stanovené ako v příklade 1 sú 1,074 dl.g a 6,75 x 10 Da.CS 273 084 B1 aa reprecipitated and dried as in Example 1. The yield of the fraction was 45.9%. The supernatant is used in Example 3. 0.55 S of the dried sediment is dissolved in 138 ml of 0.5 wt. aqueous NaCl solution. The solution is precipitated with 123 ml of acetone and the resulting suapensification is centrifuged after cooling to 10 ° C. The resulting sediment is precipitated and dried as in Example 1. Fraction I is obtained in a yield of 11%. The chromatogram of this fraction has 2 peaks, 1.5x10 ^ Da and 1.6x10 ^ Da. The supernatant obtained is further precipitated with 20 ml of acetone. A precipitate formed which was collected by cooling to 10 ° C by centrifugation. Fraction II (20.5% yield) was obtained after precipitation and drying as in Example 1. Its J ^, determined as in Example 1, is 1.193 dl.g ^ and the molecular weight from the chromatographic record is 2.3x10 ^Da. The supernatant after fraction II separation was further precipitated with an excess of acetone (40 ml) and after cooling to 10 ° C, the precipitate was centrifuged. Fraction III (9.7% yield) is obtained after precipitation and drying as in Example 1. Its limit viscosity number and molecular weight as set forth in Example 1 are 1.074 dl.g and 6.75 x 10 Da.
Přiklad 3Example 3
Supernatant z příkladu 2 sa zráža s 20 ml acetonu. Vzniknutá suspenzia sa ochladí na 10 °0, odstředí sa a sediment sa prezráža a vysuší ako v příklade 1. Získá sa frakcia IV, ktorá gélovou chromatografiou dává dvojpíkový záznam. Supernatant po oddělení frakcie IV sa dalej zráža 20 ml acetonu, suspenzia sa ochladí na 10 °C, odstředí a sediment sa prezráža a vysuší ako v příklade 1. Získá sa frakcia V (výťažok 7,7 %) s dvojpikovým chromatografickýra záznamom. Supernatant po oddělení frakcie V sa zráža s 20 ml acetonu, vzniknutá suspenzia sa ochladí na 10 °C, odstředí a spracuje ako v příklade 1. Získá sa frakcia VI (výťažok 10,5 %). Limitné viskozitné číslo a molekulová hmotnosť stanovené ako v příklade 1 sú 1,012 dl.g-1 a 2,9x10J Da. Supernatant získaný oddělením frakcie VI sa zráža s naďbytkom acetonu (60 ml), suspenzia sa ochladí na 10 °0, odstředí a sediment sa spracuje ako v příklade 1. Získá sa frakcia VII (výťažok 8,8 %). Jej limitné viskozitné číslo a molekulová hmotnost' stanovená ako v příklade 1 sú 0,657 dl.g-1 a 8,6x10^ Da.The supernatant of Example 2 is precipitated with 20 ml of acetone. The resulting suspension was cooled to 10 ° C, centrifuged, and the sediment was precipitated and dried as in Example 1. Fraction IV was obtained, which gave a two-peak gel chromatography. The supernatant after separation of Fraction IV is further precipitated with 20 ml of acetone, the suspension is cooled to 10 ° C, centrifuged and the sediment is precipitated and dried as in Example 1. Fraction V (7.7% yield) is obtained with a two-peak chromatographic record. The supernatant after separation of fraction V is precipitated with 20 ml of acetone, the resulting suspension is cooled to 10 ° C, centrifuged and worked up as in example 1. Fraction VI (yield 10.5%) is obtained. The limit viscosity number and molecular weight determined as in Example 1 are 1.012 dl.g -1 and 2.9x10 J Da. The supernatant obtained by separating Fraction VI is precipitated with excess acetone (60 ml), the suspension is cooled to 10 ° C, centrifuged and the sediment is treated as in Example 1. Fraction VII is obtained (yield 8.8%). Its limit viscosity number and molecular weight determined as in Example 1 are 0.657 dl.g -1 and 8.6x10 6 Da.
Vynález može nájsť uplatnenie v humánnej a veterinárnej medicíně ako imunostimulátor, v ohemickom priemysle ako referenčnó materiály pre kvapalinovú-chromatografiu.The invention can be used in human and veterinary medicine as an immunostimulator, in the chemical industry as reference materials for liquid chromatography.
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| CS655988A CS273084B1 (en) | 1988-10-03 | 1988-10-03 | Method of carboxymethyl-(1-6)-beta-d-gluco-(1-3)-beta-d-glucan's sodium salt's defined fractions preparation |
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| Publication Number | Publication Date |
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| CS273084B1 true CS273084B1 (en) | 1991-03-12 |
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