US3721607A - Reagent composition and process for the determination of glucose - Google Patents
Reagent composition and process for the determination of glucose Download PDFInfo
- Publication number
- US3721607A US3721607A US00170949A US3721607DA US3721607A US 3721607 A US3721607 A US 3721607A US 00170949 A US00170949 A US 00170949A US 3721607D A US3721607D A US 3721607DA US 3721607 A US3721607 A US 3721607A
- Authority
- US
- United States
- Prior art keywords
- composition
- azide
- liter
- glucose
- azino
- 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 abstract description 51
- 239000003153 chemical reaction reagent Substances 0.000 title claims abstract description 46
- 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 title claims abstract description 23
- 239000008103 glucose Substances 0.000 title claims abstract description 23
- 238000000034 method Methods 0.000 title claims description 11
- 230000008569 process Effects 0.000 title description 4
- 102000003992 Peroxidases Human genes 0.000 claims abstract description 29
- 108040007629 peroxidase activity proteins Proteins 0.000 claims abstract description 28
- 150000001540 azides Chemical class 0.000 claims abstract description 27
- 108010015776 Glucose oxidase Proteins 0.000 claims abstract description 24
- 239000004366 Glucose oxidase Substances 0.000 claims abstract description 22
- 229940116332 glucose oxidase Drugs 0.000 claims abstract description 22
- 235000019420 glucose oxidase Nutrition 0.000 claims abstract description 22
- 239000000872 buffer Substances 0.000 claims abstract description 12
- 230000002255 enzymatic effect Effects 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 22
- 239000007787 solid Substances 0.000 claims description 10
- 239000008363 phosphate buffer Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- JRBJSXQPQWSCCF-UHFFFAOYSA-N 3,3'-Dimethoxybenzidine Chemical compound C1=C(N)C(OC)=CC(C=2C=C(OC)C(N)=CC=2)=C1 JRBJSXQPQWSCCF-UHFFFAOYSA-N 0.000 claims description 6
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical group [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- -1 alkali metal azide Chemical class 0.000 claims description 3
- 239000000463 material Substances 0.000 claims description 3
- 150000002978 peroxides Chemical class 0.000 claims description 2
- ZTOJFFHGPLIVKC-YAFCTCPESA-N (2e)-3-ethyl-2-[(z)-(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound S\1C2=CC(S(O)(=O)=O)=CC=C2N(CC)C/1=N/N=C1/SC2=CC(S(O)(=O)=O)=CC=C2N1CC ZTOJFFHGPLIVKC-YAFCTCPESA-N 0.000 description 12
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZTOJFFHGPLIVKC-UHFFFAOYSA-N 3-ethyl-2-[(3-ethyl-6-sulfo-1,3-benzothiazol-2-ylidene)hydrazinylidene]-1,3-benzothiazole-6-sulfonic acid Chemical compound S1C2=CC(S(O)(=O)=O)=CC=C2N(CC)C1=NN=C1SC2=CC(S(O)(=O)=O)=CC=C2N1CC ZTOJFFHGPLIVKC-UHFFFAOYSA-N 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 108090000790 Enzymes Proteins 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 229940088598 enzyme Drugs 0.000 description 3
- 230000000087 stabilizing effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000012928 buffer substance Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000008247 solid mixture Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 239000012085 test solution Substances 0.000 description 2
- DEENCNYPFDWDSA-UHFFFAOYSA-N 2-ethyl-1,3-benzothiazole-6-sulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2SC(CC)=NC2=C1 DEENCNYPFDWDSA-UHFFFAOYSA-N 0.000 description 1
- PCDWFBFHIIKIPM-UHFFFAOYSA-N 3-ethyl-2h-1,3-benzothiazole-2-sulfonic acid Chemical compound C1=CC=C2N(CC)C(S(O)(=O)=O)SC2=C1 PCDWFBFHIIKIPM-UHFFFAOYSA-N 0.000 description 1
- 101100264195 Caenorhabditis elegans app-1 gene Proteins 0.000 description 1
- RGHNJXZEOKUKBD-UHFFFAOYSA-N D-gluconic acid Natural products OCC(O)C(O)C(O)C(O)C(O)=O RGHNJXZEOKUKBD-UHFFFAOYSA-N 0.000 description 1
- RGHNJXZEOKUKBD-SQOUGZDYSA-N Gluconic acid Natural products OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- COQLPRJCUIATTQ-UHFFFAOYSA-N Uranyl acetate Chemical compound O.O.O=[U]=O.CC(O)=O.CC(O)=O COQLPRJCUIATTQ-UHFFFAOYSA-N 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000003544 deproteinization Effects 0.000 description 1
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
- 239000000174 gluconic acid Substances 0.000 description 1
- 235000012208 gluconic acid Nutrition 0.000 description 1
- 108010046301 glucose peroxidase Proteins 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
-
- 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
-
- 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
- C12Q2326/00—Chromogens for determinations of oxidoreductase enzymes
- C12Q2326/30—2,2'-Azinobis (3-ethylbenzothiazoline-6-sulfonic acid), i.e. ABTS
Definitions
- ABSTRACT Compositions comprising glucose oxidase, peroxidase, a chromogen, a buffer, an azide, and 2,2'-azino-di-(3- ethylbenzothiazoline-6-sulfonic acid) provide remarkably stable test reagents for the enzymatic determination of glucose.
- the present invention is concerned with a reagent composition and process for the enzymatic determination of glucose by use of the enzymes glucose oxidase and peroxidase.
- test reagents In the case of test reagents, it isgenerally desired that these contain all the necessary reagents in a pre-mixed state in order, on the one hand, to reduce as much as possible the expenditure of labor in carrying out large numbers of routine investigations and, on the other hand, to prevent errors arising in the mixing of several components.
- these reagent mixtures should be in solid form but should be easily dissolved in water at the time of use and then remain stable in aqueous solution for as long as possible in order to avoid having to prepare new solutions continuously.
- the present invention provides a reagent composition for the determination of glucose, which comprises glucose oxidase, peroxidase, a chromogen and a buffer, together with an azide and 2,2-azino-di- (3-ethyl-benzothiazoline--sulphonic acid), hereinafter abbreviated as ABTS.
- ABTS can be used simultaneously as stabilizer and as the chromogen.
- it is expediently present in the reagent in an amount of 0.25 to 1.5 grams/liter, preferably of about 0.5 grams/liter, of aqueous solution or, in the case of a solid mixture intended for the preparation of one liter of solution, is present therein in an equivalent amount.
- the enzymes GOD and POD are expediently present in the reagent according to the present invention in amounts such that the mutarotation of the glucose and not the enzymes determines the rate of the reaction. This requirement is fulfilled by GOD concentrations of 2.5 to 15 X- 10 U/liter (i.e., units per liter) and of POD concentrations of 30 to I000 U/liter.
- the buffer substance used should produce, in aqueous solution, a pH value of between 6.2 and 7.5 and preferably of between 6.5 and 7.2. All buffer substances can be used which do not inhibit the reaction, a phosphate buffer (pH 7.0) being preferably used. However, tris buffer is unsuitable.
- a preferred reagent according to the present invention for the determination of blood sugar comprises:
- An especially preferred reagent according to the present invention comprises:
- a further preferred reagent according to the present invention comprises:
- the reagent according to the present invention can be in the form of an aqueous solution of. the components.
- This aqueous solution has a good stability and can, depending upon the composition and especially upon the chromogen used, be stored ready for use for several weeks.
- chromogen and enzymes had to be prepared in different solutions and, on the other hand, these solutions only had a limited period of use.
- the reagents according to the present in vention have several advantages, especially an outstanding stability. Their storage at refrigerator temperature is more than one year. Furthermore, solid mixtures according to the invention, e.g., in the form of powders or possibly of tablets, have the advantage of being very easily soluble in water.
- a further surprising advantage of the reagent according to the present invention is that the amount of POD can be substantially reduced from the previously used amount of about 250 U/liter to about 30 U/liter. Nevertheless, POD does not become the velocitydetermining reaction component. This enables a substantial saving of POD.
- a reagent solution was prepared by dissolving 1.5 grams of the above solid powder mixture in 100 ml. water. This solution contained all reagents necessary for the determination of the glucose and, when stored at +4C. can be used for at least 8 weeks.
- the reagent solution were mixed with 0.2 ml. of the glucose-containing solution (obtained, for example, by the deproteinization of blood or serum with a known deproteinisation agent, such as perchloric acid or uranyl acetate).
- a known deproteinisation agent such as perchloric acid or uranyl acetate.
- the mixture was left to stand for 25 minutes at ambient temperature and then the intensity of the colored material formed was measured. This was proportional to the glucose concentration present in the test solution.
- a standard sample of known glucose concentration which was determined at the same time, the desired glucose concentration of the test solution can easily be calculated.
- EXAMPLE 2 Stability of the peroxidase
- the reagent solution described in Example 1 was compared with a reagent solution prepared in the same way but which did not contain ABTS, by measuring the activity of the peroxidase at different times.
- the following Table shows the results obtained.
- Reagent composition for the enzymatic determination of glucose which composition comprises glucose oxidase, peroxidase, a chromogen, a buffer, an azide, and 2,2'-azino-di-(3-ethyl-benzothiazoline-o-sulfonic acid).
- composition as claimed in claim 1 which comprises:
- composition as claimed in claim 5 wherein said composition is in the form of an aqueous solution.
- composition as claimed in claim 1 which comprises:
- composition as claimed in claim 1 which comprises:
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)
- Analytical Chemistry (AREA)
- General Engineering & Computer Science (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Biophysics (AREA)
- Physics & Mathematics (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19702042828 DE2042828C (de) | 1970-08-28 | Reagens zur Bestimmung der Glucose |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3721607A true US3721607A (en) | 1973-03-20 |
Family
ID=5781013
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US00170949A Expired - Lifetime US3721607A (en) | 1970-08-28 | 1971-08-11 | Reagent composition and process for the determination of glucose |
Country Status (15)
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168205A (en) * | 1976-06-09 | 1979-09-18 | Boehringer Mannheim Gmbh | Method for the determination of substrates or enzyme activities |
| US4250254A (en) * | 1978-09-11 | 1981-02-10 | Modrovich Ivan Endre | Stabilized liquid enzyme and coenzyme compositions |
| US4271264A (en) * | 1976-09-13 | 1981-06-02 | Modrovich Ivan Endre | Stabilized liquid enzyme and coenzyme compositions |
| US4298688A (en) * | 1978-07-25 | 1981-11-03 | Veb Arzneimittelwerk Dresden | Test device for the detection and determination of glucose |
| US4409328A (en) * | 1980-09-19 | 1983-10-11 | Boehringer Mannheim Gmbh | Method and reagent for the determination of glycerol |
| WO1987007718A1 (en) * | 1986-06-02 | 1987-12-17 | Lawrence Paul J | Fecal occult blood test reagents and methods |
| US4810633A (en) * | 1984-06-04 | 1989-03-07 | Miles Inc. | Enzymatic ethanol test |
| US4818702A (en) * | 1986-06-02 | 1989-04-04 | Litmus Concepts, Inc. | Fecal occult blood test reagent |
| US4820646A (en) * | 1984-12-11 | 1989-04-11 | Litmus Concepts, Inc. | Fecal occult blood test method |
| US4937197A (en) * | 1984-12-11 | 1990-06-26 | Litmus Concepts, Inc. | Fecal occult blood test method |
| US4939097A (en) * | 1986-06-02 | 1990-07-03 | Litmus Concepts, Inc. | Fecal occult blood test methods |
| US5053342A (en) * | 1987-12-24 | 1991-10-01 | Litmus Concepts, Inc. | Fecal occult blood test reagents |
| US5068197A (en) * | 1984-12-11 | 1991-11-26 | Litmus Concepts, Inc. | Fecal occult blood test methods |
| US6586195B1 (en) | 2001-11-19 | 2003-07-01 | R.E. Davis Chemical Corporation | Method of detecting sugars |
| US20030138867A1 (en) * | 2000-11-08 | 2003-07-24 | Copeland James C. | Medium composition, method and device for selectively enhancing the isolation of anaerobic microorganisms contained in a mixed sample with facultative microorganisms |
| WO2006096691A1 (en) * | 2005-03-04 | 2006-09-14 | Bergen Teknologioverforing As | Determination of folate in samples of serum or plasma |
| US8691520B2 (en) | 2011-06-09 | 2014-04-08 | Clarkson University | Reagentless ceria-based colorimetric sensor |
| US8969085B2 (en) | 2011-06-09 | 2015-03-03 | Clarkson University | Portable nanoparticle based assay for rapid detection of food antioxidants (NanoCerac) |
-
1971
- 1971-06-29 AT AT563271A patent/AT308049B/de not_active IP Right Cessation
- 1971-07-16 IL IL37324A patent/IL37324A/xx unknown
- 1971-07-21 DK DK359271A patent/DK134796C/da active
- 1971-07-29 CA CA119,471A patent/CA952416A/en not_active Expired
- 1971-08-11 US US00170949A patent/US3721607A/en not_active Expired - Lifetime
- 1971-08-11 IT IT27438/71A patent/IT941678B/it active
- 1971-08-23 SU SU1696900A patent/SU513645A3/ru active
- 1971-08-24 GB GB39579/71A patent/GB1300338A/en not_active Expired
- 1971-08-24 JP JP6467371A patent/JPS5335479B1/ja active Pending
- 1971-08-25 NL NL717111668A patent/NL154832B/xx not_active IP Right Cessation
- 1971-08-25 CH CH1242771A patent/CH560900A5/xx not_active IP Right Cessation
- 1971-08-25 SE SE10768/71A patent/SE368872B/xx unknown
- 1971-08-25 CH CH1242871A patent/CH560901A5/xx not_active IP Right Cessation
- 1971-08-27 FI FI712405A patent/FI51638C/fi active
- 1971-08-27 FR FR7131226A patent/FR2131198A5/fr not_active Expired
- 1971-08-27 HU HUBO1316A patent/HU163669B/hu unknown
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4168205A (en) * | 1976-06-09 | 1979-09-18 | Boehringer Mannheim Gmbh | Method for the determination of substrates or enzyme activities |
| US4271264A (en) * | 1976-09-13 | 1981-06-02 | Modrovich Ivan Endre | Stabilized liquid enzyme and coenzyme compositions |
| US4298688A (en) * | 1978-07-25 | 1981-11-03 | Veb Arzneimittelwerk Dresden | Test device for the detection and determination of glucose |
| US4250254A (en) * | 1978-09-11 | 1981-02-10 | Modrovich Ivan Endre | Stabilized liquid enzyme and coenzyme compositions |
| US4409328A (en) * | 1980-09-19 | 1983-10-11 | Boehringer Mannheim Gmbh | Method and reagent for the determination of glycerol |
| US4810633A (en) * | 1984-06-04 | 1989-03-07 | Miles Inc. | Enzymatic ethanol test |
| US4820646A (en) * | 1984-12-11 | 1989-04-11 | Litmus Concepts, Inc. | Fecal occult blood test method |
| US4937197A (en) * | 1984-12-11 | 1990-06-26 | Litmus Concepts, Inc. | Fecal occult blood test method |
| US5068197A (en) * | 1984-12-11 | 1991-11-26 | Litmus Concepts, Inc. | Fecal occult blood test methods |
| US4818702A (en) * | 1986-06-02 | 1989-04-04 | Litmus Concepts, Inc. | Fecal occult blood test reagent |
| WO1987007718A1 (en) * | 1986-06-02 | 1987-12-17 | Lawrence Paul J | Fecal occult blood test reagents and methods |
| US4939097A (en) * | 1986-06-02 | 1990-07-03 | Litmus Concepts, Inc. | Fecal occult blood test methods |
| US5053342A (en) * | 1987-12-24 | 1991-10-01 | Litmus Concepts, Inc. | Fecal occult blood test reagents |
| US20030138867A1 (en) * | 2000-11-08 | 2003-07-24 | Copeland James C. | Medium composition, method and device for selectively enhancing the isolation of anaerobic microorganisms contained in a mixed sample with facultative microorganisms |
| US7374905B2 (en) * | 2000-11-08 | 2008-05-20 | Oxyrase, Inc. | Medium composition, method and device for selectively enhancing the isolation of anaerobic microorganisms contained in a mixed sample with facultative microorganisms |
| US6586195B1 (en) | 2001-11-19 | 2003-07-01 | R.E. Davis Chemical Corporation | Method of detecting sugars |
| WO2006096691A1 (en) * | 2005-03-04 | 2006-09-14 | Bergen Teknologioverforing As | Determination of folate in samples of serum or plasma |
| US8691520B2 (en) | 2011-06-09 | 2014-04-08 | Clarkson University | Reagentless ceria-based colorimetric sensor |
| US8969085B2 (en) | 2011-06-09 | 2015-03-03 | Clarkson University | Portable nanoparticle based assay for rapid detection of food antioxidants (NanoCerac) |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7111668A (enrdf_load_stackoverflow) | 1972-03-01 |
| FI51638B (enrdf_load_stackoverflow) | 1976-11-01 |
| CH560901A5 (enrdf_load_stackoverflow) | 1975-04-15 |
| DE2042828A1 (de) | 1972-03-09 |
| GB1300338A (en) | 1972-12-20 |
| SE368872B (enrdf_load_stackoverflow) | 1974-07-22 |
| IL37324A (en) | 1974-05-16 |
| CA952416A (en) | 1974-08-06 |
| DE2042828B2 (de) | 1972-07-20 |
| DK134796C (da) | 1977-07-25 |
| AT308049B (de) | 1973-06-25 |
| HU163669B (enrdf_load_stackoverflow) | 1973-10-27 |
| FI51638C (fi) | 1977-02-10 |
| FR2131198A5 (enrdf_load_stackoverflow) | 1972-11-10 |
| IT941678B (it) | 1973-03-10 |
| JPS5335479B1 (enrdf_load_stackoverflow) | 1978-09-27 |
| IL37324A0 (en) | 1971-10-20 |
| DK134796B (da) | 1977-01-17 |
| NL154832B (nl) | 1977-10-17 |
| CH560900A5 (enrdf_load_stackoverflow) | 1975-04-15 |
| SU513645A3 (ru) | 1976-05-05 |
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