WO1991009314A1 - Procede de detection de fructosamine - Google Patents
Procede de detection de fructosamine Download PDFInfo
- Publication number
- WO1991009314A1 WO1991009314A1 PCT/JP1990/001653 JP9001653W WO9109314A1 WO 1991009314 A1 WO1991009314 A1 WO 1991009314A1 JP 9001653 W JP9001653 W JP 9001653W WO 9109314 A1 WO9109314 A1 WO 9109314A1
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- WIPO (PCT)
- Prior art keywords
- formula
- carbon atoms
- active oxygen
- substance
- generating substance
- Prior art date
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Classifications
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- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12Q—MEASURING OR TESTING PROCESSES INVOLVING ENZYMES, NUCLEIC ACIDS OR MICROORGANISMS; COMPOSITIONS OR TEST PAPERS THEREFOR; PROCESSES OF PREPARING SUCH COMPOSITIONS; CONDITION-RESPONSIVE CONTROL IN MICROBIOLOGICAL OR ENZYMOLOGICAL PROCESSES
- C12Q1/00—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions
- C12Q1/26—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase
- C12Q1/28—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving oxidoreductase involving peroxidase
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/66—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving blood sugars, e.g. galactose
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S436/00—Chemistry: analytical and immunological testing
- Y10S436/904—Oxidation - reduction indicators
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, etc.]
- Y10T436/144444—Glucose
Definitions
- the present invention relates to a method for measuring fructosamine in an aqueous liquid.
- Japanese Patent Publication No. 1133062 discloses that a colorant (eg, tetrazolium salt) is colored by utilizing the fact that fructosamine has a reducing property under alkaline conditions, and the concentration of fructosamine in a blood sample is determined. Is described. This method is preferable because it can be applied to an automatic measuring device.
- serum samples contain reducing substances (for example, ascorbic acid, glutathione, and uric acid) in addition to fructosamine, so that the effects of these non-specific reducing substances should be reduced or avoided.
- reducing substances for example, ascorbic acid, glutathione, and uric acid
- Japanese Unexamined Patent Publication (Kokai) No. 63-151168 discloses a non-specific reducing component. It describes a method for removing components and turbidity-inducing components at a neutral PH value.
- Japanese Patent Application Laid-Open No. 63-34999 describes a method in which non-specific reducing components and turbidity-inducing components are removed by peroxidase or a surfactant, and measurement is performed in one step. Has been described. Further, Japanese Patent Application Laid-Open No.
- Japanese Patent Application Laid-Open No. No. 997 also discloses a method for removing interfering substances using an enzyme oxidizing agent or the like.
- a tetrazolium salt is used as each of the optimal coloring agents, similarly to the method described in the above-mentioned Japanese Patent Publication No. 11-132. I have.
- This tetrazolium salt produces a water-insoluble colored substance, hormazan, as a result of the reaction. Formazan easily adheres to the measuring instrument and is difficult to remove.
- surfactants eg, lipids and proteins
- the measurement results are affected by the amount of lipids and proteins, resulting in lower measurement accuracy. The problem of doing so was also a problem.
- the present inventor has conducted intensive studies to solve the above-mentioned drawbacks. As a result, when a specific compound is brought into contact with fructosamine, active oxygen is generated, and hydrogen peroxide is derived from the active oxygen. It has been found that fructosamine can be measured by measuring the amount of hydrogen. The present invention is based on this finding. Disclosure of the invention Therefore, the present invention
- step (b) contacting a reagent that produces a detectable change in the presence of hydrogen peroxide derived from active oxygen with the product of step (a);
- FIG. 1 is a graph showing the relationship between the amount of glycated albumin and the absorbance.
- FIG. 2 is a graph showing the correlation between the method of the present invention and the conventional HPLC method.
- the “active oxygen generating substance” used in the method of the present invention means a compound capable of generating active oxygen ( ⁇ ⁇ 2-) when contacted with fructosamine having a reducing property.
- the active oxygen generating substance for example, a general formula
- R i is a lower alkyl group having 1 to 4 carbon atoms, particularly a methyl group or an ethyl group
- R 2 is a hydrogen atom, a lower alkyl group having 1 to 4 carbon atoms, particularly a methyl group.
- X 1 is an anion, for example, a lower alkyl sulfate having 1 to 4 carbon atoms, particularly methyl or ethylsulfur
- the compound can be used.
- the phenazine compound represented by the formula (1) is brought into contact with a test sample in a pH range of 8.5 to 11.0, preferably 9.5 to 10.3. '
- R 3 and R 4 are each independently a lower alkyl group having 1 to 4 carbon atoms, especially. Is a methyl group or an ethyl group, and X 2 is an anion such as a halogen, especially chlorine or bromine. Is)
- biviridine compound represented by the formula (2) examples include 1,1'-dimethyl-'4,4'-biviridylium dichloride [methylviologen] It is preferable to use The bipyridine compound represented by the formula (2) is brought into contact with a test sample in a pH range of 8.5 to 11., Preferably 9.5 to 10.3.
- the active oxygen-generating substance is represented by a general formula
- R 5 is a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, particularly a methyl group or an ethyl group, and 81 and 82 are each a hydrogen atom or 2 1,4-type quinone compound represented by the following formula: is an atom necessary to form a benzene ring together with carbon atoms.
- 1,4-type quinone compound represented by (3) it is preferable to use benzoquinone, 1, '4-naphthoquinone or 2-methyl-1,4-naphthoquinone.
- the 1,4-type quinone compound represented by the formula (3) is brought into contact with a test sample in the range of 8.5 to 11.0, preferably 9.5 to 10.5.
- B 3 and B 4 are each a hydrogen atom, or a force capable of forming a benzene ring together with two carbon atoms in the formula, or substituted or unsubstituted Atoms required to form a pyridin ring, and B 5 and B 6 together with the two carbon atoms in the formula form a benzene ring, or are substituted or substituted Atoms necessary to form an unsubstituted pyrrole ring
- the substituent which may be present on the t- pyridine ring or the pyrrole ring in which the 1,2-type quinone compound represented by the formula (1) can be used is, for example, a group having 1 to 4 carbon atoms. It is a lower alkyl group or a carboxylic acid group.
- Examples of the 1,2-type quinone compound represented by the formula (4) include 1,2-naphthoquinone, 9,10-phenanthrene quinone, and quinoline quinone (2,7,9-tricarboxy-1H— It is preferable to use a pyro [2,3 -—] quinoline (1,4,5-dione).
- the 1,2-type quinone compound represented by the formula (4) is brought into contact with the test sample in the range of 8.5 to 11.0, preferably 9.5 to 10.5.
- ⁇ represents a halogenated phenyl group (particularly, Group), substituted or unsubstituted thiazolyl group
- R 6 is a hydrogen atom or a nitro group
- R 7 and R 8 are each independently a lower alkyl group having 1 to 4 carbon atoms, particularly a methyl group or an ethyl group.
- X3 and X4 are each independently an anions, such as halogen, especially chlorine or bromine.
- Examples of the tetrazolium salt represented by the formula (5) include 3- (P-phenyl) -2- (P-dinitrophenyl) -1-5-phenyl-2H tetrazolium chloride [IN-cho] , 3— (4,5-dimethyl-2, thiazolyl) -1,2,5-diphenyl-12H tetrazolium bromide [MTT], or 3,3 ′ mono (3,3′dimethoxy 4,4′—biphenylenyl) ⁇ Bis [2- (P-d-phenyl) 1-5-phenyl 2H tetrazolium chloride [N itro— TB] is preferably used.
- the tetrazolium salt represented by the formula (5) is brought into contact with a test sample in the range of pH 8.5 to 11.0, preferably 9.5 to 10.5.
- the method according to the invention measures fructosamine contained in aqueous liquids, in particular biological aqueous liquids, for example blood or blood-derived liquids (especially serum or plasma), or urine or tissue extracts.
- aqueous liquids in particular biological aqueous liquids, for example blood or blood-derived liquids (especially serum or plasma), or urine or tissue extracts.
- Interfering substances are, for example, reducing substances other than fructosamine (eg ascorbic acid, glutathione or uric acid), turbidity-inducing components (eg chyle).
- reducing substances other than fructosamine eg ascorbic acid, glutathione or uric acid
- turbidity-inducing components eg chyle.
- Known methods for removing interfering substances are described, for example, in JP-A-63-15168, JP-A-63-304999, JP-A-63-182567, and JP-A-11-108997. The following method can be used.
- test sample is left for a long time (for example, 30 minutes or more) for dialysis or gel over-desalting to remove interfering substances.
- an enzyme that does not ultimately affect the measurement system of the present invention can be added.
- ascorbic acid oxidase can be added to remove ascorbic acid.
- a surfactant eg, sodium lauryl sulfate
- Fructosamine becomes a reductive enol form under alkaline conditions.
- alkaline conditions for example, pH 8.5 to 11.0, preferably PH 9.0 to Any buffer can be used which can be 10.5, especially PH9.5 ⁇ : L0.3).
- a buffer for example, a good buffer or preferably a carbonate buffer (for example, sodium hydrogen carbonate or sodium carbonate) can be used.
- the test sample, the active oxygen-generating substance, and the buffer can be brought into contact with each other in any order. However, it is preferable to bring the buffer into contact with the test sample, and then contact the active oxygen-generating substance.
- the buffer is generally used at a concentration of 10 to 5OmM, preferably 20 to 10OmM.
- the active oxygen generating substance is generally used at a concentration of 10 M to 4 mM, but the optimum concentration varies depending on the type of compound used.
- the phenazine compound represented by the formula (1) is generally used at a concentration of 10 M to 500 M, preferably 40> M to 200 / M.
- the biviridine compound represented by the formula (2) is generally used at a concentration of 0.2 mM to 4 mM, preferably 0.5 mM to 2 mM.
- the 1,4-type quinone compound represented by the formula (3) or the 1,2-type quinone compound represented by the formula (4) is generally 10 M to 2 mM, preferably 25 M to 1 mM.
- Use at a concentration of The tetrazolium salt represented by the formula (5) is generally 0.1 m] V! It is used at a concentration of 22 mM, preferably 0.2-1 mM.
- the contact between the test sample, the active oxygen-generating substance and the buffer can be carried out at a temperature usually used, that is, from room temperature to about 40 ° C (preferably about 25 to 37 ° C). As the contact time increases, the amount of the product also increases, so the contact time is not particularly limited. When applied to an automatic analyzer or from the viewpoint of measurement accuracy, it is preferable to make contact for about 5 minutes or more. When reducing fructosamine is present in the test sample, active oxygen is generated by the fructosamine and the active oxygen generating substance, and the active oxygen subsequently induces hydrogen peroxide.
- superoxide dismutase (generally 60 MS / m 1-4 ms / m 1, preferably 125 / ig / ml) 22 mgZ ml) to induce only hydrogen peroxide without producing a water-insoluble formazan dye.
- a “reagent that produces a detectable change in the presence of hydrogen peroxide” derived from active oxygen is defined as (i) a substance having a peroxidative activity (hereinafter referred to as a “peroxide active substance”; typically, (Peroxidase) and (ii) a color precursor or a substance that emits or emits fluorescence in the presence of a peroxide active substance.
- H2A reduced form
- A oxidized form: detectable substance
- the peroxide active substance is, for example, peroxidase.
- Peroxidase is a horseradish, potato, fig sap or power bra, milk (lactoperoxidase) white blood cells Luoxidase) or present in microorganisms. Synthetic peroxidases can also be used.
- peroxidation active substances other than enzymes include iron thiocyanate, iron tannate, ferrous ferrocyanide, and dichromate (potassium chromium sulfate) adsorbed on silica gel.
- Dye precursors that change color or discolor in the presence of a peroxide active substance include, for example, monoamines (aniline or its derivatives, o-toluidine, P-toluidine, etc.), diamines (o-phenylene diamine, benzidine) , Dianididine, etc.), phenols
- peroxidase generally 2.5 to 50 ⁇ g Zm 1
- 4-aminoantipyrine as an electron donor
- 3-hydroxy-2,4,6-triodobenzoic acid generally each ⁇ .2 to 2 mM
- step (a) is added to the product of step (a) and the absorbance at a wavelength of 51 nm is measured within about 2 to 60 minutes. Use distilled water as a control.
- a luminescence method using luminol-microbexoxidase can be used for the generated hydrogen peroxide.
- a fluorescence method using a fluorescent substance for example, homovanillic acid
- the measurement method of the present invention is a one-step method in which all the reagents are contacted simultaneously (that is, the test liquid is placed in a system containing an active oxygen generating substance and a reagent that produces a detectable change in the presence of hydrogen peroxide). Addition) can be used, but it is preferable to perform it in two stages. That is, in the first stage, the test sample is brought into contact with the active oxygen generating substance to induce hydrogen peroxide, and then in the second stage, a detectable change is generated from the hydrogen peroxide, and the change is detected. Measure the amount.
- any standard solution whose content can be determined according to Menet et al., J. Chromatography, 297, 339350, 1984] can be used.
- a standard solution prepared from albumin and 1-deoxy 1-morpholino fructose described in Japanese Patent Application Publication No. H07-115, or fructosylglutamic acid (see Japanese Patent Application No. 11-2067221) can be used.
- the measurement principle according to the present invention is based on the fact that electrons from a reductive phenolic fructosamine are used in the presence of an oxidized substance in a dissolved oxygen-dependent peroxidation reaction.
- a suitable oxidized substance the active oxygen-generating substance of the present invention
- electrons from the reducing enol-type fructosamine are transferred to dissolved oxygen to generate active oxygen ( ⁇ 2-).
- This neutral oxygen is followed by a disproportionation reaction
- Disproportionation reactions are generally Although the reaction proceeds even in the absence of oxygen, etc., when a tetrazolium salt is used as an active oxygen-generating substance, the reaction from the tetrazolium salt to the formazan dye is prevented, and the disproportionation reaction proceeds. Therefore, it is necessary to use superoxide dismutase. Hydrogen peroxide induced by the disproportionation reaction can be measured by a method well known to those skilled in the art. Example
- Glucose (Wako Pure Chemical Industries) To a Ringer solution containing 0.4 mM, albumin extracted and purified from serum was added at 4.3 mg / m 1 and incubated at 37 ° C for 4 days. The amount of saccharified albumin obtained was determined by HPLC method [Parker, etc.
- a 0.2 M phosphate buffer (PH 7.0) was prepared and used as reagent B.
- a 20 mM carbonate buffer ( ⁇ 9.8) was prepared and used as reagent A.
- 1-Methoxy-5-methylphenazine methyl sulfate (1-methoxy PMS) An aqueous solution containing 1 OmM was used as Reagent B.
- 3-hydroxy-1,2,4,6-triiodobenzoic acid 2.8 ⁇ 2.8 mM of 4-aminoantipyrine, 0.55 mM of ethylenediaminetetraacetic acid, and 1 l / gZm1 of peroxidase, to prepare a 0.2 M phosphate buffer (pH 7.0).
- 4-aminoantipyrine 0.55 mM of ethylenediaminetetraacetic acid
- 1 l / gZm1 of peroxidase to prepare a 0.2 M phosphate buffer (pH 7.0).
- Reagent A ( ⁇ 1), while handling the standard solution 50 1 prepared in Example 1 was added further reagent beta 1 Ou I, and the 5 minutes the reaction takes place. Was at 37 e C. To this reaction solution, 9 ml of reagent CO. was added, and the mixture was allowed to stand at room temperature for 10 minutes, and then the absorbance at a wavelength of 510 nm was measured. Ma A control test was also performed using distilled water instead of the standard solution. The results are indicated by ⁇ in FIG. Preparation of reagents
- a 1 OmM carbonate buffer (PH I 0.3) containing 0.25 mM, 0.25 mM 4-aminoantipyrine, and 125 g / m 1 of superoxide dismutase (S ⁇ D). This was designated as Reagent A.
- 0.1 M phosphate buffer (pH 6) containing 1.3 mM of 3-hydroxy-1,2,4,6-triobenzoic acid, 1.8% Triton X-100 ′, and 260 gZm 1 of peroxidase. 0> was prepared, and this was used as reagent B.
- a 20-mM carbonate buffer (pH 10.0) containing 0.3 mM of 2-methyl-1,4-naphthoquinone was prepared.
- 3-hydroxy-2,4,6-triodobenzoic acid 2.8
- a 2 OmM carbonate buffer (pH 10.3) containing 1 mM methyl viologen was prepared and used as reagent A.
- a 0.2 M phosphate buffer solution (pH 7.0) containing the above was prepared and used as reagent B.
- Serum was collected from 24 humans, and the fructosamine content was measured by the method described in Example 1.
- Example 7 The procedure described in Example 6 was repeated, except that 9,10-phenanthrenequinone was replaced by 1-methoxy-5-methylphenazine (Example 7), 2-methyl-11,41-naphthoquinone (Example 8), and N itro—TB and superoxide dismutase (Example 9) or methylviologen (Example 10) were used.
- Example 7 The procedure described in Example 6 was repeated, except that 9,10-phenanthrenequinone was replaced by 1-methoxy-5-methylphenazine (Example 7), 2-methyl-11,41-naphthoquinone (Example 8), and N itro—TB and superoxide dismutase (Example 9) or methylviologen (Example 10) were used.
- Table 1 The results are shown in Table 1 below.
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Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/741,432 US5312759A (en) | 1989-12-20 | 1989-12-20 | Method for measurement of fructosamines using 1,2-quinones |
KR1019910700931A KR910701823A (ko) | 1989-12-20 | 1990-12-19 | 프룩토사민의 측정 방법 |
EP91900927A EP0463171B1 (en) | 1989-12-20 | 1990-12-19 | Method of determining fructosamines |
DE69026611T DE69026611T2 (de) | 1989-12-20 | 1990-12-19 | Verfahren zur Bestimmung von Fruktosaminen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1/330165 | 1989-12-20 | ||
JP1330165A JP2796150B2 (ja) | 1989-12-20 | 1989-12-20 | フルクトサミンの測定方法 |
Publications (1)
Publication Number | Publication Date |
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WO1991009314A1 true WO1991009314A1 (fr) | 1991-06-27 |
Family
ID=18229546
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP1990/001653 WO1991009314A1 (fr) | 1989-12-20 | 1990-12-19 | Procede de detection de fructosamine |
Country Status (8)
Country | Link |
---|---|
US (1) | US5312759A (ja) |
EP (1) | EP0463171B1 (ja) |
JP (1) | JP2796150B2 (ja) |
KR (1) | KR910701823A (ja) |
AU (1) | AU638524B2 (ja) |
CA (1) | CA2045665A1 (ja) |
DE (1) | DE69026611T2 (ja) |
WO (1) | WO1991009314A1 (ja) |
Families Citing this family (10)
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CA2127679A1 (en) * | 1993-07-27 | 1995-01-28 | Ewald Vorberg | Set of reagents for determining the fructosamine content |
US5712167A (en) * | 1995-07-19 | 1998-01-27 | Kyoto Dai-Ichi Kagaku Co., Ltd. | Method of measuring Amadori compound by light scattering |
US6352835B1 (en) * | 1998-11-17 | 2002-03-05 | Kyoto Daiichi Kagaku Co. Ltd. | Method of measuring substance in sample using a redox reaction |
JP4647742B2 (ja) * | 2000-03-13 | 2011-03-09 | 三菱化学メディエンス株式会社 | アスコルビン酸の分析方法及び分析用試薬 |
US7153666B2 (en) * | 2003-07-17 | 2006-12-26 | General Atomics | Methods and compositions for determination of glycated proteins |
ES2404059T3 (es) * | 2006-07-25 | 2013-05-23 | General Atomics | Procedimientos para analizar el porcentaje de hemoglobina glicada |
US7943385B2 (en) * | 2006-07-25 | 2011-05-17 | General Atomics | Methods for assaying percentage of glycated hemoglobin |
MX2010009253A (es) * | 2008-02-22 | 2010-09-14 | Glaxosmithkline Llc | Un aparato y metodo para fabricar dentaduras personalizadas. |
US8673646B2 (en) | 2008-05-13 | 2014-03-18 | General Atomics | Electrochemical biosensor for direct determination of percentage of glycated hemoglobin |
KR101789787B1 (ko) * | 2016-08-17 | 2017-10-25 | 주식회사 바이오맥스 | 염료를 이용한 마이코플라즈마 검출방법 |
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JPS63180861A (ja) * | 1987-01-22 | 1988-07-25 | Sogo Seibutsu Igaku Kenkyusho:Kk | 簡易血中蛋白質結合性グルコ−ス測定法 |
JPS63280955A (ja) * | 1987-05-12 | 1988-11-17 | Honda Motor Co Ltd | 無段変速機の変速比制御方法および変速比制御装置 |
DE3743405A1 (de) * | 1987-05-14 | 1988-11-24 | Boehringer Mannheim Gmbh | Verfahren zur bestimmung von fructosamin |
JPH02184758A (ja) * | 1989-01-11 | 1990-07-19 | Daiso Co Ltd | 糖化蛋白の測定方法 |
JP2775847B2 (ja) * | 1989-05-12 | 1998-07-16 | 東洋紡績株式会社 | フルクトサミン測定用試薬 |
US5110745A (en) * | 1989-06-01 | 1992-05-05 | The Trustees Of The University Of Pennsylvania | Methods of detecting glycated proteins |
US4956301A (en) * | 1989-11-02 | 1990-09-11 | Miles Inc. | Test device and method of assaying for fructosamines |
-
1989
- 1989-12-20 JP JP1330165A patent/JP2796150B2/ja not_active Expired - Fee Related
- 1989-12-20 US US07/741,432 patent/US5312759A/en not_active Expired - Lifetime
-
1990
- 1990-12-19 EP EP91900927A patent/EP0463171B1/en not_active Expired - Lifetime
- 1990-12-19 DE DE69026611T patent/DE69026611T2/de not_active Expired - Fee Related
- 1990-12-19 AU AU69067/91A patent/AU638524B2/en not_active Ceased
- 1990-12-19 WO PCT/JP1990/001653 patent/WO1991009314A1/ja active IP Right Grant
- 1990-12-19 KR KR1019910700931A patent/KR910701823A/ko not_active Application Discontinuation
- 1990-12-19 CA CA002045665A patent/CA2045665A1/en not_active Abandoned
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63182567A (ja) * | 1986-01-06 | 1988-07-27 | アイソラブ,インク. | フルクトサミン測定方法 |
JPS6315168A (ja) * | 1986-06-21 | 1988-01-22 | ベ−リンガ−・マンハイム・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 血液又は血液から誘導された試料中の血清フルクトサミン含量を特異的に測定する際に蛋白質基質効果を回避するための方法及び製剤 |
JPH01108997A (ja) * | 1987-09-29 | 1989-04-26 | Boehringer Mannheim Gmbh | 血液又は血液から導出した試料中の血清のフルクトスアミン含量を特異的に測定する方法及び試薬、及び非特異的還元作用を有するか、又は/及び溷濁を惹起する試料成分を除去する方法 |
Non-Patent Citations (1)
Title |
---|
See also references of EP0463171A4 * |
Also Published As
Publication number | Publication date |
---|---|
US5312759A (en) | 1994-05-17 |
KR910701823A (ko) | 1992-08-12 |
JP2796150B2 (ja) | 1998-09-10 |
DE69026611D1 (de) | 1996-05-23 |
AU638524B2 (en) | 1993-07-01 |
EP0463171A4 (en) | 1993-03-10 |
CA2045665A1 (en) | 1991-06-21 |
EP0463171A1 (en) | 1992-01-02 |
DE69026611T2 (de) | 1996-08-14 |
JPH03189561A (ja) | 1991-08-19 |
AU6906791A (en) | 1991-07-18 |
EP0463171B1 (en) | 1996-04-17 |
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