FR2459226A1 - Nouveaux amides de tripeptides, utiles dans la determination quantitative d'enzymes proteolytiques - Google Patents
Nouveaux amides de tripeptides, utiles dans la determination quantitative d'enzymes proteolytiques Download PDFInfo
- Publication number
- FR2459226A1 FR2459226A1 FR8013218A FR8013218A FR2459226A1 FR 2459226 A1 FR2459226 A1 FR 2459226A1 FR 8013218 A FR8013218 A FR 8013218A FR 8013218 A FR8013218 A FR 8013218A FR 2459226 A1 FR2459226 A1 FR 2459226A1
- Authority
- FR
- France
- Prior art keywords
- nitroanilide
- arginyl
- prolyl
- alanyl
- carbobenzoxy
- 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.)
- Granted
Links
- 108091005804 Peptidases Proteins 0.000 title claims abstract description 7
- 102000035195 Peptidases Human genes 0.000 title claims abstract description 7
- 229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 title claims abstract description 6
- 150000001408 amides Chemical class 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 30
- -1 AMINO Chemical class 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 239000002253 acid Substances 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000006501 nitrophenyl group Chemical group 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 241000238876 Acari Species 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 description 21
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- 229960004072 thrombin Drugs 0.000 description 18
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- 238000006243 chemical reaction Methods 0.000 description 14
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- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
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- 238000003756 stirring Methods 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
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- STQMDRQJSNKUAW-UHFFFAOYSA-N 4-(phenylmethoxycarbonylamino)butanoic acid Chemical compound OC(=O)CCCNC(=O)OCC1=CC=CC=C1 STQMDRQJSNKUAW-UHFFFAOYSA-N 0.000 description 3
- AFJHAQCIJGPIFV-UHFFFAOYSA-N 4-[ethyl(phenylmethoxycarbonyl)amino]butanoic acid Chemical compound OC(=O)CCCN(CC)C(=O)OCC1=CC=CC=C1 AFJHAQCIJGPIFV-UHFFFAOYSA-N 0.000 description 3
- 239000004475 Arginine Substances 0.000 description 3
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- 229930182821 L-proline Natural products 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- KZNQNBZMBZJQJO-UHFFFAOYSA-N N-glycyl-L-proline Natural products NCC(=O)N1CCCC1C(O)=O KZNQNBZMBZJQJO-UHFFFAOYSA-N 0.000 description 3
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- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
- 235000009697 arginine Nutrition 0.000 description 3
- 238000004587 chromatography analysis Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
- KZNQNBZMBZJQJO-YFKPBYRVSA-N glyclproline Chemical compound NCC(=O)N1CCC[C@H]1C(O)=O KZNQNBZMBZJQJO-YFKPBYRVSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
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- 108060005987 Kallikrein Proteins 0.000 description 2
- 102000001399 Kallikrein Human genes 0.000 description 2
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- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 2
- 239000004472 Lysine Substances 0.000 description 2
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- 125000002947 alkylene group Chemical group 0.000 description 2
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- 239000000872 buffer Substances 0.000 description 2
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- 150000001412 amines Chemical class 0.000 description 1
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- 125000003277 amino group Chemical group 0.000 description 1
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- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/08—Tripeptides
- C07K5/0802—Tripeptides with the first amino acid being neutral
- C07K5/0804—Tripeptides with the first amino acid being neutral and aliphatic
- C07K5/0808—Tripeptides with the first amino acid being neutral and aliphatic the side chain containing 2 to 4 carbon atoms, e.g. Val, Ile, Leu
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- 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
- Y10S530/00—Chemistry: natural resins or derivatives; peptides or proteins; lignins or reaction products thereof
- Y10S530/802—Chromogenic or luminescent peptides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Genetics & Genomics (AREA)
- Biochemistry (AREA)
- Biophysics (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/048,409 US4221706A (en) | 1979-06-14 | 1979-06-14 | Chromogenic substrates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2459226A1 true FR2459226A1 (fr) | 1981-01-09 |
| FR2459226B1 FR2459226B1 (OSRAM) | 1984-02-03 |
Family
ID=21954411
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8013218A Granted FR2459226A1 (fr) | 1979-06-14 | 1980-06-13 | Nouveaux amides de tripeptides, utiles dans la determination quantitative d'enzymes proteolytiques |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US4221706A (OSRAM) |
| FR (1) | FR2459226A1 (OSRAM) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0018002B1 (de) * | 1979-04-24 | 1983-02-09 | Marcel Jozefonvicz | Neues Bestimmungsverfahren für Proteasen und Antiproteasen |
| JPS57501234A (OSRAM) * | 1980-08-25 | 1982-07-15 | ||
| US4406832A (en) * | 1981-09-03 | 1983-09-27 | Mallinckrodt, Inc. | Peptide-type substrates useful in the quantitative determination of endotoxin |
| US4510241A (en) * | 1981-09-03 | 1985-04-09 | Mallinckrodt, Inc. | Peptide-type substrates useful in the quantitative determination of endotoxin |
| JPS5856695A (ja) * | 1981-09-28 | 1983-04-04 | Nitto Boseki Co Ltd | 新規なトロンビン測定用基質 |
| US4448715A (en) * | 1981-11-02 | 1984-05-15 | University Of Miami | Tagged pyroglu-L-Phe-L-Arg derivatives, substrates and assays for kallikrein |
| US4473639A (en) * | 1982-09-15 | 1984-09-25 | Miles Laboratories, Inc. | Reagent strip test for antithrombin-III |
| DE3244030A1 (de) * | 1982-11-27 | 1984-05-30 | Behringwerke Ag, 3550 Marburg | Chromogene verbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| US4499186A (en) * | 1982-12-30 | 1985-02-12 | University Of Illinois, Board Of Trustees | Diagnosing autoimmune rheumatoid arthritis by measuring proteolytic activity of α2 -macroglobulin |
| DE3484912D1 (de) * | 1983-06-03 | 1991-09-19 | Pentapharm Ag | Peptidderivate und deren verwendung als substrate zur quantitativen bestimmung von enzymen. |
| JP2662998B2 (ja) * | 1988-10-21 | 1997-10-15 | 第一製薬株式会社 | プロリン含有ペプチド |
| US5391705A (en) * | 1991-03-15 | 1995-02-21 | Merrell Dow Pharmaceuticals Inc. | Polyfluorinated tripeptide thrombin inhibitors |
| US6069232A (en) * | 1995-10-02 | 2000-05-30 | Hoechst Marion Roussel, Inc. | Polyfluoroalkyl tryptophan tripeptide thrombin inhibitors |
| NL1006429C2 (nl) * | 1997-06-27 | 1998-12-29 | Univ Maastricht | Werkwijze voor het bepalen van het heparinegehalte. |
| US6297024B1 (en) | 1998-10-15 | 2001-10-02 | Cell Activation, Inc. | Methods for assessing complement activation |
| US6235494B1 (en) | 1999-02-08 | 2001-05-22 | The Scripps Research Institute | Substrates for assessing mannan-binding protein-associated serine protease activity and methods using the substrates |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3884896A (en) * | 1972-05-02 | 1975-05-20 | Bofors Ab | New substrates for diagnostic use, with high susceptibility to thrombin and other proteolytic |
| US4061625A (en) * | 1975-07-11 | 1977-12-06 | Ab Kabi | Novel chromogenic thrombin substrates |
| US4070245A (en) * | 1975-06-23 | 1978-01-24 | Pentapharm A.G. | Substrate for the quantitative determination of proteolytic enzymes |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3748044A (en) * | 1969-09-02 | 1973-07-24 | Abbott Lab | Digital chemical analysis apparatus |
-
1979
- 1979-06-14 US US06/048,409 patent/US4221706A/en not_active Expired - Lifetime
-
1980
- 1980-06-13 FR FR8013218A patent/FR2459226A1/fr active Granted
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3884896A (en) * | 1972-05-02 | 1975-05-20 | Bofors Ab | New substrates for diagnostic use, with high susceptibility to thrombin and other proteolytic |
| US4070245A (en) * | 1975-06-23 | 1978-01-24 | Pentapharm A.G. | Substrate for the quantitative determination of proteolytic enzymes |
| US4061625A (en) * | 1975-07-11 | 1977-12-06 | Ab Kabi | Novel chromogenic thrombin substrates |
Also Published As
| Publication number | Publication date |
|---|---|
| US4221706A (en) | 1980-09-09 |
| FR2459226B1 (OSRAM) | 1984-02-03 |
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| ST | Notification of lapse |