US3042496A - Diagnostic composition - Google Patents
Diagnostic composition Download PDFInfo
- Publication number
- US3042496A US3042496A US802281A US80228159A US3042496A US 3042496 A US3042496 A US 3042496A US 802281 A US802281 A US 802281A US 80228159 A US80228159 A US 80228159A US 3042496 A US3042496 A US 3042496A
- Authority
- US
- United States
- Prior art keywords
- glucose
- hemin
- metalloporphyrin
- solution
- urine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 25
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 26
- 239000008103 glucose Substances 0.000 claims description 26
- 239000004366 Glucose oxidase Substances 0.000 claims description 16
- 108010015776 Glucose oxidase Proteins 0.000 claims description 16
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
- 229940116332 glucose oxidase Drugs 0.000 claims description 16
- 235000019420 glucose oxidase Nutrition 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- SNCJAJRILVFXAE-UHFFFAOYSA-N 9h-fluorene-2,7-diamine Chemical compound NC1=CC=C2C3=CC=C(N)C=C3CC2=C1 SNCJAJRILVFXAE-UHFFFAOYSA-N 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- UHGULLIUJBCTEF-UHFFFAOYSA-N 2-aminobenzothiazole Chemical compound C1=CC=C2SC(N)=NC2=C1 UHGULLIUJBCTEF-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 description 26
- 229940025294 hemin Drugs 0.000 description 21
- 210000002700 urine Anatomy 0.000 description 20
- 239000000243 solution Substances 0.000 description 19
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 16
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000012360 testing method Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 229960003512 nicotinic acid Drugs 0.000 description 8
- 239000011664 nicotinic acid Substances 0.000 description 8
- 235000001968 nicotinic acid Nutrition 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 108010010803 Gelatin Proteins 0.000 description 5
- 239000007853 buffer solution Substances 0.000 description 5
- 238000001514 detection method Methods 0.000 description 5
- 229920000159 gelatin Polymers 0.000 description 5
- 239000008273 gelatin Substances 0.000 description 5
- 235000019322 gelatine Nutrition 0.000 description 5
- 235000011852 gelatine desserts Nutrition 0.000 description 5
- NUIURNJTPRWVAP-UHFFFAOYSA-N 3,3'-Dimethylbenzidine Chemical compound C1=C(N)C(C)=CC(C=2C=C(C)C(N)=CC=2)=C1 NUIURNJTPRWVAP-UHFFFAOYSA-N 0.000 description 4
- 229960004543 anhydrous citric acid Drugs 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- UBVSIAHUTXHQTD-UHFFFAOYSA-N 2-n-(4-bromophenyl)-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(NC=2C=CC(Br)=CC=2)=N1 UBVSIAHUTXHQTD-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 210000001124 body fluid Anatomy 0.000 description 2
- 239000010839 body fluid Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- 229940088598 enzyme Drugs 0.000 description 2
- 235000012732 erythrosine Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 150000002303 glucose derivatives Chemical class 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- PKIDNTKRVKSLDB-UHFFFAOYSA-K trisodium;2-hydroxypropane-1,2,3-tricarboxylate;hydrate Chemical compound O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PKIDNTKRVKSLDB-UHFFFAOYSA-K 0.000 description 2
- LUKPNZHXJRJBAN-UHFFFAOYSA-N 4-(4-amino-3-methylphenyl)-2-methylaniline;hydron;dichloride Chemical compound [Cl-].[Cl-].C1=C([NH3+])C(C)=CC(C=2C=C(C)C([NH3+])=CC=2)=C1 LUKPNZHXJRJBAN-UHFFFAOYSA-N 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- 102000016938 Catalase Human genes 0.000 description 1
- 108010053835 Catalase Proteins 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000001856 Ethyl cellulose Substances 0.000 description 1
- ZZSNKZQZMQGXPY-UHFFFAOYSA-N Ethyl cellulose Chemical compound CCOCC1OC(OC)C(OCC)C(OCC)C1OC1C(O)C(O)C(OC)C(CO)O1 ZZSNKZQZMQGXPY-UHFFFAOYSA-N 0.000 description 1
- 206010018473 Glycosuria Diseases 0.000 description 1
- 241001417516 Haemulidae Species 0.000 description 1
- 239000011358 absorbing material Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000013060 biological fluid Substances 0.000 description 1
- -1 bipyridylpyridine Chemical compound 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002405 diagnostic procedure Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 1
- 238000013399 early diagnosis Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 235000019325 ethyl cellulose Nutrition 0.000 description 1
- 229920001249 ethyl cellulose Polymers 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical class [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000035780 glucosuria Effects 0.000 description 1
- JHGVLAHJJNKSAW-UHFFFAOYSA-N herniarin Natural products C1CC(=O)OC2=CC(OC)=CC=C21 JHGVLAHJJNKSAW-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- BAUYGSIQEAFULO-UHFFFAOYSA-L iron(2+) sulfate (anhydrous) Chemical compound [Fe+2].[O-]S([O-])(=O)=O BAUYGSIQEAFULO-UHFFFAOYSA-L 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- JZRYQZJSTWVBBD-UHFFFAOYSA-N pentaporphyrin i Chemical class N1C(C=C2NC(=CC3=NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 JZRYQZJSTWVBBD-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 150000004032 porphyrins Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
- C12Q1/54—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving glucose or galactose
-
- 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
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/805—Test papers
Definitions
- This invention relates to a new and improved diagnostic composition and is particularly concerned with a diagnostic test which is useful for the qualitative detection and quantitative determination of glucose in biological fluids, such as urine, and wherein the reagent composition is incorporated upon a bibulous carrier.
- glucose indicator may also be used efiiciently in routine urinalyses in hospitals and physicians oflices, in diabetes detection screening programs, in the difierentiation of glucosuria from other meliturias, and the like.
- a urine-sugar test to be of greatest value, must be conveniently rapid, simple enough for any patient to learn with ease, accurate enough to serve the clinician, and sensitive enough to reflect variations in the patients condition.
- the reagent composition must be adequately stable.
- metalloporphyrins which are not operable per so, are, however, when activated by certain nitrogenous substances, surprisingly and unexpectedly capable of acting as catalysts to induce the oxidation of indicators by hydrogen peroxide formed when glucose is aerobically oxidized in the presence of glucose oxidase.
- the principles underlying these reactions are well known and need not be expounded.
- a diagnostic composition according to the present invention comprises as essential constituents glucose oxidase, a metalloporphyrin, such as hemin, complex-forming compounds containing amino-donor groups, such as Z-aminobenzothiazole, pyridine, bipyridyl, bipyridylpyridine, nicotinic acid or the like, and color-forming substances or indicators, such as 2,7-diaminofluorene, o-tolidine, leucoindophenols, etc.
- a metalloporphyrin such as hemin
- complex-forming compounds containing amino-donor groups such as Z-aminobenzothiazole
- pyridine bipyridyl, bipyridylpyridine, nicotinic acid or the like
- color-forming substances or indicators such as 2,7-diaminofluorene, o-tolidine, leucoindophenols, etc.
- the metalloporphyrin used in the preferred embodiments of this invention is hemin, which is commercially available and whose full chemical name is 1,3,5,8-tetramethyl-2,4-diviny1porphine-6,7-dipropionic acid ferrichloride, (C H N O FeCl).
- the following structural formula characterizes its complex chemical nature:
- H3C CH CH n 1 CH3 l /N Fe 4% nooccn cn 2 Haw H nooccn ca CH3 Hernin and the other 'metalloporphyrins that can be 0 employed in accordance with the inventive concept react wherein the 4-membered ring represents an octahedral porphyrin ring system, M represents Fe, Co, Ni, Mn, Mg,
- a metalloporphyrin it is also contemplated to employ other equivalent metallic complexes or chelates, such as phthalocyanines, the structure of which is closely analogous to that of the porphine nucleus present in hemin.
- phthalocyanines the structure of which is closely analogous to that of the porphine nucleus present in hemin.
- Further catalytic materials useful in the practice of this invention are ferrocene compounds, the ferrous salt of dimethylglyoxime and the like.
- the diagnostic composition of our invention is prepared, due to incompatibility of ingredients, by way of two separate solutions, one comprising the glucose oxidase and the indicator substance dissolved in 1:1 alcohol-water and the other containing hemin and the nitrogenous substance in an alcoholic medium.
- this glucose test may contain a suitable inert dye to impart to the composition a uniform background color as well as an appropriate buffer system to maintain a desired pH range (pH 3 to 7 with a pH of 5.4 being preferred).
- a pH 5.4 buffer solution (prepared by dissolving 352.8 g. of sodium citrate monohydrate and 25.6 g. of anhydrous citric acid in water and diluting to 1000 ml.) was added with stirring.
- a solution of 2 g. of gelatin and 150 mg. of ED. & C. Red No. 3 (disodium salt of 9-o-carboxyphenyl 6 hydroxy 2,4,5,7 tetraiodo-3-isoxanthone) in 100 ml. of hot water was prepared and 20 ml. of this solution was added to the algin-bufier solution with stirring. Then a solution of 200 mg. of 2,7diamino-fiuorene dihydrochloride in 20 m1.
- Solution B.Hemin, 50 mg, and 500 mg. of 2-aminobenzothiazole were added to 50 ml. of 95 ethanol and 50 ml. of 10% aqueous polyvinyl alcohol and the mixture was heated to boiling and shaken for two minutes. The excess hemin was removed by filtration, and the filtrate was allowed to cool to room temperature.
- Bilbulous strips such as filter paper cut into narrow strips, small sticks of wood, or other porous or absorbing material with a water-impervious barrier of ethyl cellulose, one-half inch from the tip, were dipped into 'solution A so that through the process of submersion Procedure of Testing In use, an impregnated strip made as described above is dipped into the liquid specimen to be tested. When contacted with urine containing glucose, test strips gave positive reactions in about one minute evidenced by various shades of blue color as follows:
- EXAMPLE II Twelve ml. of a buffer solution (which was prepared by dissolving 7.4 g. of anhydrous citric acid and 32.6 g. of trisodium citrate dihydrate in 100 ml. of water) was added rapidly with good stirring to 10 ml. of a warm gelatin solution (which was prepared by dissolving 4.8 g. of gelatin in 100 ml. of boiling water). One hundred mg. of o-tolidine dihydrochloride was mixed with 10 ml. of 95% ethanol (2B), and the mixture was added rapidly to the gelatin-buffer solution with good stirring. Then 10 ml. of a glucose oxid-ase solution was added, which was prepared by dissolving 0.5 g. of glucose oxidase (having an activity of 16,000 units per gram) in 50 ml. of water, and the mixture was stirred until well mixed. Paper strips were dipped into this solution and dried at 100 C. for 10 minutes.
- EXAMPLE III A mixture of 50 mg. of hemin, 500 mg. of nicotinic acid, 50 ml. of ethanol and 50 ml. of 10% aqueous polyvinyl alcohol was warmed and shaken for 5 minutes. The excess hemin was removed by filtration. Strips described in Example IIA were impregnated with this mixture and dried at for 10 minutes. These strips developed a blue-green color after 5 minutes with urine containing 1% glucose and only a very faint green color with urine containing glucose.
- EXAMPLE IV When 50 mg. of Z-aminobenzothiazole was substituted for the nicotinic acid in Example III, the strips were a little more active, and a blue-green color developed with 1% glucose in urine in 3 minutes.
- EXAMPLE V (A) Twenty ml. of hot buffer solution (which was prepared by dissolving 352.8 g. of sodium citrate monohydrate and 25.6 g. of anhydrous citric acid in water and diluting to 1000 ml.) was added with stirring to a solution of 200 mg. of algin in 20 ml. of water. Then 20 ml. of a hot gelatin-dye solution (Which was prepared by dissolving 2 g. of gelatin and mg. of ED. & C. Red No. 3 dye in 100 ml. of water) was added with stirring and followed by a solution of 2,7-diaminofiuorene dihydrochloride (200 mg.) in 20 ml.
- hot buffer solution which was prepared by dissolving 352.8 g. of sodium citrate monohydrate and 25.6 g. of anhydrous citric acid in water and diluting to 1000 ml.
- this invention pertains to a diagnostic composition for the detection of glucose in body fluids
- a bibulous strip or stick that has been impregnated with a composition comprising glucose oxidase, a metalloporphyrin, such as hemin, a complex-forming compound containing aminodonor groups, such as 2-aminobenzothiazole, nicotinic acid or pyridine to activate the metalloporphyrin and a color-forming substance, such as 2,7-diaminolluorene or o-tolidine, which is oxidizable by hydrogen peroxide in the presence of the activated metalloporphyrin.
- the composition containing glucose oxidase, hemin, Z-aminobenzothiazole and 2,7-diaminofiuorene constitutes the preferred embodiment of this invention.
- a diagnostic composition for detecting glucose which comprises glucose oxidase, a metalloporphyrin, a complexforming compound containing amino-donor groups selected from the class consisting of 2-aminobenzothiazole, nicotinic acid and pyridine to activate said metalloporphyrin and a color-forming substance taken from the group consisting of 2,7-diaminofluorene and o-tolidine, oxidizable by hydrogen peroxide in the presence of the activated metalloporphyrin.
- a diagnostic composition for detecting glucose which comprises glucose oxidase, hemin, a complex-forming compound selected from the class consisting of Z-aminobenzothiazole, nicotinic acid and pyridine to activate said hemin and a color-forming substance taken from the group consisting of 2,7-diaminofiuorene and o-tolidine, oxidizable by hydrogen peroxide in the presence of the activated hemin.
- a diagnostic composition for detecting glucose which comprises glucose oxidase, hemin, Z-aminobenzothiazole to activate said hemin by forming a complex therewith and 2,7-diaminofluorene oxidizable by hydrogen peroxide in the presence of the activated hemin.
- a glucose-detecting means including a bibulous carrier impregnated with a diagnostic composition comprising glucose oxidase, hemin, Z-aminobenzothiazole to activate said hemin, and 2,7-dia-minofluorene oxidizable by hydrogen peroxide in the presence of the activated hemin.
- a glucose-detecting means including a bibulous carrier impregnated with a diagnostic composition comprising glucose oxidase, hemin, an amino-donor selected from the group consisting of Z-aminobenzothiazole, nicotinic acid and pyridine to activate said hemin and 2,7-diaminofluorene oxidizable by hydrogen peroxide in the presence of the activated hemin.
- rier impregnated with a diagnostic composition comprising glucose oxidase, hemin, pyridine to activate said hemin and 2,7-diaminofiuorene oxidizable by hydrogen peroxide in the presence of the activated hemin.
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Molecular Biology (AREA)
- Emergency Medicine (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Physics & Mathematics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL102893D NL102893C (en)) | 1959-03-27 | ||
| US802281A US3042496A (en) | 1959-03-27 | 1959-03-27 | Diagnostic composition |
| DEM44720A DE1185841B (de) | 1959-03-27 | 1960-03-19 | Diagnostisches Reagens zum Nachweis von Glukose und Diagnosehilfsmittel |
| FR822349A FR1251916A (fr) | 1959-03-27 | 1960-03-24 | Composition pour la détection colorimétrique du glucose dans les liquides biologiques |
| GB10679/60A GB886778A (en) | 1959-03-27 | 1960-03-25 | Diagnostic composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US802281A US3042496A (en) | 1959-03-27 | 1959-03-27 | Diagnostic composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3042496A true US3042496A (en) | 1962-07-03 |
Family
ID=25183293
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US802281A Expired - Lifetime US3042496A (en) | 1959-03-27 | 1959-03-27 | Diagnostic composition |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3042496A (en)) |
| DE (1) | DE1185841B (en)) |
| GB (1) | GB886778A (en)) |
| NL (1) | NL102893C (en)) |
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3252762A (en) * | 1961-05-04 | 1966-05-24 | Miles Lab | Stabilized occult blood diagnostic |
| US3266868A (en) * | 1962-01-24 | 1966-08-16 | Miles Lab | Diagnostic composition and test indicator |
| US3278394A (en) * | 1963-07-22 | 1966-10-11 | Miles Lab | Method and composition for diagnosing glucose |
| DE1260827B (de) * | 1964-12-09 | 1968-02-08 | Miles Lab | Zubereitung zum Glukosenachweis in Harn |
| EP0140322A3 (en) * | 1983-11-02 | 1986-07-16 | Miles Laboratories, Inc. | Polymer catalyst transducers and use thereof in test kits for analytical methods |
| US4722894A (en) * | 1984-02-03 | 1988-02-02 | Kyowa Medex Co., Ltd. | Method for the determination of ceruloplasmin activity |
| US4956300A (en) * | 1982-01-05 | 1990-09-11 | Helena Laboratories Corporation | Aid for determining the presence of occult blood, method of making the aid, and method of using the aid |
| US5081040A (en) * | 1987-06-29 | 1992-01-14 | Helena Laboratories Corporation | Composition and kit for testing for occult blood in human and animal excretions, fluids, or tissue matrixes |
| US5196167A (en) * | 1989-04-04 | 1993-03-23 | Helena Laboratories Corporation | Fecal occult blood test product with positive and negative controls |
| US5217874A (en) * | 1989-04-04 | 1993-06-08 | Helena Laboratories Corporation | Fecal occult blood test product with positive and negative controls |
| US5273888A (en) * | 1984-01-16 | 1993-12-28 | Helena Laboratories Corporation | Chemical test kit and method for determining the presence of blood in a specimen and for verifying the effectiveness of the chemicals |
| US5702913A (en) * | 1983-12-21 | 1997-12-30 | Helena Laboratories Corporation | Chromgen-reagent test system |
-
0
- NL NL102893D patent/NL102893C/xx active
-
1959
- 1959-03-27 US US802281A patent/US3042496A/en not_active Expired - Lifetime
-
1960
- 1960-03-19 DE DEM44720A patent/DE1185841B/de active Pending
- 1960-03-25 GB GB10679/60A patent/GB886778A/en not_active Expired
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3252762A (en) * | 1961-05-04 | 1966-05-24 | Miles Lab | Stabilized occult blood diagnostic |
| US3266868A (en) * | 1962-01-24 | 1966-08-16 | Miles Lab | Diagnostic composition and test indicator |
| US3278394A (en) * | 1963-07-22 | 1966-10-11 | Miles Lab | Method and composition for diagnosing glucose |
| DE1260827B (de) * | 1964-12-09 | 1968-02-08 | Miles Lab | Zubereitung zum Glukosenachweis in Harn |
| US4956300A (en) * | 1982-01-05 | 1990-09-11 | Helena Laboratories Corporation | Aid for determining the presence of occult blood, method of making the aid, and method of using the aid |
| EP0140322A3 (en) * | 1983-11-02 | 1986-07-16 | Miles Laboratories, Inc. | Polymer catalyst transducers and use thereof in test kits for analytical methods |
| US5702913A (en) * | 1983-12-21 | 1997-12-30 | Helena Laboratories Corporation | Chromgen-reagent test system |
| US5273888A (en) * | 1984-01-16 | 1993-12-28 | Helena Laboratories Corporation | Chemical test kit and method for determining the presence of blood in a specimen and for verifying the effectiveness of the chemicals |
| US4722894A (en) * | 1984-02-03 | 1988-02-02 | Kyowa Medex Co., Ltd. | Method for the determination of ceruloplasmin activity |
| US5081040A (en) * | 1987-06-29 | 1992-01-14 | Helena Laboratories Corporation | Composition and kit for testing for occult blood in human and animal excretions, fluids, or tissue matrixes |
| US5196167A (en) * | 1989-04-04 | 1993-03-23 | Helena Laboratories Corporation | Fecal occult blood test product with positive and negative controls |
| US5217874A (en) * | 1989-04-04 | 1993-06-08 | Helena Laboratories Corporation | Fecal occult blood test product with positive and negative controls |
Also Published As
| Publication number | Publication date |
|---|---|
| NL102893C (en)) | |
| DE1185841B (de) | 1965-01-21 |
| GB886778A (en) | 1962-01-10 |
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