CA2426479C - Dye pair for fluorescence resonance energy transfer (fret) measurements - Google Patents
Dye pair for fluorescence resonance energy transfer (fret) measurements Download PDFInfo
- Publication number
- CA2426479C CA2426479C CA002426479A CA2426479A CA2426479C CA 2426479 C CA2426479 C CA 2426479C CA 002426479 A CA002426479 A CA 002426479A CA 2426479 A CA2426479 A CA 2426479A CA 2426479 C CA2426479 C CA 2426479C
- Authority
- CA
- Canada
- Prior art keywords
- fret
- fluorescence
- alkyl
- labelled
- 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 - Fee Related
Links
- 238000002866 fluorescence resonance energy transfer Methods 0.000 title claims abstract description 87
- 238000005259 measurement Methods 0.000 title claims abstract description 29
- 230000003993 interaction Effects 0.000 claims abstract description 25
- 239000000370 acceptor Substances 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 41
- 239000013522 chelant Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 230000007704 transition Effects 0.000 claims description 15
- 229910021645 metal ion Inorganic materials 0.000 claims description 14
- 238000012360 testing method Methods 0.000 claims description 14
- -1 sulfo, carboxy Chemical group 0.000 claims description 13
- 229910052751 metal Inorganic materials 0.000 claims description 12
- 239000002184 metal Substances 0.000 claims description 12
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 150000004893 oxazines Chemical class 0.000 claims description 8
- 150000004697 chelate complex Chemical class 0.000 claims description 7
- 239000012327 Ruthenium complex Substances 0.000 claims description 6
- 125000003884 phenylalkyl group Chemical group 0.000 claims description 6
- 150000003732 xanthenes Chemical class 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 claims description 3
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 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
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000000975 dye Substances 0.000 abstract description 45
- 239000012491 analyte Substances 0.000 abstract description 15
- 239000007850 fluorescent dye Substances 0.000 abstract description 3
- 238000001514 detection method Methods 0.000 description 23
- 230000035945 sensitivity Effects 0.000 description 19
- 108010090804 Streptavidin Proteins 0.000 description 15
- 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 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 238000012546 transfer Methods 0.000 description 12
- HVLSXIKZNLPZJJ-TXZCQADKSA-N HA peptide Chemical compound C([C@@H](C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](C)C(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 HVLSXIKZNLPZJJ-TXZCQADKSA-N 0.000 description 10
- 238000003556 assay Methods 0.000 description 9
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- 150000003303 ruthenium Chemical class 0.000 description 9
- 229910052693 Europium Inorganic materials 0.000 description 7
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 229910052747 lanthanoid Inorganic materials 0.000 description 7
- 150000002602 lanthanoids Chemical class 0.000 description 7
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- 239000000047 product Substances 0.000 description 7
- 229910052707 ruthenium Inorganic materials 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229960002685 biotin Drugs 0.000 description 6
- 235000020958 biotin Nutrition 0.000 description 6
- 239000011616 biotin Substances 0.000 description 6
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
- 235000017557 sodium bicarbonate Nutrition 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000000427 antigen Substances 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 108060006184 phycobiliprotein Proteins 0.000 description 4
- 239000001022 rhodamine dye Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 102000008100 Human Serum Albumin Human genes 0.000 description 3
- 108091006905 Human Serum Albumin Proteins 0.000 description 3
- 150000001217 Terbium Chemical class 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 230000005284 excitation Effects 0.000 description 3
- 230000002452 interceptive effect Effects 0.000 description 3
- 238000004020 luminiscence type Methods 0.000 description 3
- 150000007523 nucleic acids Chemical group 0.000 description 3
- 238000002165 resonance energy transfer Methods 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 102000004856 Lectins Human genes 0.000 description 2
- 108090001090 Lectins Proteins 0.000 description 2
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 108010004469 allophycocyanin Proteins 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- LWISPDYGRSGXME-YDHLFZDLSA-N biotin peg2 amine Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCOCCOCCN)SC[C@@H]21 LWISPDYGRSGXME-YDHLFZDLSA-N 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 230000002255 enzymatic effect Effects 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 238000003018 immunoassay Methods 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 239000002523 lectin Substances 0.000 description 2
- 230000001795 light effect Effects 0.000 description 2
- UYEUUXMDVNYCAM-UHFFFAOYSA-N lumazine Chemical compound N1=CC=NC2=NC(O)=NC(O)=C21 UYEUUXMDVNYCAM-UHFFFAOYSA-N 0.000 description 2
- 238000001906 matrix-assisted laser desorption--ionisation mass spectrometry Methods 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 238000006862 quantum yield reaction Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 235000000346 sugar Nutrition 0.000 description 2
- 125000000542 sulfonic acid group Chemical group 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
- CKRJGDYKYQUNIM-UHFFFAOYSA-N 3-fluoro-2,2-dimethylpropanoic acid Chemical compound FCC(C)(C)C(O)=O CKRJGDYKYQUNIM-UHFFFAOYSA-N 0.000 description 1
- 102000006306 Antigen Receptors Human genes 0.000 description 1
- 108010083359 Antigen Receptors Proteins 0.000 description 1
- 101100248451 Arabidopsis thaliana RICE2 gene Proteins 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 150000000918 Europium Chemical class 0.000 description 1
- MNLIKWSOXBSLMV-UHFFFAOYSA-N NC(OO)(CCCCC)N Chemical compound NC(OO)(CCCCC)N MNLIKWSOXBSLMV-UHFFFAOYSA-N 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 229910052771 Terbium Inorganic materials 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- DGOBMKYRQHEFGQ-UHFFFAOYSA-L acid green 5 Chemical compound [Na+].[Na+].C=1C=C(C(=C2C=CC(C=C2)=[N+](CC)CC=2C=C(C=CC=2)S([O-])(=O)=O)C=2C=CC(=CC=2)S([O-])(=O)=O)C=CC=1N(CC)CC1=CC=CC(S([O-])(=O)=O)=C1 DGOBMKYRQHEFGQ-UHFFFAOYSA-L 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000003149 assay kit Methods 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229960004407 chorionic gonadotrophin Drugs 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 230000009918 complex formation Effects 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- ZWWWLCMDTZFSOO-UHFFFAOYSA-N diethoxyphosphorylformonitrile Chemical compound CCOP(=O)(C#N)OCC ZWWWLCMDTZFSOO-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- STWJKLMRMTWJEY-UHFFFAOYSA-N diphenyl 1,10-phenanthroline-4,7-disulfonate Chemical compound C=1C=NC(C2=NC=CC(=C2C=C2)S(=O)(=O)OC=3C=CC=CC=3)=C2C=1S(=O)(=O)OC1=CC=CC=C1 STWJKLMRMTWJEY-UHFFFAOYSA-N 0.000 description 1
- IWBOPFCKHIJFMS-UHFFFAOYSA-N ethylene glycol bis(2-aminoethyl) ether Chemical compound NCCOCCOCCN IWBOPFCKHIJFMS-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000002875 fluorescence polarization Methods 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 230000010363 phase shift Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 238000002821 scintillation proximity assay Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
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
- G01N33/58—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances
- G01N33/582—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving labelled substances 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
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/536—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase
- G01N33/542—Immunoassay; Biospecific binding assay; Materials therefor with immune complex formed in liquid phase with steric inhibition or signal modification, e.g. fluorescent quenching
-
- 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
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T436/00—Chemistry: analytical and immunological testing
- Y10T436/14—Heterocyclic carbon compound [i.e., O, S, N, Se, Te, as only ring hetero atom]
- Y10T436/142222—Hetero-O [e.g., ascorbic acid, etc.]
- Y10T436/143333—Saccharide [e.g., DNA, etc.]
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)
- Cell Biology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00124995.2 | 2000-11-16 | ||
| EP00124995 | 2000-11-16 | ||
| PCT/EP2001/013152 WO2002041001A1 (de) | 2000-11-16 | 2001-11-14 | Farbstoffpaare für fluoreszenz-resonanz-energie-transfer (fret) messungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2426479A1 CA2426479A1 (en) | 2003-04-22 |
| CA2426479C true CA2426479C (en) | 2007-08-07 |
Family
ID=8170391
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002426479A Expired - Fee Related CA2426479C (en) | 2000-11-16 | 2001-11-14 | Dye pair for fluorescence resonance energy transfer (fret) measurements |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6908769B2 (enExample) |
| EP (1) | EP1337851B1 (enExample) |
| JP (1) | JP3905838B2 (enExample) |
| AT (1) | ATE300050T1 (enExample) |
| AU (1) | AU2002221848A1 (enExample) |
| CA (1) | CA2426479C (enExample) |
| DE (1) | DE50106822D1 (enExample) |
| ES (1) | ES2245995T3 (enExample) |
| WO (1) | WO2002041001A1 (enExample) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE518913T1 (de) * | 2000-09-06 | 2011-08-15 | Evotec Ag | Verfahren zur gezielten markierung mittels affinitätsmarkierter detektionsmarker |
| AU2003251986A1 (en) * | 2002-07-17 | 2004-02-02 | U.S.Genomics, Inc. | Methods and compositions for analyzing polymers using chimeric tags |
| GB2421412B (en) * | 2003-02-26 | 2007-08-29 | Tomtom Bv | Navigation device with touch screen |
| CN100447145C (zh) * | 2003-08-18 | 2008-12-31 | 诺瓦提斯公司 | 适宜作为近红外显像剂的3h－吩嗪衍生物、其制备和用途 |
| ATE403870T1 (de) | 2003-10-01 | 2008-08-15 | Wallac Oy | Verbesserter homogenener zeitaufgelöster energietransfertest |
| US8105849B2 (en) * | 2004-02-27 | 2012-01-31 | Board Of Regents, The University Of Texas System | Integration of fluids and reagents into self-contained cartridges containing sensor elements |
| EP1725587A2 (en) * | 2004-03-19 | 2006-11-29 | U.S. Genomics, Inc. | Compositions and methods for detection of single molecules |
| US8883486B2 (en) | 2004-05-04 | 2014-11-11 | Universite De Montreal | Arrestin biosensor |
| CN100473988C (zh) * | 2004-07-08 | 2009-04-01 | 厦门大学 | 具有荧光共振能量转移特点的蛋白组合及其用途 |
| WO2006080396A1 (ja) * | 2005-01-28 | 2006-08-03 | Shionogi & Co., Ltd. | 組換え蛋白質の定量法 |
| WO2006125855A1 (en) * | 2005-05-24 | 2006-11-30 | Hidex Oy | Correction method and measurement device for anti-stokes photoluminescence measurement |
| WO2007016975A1 (en) | 2005-07-29 | 2007-02-15 | F. Hoffmann-La Roche Ag | Kinase and phosphatase assays based on fret |
| FR2890174B1 (fr) * | 2005-08-30 | 2009-04-24 | Cis Bio Internat Sa | Procede pour la mise en evidence d'un processus biologique par mesure d'un fret |
| US20100035247A1 (en) * | 2005-11-04 | 2010-02-11 | U.S. Genomics, Inc. | Heterogeneous Assay of Analytes in Solution Using Polymers |
| WO2007135368A2 (en) | 2006-05-18 | 2007-11-29 | Solexa Limited | Dye compounds and the use of their labelled conjugates |
| US20110098309A1 (en) * | 2007-07-12 | 2011-04-28 | Acumen Pharmaceuticals, Inc. | Methods of inhibiting the formation of amyloid-beta diffusable ligands using acylhydrazide compounds |
| US8962677B2 (en) * | 2007-07-12 | 2015-02-24 | Acumen Pharmaceuticals, Inc. | Methods of restoring cognitive ability using non-peptidic compounds |
| US9006283B2 (en) | 2007-07-12 | 2015-04-14 | Acumen Pharmaceuticals, Inc. | Methods of modifying amyloid β oligomers using non-peptidic compounds |
| US20100294665A1 (en) * | 2007-07-12 | 2010-11-25 | Richard Allen | Method and system for transferring and/or concentrating a sample |
| CA2707309A1 (en) | 2007-12-18 | 2009-06-25 | Acumen Pharmaceuticals, Inc. | Novel addl receptor polypeptides, polynucleotides and host cells for recombinant production |
| WO2010117420A2 (en) * | 2009-03-30 | 2010-10-14 | Pacific Biosciences Of California, Inc. | Fret-labeled compounds and uses therefor |
| EP2425249B1 (fr) * | 2009-04-30 | 2014-07-16 | Cisbio Bioassays | Procede de detection de composes modulateurs de dimeres de proteines membranaires a domaine vft |
| CA2810725A1 (en) | 2010-09-15 | 2012-03-22 | Constance Neely Wilson | Methods of use and kit for measurement of lipopolysaccharide with a time resolved fluorescence based assay |
| US9435805B2 (en) | 2010-09-23 | 2016-09-06 | Woundchek Laboratories (Us), Inc. | Ultrasensitive detection of beta hemolytic Streptococcus |
| US8569254B2 (en) | 2010-12-10 | 2013-10-29 | National Yang Ming University | Methods for modulating the expression and aggregation of CAG-expanded gene product in cells and methods for identifying agents useful for doing the same |
| CN109752552A (zh) * | 2017-11-05 | 2019-05-14 | 江苏维赛科技生物发展有限公司 | 检测联苯的时间分辨荧光免疫试剂盒及其检测方法 |
| WO2019212946A1 (en) | 2018-04-30 | 2019-11-07 | Ribon Therapeutics Inc. | Screening methods for parp modulators |
| KR102267067B1 (ko) * | 2020-01-16 | 2021-06-21 | 경희대학교 산학협력단 | 다이에틸싸이아노포스포네이트 검출용 형광 프로브 화합물 및 이의 용도 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3262442D1 (en) | 1981-10-06 | 1985-03-28 | Univ Leland Stanford Junior | Fluorescent conjugates for analysis of molecules and cells |
| US4822733A (en) * | 1985-05-28 | 1989-04-18 | Amoco Corporation | Lifetime-resolved assay procedures |
| DE4137934A1 (de) | 1991-11-18 | 1993-05-19 | Boehringer Mannheim Gmbh | Neue pentacyklische verbindungen und ihre verwendung als absorptions- oder fluoreszenzfarbstoffe |
| US5246867A (en) * | 1992-01-17 | 1993-09-21 | University Of Maryland At Baltimore | Determination and quantification of saccharides by luminescence lifetimes and energy transfer |
| US5622821A (en) * | 1994-06-29 | 1997-04-22 | The Regents Of The University Of California | Luminescent lanthanide chelates and methods of use |
| PT912766E (pt) * | 1996-06-04 | 2009-07-16 | Univ Utah Res Found | Monitorização da hibridização durante a pcr |
| EP0968411A1 (en) | 1997-03-25 | 2000-01-05 | Photonic Research Systems Limited | Luminescence assays |
| AU3487499A (en) | 1998-04-08 | 1999-10-25 | Regents Of The University Of California, The | Methods and reagents for targeting organic compounds to selected cellular locations |
| GB9811483D0 (en) * | 1998-05-29 | 1998-07-29 | Photonic Research Systems Limi | Luminescence assay using cyclical excitation wavelength sequence |
| US5998146A (en) * | 1998-07-17 | 1999-12-07 | Wallac Oy | Homogeneous luminescence assay method based on energy transfer |
| AU3488700A (en) | 1999-02-12 | 2000-08-29 | Ljl Biosystems, Inc. | Luminescent metal-ligand complexes |
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2001
- 2001-11-14 US US10/432,132 patent/US6908769B2/en not_active Expired - Fee Related
- 2001-11-14 ES ES01996741T patent/ES2245995T3/es not_active Expired - Lifetime
- 2001-11-14 JP JP2002542878A patent/JP3905838B2/ja not_active Expired - Fee Related
- 2001-11-14 WO PCT/EP2001/013152 patent/WO2002041001A1/de not_active Ceased
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- 2001-11-14 DE DE50106822T patent/DE50106822D1/de not_active Expired - Lifetime
- 2001-11-14 AU AU2002221848A patent/AU2002221848A1/en not_active Abandoned
- 2001-11-14 CA CA002426479A patent/CA2426479C/en not_active Expired - Fee Related
- 2001-11-14 EP EP01996741A patent/EP1337851B1/de not_active Expired - Lifetime
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| JP2004514139A (ja) | 2004-05-13 |
| US20040076979A1 (en) | 2004-04-22 |
| AU2002221848A1 (en) | 2002-05-27 |
| CA2426479A1 (en) | 2003-04-22 |
| ES2245995T3 (es) | 2006-02-01 |
| EP1337851A1 (de) | 2003-08-27 |
| ATE300050T1 (de) | 2005-08-15 |
| WO2002041001A1 (de) | 2002-05-23 |
| EP1337851B1 (de) | 2005-07-20 |
| US6908769B2 (en) | 2005-06-21 |
| JP3905838B2 (ja) | 2007-04-18 |
| DE50106822D1 (de) | 2005-08-25 |
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