US20080108114A1 - Glucan preparations - Google Patents

Glucan preparations Download PDF

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US20080108114A1
US20080108114A1 US11/818,804 US81880407A US2008108114A1 US 20080108114 A1 US20080108114 A1 US 20080108114A1 US 81880407 A US81880407 A US 81880407A US 2008108114 A1 US2008108114 A1 US 2008108114A1
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glucan
particulate
surfactant
soluble
yeast
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Donald Cox
Ren-Der Yang
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Biopolymer Engineering Inc
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Biopolymer Engineering Inc
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Assigned to QUEENWOOD CAPITAL PARTNERS LLC reassignment QUEENWOOD CAPITAL PARTNERS LLC SECURITY AGREEMENT Assignors: BIOPOLYMER ENGINEERING, INC. (D/B/A BIOTHERA)
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • A61K31/716—Glucans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/04—Immunostimulants
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
    • C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
    • C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
    • C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L5/00—Compositions of polysaccharides or of their derivatives not provided for in groups C08L1/00 or C08L3/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K39/00—Medicinal preparations containing antigens or antibodies
    • A61K2039/545—Medicinal preparations containing antigens or antibodies characterised by the dose, timing or administration schedule

Definitions

  • the present invention relates to compositions that include ⁇ -glucan. More particularly, the present invention relates to soluble ⁇ -glucan compositions and their use in stem cell mobilization.
  • Glucans are generally described as polymers of glucose and are derived from yeast, bacteria, fungi and plants such as oats and barley. Glucans containing a ⁇ (1-3)-linked glucopyranose backbone are known to have biological activity, specifically they have been shown to modulate the immune system and more recently to induce hematopoietic stem and progenitor cell (HSPC) mobilization.
  • HSPC hematopoietic stem and progenitor cell
  • cytoreductive therapy including high dose chemotherapy or radiation.
  • These therapies decrease a patient's white blood cell counts, suppress bone marrow hematopoietic activity, and increase their risk of infection and/or hemorrhage.
  • patients who undergo cytoreductive therapy must also receive therapy to reconstitute bone marrow function (hematopoiesis).
  • PGG ⁇ -glucan is a soluble yeast-derived polysaccharide and has been shown previously to induce hematopoietic stem and progenitor cell (HSPC) mobilization.
  • yeast is cultured, harvested and purified to yield particulate ⁇ -glucan essentially free of contaminating volatile organic compounds (VOCs).
  • Particulate ⁇ -glucan is prepared by subjecting yeast cells or fragments thereof to a series of alkaline, surfactant, and acidic extractions that remove host cell impurities.
  • FIG. 1 is a schematic representation of a process for producing particulate ⁇ -glucan.
  • FIG. 2 is a schematic representation of a process for producing soluble ⁇ -glucan.
  • FIG. 1 is an overview of method 10 , which includes steps 12 - 22 , for producing insoluble, or particulate, ⁇ -glucan from yeast.
  • a yeast culture is grown, typically, in a shake flask or fermenter.
  • the yeast strain utilized for the present invention can be any strain, examples of which include Saccharomyces ( S .) cerevisiae, S. delbrueckii, S. rosei, S. microellipsodes, S. carlsbergensis, S. bisporus, S. fermentati, S. rouxii, Schizosaccharomyces pombe, Kluyveromyces ( K .) lactis, K. fragilis, K.
  • a culture of yeast is started and expanded stepwise through a shake flask culture into a 250-L scale production fermenter.
  • the yeast are grown in a glucose-ammonium sulfate medium enriched with vitamins, such as folic acid, inositol, nicotinic acid, pantothenic acid (calcium and sodium salt), pyridoxine HCl and thymine HCl and trace metals from compounds such as ferric chloride, hexahydrate; zinc chloride; calcium chloride, dihydrate; molybdic acid; cupric sulfate, pentahydrate and boric acid.
  • An antifoaming agent such as Antifoam 204 may also be added at a concentration of about 0.02%.
  • the production culture is maintained under glucose limitation in a fed batch mode.
  • samples are taken periodically to measure the optical density of the culture before inoculating the production fermenter.
  • samples are also taken periodically to measure the optical density of the culture.
  • samples are taken to measure the optical density, the dry weight, and the microbial purity.
  • fermentation may be terminated by raising the pH of the culture to at least 11.5 or by centrifuging the culture to separate the cells from the growth medium.
  • steps to disrupt or fragment the yeast cells may be carried out. Any known chemical, enzymatic or mechanical methods, or any combination thereof may be used to carry out disruption or fragmentation of the yeast cells.
  • the yeast cells containing the ⁇ -glucan are harvested.
  • yeast cells are typically harvested using continuous-flow centrifugation.
  • Step 16 represents the initial extraction of the yeast cells utilizing one or more of an alkaline solution, a surfactant, or a combination thereof.
  • a suitable alkaline solution is, for example, 0.1 M-5 M NaOH.
  • Suitable surfactants include, for example, octylthioglucoside, Lubrol PX, Triton X-100, sodium lauryl sulfate, sodium dodecyl sulfate, Nonidet P-40, Tween 20 and the like.
  • Ionic (anionic, cationic, amphoteric) surfactants e.g., alkyl sulfonates, benzalkonium chlorides, and the like
  • nonionic surfactants e.g., polyoxyethylene hydrogenated castor oils, polyoxyethylene sorbitol fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene glycerol fatty acid esters, polyethylene glycol fatty acid esters, polyoxyethylene alkyl phenyl ethers, and the like
  • concentration of surfactant will vary and depend, in part, on which surfactant is used.
  • Yeast cell material may be extracted one or more times.
  • Extractions are usually carried out at temperatures between about 70° C. and about 90° C. Depending on the temperature, the reagents used and their concentrations, the duration of each extraction is between about 30 minutes and about 3 hours.
  • the solid phase containing the ⁇ -glucan is collected using centrifugation or continuous-flow centrifugation and resuspended for the subsequent step.
  • the solubilized contaminants are removed in the liquid phase during the centrifugations, while the ⁇ -glucan remains in the insoluble cell wall material.
  • the first extraction harvested yeast cells are mixed with 1.0 M NaOH and heated to 90° C. for approximately 60 minutes.
  • the second extraction is an alkaline/surfactant extraction whereby the insoluble material is resuspended in 0.1 M NaOH and about 0.5% to 0.6% Triton X-100 and heated to 90° C. for approximately 120 minutes.
  • the third extraction is similar to the second extraction except that the concentration of Triton X-100 is about 0.05%, and the duration is shortened to about 60 minutes.
  • the insoluble material is resuspended in about 0.5% Triton-X 100 and heated to 75° C. for approximately 60 minutes.
  • the alkaline and/or surfactant extractions solubilize and remove some of the extraneous yeast cell materials.
  • the alkaline solution hydrolyzes proteins, nucleic acids, mannans, and lipids.
  • Surfactant enhances the removal of lipids and other hydrophobic impurities, which provides an additional advantage yielding an improved. ⁇ -glucan product.
  • VOCs volatile organic compounds
  • Fat content of the yeast Saccharomyces cerevisiae produced by aerobic and anaerobic growth ranges from about 3% to about 8%. The fat content varies depending on growth conditions of the yeast. Table 1 provides an overview of the typical fat composition of the yeast Saccharomyces cerevisiae . The data is from the following references:
  • Yeast cell wall material typically contains 10-25% fat depending on yeast type and growth conditions.
  • some, but not all fat was removed by centrifugation and wash steps.
  • a typical preparation might yield a fat content of 3-7%.
  • the manufacturing process typically involves steps to remove mannoproteins, lipids and other undesirable components of the yeast cell wall.
  • Some key steps common to this processing are various wash steps that employ acid and alkali in separate washing steps to liberate certain cell wall components.
  • Several of the steps use an alkali wash process where an alkali, usually sodium hydroxide, is added to the liquid cell wall suspension.
  • an alkali usually sodium hydroxide
  • One of the purposes of the alkali is to remove lipid by forming the free fatty acids of the lipid. The result is a reduction in fat content of the ⁇ -glucan.
  • the alkali wash steps commonly used in production of yeast ⁇ -glucan leave behind residual fatty acids and partially degraded fat triglycerides that have increased reactivity.
  • the direct result of the alkali wash process is the release of reactive free fatty acids that quickly decompose to various oxidative products of fat decomposition.
  • the process of fat oxidation has several mechanisms. The most common mechanism is autoxidation.
  • the process is initiated by the removal of a hydrogen from an olefenic compound to create a free radical. The removal of hydrogen takes place at the carbon atom next to the double bond in the fat.
  • the reaction is initiated by various free-radical generating factors such as UV light, metals, singlet oxygen etc. RH ⁇ R*+H* (creation of a free radical electron)
  • the second step is the addition of oxygen to cause formation of a peroxy-free radical, which propagates the chain reaction by extracting hydrogen from another unsaturated fatty acid.
  • ROOH is the reactive hydroperoxide that decomposes to secondary reaction products such as VOCs
  • the chain reaction continues until it is terminated by free radicals combining with themselves to yield nonreactive products.
  • R*+R* ⁇ R—R R*+RO 2 *RO 2 R The following are the chemical reactions that occur to form the VOCs. Linoleic acid is used as a model for the chemistry, but there are other unsaturated fatty acids present in the yeast cell wall and in yeast ⁇ -glucan preparations that produce the same end products.
  • ROOH ⁇ RO*+OH— RO* ⁇ cleavage reactions form aldehydes, alkyl radicals (which form hydrocarbons and alcohols), esters, alcohols, and hydrocarbons.
  • the next step in the purification process is an acidic extraction shown at step 18 , which removes glycogen.
  • One or more acidic extractions are accomplished by adjusting the pH of the alkaline/surfactant extracted material to between about 5 and 9 and mixing the material in about 0.05 M to about 1.0 M acetic acid at a temperature between about 70° C. and 100° C. for approximately 30 minutes to about 12 hours.
  • the insoluble material remaining after centrifugation of the alkaline/surfactant extraction is resuspended in water, and the pH of the solution is adjusted to about 7 with concentrated HCl.
  • the material is mixed with enough glacial acetic acid to make a 0.1 M acetic acid solution, which is heated to 90° C. for approximately 5 hours.
  • the insoluble material is washed.
  • the material is mixed in purified water at about room temperature for a minimum of about 20 minutes.
  • the water wash is carried out two times.
  • the purified ⁇ -glucan product is then collected, as shown by step 22 . Again, collection is typically carried out by centrifugation or continuous-flow centrifugation.
  • the product may be in the form of whole glucan particles or any portion thereof, depending on the starting material.
  • larger sized particles may be broke down into smaller particles.
  • the range of product includes ⁇ -glucan particles that have substantially retained in vivo morphology (whole glucan particles) down to submicron-size particles.
  • particulate ⁇ -glucan is useful in many food, supplement and pharmaceutical applications.
  • particulate ⁇ -glucan can be processed further to form aqueous, soluble ⁇ -glucan.
  • FIG. 2 is an overview of method 24 , which includes steps 26 - 32 , for producing aqueous, soluble ⁇ -glucan.
  • the starting material used in method 24 is particulate ⁇ -glucan, which may be produced by method 10 or produced by any of a number of previously used methods.
  • the particulate ⁇ -glucan starting material may range in size from whole glucan particles down to submicron-sized particles.
  • step 26 particulate ⁇ -glucan undergoes an acidic treatment under pressure and elevated temperature to produce soluble ⁇ -glucan.
  • Pelleted, particulate ⁇ -glucan is resuspended and mixed in a sealable reaction vessel in a buffer solution and brought to pH 3.6. Buffer reagents are added such that every liter, total volume, of the final suspension mixture contains about 0.61 g sodium acetate, 5.24 ml glacial acetic acid and 430 g pelleted, particulate ⁇ -glucan.
  • the vessel is purged with nitrogen to remove oxygen and increase the pressure within the reaction vessel.
  • the pressure inside the vessel is brought to 35 PSI, and the suspension is heated to about 135° C. for between about 4.5 and 5.5 hours. It was found that under these conditions the ⁇ -glucan will solubilize. As the temperature decreases from 135° C., the amount of solubilization also decreases.
  • Hazardous chemicals that have previously been used include, for example, flammable VOCs such as ether and ethanol, very strong acids such as formic acid and sulphuric acid and caustic solutions of very high pH.
  • flammable VOCs such as ether and ethanol
  • very strong acids such as formic acid and sulphuric acid and caustic solutions of very high pH.
  • the present process is not only safer, but, by reducing the number of different chemicals used and the number of steps involved, is more economical.
  • the exact duration of heat treatment is typically determined experimentally by sampling reactor contents and performing gel permeation chromatography (GPC) analyses.
  • the objective is to maximize the yield of soluble material that meets specifications for high resolution-GPC(HR-GPC) profile and impurity levels, which are discussed below.
  • the crude, solubilized ⁇ -glucan may be washed and utilized in some applications at this point, however, for pharmaceutical applications further purification is performed. Any combination of one or more of the following steps may be used to purify the soluble ⁇ -glucan. Other means known in the art may also be used if desired.
  • the soluble ⁇ -glucan is clarified. Suitable clarification means include, for example, centrifugation or continuous-flow centrifugation.
  • the soluble ⁇ -glucan may be filtered as shown by step 30 .
  • the material is filtered, for example, through a depth filter followed by a 0.2 ⁇ m filter.
  • Step 32 utilizes chromatography for further purification.
  • the soluble ⁇ -glucan may be conditioned at some point during step 28 or step 30 in preparation for chromatography.
  • a chromatographic step includes hydrophobic interaction chromatography (HIC)
  • the soluble ⁇ -glucan can be conditioned to the appropriate conductivity and pH with a solution of ammonium sulphate and sodium acetate.
  • a suitable solution is 3.0 M ammonium sulfate, 0.1 M sodium acetate, which is used to adjust the pH to 5.5.
  • a column is packed with Tosah Toyopearl Butyl 650M resin (or equivalent). The column is packed and qualified according to the manufacturer's recommendations.
  • the column equilibration flow-through Prior to loading, the column equilibration flow-through is sampled for pH, conductivity and endotoxin analyses.
  • the soluble ⁇ -glucan conditioned in the higher concentration ammonium sulphate solution, is loaded and then washed.
  • the nature of the soluble ⁇ -glucan is such that a majority of the product will bind to the HIC column. Low molecular weight products as well as some high molecular weight products are washed through. Soluble ⁇ -glucan remaining on the column is eluted with a buffer such as 0.2 M ammonium sulfate, 0.1 M sodium acetate, pH 5.5. Multiple cycles may be necessary to ensure that the hexose load does not exceed the capacity of the resin. Fractions are collected and analyzed for the soluble ⁇ -glucan product.
  • GPC gel permeation chromatography
  • a Tosah Toyopearl HW55F resin, or equivalent is utilized and packed and qualified as recommended by the manufacturer.
  • the column is equilibrated and eluted using citrate-buffered saline (0.14 M sodium chloride, 0.011 M sodium citrate, pH 6.3).
  • citrate-buffered saline 0.14 M sodium chloride, 0.011 M sodium citrate, pH 6.3.
  • column wash samples are taken for pH, conductivity and endotoxin analyses. Again, multiple chromatography cycles may be needed to ensure that the load does not exceed the capacity of the column.
  • the eluate is collected in fractions, and various combinations of samples from the fractions are analyzed to determine the combination with the optimum profile.
  • sample combinations may be analyzed by HR-GPC to yield the combination having an optimized HR-GPC profile.
  • HR-GPC HR-GPC
  • the amount of high molecular weight (HMW) impurity, that is soluble ⁇ -glucans over 380,000 Da, is less than or equal to 10%.
  • the amount of low molecular weight (LMW) impurity, under 25,000 Da, is less than or equal to 17%.
  • the selected combination of fractions is subsequently pooled.
  • the soluble ⁇ -glucan is purified and ready for use. Further filtration may be performed in order to sterilize the product. If desired, the hexose concentration of the product can be adjusted to about 1.0 ⁇ 0.15 mg/ml with sterile citrate-buffered saline.
  • the purification techniques described above result in an improved soluble ⁇ -glucan that provides specific advantages as a pharmaceutical agent, which is discussed below.
  • the soluble ⁇ -glucan has an average molecular weight between about 120,000 Da and about 205,000 Da and a molecular weight distribution (polydispersity) of not more than 2.5 as determined by HR-GPC with multiple angle light scattering (HR-GPC/MALS) and differential refractive index detection. Powder X-ray diffraction and magic-angle spinning NMR determined that the product consists of polymeric chains associated into triple helices.
  • the soluble ⁇ -glucan is typically uncharged and therefore has no pK a . It is soluble in water independent of pH, and the viscosity increases as the concentration increases.
  • Table 2 summarizes the typical levels of impurities in a soluble ⁇ -glucan product utilizing whole glucan particles produced by method 10 .
  • Sugar polymers are hydrolyzed in sulphuric acid and anthrone to form furfurals.
  • the furfurals conjugate with the anthrone to yield a chromophore, which is measured spectrophotometrically. **Limits were not specified.
  • Product-related impurities include material with molecular weights greater than 380,000 daltons or less than 25,000 daltons, because it has been found that the improved soluble ⁇ -glucan falls between those molecular weight ranges.
  • reducing sugar An additional measure of product-related impurities is reducing sugar.
  • Each glucan polysaccharide chain ends in the aldehyde form (reducing sugar) of the sugar.
  • the amount of reducing sugar serves as an indication of the number of chains in the preparation.
  • BCA bicinchoninic acid
  • Potential process impurities include other yeast cell constituents such as DNA, yeast cell proteins, lipids and other polysaccharides such as glycogen, miannan and chitin.
  • DNA levels can be analyzed using the slot hybridization assay (MDS PanLabs, Seattle, Wash.).
  • Residual protein may be determined by a colorimetric assay for protein or by a more sensitive commercial enzyme-linked immunosorbent assay (ELISA) that measures S. cerevisiae cell proteins (Cygnus Technology, Southport, N.C.).
  • Residual lipids may be monitored by evaluating ergosterol levels using reversed-phase high-performance liquid chromatography (RP-HPLC) with detection at 280 nm.
  • RP-HPLC reversed-phase high-performance liquid chromatography
  • Glycogen is a polysaccharide comprised primarily of ⁇ -1,4-linked glucose, and its presence can be determined by an enzymatic assay.
  • the product is added to an enzymatic reaction containing amyloglucosidase, which liberates glucose from glycogen, generating reducing sugars.
  • the reducing sugars are measured by the BCA assay.
  • Mannan is a branched polymer of ⁇ -1,6-linked mannose with ⁇ -1,2- and ⁇ -1,3-branches that is monitored, as mannose, by its monosaccharide composition.
  • the product is added to a reaction, and the mannose is hydrolyzed with trifluoroacetic acid and analyzed by HPLC.
  • Chitin is a polymer of ⁇ -1,4-N-acetyl glucosamine, which is monitored by a calorimetric assay. Soluble O-glucan is hydrolyzed with sulphuric acid, and the resulting glucosamine forms a complex with Ehrlich's reagent that is measured calorimetrically. These and other suitable assays are known to those skilled in the art.
  • Non-yeast impurities originating from components added during the manufacturing process include Triton X-100 (surfactant) and Antifoam 204 (antifoaming agent).
  • Reversed-phase HPLC (RP-HPLC) with detection at 280 nm can be used to discern any residual Triton X-100.
  • Antifoam 204 is assessed by a RP-HPLC method using selective ion monitoring with an electrospray mass spectroscopy detector in positive mode.
  • soluble ⁇ -glucan produced by methods 10 and 24 is an improved product over prior art soluble ⁇ -glucan materials. Improvement is seen in clinical trial results where soluble ⁇ -glucan of the present invention given at a much higher maximum dose showed the same or fewer adverse events (AEs) as lower maximum doses of prior art soluble ⁇ -glucan. The results are shown in Table 4.
  • BetafectinTM a soluble ⁇ -glucan product developed by Alpha-Beta Technology, Inc.
  • the process to produce BetafectinTM utilized formic acid to solubilize particulate ⁇ -glucan material.
  • Bf1 was not subjected to any chromatography in its purification process.
  • the processes of the present invention provide several advantages over prior alt processes and result in improved O-glucan products.
  • the particulate ⁇ -glucan is essentially free of harmful VOCs. Solubilization of ⁇ -glucan is safer and more economical. In addition, solubilization of particulate ⁇ -glucan made by the present process results in soluble ⁇ -glucan with improved pharmaceutical qualities.

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* Cited by examiner, † Cited by third party
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US20080167268A1 (en) * 2006-09-01 2008-07-10 Jun Yan Particulate beta-glucan compositions for regulating dendritic cells
US20090005340A1 (en) * 2005-06-15 2009-01-01 Medimush A/S Bioactive Agents Produced By Submerged Cultivation of a Basidiomycete Cell
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US9072776B2 (en) 2005-06-15 2015-07-07 Glycanova As Anti-cancer combination treatment and kit-of-parts
US10111900B2 (en) 2014-11-06 2018-10-30 Biothera, Inc. β-glucan methods and compositions that affect the tumor microenvironment
US10111901B2 (en) 2014-07-10 2018-10-30 Biothera, Inc. Beta-glucan in combination with anti-cancer agents affecting the tumor microenvironment
US10265340B2 (en) 2012-02-22 2019-04-23 Kemin Industries, Inc. Animal feed compositions and methods of using the same
US11140912B1 (en) 2020-12-22 2021-10-12 Agvault, Llc Process for manufacturing yeast strains having increased mannan oligosaccharides and improved amino acid profiles
US11815435B2 (en) 2017-02-24 2023-11-14 Hibercell, Inc. Beta glucan immunopharmacodynamics

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NO20014256D0 (no) * 2001-09-03 2001-09-03 Bjoern Kristiansen Fremstilling av immunstimulerende forbindelse
US7514085B2 (en) 2004-07-16 2009-04-07 Medimush A/S Immune modulating compounds from fungi
FI20080665A0 (fi) * 2008-12-18 2008-12-18 Glykos Finland Oy Luonnollisen tyyppiset sakkaridikoostumukset
JP5172930B2 (ja) * 2009-10-20 2013-03-27 国立大学法人佐賀大学 高粘性培養液の粘性低下方法
WO2012154818A1 (en) 2011-05-09 2012-11-15 Biothera, Inc. B-glucan compounds, compositions, and methods
EP2714053B1 (en) 2011-06-03 2020-12-09 Hibercell, Inc. Opsonized beta-glucan preparations and methods
EP3373006A1 (en) 2012-04-30 2018-09-12 Biothera, Inc. Beta-glucan immunotherapeutic methods
JP6673829B2 (ja) 2013-12-05 2020-03-25 バイオセラ インコーポレイテッド β−グルカンアッセイ方法
LT6145B (lt) 2014-04-14 2015-04-27 Uab "Biocentras" TERAPINĖ ß-GLIUKANŲ KOMPOZICIJA, MODULIUOJANTI ŽMOGAUS IMUNINĘ SISTEMĄ IR INICIJUOJANTI VĖŽINIŲ LĄSTELIŲ ARDYMĄ
KR102524964B1 (ko) 2014-11-19 2023-04-24 테이부루마크 가부시키가이샤 효모 세포의 풍미 개선방법 및 식품 품질 개량제
JP2016208909A (ja) * 2015-05-08 2016-12-15 株式会社カネカ 脂溶性生理活性物質の製造方法
JP6935877B2 (ja) * 2017-01-27 2021-09-15 日本製紙株式会社 免疫調整剤
JP6530846B1 (ja) * 2018-10-09 2019-06-12 アサヒグループホールディングス株式会社 免疫賦活剤及び感染予防方法
WO2023107712A1 (en) 2021-12-10 2023-06-15 Hibercell, Inc. SOLUBLE β-GLUCANS FOR INDUCING TRAINED IMMUNITY
CN115028755B (zh) * 2022-07-01 2023-08-11 福建省农业科学院食用菌研究所 一种高分子量绣球菌β-葡聚糖的制备方法

Citations (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4962094A (en) * 1988-10-28 1990-10-09 Alpha Beta Technology, Inc. Glucan dietary additives
US5032401A (en) * 1989-06-15 1991-07-16 Alpha Beta Technology Glucan drug delivery system and adjuvant
US5082936A (en) * 1984-11-28 1992-01-21 Massachusetts Institute Of Technology Glucan composition and process for preparation thereof
US5250436A (en) * 1984-11-28 1993-10-05 Massachusetts Institute Of Technology Glucan compositions and process for preparation thereof
US5322841A (en) * 1989-09-08 1994-06-21 Alpha-Beta Technology, Inc. Method for producing neutral glucans for pharmaceutical applications
US5397773A (en) * 1989-11-09 1995-03-14 Donzis; Byron A. Photoprotective composition containing yeast extract
US5488040A (en) * 1989-09-08 1996-01-30 Alpha-Beta Technology, Inc. Use of neutral soluble glucan preparations to stimulate platelet production
US5504079A (en) * 1989-09-08 1996-04-02 Alpha-Beta Technology, Inc. Method for immune system activation by administration of a β(1-3) glucan which is produced by Saccharomyces cerevisiae strain R4
US5519009A (en) * 1993-10-01 1996-05-21 Donzis; Byron A. Solubilized yeast glucan
US5576015A (en) * 1995-03-02 1996-11-19 Donzis; Byron A. Substantially purified beta (1,3) finely ground yeast cell wall glucan composition with dermatological and nutritional uses
US5622940A (en) * 1994-07-14 1997-04-22 Alpha-Beta Technology Inhibition of infection-stimulated oral tissue destruction by β(1,3)-glucan
US5622939A (en) * 1992-08-21 1997-04-22 Alpha-Beta Technology, Inc. Glucan preparation
US5633369A (en) * 1989-09-08 1997-05-27 Alpha-Beta Technology, Inc. Method for producing soluble glucans
US6020324A (en) * 1989-10-20 2000-02-01 The Collaborative Group, Ltd. Glucan dietary additives
US6046323A (en) * 1997-07-29 2000-04-04 The Collaborative Group, Ltd. Conformations of PPG-glucan
US6084092A (en) * 1997-01-31 2000-07-04 The Collaborative Group, Ltd. β(1-3)-glucan diagnostic assays
US6090938A (en) * 1996-05-01 2000-07-18 Collaborative Group, Ltd. Activation of signal transduction by underivatized, aqueous soluble . .beta(1-3)-Glucan
US6110692A (en) * 1996-05-01 2000-08-29 The Collaborative Group, Ltd. Receptor for underivatized aqueous soluble β(1-3)-glucan
US6117850A (en) * 1995-08-28 2000-09-12 The Collaborative Group, Ltd. Mobilization of peripheral blood precursor cells by β(1,3)-glucan
US6143731A (en) * 1989-10-20 2000-11-07 The Collaborative Group, Ltd. Glucan dietary additives
US6369216B1 (en) * 1998-09-25 2002-04-09 Biopolymer Engineering Pharmaceutical, Inc. Very high molecular weight β-glucans
US6413715B2 (en) * 1997-01-31 2002-07-02 The Collaborative Group β(1-3)-glucan diagnostic assays
US7022685B2 (en) * 1998-09-25 2006-04-04 Biopolymer Engineering, Inc. Very high molecular weight β-glucans

Family Cites Families (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5028703A (en) 1988-03-11 1991-07-02 Massachusetts Institute Of Technology Glucan composition and process for preparation thereof
US4810646A (en) 1984-11-28 1989-03-07 Massachusetts Institute Of Technology Glucan compositions and process for preparation thereof
JP2547220Y2 (ja) 1990-07-19 1997-09-10 株式会社ユニシアジェックス アクチュエータ
AUPN166195A0 (en) * 1995-03-13 1995-04-06 Norvet Research Pty Limited Process for glucan extraction
US6214337B1 (en) 1995-04-18 2001-04-10 Biotec Asa Animal feeds comprising yeast glucan
RU2233599C2 (ru) * 1998-10-26 2004-08-10 Себа Аб СПОСОБ ПОЛУЧЕНИЯ КОМПОЗИЦИИ, СОДЕРЖАЩЕЙ ВОДОРАСТВОРИМЫЙ β-ГЛЮКАН, (ВАРИАНТЫ) И ИЗГОТАВЛИВАЕМЫЕ ИЗ НЕЕ ПРОДУКТЫ
US6143883A (en) * 1998-12-31 2000-11-07 Marlyn Nutraceuticals, Inc. Water-soluble low molecular weight beta-glucans for modulating immunological responses in mammalian system
JP2001342257A (ja) 2000-06-01 2001-12-11 Fuji Photo Film Co Ltd セルロース系ポリマーの製造方法
JP2002105101A (ja) * 2000-10-03 2002-04-10 Ajinomoto Co Inc 水溶性高分子の製造法
US7786094B2 (en) 2001-10-09 2010-08-31 Biopolymer Engineering, Inc. Use of beta-glucans against biological warfare weapons and pathogens including anthrax
US20070042930A1 (en) 2002-08-13 2007-02-22 Ross Gordon D Effect of beta-glucan on stem cell recruitment and tissue repair
EP1545208A4 (en) 2002-08-13 2006-04-12 Biopolymer Engineering Inc METHODS OF USING BETA-GLUCAN AS RADIOPROTECTIVE AGENT
US20060165700A1 (en) 2002-09-04 2006-07-27 Ostroff Gary R Cancer therapy using whole glucan particles and antibodies
JP2006502167A (ja) 2002-09-04 2006-01-19 バイオポリマー エンジニアリング，インコーポレイテッド 全グルカン粒子および抗体を用いた癌治療
CA2501820C (en) 2002-10-08 2009-12-15 Ricom Corporation Chitosan-containing polysaccharide, method for preparing the same and use thereof
EP1721990B1 (en) * 2004-02-13 2009-03-18 Alpron Co., Ltd Process for producing yeast-derived glucan
US20090169557A1 (en) 2004-05-10 2009-07-02 Biopolymer Engineering, Inc. D/B/A Biothera Whole glucan particles in combination with antibiotics, vaccines and viral monoclonal antibodies
GB0411880D0 (en) 2004-05-27 2004-06-30 Imagination Tech Ltd Method and apparatus for efficient evaluation of "table-based" mathematical functions
FI20040804A (fi) 2004-06-11 2005-12-12 Glubikan Ab Oy Menetelmä viljan ainesosan erottamiseksi
US20050020490A1 (en) * 2004-10-18 2005-01-27 Progressive Bioactives Incorporated A Method of Producing an Economical and Ecologically Sound Natural Immunobiotic Extract for Use as a Health Management Instrument and a Replacement for Growth Promotion Antibiotics in Livestock and Companion Animals.
US20070059310A1 (en) 2005-05-03 2007-03-15 Karel Steven J Therapeutic combination compositions and methods of using same
CN101558165B (zh) 2005-11-01 2013-07-03 Cp凯尔科美国股份有限公司 高粘度迪优坦胶及其制备方法
EP2032591A2 (en) 2006-06-15 2009-03-11 Biopolymer Engineering, Inc. Dba Biothera, Inc. Glucan compositions and methods of enhancing cr3 dependent neutrophil-mediated cytotoxicity
EP2032180B1 (en) 2006-06-15 2017-03-15 Biothera, Inc. Glucan preparations
WO2008027581A1 (en) 2006-09-01 2008-03-06 University Of Louisville Mcrp antagonists and their uses
US20080167268A1 (en) 2006-09-01 2008-07-10 Jun Yan Particulate beta-glucan compositions for regulating dendritic cells
WO2008130719A1 (en) 2007-04-24 2008-10-30 University Of Louisville Therapeutic beta-glucan combinations
KR101547970B1 (ko) 2007-05-08 2015-08-28 바이오테라, 인크. 미립자-가용성 글루칸 제제
CN101952023B (zh) 2007-10-08 2013-09-04 巴斯夫欧洲公司 具有催化性能的成型体作为反应器内件的用途
JP5503952B2 (ja) 2009-12-09 2014-05-28 富士フイルム株式会社 印刷装置及び印刷制御方法

Patent Citations (36)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5506124A (en) * 1984-11-28 1996-04-09 Massachusetts Institute Of Technology Process for preparing glucanase resistant yeast mutants
US5082936A (en) * 1984-11-28 1992-01-21 Massachusetts Institute Of Technology Glucan composition and process for preparation thereof
US5250436A (en) * 1984-11-28 1993-10-05 Massachusetts Institute Of Technology Glucan compositions and process for preparation thereof
US4962094A (en) * 1988-10-28 1990-10-09 Alpha Beta Technology, Inc. Glucan dietary additives
US5032401A (en) * 1989-06-15 1991-07-16 Alpha Beta Technology Glucan drug delivery system and adjuvant
US5741495A (en) * 1989-06-15 1998-04-21 Alpha-Beta Technology, Inc. Glucan drug delivery system and adjuvant
US5607677A (en) * 1989-06-15 1997-03-04 Alpha-Beta Technology, Inc. Glucan drug delivery system and adjuvant
US5633369A (en) * 1989-09-08 1997-05-27 Alpha-Beta Technology, Inc. Method for producing soluble glucans
US5849720A (en) * 1989-09-08 1998-12-15 Alpha-Beta Technology, Inc. Enhancement of non-specific immune defenses by administration of underivatized, aqueous soluble glucans
US5811542A (en) * 1989-09-08 1998-09-22 Alpha-Beta Technology, Inc. Method for producing soluble glucans
US5532223A (en) * 1989-09-08 1996-07-02 Alpha-Beta Technology, Inc. Use of aqueous soluble glucan preparations to stimulate platelet production
US5322841A (en) * 1989-09-08 1994-06-21 Alpha-Beta Technology, Inc. Method for producing neutral glucans for pharmaceutical applications
US5488040A (en) * 1989-09-08 1996-01-30 Alpha-Beta Technology, Inc. Use of neutral soluble glucan preparations to stimulate platelet production
US5504079A (en) * 1989-09-08 1996-04-02 Alpha-Beta Technology, Inc. Method for immune system activation by administration of a β(1-3) glucan which is produced by Saccharomyces cerevisiae strain R4
US5663324A (en) * 1989-09-08 1997-09-02 Alpha-Beta Technology, Inc. Method for producing underivatized, aqueous soluble β(1-3) glucan
US6020324A (en) * 1989-10-20 2000-02-01 The Collaborative Group, Ltd. Glucan dietary additives
US6143731A (en) * 1989-10-20 2000-11-07 The Collaborative Group, Ltd. Glucan dietary additives
US5397773A (en) * 1989-11-09 1995-03-14 Donzis; Byron A. Photoprotective composition containing yeast extract
US5622939A (en) * 1992-08-21 1997-04-22 Alpha-Beta Technology, Inc. Glucan preparation
US5783569A (en) * 1992-08-21 1998-07-21 Alpha-Beta Technology, Inc. Uses for underivatized, aqueous soluble β(1-3) glucan and compositions comprising same
US5817643A (en) * 1992-08-21 1998-10-06 Alpha-Beta Technology, Inc. Underivatized, aqueous soluable β(1-3) glucan, composition and method of making same
US5519009A (en) * 1993-10-01 1996-05-21 Donzis; Byron A. Solubilized yeast glucan
US5622940A (en) * 1994-07-14 1997-04-22 Alpha-Beta Technology Inhibition of infection-stimulated oral tissue destruction by β(1,3)-glucan
US5705184A (en) * 1995-03-02 1998-01-06 Donzis; Byron A. Substantially purified beta (1,3) finely ground yeast cell wall glucan composition with dermatological and nutritional uses
US5702719A (en) * 1995-03-02 1997-12-30 Donzis; Byron A. Substantially purified beta (1,3) finely ground yeast cell wall glucan composition with dermatological and nutritional uses
US5576015A (en) * 1995-03-02 1996-11-19 Donzis; Byron A. Substantially purified beta (1,3) finely ground yeast cell wall glucan composition with dermatological and nutritional uses
US6117850A (en) * 1995-08-28 2000-09-12 The Collaborative Group, Ltd. Mobilization of peripheral blood precursor cells by β(1,3)-glucan
US6090938A (en) * 1996-05-01 2000-07-18 Collaborative Group, Ltd. Activation of signal transduction by underivatized, aqueous soluble . .beta(1-3)-Glucan
US6110692A (en) * 1996-05-01 2000-08-29 The Collaborative Group, Ltd. Receptor for underivatized aqueous soluble β(1-3)-glucan
US6294321B1 (en) * 1996-05-01 2001-09-25 The Collaborative Group β(1-3)-glucan diagnostic assays
US6630310B1 (en) * 1996-05-01 2003-10-07 Biopolymer Engineering Pharmaceutical, Inc. Assay for binding between carbohydrate and glycolipid
US6084092A (en) * 1997-01-31 2000-07-04 The Collaborative Group, Ltd. β(1-3)-glucan diagnostic assays
US6413715B2 (en) * 1997-01-31 2002-07-02 The Collaborative Group β(1-3)-glucan diagnostic assays
US6046323A (en) * 1997-07-29 2000-04-04 The Collaborative Group, Ltd. Conformations of PPG-glucan
US6369216B1 (en) * 1998-09-25 2002-04-09 Biopolymer Engineering Pharmaceutical, Inc. Very high molecular weight β-glucans
US7022685B2 (en) * 1998-09-25 2006-04-04 Biopolymer Engineering, Inc. Very high molecular weight β-glucans

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090005340A1 (en) * 2005-06-15 2009-01-01 Medimush A/S Bioactive Agents Produced By Submerged Cultivation of a Basidiomycete Cell
US9072776B2 (en) 2005-06-15 2015-07-07 Glycanova As Anti-cancer combination treatment and kit-of-parts
US9610303B2 (en) 2006-06-15 2017-04-04 Biothera, Inc. Glucan preparations
US20080103112A1 (en) * 2006-06-15 2008-05-01 MAGEE Andrew Glucan preparations
US10272101B2 (en) 2006-06-15 2019-04-30 Biothera Inc. Glucan preparations
US20080167268A1 (en) * 2006-09-01 2008-07-10 Jun Yan Particulate beta-glucan compositions for regulating dendritic cells
US20080063650A1 (en) * 2006-09-01 2008-03-13 Jun Yan mCRP antagonists and their uses
CN101407559B (zh) * 2008-11-25 2011-01-26 天津科技大学 一种快速制备酵母β-1,3-葡聚糖的方法
US10265340B2 (en) 2012-02-22 2019-04-23 Kemin Industries, Inc. Animal feed compositions and methods of using the same
US10869882B2 (en) 2012-02-22 2020-12-22 Kemin Industries, Inc. Animal feed compositions and methods of using the same
US10111901B2 (en) 2014-07-10 2018-10-30 Biothera, Inc. Beta-glucan in combination with anti-cancer agents affecting the tumor microenvironment
US10111900B2 (en) 2014-11-06 2018-10-30 Biothera, Inc. β-glucan methods and compositions that affect the tumor microenvironment
US11815435B2 (en) 2017-02-24 2023-11-14 Hibercell, Inc. Beta glucan immunopharmacodynamics
US11140912B1 (en) 2020-12-22 2021-10-12 Agvault, Llc Process for manufacturing yeast strains having increased mannan oligosaccharides and improved amino acid profiles
US11484045B2 (en) 2020-12-22 2022-11-01 Agvault Properties, Llc Process for manufacturing yeast strains having increased mannan oligosaccharides and improved amino acid profiles

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