GB1565154A - Tetrapeptides as specific chromogenic enzyme substrates - Google Patents
Tetrapeptides as specific chromogenic enzyme substrates Download PDFInfo
- Publication number
- GB1565154A GB1565154A GB48288/77A GB4828877A GB1565154A GB 1565154 A GB1565154 A GB 1565154A GB 48288/77 A GB48288/77 A GB 48288/77A GB 4828877 A GB4828877 A GB 4828877A GB 1565154 A GB1565154 A GB 1565154A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substrate
- gly
- glu
- arg
- group
- 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
Links
- 239000000758 substrate Substances 0.000 title claims description 42
- 108090000790 Enzymes Proteins 0.000 title claims description 12
- 102000004190 Enzymes Human genes 0.000 title claims description 12
- 238000000034 method Methods 0.000 claims description 22
- -1 4-methoxy-2-naphthyl Chemical group 0.000 claims description 11
- 239000003593 chromogenic compound Substances 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
- 108010022999 Serine Proteases Proteins 0.000 claims description 5
- 102000012479 Serine Proteases Human genes 0.000 claims description 5
- 238000003556 assay Methods 0.000 claims description 5
- 230000009435 amidation Effects 0.000 claims description 4
- 238000007112 amidation reaction Methods 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000007850 fluorescent dye Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 230000007071 enzymatic hydrolysis Effects 0.000 claims description 2
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 claims description 2
- 125000004193 piperazinyl group Chemical group 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 150000001408 amides Chemical class 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 238000006467 substitution reaction Methods 0.000 claims 2
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 1
- 239000007844 bleaching agent Substances 0.000 claims 1
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 108010074860 Factor Xa Proteins 0.000 description 9
- 150000001413 amino acids Chemical group 0.000 description 9
- 108090000765 processed proteins & peptides Proteins 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 7
- 229940088598 enzyme Drugs 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 235000001014 amino acid Nutrition 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 101000939500 Homo sapiens UBX domain-containing protein 11 Proteins 0.000 description 5
- 102100029645 UBX domain-containing protein 11 Human genes 0.000 description 5
- 238000004587 chromatography analysis Methods 0.000 description 5
- 239000012847 fine chemical Substances 0.000 description 5
- 108010094028 Prothrombin Proteins 0.000 description 4
- 102100027378 Prothrombin Human genes 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- 229940039716 prothrombin Drugs 0.000 description 4
- 230000035945 sensitivity Effects 0.000 description 4
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000003776 cleavage reaction Methods 0.000 description 3
- 102000004196 processed proteins & peptides Human genes 0.000 description 3
- 230000007017 scission Effects 0.000 description 3
- ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 2
- HYOUYNIRTMZPLG-UHFFFAOYSA-N 1-hydroxyethyl(dimethyl)azanium;chloride Chemical compound [Cl-].CC(O)[NH+](C)C HYOUYNIRTMZPLG-UHFFFAOYSA-N 0.000 description 2
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 108010014173 Factor X Proteins 0.000 description 2
- 229920002684 Sepharose Polymers 0.000 description 2
- 108090000190 Thrombin Proteins 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 210000004369 blood Anatomy 0.000 description 2
- 239000008280 blood Substances 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000006225 natural substrate Substances 0.000 description 2
- 239000011877 solvent mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229960004072 thrombin Drugs 0.000 description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 2
- KQJTXYQXRHCWKW-PJSBSAQXSA-N (4s)-4-[[(2s,3s)-2-benzamido-3-methylpentanoyl]amino]-5-[[2-[[(2s)-5-(diaminomethylideneamino)-1-(4-nitroanilino)-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-5-oxopentanoic acid;hydrochloride Chemical compound Cl.N([C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCC(O)=O)C(=O)NCC(=O)N[C@@H](CCCN=C(N)N)C(=O)NC=1C=CC(=CC=1)[N+]([O-])=O)C(=O)C1=CC=CC=C1 KQJTXYQXRHCWKW-PJSBSAQXSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- FOYWCEUVVIHJKD-UHFFFAOYSA-N 2-methyl-5-(1h-pyrazol-5-yl)pyridine Chemical compound C1=NC(C)=CC=C1C1=CC=NN1 FOYWCEUVVIHJKD-UHFFFAOYSA-N 0.000 description 1
- TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
- 239000004475 Arginine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- HTTJABKRGRZYRN-UHFFFAOYSA-N Heparin Chemical compound OC1C(NC(=O)C)C(O)OC(COS(O)(=O)=O)C1OC1C(OS(O)(=O)=O)C(O)C(OC2C(C(OS(O)(=O)=O)C(OC3C(C(O)C(O)C(O3)C(O)=O)OS(O)(=O)=O)C(CO)O2)NS(O)(=O)=O)C(C(O)=O)O1 HTTJABKRGRZYRN-UHFFFAOYSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 102000035195 Peptidases Human genes 0.000 description 1
- 241001620634 Roger Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PPWHTZKZQNXVAE-UHFFFAOYSA-N Tetracaine hydrochloride Chemical compound Cl.CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 PPWHTZKZQNXVAE-UHFFFAOYSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000003708 ampul Substances 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 108010031969 benzoyl-Ile-Glu-Gly-Arg-p-nitroanilide Proteins 0.000 description 1
- 125000001589 carboacyl group Chemical group 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 230000015271 coagulation Effects 0.000 description 1
- 238000005345 coagulation Methods 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000006639 cyclohexyl carbonyl group Chemical group 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
- 229920000669 heparin Polymers 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- VBEGHXKAFSLLGE-UHFFFAOYSA-N n-phenylnitramide Chemical compound [O-][N+](=O)NC1=CC=CC=C1 VBEGHXKAFSLLGE-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000006501 nitrophenyl group Chemical group 0.000 description 1
- 210000002381 plasma Anatomy 0.000 description 1
- XUWVIABDWDTJRZ-UHFFFAOYSA-N propan-2-ylazanide Chemical compound CC(C)[NH-] XUWVIABDWDTJRZ-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
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
- C07K5/10—Tetrapeptides
- C07K5/1002—Tetrapeptides with the first amino acid being neutral
- C07K5/1005—Tetrapeptides with the first amino acid being neutral and aliphatic
- C07K5/101—Tetrapeptides 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
- 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
- C12Q1/56—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving blood clotting factors, e.g. involving thrombin, thromboplastin, fibrinogen
-
- 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
- C12Q2337/00—N-linked chromogens for determinations of peptidases and proteinases
- C12Q2337/10—Anilides
- C12Q2337/12—Para-Nitroanilides p-NA
-
- 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
-
- 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
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/28—Bound to a nonpeptide drug, nonpeptide label, nonpeptide carrier, or a nonpeptide resin
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Molecular Biology (AREA)
- General Health & Medical Sciences (AREA)
- Biophysics (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Neurosurgery (AREA)
- Biotechnology (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Hematology (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Peptides Or Proteins (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Cosmetics (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE7613463A SE437153B (sv) | 1976-12-01 | 1976-12-01 | Specifika kromogena enzymsubstrat for serinproteaser |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1565154A true GB1565154A (en) | 1980-04-16 |
Family
ID=20329625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB48288/77A Expired GB1565154A (en) | 1976-12-01 | 1977-11-21 | Tetrapeptides as specific chromogenic enzyme substrates |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US4207232A (enExample) |
| JP (1) | JPS5369693A (enExample) |
| AT (1) | AT358203B (enExample) |
| AU (1) | AU514768B2 (enExample) |
| BE (1) | BE861295A (enExample) |
| CA (1) | CA1098428A (enExample) |
| CH (1) | CH637627A5 (enExample) |
| DD (1) | DD136896A5 (enExample) |
| DE (2) | DE2760116C2 (enExample) |
| DK (1) | DK155333C (enExample) |
| ES (1) | ES464117A1 (enExample) |
| FI (1) | FI773242A7 (enExample) |
| FR (1) | FR2372798A1 (enExample) |
| GB (1) | GB1565154A (enExample) |
| HU (1) | HU176983B (enExample) |
| IL (1) | IL53187A (enExample) |
| IT (1) | IT1092154B (enExample) |
| NL (1) | NL178600C (enExample) |
| NO (1) | NO774092L (enExample) |
| PL (2) | PL109588B1 (enExample) |
| SE (1) | SE437153B (enExample) |
| SU (1) | SU736889A3 (enExample) |
| ZA (1) | ZA776460B (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016800A4 (en) * | 1978-08-03 | 1981-01-08 | American Hospital Supply Corp | Determination of proteolytic enzymes in biological fluids and fluorogenic substrates. |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7801373L (sv) * | 1978-02-07 | 1979-08-08 | Kabi Ab | Lett spjelkbara substrat for kvantifiering av proteaser |
| US4409140A (en) * | 1979-04-23 | 1983-10-11 | Smith Robert E | Substrates and method for determining enzymes |
| CA1161432A (en) * | 1980-02-12 | 1984-01-31 | Lars G. Svendsen | Tripeptide derivatives and their application in assaying enzymes |
| EP0046742B1 (en) * | 1980-08-25 | 1984-06-27 | KabiVitrum AB | Peptide substrates for determination of protease activity |
| US4510241A (en) * | 1981-09-03 | 1985-04-09 | Mallinckrodt, Inc. | Peptide-type substrates useful in the quantitative determination of endotoxin |
| US4406832A (en) * | 1981-09-03 | 1983-09-27 | Mallinckrodt, Inc. | Peptide-type substrates useful in the quantitative determination of endotoxin |
| US4448715A (en) * | 1981-11-02 | 1984-05-15 | University Of Miami | Tagged pyroglu-L-Phe-L-Arg derivatives, substrates and assays for kallikrein |
| DE3211254A1 (de) * | 1982-03-26 | 1983-09-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren zum nachweis des vorliegens einer allergie und zum spezifischen nachweis des fuer die allergie verantwortlichen allergens |
| JPH04501460A (ja) | 1988-09-30 | 1992-03-12 | ザ ユニバーシティ オブ バーモント アンド ステイト アグリカルチュラル カレッジ | 触媒活性セリンプロテアーゼに関する免疫検定法 |
| WO1995004281A1 (en) * | 1993-07-27 | 1995-02-09 | THE UNITED STATES GOVERNMENT, represented by THE ADMINISTRATOR OF THE NATIONAL AERONAUTICS AND SPACE ADMINISTRATION | Quantitative method of measuring cancer cell urokinase and metastatic potential |
| 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 |
| US20050159362A1 (en) * | 2003-04-22 | 2005-07-21 | Sircar Jagadish C. | Mediators of reverse cholesterol transport for the treatment of hypercholesterolemia |
| BRPI0409609A (pt) * | 2003-04-22 | 2006-04-18 | Avanir Pharmaceuticals | mediadores do transporte reverso de colesterol para o tratamento da hipercolesterolemia |
| US8329168B2 (en) | 2005-11-15 | 2012-12-11 | The Children's Hospital Of Philadelphia | Compositions and methods for modulating hemostasis |
| WO2012154272A1 (en) * | 2011-02-25 | 2012-11-15 | Wellstat Diagnostics, Llc | Assays for detecting enzymatic activity |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2527932C2 (de) * | 1974-07-02 | 1983-04-21 | Pentapharm AG, 4052 Basel | Säureadditionssalze von Tripeptidderivaten und deren Verwendung als Substrate zur Bestimmung von Plasmakallikrein |
| SE407058B (sv) * | 1974-12-05 | 1979-03-12 | Kabi Ab | Nya kromogena enzymsubstrat for serinproteaser |
| CH622286A5 (enExample) * | 1975-06-23 | 1981-03-31 | Pentapharm Ag | |
| US4137225A (en) * | 1975-07-11 | 1979-01-30 | Ab Kabi | Novel chromogenic enzyme substrates |
| US4061625A (en) * | 1975-07-11 | 1977-12-06 | Ab Kabi | Novel chromogenic thrombin substrates |
-
1976
- 1976-12-01 SE SE7613463A patent/SE437153B/xx unknown
-
1977
- 1977-10-21 IL IL53187A patent/IL53187A/xx unknown
- 1977-10-27 NL NLAANVRAGE7711791,A patent/NL178600C/xx not_active IP Right Cessation
- 1977-10-31 ZA ZA00776460A patent/ZA776460B/xx unknown
- 1977-10-31 FI FI773242A patent/FI773242A7/fi not_active Application Discontinuation
- 1977-11-14 ES ES464117A patent/ES464117A1/es not_active Expired
- 1977-11-14 IT IT51808/77A patent/IT1092154B/it active
- 1977-11-16 US US05/852,006 patent/US4207232A/en not_active Expired - Lifetime
- 1977-11-18 AU AU30771/77A patent/AU514768B2/en not_active Expired
- 1977-11-21 GB GB48288/77A patent/GB1565154A/en not_active Expired
- 1977-11-29 PL PL1977202501A patent/PL109588B1/pl unknown
- 1977-11-29 DD DD77202299A patent/DD136896A5/xx unknown
- 1977-11-29 FR FR7735870A patent/FR2372798A1/fr active Granted
- 1977-11-29 PL PL1977216410A patent/PL110803B1/pl unknown
- 1977-11-29 BE BE183005A patent/BE861295A/xx not_active IP Right Cessation
- 1977-11-29 CH CH1461877A patent/CH637627A5/de not_active IP Right Cessation
- 1977-11-30 SU SU772548501A patent/SU736889A3/ru active
- 1977-11-30 NO NO774092A patent/NO774092L/no unknown
- 1977-11-30 CA CA292,077A patent/CA1098428A/en not_active Expired
- 1977-12-01 JP JP14334077A patent/JPS5369693A/ja active Granted
- 1977-12-01 AT AT859677A patent/AT358203B/de not_active IP Right Cessation
- 1977-12-01 DE DE2760116A patent/DE2760116C2/de not_active Expired
- 1977-12-01 HU HU77KA1497A patent/HU176983B/hu unknown
- 1977-12-01 DE DE2753653A patent/DE2753653C2/de not_active Expired
- 1977-12-01 DK DK535377A patent/DK155333C/da not_active IP Right Cessation
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1979
- 1979-10-22 US US06/086,970 patent/US4276375A/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0016800A4 (en) * | 1978-08-03 | 1981-01-08 | American Hospital Supply Corp | Determination of proteolytic enzymes in biological fluids and fluorogenic substrates. |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19961121 |