JP4312953B2 - 生物学的物質のリン酸化活性を検出および／または測定するための均質方法およびその方法の実施に使用されるキット - Google Patents
生物学的物質のリン酸化活性を検出および／または測定するための均質方法およびその方法の実施に使用されるキット Download PDFInfo
- Publication number
- JP4312953B2 JP4312953B2 JP2000513143A JP2000513143A JP4312953B2 JP 4312953 B2 JP4312953 B2 JP 4312953B2 JP 2000513143 A JP2000513143 A JP 2000513143A JP 2000513143 A JP2000513143 A JP 2000513143A JP 4312953 B2 JP4312953 B2 JP 4312953B2
- Authority
- JP
- Japan
- Prior art keywords
- luminescent
- molecule
- bound
- fluorescent
- specific receptor
- 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 - Fee Related
Links
- 238000000034 method Methods 0.000 title claims abstract description 42
- 230000000694 effects Effects 0.000 title claims description 39
- 238000006366 phosphorylation reaction Methods 0.000 title claims description 35
- 230000026731 phosphorylation Effects 0.000 title claims description 34
- 239000000126 substance Substances 0.000 title claims description 21
- 239000000758 substrate Substances 0.000 claims abstract description 27
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims abstract description 8
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000004473 Threonine Substances 0.000 claims abstract description 8
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims abstract description 7
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000012620 biological material Substances 0.000 claims abstract 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 49
- 150000001875 compounds Chemical class 0.000 claims description 35
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 30
- 239000003550 marker Substances 0.000 claims description 28
- 108020003175 receptors Proteins 0.000 claims description 24
- 229920001184 polypeptide Polymers 0.000 claims description 19
- -1 rare earth ion Chemical class 0.000 claims description 14
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 14
- GWQVMPWSEVRGPY-UHFFFAOYSA-N europium cryptate Chemical compound [Eu+3].N=1C2=CC=CC=1CN(CC=1N=C(C=CC=1)C=1N=C(C3)C=CC=1)CC(N=1)=CC(C(=O)NCCN)=CC=1C(N=1)=CC(C(=O)NCCN)=CC=1CN3CC1=CC=CC2=N1 GWQVMPWSEVRGPY-UHFFFAOYSA-N 0.000 claims description 11
- 229910052771 Terbium Inorganic materials 0.000 claims description 9
- 238000004020 luminiscence type Methods 0.000 claims description 9
- 150000002678 macrocyclic compounds Chemical class 0.000 claims description 9
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 9
- 108010053210 Phycocyanin Proteins 0.000 claims description 8
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims description 7
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims description 7
- 238000001514 detection method Methods 0.000 claims description 7
- 108010004729 Phycoerythrin Proteins 0.000 claims description 6
- 239000007983 Tris buffer Substances 0.000 claims description 6
- 108010004469 allophycocyanin Proteins 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007850 fluorescent dye Substances 0.000 claims description 6
- 150000002910 rare earth metals Chemical group 0.000 claims description 6
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 6
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical compound N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 5
- 230000003993 interaction Effects 0.000 claims description 5
- 238000005259 measurement Methods 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 239000013522 chelant Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 150000002430 hydrocarbons Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 229910052693 Europium Inorganic materials 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 3
- 230000002285 radioactive effect Effects 0.000 claims description 3
- XEROZRUZBZDEDD-UHFFFAOYSA-N C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=CC=C1C1=CC=CC=C1 Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.C1=CC=CC=C1C1=CC=CC=C1 XEROZRUZBZDEDD-UHFFFAOYSA-N 0.000 claims description 2
- 229910052692 Dysprosium Inorganic materials 0.000 claims description 2
- 229910052779 Neodymium Inorganic materials 0.000 claims description 2
- 229910052772 Samarium Inorganic materials 0.000 claims description 2
- 108010067010 allophycocyanin B Proteins 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- UMVFZJRCHRLAGC-UHFFFAOYSA-N anthracene-1-carboxamide Chemical compound C1=CC=C2C=C3C(C(=O)N)=CC=CC3=CC2=C1 UMVFZJRCHRLAGC-UHFFFAOYSA-N 0.000 claims description 2
- KBQHZAAAGSGFKK-UHFFFAOYSA-N dysprosium atom Chemical compound [Dy] KBQHZAAAGSGFKK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 claims description 2
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 claims description 2
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 claims description 2
- MVVRNAUFPUDQIB-UHFFFAOYSA-N 1-isoquinolin-1-ylisoquinoline Chemical compound C1=CC=C2C(C=3C4=CC=CC=C4C=CN=3)=NC=CC2=C1 MVVRNAUFPUDQIB-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 238000002372 labelling Methods 0.000 claims 1
- 108010004335 phycoerythrocyanin Proteins 0.000 claims 1
- 230000009870 specific binding Effects 0.000 claims 1
- 230000000865 phosphorylative effect Effects 0.000 abstract 1
- 102000005962 receptors Human genes 0.000 description 23
- 239000008363 phosphate buffer Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 108010026479 Src peptide Proteins 0.000 description 9
- 239000000863 peptide conjugate Substances 0.000 description 7
- JWDFQMWEFLOOED-UHFFFAOYSA-N (2,5-dioxopyrrolidin-1-yl) 3-(pyridin-2-yldisulfanyl)propanoate Chemical compound O=C1CCC(=O)N1OC(=O)CCSSC1=CC=CC=N1 JWDFQMWEFLOOED-UHFFFAOYSA-N 0.000 description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 230000004913 activation Effects 0.000 description 6
- 239000003456 ion exchange resin Substances 0.000 description 6
- 229920003303 ion-exchange polymer Polymers 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 102000004190 Enzymes Human genes 0.000 description 5
- 108090000790 Enzymes Proteins 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000002947 alkylene group Chemical group 0.000 description 4
- 125000000732 arylene group Chemical group 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000004587 chromatography analysis Methods 0.000 description 4
- 125000002993 cycloalkylene group Chemical group 0.000 description 4
- 238000009792 diffusion process Methods 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000562 conjugate Substances 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 230000007717 exclusion Effects 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 239000000700 radioactive tracer Substances 0.000 description 3
- VUFNRPJNRFOTGK-UHFFFAOYSA-M sodium;1-[4-[(2,5-dioxopyrrol-1-yl)methyl]cyclohexanecarbonyl]oxy-2,5-dioxopyrrolidine-3-sulfonate Chemical compound [Na+].O=C1C(S(=O)(=O)[O-])CC(=O)N1OC(=O)C1CCC(CN2C(C=CC2=O)=O)CC1 VUFNRPJNRFOTGK-UHFFFAOYSA-M 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 125000006850 spacer group Chemical group 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- YBJHBAHKTGYVGT-ZKWXMUAHSA-N (+)-Biotin Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 YBJHBAHKTGYVGT-ZKWXMUAHSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- HKOAFLAGUQUJQG-UHFFFAOYSA-N 2-pyrimidin-2-ylpyrimidine Chemical compound N1=CC=CN=C1C1=NC=CC=N1 HKOAFLAGUQUJQG-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GHAZCVNUKKZTLG-UHFFFAOYSA-N N-ethyl-succinimide Natural products CCN1C(=O)CCC1=O GHAZCVNUKKZTLG-UHFFFAOYSA-N 0.000 description 2
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical group [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000012190 activator Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000000502 dialysis Methods 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000000295 emission spectrum Methods 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 230000000155 isotopic effect Effects 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229910052698 phosphorus Chemical group 0.000 description 2
- 239000011574 phosphorus Chemical group 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- WHMDPDGBKYUEMW-UHFFFAOYSA-N pyridine-2-thiol Chemical compound SC1=CC=CC=N1 WHMDPDGBKYUEMW-UHFFFAOYSA-N 0.000 description 2
- 239000007790 solid phase Substances 0.000 description 2
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 2
- VBEQCZHXXJYVRD-GACYYNSASA-N uroanthelone Chemical compound C([C@@H](C(=O)N[C@H](C(=O)N[C@@H](CS)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CS)C(=O)N[C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCC(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CO)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CS)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCNC(N)=N)C(O)=O)C(C)C)[C@@H](C)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCSC)NC(=O)[C@H](CS)NC(=O)[C@@H](NC(=O)CNC(=O)CNC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CS)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)CNC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CS)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CO)NC(=O)[C@@H](N)CC(N)=O)C(C)C)[C@@H](C)CC)C1=CC=C(O)C=C1 VBEQCZHXXJYVRD-GACYYNSASA-N 0.000 description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- FAAYDFBUMOADEP-UHFFFAOYSA-N 3-(2,5-dioxopyrrol-1-yl)-3-hexanoyl-1-hydroxypyrrolidine-2,5-dione Chemical compound O=C1C=CC(=O)N1C1(C(=O)CCCCC)CC(=O)N(O)C1=O FAAYDFBUMOADEP-UHFFFAOYSA-N 0.000 description 1
- 108090001008 Avidin Proteins 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102000001301 EGF receptor Human genes 0.000 description 1
- 108060006698 EGF receptor Proteins 0.000 description 1
- 102400001368 Epidermal growth factor Human genes 0.000 description 1
- 101800003838 Epidermal growth factor Proteins 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000007987 MES buffer Substances 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 108091005461 Nucleic proteins Proteins 0.000 description 1
- 208000037273 Pathologic Processes Diseases 0.000 description 1
- 108091000080 Phosphotransferase Proteins 0.000 description 1
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 description 1
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000012505 Superdex™ Substances 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- HAXFWIACAGNFHA-UHFFFAOYSA-N aldrithiol Chemical group C=1C=CC=NC=1SSC1=CC=CC=N1 HAXFWIACAGNFHA-UHFFFAOYSA-N 0.000 description 1
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
- 230000007321 biological mechanism Effects 0.000 description 1
- 229960002685 biotin Drugs 0.000 description 1
- 235000020958 biotin Nutrition 0.000 description 1
- 239000011616 biotin Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 125000005392 carboxamide group Chemical group NC(=O)* 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 230000019522 cellular metabolic process Effects 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical group SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
- 229940116977 epidermal growth factor Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 229940027941 immunoglobulin g Drugs 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 230000009054 pathological process Effects 0.000 description 1
- 102000020233 phosphotransferase Human genes 0.000 description 1
- 108060006184 phycobiliprotein Proteins 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 239000000941 radioactive substance Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000026683 transduction Effects 0.000 description 1
- 238000010361 transduction Methods 0.000 description 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Images
Classifications
-
- 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
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6842—Proteomic analysis of subsets of protein mixtures with reduced complexity, e.g. membrane proteins, phosphoproteins, organelle proteins
-
- 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
-
- 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
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or 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
- Y10S435/00—Chemistry: molecular biology and microbiology
- Y10S435/975—Kit
-
- 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
- Y10S436/815—Test for named compound or class of compounds
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Pathology (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Bioinformatics & Computational Biology (AREA)
- Biophysics (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Peptides Or Proteins (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR97/11721 | 1997-09-19 | ||
| FR9711721A FR2768817B1 (fr) | 1997-09-19 | 1997-09-19 | Methode homogene pour la detection et/ou la determination de l'activite phosphorylante d'un materiel biologique |
| PCT/FR1998/001976 WO1999015896A1 (fr) | 1997-09-19 | 1998-09-16 | Methode homogene pour la detection et/ou la determination de l'activite phosphorylante d'un materiel biologique |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2001517796A JP2001517796A (ja) | 2001-10-09 |
| JP2001517796A5 JP2001517796A5 (enExample) | 2009-04-23 |
| JP4312953B2 true JP4312953B2 (ja) | 2009-08-12 |
Family
ID=9511294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2000513143A Expired - Fee Related JP4312953B2 (ja) | 1997-09-19 | 1998-09-16 | 生物学的物質のリン酸化活性を検出および／または測定するための均質方法およびその方法の実施に使用されるキット |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US6753156B1 (enExample) |
| EP (1) | EP1018009B1 (enExample) |
| JP (1) | JP4312953B2 (enExample) |
| AT (1) | ATE238551T1 (enExample) |
| DE (1) | DE69813850T2 (enExample) |
| ES (1) | ES2198744T3 (enExample) |
| FR (1) | FR2768817B1 (enExample) |
| WO (1) | WO1999015896A1 (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6938493B2 (en) | 1997-07-21 | 2005-09-06 | Helix Technology Corporation | Apparatus and methods for heat loss pressure measurement |
| WO2001007638A2 (en) * | 1999-07-27 | 2001-02-01 | University Of Utah Research Foundation | Homogeneous fluorescence method for assaying structural modifications of biomolecules |
| AU3599601A (en) * | 2000-02-28 | 2001-09-03 | Daiichi Pure Chemicals Co Ltd | Measuring method using long life fluorescence of excitation type |
| EP1553408A4 (en) | 2002-07-08 | 2005-08-17 | Tetsuo Nagano | FLUORESCENCE PROBE |
| US20060211122A1 (en) * | 2002-10-16 | 2006-09-21 | Tetsuo Nagano | Reagents for the measurement of peroxynitrites |
| US7696245B2 (en) | 2003-03-28 | 2010-04-13 | Sekisui Medical Co., Ltd. | Fluorescent probe for zinc |
| DE10321901A1 (de) * | 2003-05-06 | 2004-12-02 | Proteosys Ag | Affinitätsanreicherung von phosphorylierten Peptiden und/oder Proteinen |
| JP2005194244A (ja) | 2004-01-09 | 2005-07-21 | Shigenobu Yano | 亜鉛イオン蛍光センサー |
| DE102004022628A1 (de) * | 2004-05-07 | 2005-12-15 | Sensient Imaging Technologies Gmbh | FRET-Bioassay |
| EP1749014B1 (de) * | 2004-05-19 | 2010-07-07 | Merck Patent GmbH | Metallkomplexe |
| DE102004034517A1 (de) | 2004-07-16 | 2006-02-16 | Covion Organic Semiconductors Gmbh | Metallkomplexe |
| FR2899689B1 (fr) * | 2006-04-10 | 2016-05-20 | Cis Bio Int | Procede de suppression d'un signal fret, agents suppresseurs d'un signal de fret et utilisation dans un procede de multiplexage biologiques |
| US7605009B2 (en) * | 2007-03-12 | 2009-10-20 | Silverbrook Research Pty Ltd | Method of fabrication MEMS integrated circuits |
| DE102011001368B4 (de) | 2011-03-17 | 2013-01-31 | Bundesanstalt für Materialforschung und -Prüfung (BAM) | Lanthanoid-Chelate enthaltende Partikel, deren Herstellung sowie deren Verwendung in der Bioanalytik |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2570703B1 (fr) * | 1984-09-26 | 1988-07-08 | Commissariat Energie Atomique | Complexes macropolycycliques de terres rares et application a titre de marqueurs fluorescents |
| US5279943A (en) * | 1985-08-02 | 1994-01-18 | Compagnie Oris Industrie | Homogeneous process for the detection and/or determination by luminescence of an analyte in a medium in which it may be present |
| FR2585836B1 (fr) * | 1985-08-02 | 1987-11-27 | Commissariat Energie Atomique | Procede homogene de detection et/ou de determination par luminescence d'un analyte dans un milieu susceptible de le contenir |
| EP0537270B1 (en) * | 1990-07-02 | 1998-09-09 | The Regents Of The University Of California | Detection of analytes using fluorescent energy transfer |
| FR2680787B1 (fr) * | 1991-08-30 | 1994-11-04 | Cis Bio Int | Complexes macrocycliques de terres rares et leur utilisation pour reduire les interferences dans un dosage par fluorescence. |
| US5622821A (en) * | 1994-06-29 | 1997-04-22 | The Regents Of The University Of California | Luminescent lanthanide chelates and methods of use |
| FR2735238B1 (fr) * | 1995-06-09 | 1997-09-05 | Cis Bio Int | Utilisation d'un complexe phycobiliproteine-peptide de liaison en tant que traceur fluorescent |
| AU3801997A (en) * | 1996-07-16 | 1998-02-09 | Regents Of The University Of California, The | Assays for protein kinases using fluorescent protein substrates |
| US5925558A (en) * | 1996-07-16 | 1999-07-20 | The Regents Of The University Of California | Assays for protein kinases using fluorescent protein substrates |
| US5759787A (en) * | 1996-08-26 | 1998-06-02 | Tularik Inc. | Kinase assay |
| PT1036192E (pt) * | 1997-12-05 | 2003-06-30 | Upjohn Co | Ensaios de pesquisa de alto rendimento a base de fluorescencia para proteina-quinases e -fosfatases |
-
1997
- 1997-09-19 FR FR9711721A patent/FR2768817B1/fr not_active Expired - Fee Related
-
1998
- 1998-09-16 EP EP98943995A patent/EP1018009B1/fr not_active Expired - Lifetime
- 1998-09-16 DE DE69813850T patent/DE69813850T2/de not_active Expired - Fee Related
- 1998-09-16 JP JP2000513143A patent/JP4312953B2/ja not_active Expired - Fee Related
- 1998-09-16 ES ES98943995T patent/ES2198744T3/es not_active Expired - Lifetime
- 1998-09-16 AT AT98943995T patent/ATE238551T1/de not_active IP Right Cessation
- 1998-09-16 WO PCT/FR1998/001976 patent/WO1999015896A1/fr not_active Ceased
- 1998-09-16 US US09/486,701 patent/US6753156B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JP2001517796A (ja) | 2001-10-09 |
| US6753156B1 (en) | 2004-06-22 |
| ATE238551T1 (de) | 2003-05-15 |
| EP1018009A1 (fr) | 2000-07-12 |
| EP1018009B1 (fr) | 2003-04-23 |
| DE69813850T2 (de) | 2004-04-01 |
| ES2198744T3 (es) | 2004-02-01 |
| FR2768817B1 (fr) | 1999-12-10 |
| FR2768817A1 (fr) | 1999-03-26 |
| WO1999015896A1 (fr) | 1999-04-01 |
| DE69813850D1 (de) | 2003-05-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5512493A (en) | Method of amplifying the emission signal of a luminescent compound | |
| JP3233285B2 (ja) | 冷光分析における放射冷光測定方法 | |
| US7314711B2 (en) | Assays employing electrochemiluminescent labels and electrochemiluminescence quenchers | |
| EP2021778B1 (en) | Nonseparation assay methods | |
| US6753156B1 (en) | Homogeneous method for detecting and/or determining phosphorylating activity in a biological material | |
| EP0335902B1 (en) | Monomeric phthalocyanine reagents | |
| WO1998015830A2 (en) | Homogenous luminescence energy transfer assays | |
| US6352672B1 (en) | Apparatus for measuring the luminescence emitted in a luminescent assay | |
| WO1992016841A1 (en) | Method for specific binding assays using a releasable ligand | |
| US5627074A (en) | Method of reducing interference in a fluorescent assay | |
| JP3583441B2 (ja) | フィコビリン蛋白質−結合ペプチド複合体の螢光トレーサとしての利用方法 | |
| US6013457A (en) | Method for carrying out an immunoassay in a multiphase system | |
| US6861264B2 (en) | Method of measuring the luminescence emitted in a luminescent assay | |
| JP2953501B2 (ja) | 発光可能な金属錯体を用いてアナライトを測定するための干渉除去試薬 | |
| BRPI0711388B1 (pt) | método para detectar um analito em uma amostra em um procedimento de ensaio | |
| CN117769588B (zh) | 增强化学发光信号的方法和试剂 | |
| JP3907919B2 (ja) | 抗原又は抗体の高感度検出法 | |
| EP1359416A2 (en) | Assays employing electrochemiluminescent labels and electrochemiluminescence quenchers | |
| US6994980B2 (en) | Chemiluminescent compounds and use thereof | |
| JPH0454455A (ja) | 多座配位蛍光キレートで標識した生物物質 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20050831 |
|
| A977 | Report on retrieval |
Free format text: JAPANESE INTERMEDIATE CODE: A971007 Effective date: 20080717 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20080909 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20081208 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20081215 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20090306 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20090306 |
|
| TRDD | Decision of grant or rejection written | ||
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20090414 |
|
| A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20090514 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120522 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| LAPS | Cancellation because of no payment of annual fees |