DE29915165U1 - Energy Transfer Dyes - Google Patents
Energy Transfer DyesInfo
- Publication number
- DE29915165U1 DE29915165U1 DE29915165U DE29915165U DE29915165U1 DE 29915165 U1 DE29915165 U1 DE 29915165U1 DE 29915165 U DE29915165 U DE 29915165U DE 29915165 U DE29915165 U DE 29915165U DE 29915165 U1 DE29915165 U1 DE 29915165U1
- Authority
- DE
- Germany
- Prior art keywords
- dye
- energy transfer
- group
- phe
- fam
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000975 dye Substances 0.000 title claims abstract description 308
- 238000012546 transfer Methods 0.000 title claims abstract description 145
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 25
- 125000003118 aryl group Chemical group 0.000 claims abstract description 25
- 125000005647 linker group Chemical group 0.000 claims abstract description 24
- 125000000524 functional group Chemical group 0.000 claims abstract description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
- 239000013077 target material Substances 0.000 claims abstract description 13
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000012620 biological material Substances 0.000 claims abstract description 12
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 10
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000001301 oxygen Substances 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 6
- 239000011574 phosphorus Substances 0.000 claims abstract description 6
- 239000011593 sulfur Substances 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- 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 37
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 cells Substances 0.000 claims description 28
- 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 18
- 229940075420 xanthine Drugs 0.000 claims description 17
- 108020004707 nucleic acids Proteins 0.000 claims description 13
- 102000039446 nucleic acids Human genes 0.000 claims description 13
- 150000007523 nucleic acids Chemical class 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 108090000790 Enzymes Proteins 0.000 claims description 8
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- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 claims description 7
- 239000000463 material Substances 0.000 claims description 6
- UNGMOMJDNDFGJG-UHFFFAOYSA-N 5-carboxy-X-rhodamine Chemical compound [O-]C(=O)C1=CC(C(=O)O)=CC=C1C1=C(C=C2C3=C4CCCN3CCC2)C4=[O+]C2=C1C=C1CCCN3CCCC2=C13 UNGMOMJDNDFGJG-UHFFFAOYSA-N 0.000 claims description 5
- NJYVEMPWNAYQQN-UHFFFAOYSA-N 5-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C21OC(=O)C1=CC(C(=O)O)=CC=C21 NJYVEMPWNAYQQN-UHFFFAOYSA-N 0.000 claims description 5
- IDLISIVVYLGCKO-UHFFFAOYSA-N 6-carboxy-4',5'-dichloro-2',7'-dimethoxyfluorescein Chemical compound O1C(=O)C2=CC=C(C(O)=O)C=C2C21C1=CC(OC)=C(O)C(Cl)=C1OC1=C2C=C(OC)C(O)=C1Cl IDLISIVVYLGCKO-UHFFFAOYSA-N 0.000 claims description 5
- BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 claims description 5
- 101100301524 Drosophila melanogaster Reg-5 gene Proteins 0.000 claims description 5
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 5
- 239000012876 carrier material Substances 0.000 claims description 5
- VYXSBFYARXAAKO-UHFFFAOYSA-N ethyl 2-[3-(ethylamino)-6-ethylimino-2,7-dimethylxanthen-9-yl]benzoate;hydron;chloride Chemical compound [Cl-].C1=2C=C(C)C(NCC)=CC=2OC2=CC(=[NH+]CC)C(C)=CC2=C1C1=CC=CC=C1C(=O)OCC VYXSBFYARXAAKO-UHFFFAOYSA-N 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 239000002245 particle Substances 0.000 claims description 5
- 102000004169 proteins and genes Human genes 0.000 claims description 5
- ABZLKHKQJHEPAX-UHFFFAOYSA-N tetramethylrhodamine Chemical compound C=12C=CC(N(C)C)=CC2=[O+]C2=CC(N(C)C)=CC=C2C=1C1=CC=CC=C1C([O-])=O ABZLKHKQJHEPAX-UHFFFAOYSA-N 0.000 claims description 5
- 150000001720 carbohydrates Chemical class 0.000 claims description 4
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- 150000002540 isothiocyanates Chemical class 0.000 claims description 4
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- 239000001022 rhodamine dye Substances 0.000 claims description 4
- GNBHRKFJIUUOQI-UHFFFAOYSA-N fluorescein Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(O)C=C1OC1=CC(O)=CC=C21 GNBHRKFJIUUOQI-UHFFFAOYSA-N 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
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- 239000011324 bead Substances 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- WQZIDRAQTRIQDX-UHFFFAOYSA-N 6-carboxy-x-rhodamine Chemical compound OC(=O)C1=CC=C(C([O-])=O)C=C1C(C1=CC=2CCCN3CCCC(C=23)=C1O1)=C2C1=C(CCC1)C3=[N+]1CCCC3=C2 WQZIDRAQTRIQDX-UHFFFAOYSA-N 0.000 claims 4
- VWOLRKMFAJUZGM-UHFFFAOYSA-N 6-carboxyrhodamine 6G Chemical compound [Cl-].C=12C=C(C)C(NCC)=CC2=[O+]C=2C=C(NCC)C(C)=CC=2C=1C1=CC(C(O)=O)=CC=C1C(=O)OCC VWOLRKMFAJUZGM-UHFFFAOYSA-N 0.000 claims 4
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 239000000298 carbocyanine Substances 0.000 claims 3
- 150000008300 phosphoramidites Chemical class 0.000 claims 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 125000004429 atom Chemical group 0.000 abstract description 28
- 238000002360 preparation method Methods 0.000 abstract description 7
- 125000001475 halogen functional group Chemical group 0.000 abstract description 2
- 238000001429 visible spectrum Methods 0.000 abstract description 2
- 244000309464 bull Species 0.000 description 24
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 18
- 108020004414 DNA Proteins 0.000 description 16
- 229960005190 phenylalanine Drugs 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
- 239000000523 sample Substances 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
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- 125000003545 alkoxy group Chemical group 0.000 description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 5
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
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- 238000001712 DNA sequencing Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
- ARLKCWCREKRROD-POYBYMJQSA-N [[(2s,5r)-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] phosphono hydrogen phosphate Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)CC1 ARLKCWCREKRROD-POYBYMJQSA-N 0.000 description 2
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- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000004163 cytometry Methods 0.000 description 1
- SUYVUBYJARFZHO-RRKCRQDMSA-N dATP Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@H]1C[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 SUYVUBYJARFZHO-RRKCRQDMSA-N 0.000 description 1
- SUYVUBYJARFZHO-UHFFFAOYSA-N dATP Natural products C1=NC=2C(N)=NC=NC=2N1C1CC(O)C(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)O1 SUYVUBYJARFZHO-UHFFFAOYSA-N 0.000 description 1
- RGWHQCVHVJXOKC-SHYZEUOFSA-J dCTP(4-) Chemical compound O=C1N=C(N)C=CN1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)C1 RGWHQCVHVJXOKC-SHYZEUOFSA-J 0.000 description 1
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- 230000007613 environmental effect Effects 0.000 description 1
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- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000000799 fluorescence microscopy Methods 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 125000003709 fluoroalkyl group Chemical group 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010166 immunofluorescence Methods 0.000 description 1
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- 238000010348 incorporation Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012160 loading buffer Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
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- 125000002950 monocyclic group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000002777 nucleoside Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000011002 quantification Methods 0.000 description 1
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- 230000000171 quenching effect Effects 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000002165 resonance energy transfer Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 230000035945 sensitivity 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
- 238000010561 standard procedure Methods 0.000 description 1
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- 238000005382 thermal cycling Methods 0.000 description 1
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
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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
- G01N33/53—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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B11/00—Diaryl- or thriarylmethane dyes
- C09B11/04—Diaryl- or thriarylmethane dyes derived from triarylmethanes, i.e. central C-atom is substituted by amino, cyano, alkyl
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
-
- 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
- C12Q1/68—Measuring or testing processes involving enzymes, nucleic acids or microorganisms; Compositions therefor; Processes of preparing such compositions involving nucleic acids
- C12Q1/6813—Hybridisation assays
- C12Q1/6816—Hybridisation assays characterised by the detection means
- C12Q1/6818—Hybridisation assays characterised by the detection means involving interaction of two or more labels, e.g. resonant energy transfer
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Immunology (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Urology & Nephrology (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Genetics & Genomics (AREA)
- General Engineering & Computer Science (AREA)
- Biophysics (AREA)
- Medicinal Chemistry (AREA)
- Food Science & Technology (AREA)
- Cell Biology (AREA)
- General Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pathology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
- Coloring (AREA)
- Peptides Or Proteins (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9846998P | 1998-08-31 | 1998-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE29915165U1 true DE29915165U1 (de) | 2000-03-02 |
Family
ID=22269416
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE29915165U Expired - Lifetime DE29915165U1 (de) | 1998-08-31 | 1999-08-30 | Energy Transfer Dyes |
| DE69912139T Expired - Lifetime DE69912139T2 (de) | 1998-08-31 | 1999-08-30 | Energieübertragungsfarbstoffe |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69912139T Expired - Lifetime DE69912139T2 (de) | 1998-08-31 | 1999-08-30 | Energieübertragungsfarbstoffe |
Country Status (9)
| Country | Link |
|---|---|
| EP (1) | EP1110088B1 (enExample) |
| JP (1) | JP4659213B2 (enExample) |
| AT (1) | ATE252239T1 (enExample) |
| AU (1) | AU767840B2 (enExample) |
| CA (1) | CA2341520C (enExample) |
| DE (2) | DE29915165U1 (enExample) |
| ES (1) | ES2209492T3 (enExample) |
| GB (1) | GB2341189B (enExample) |
| WO (1) | WO2000013026A1 (enExample) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6967250B1 (en) * | 1998-08-31 | 2005-11-22 | Amersham Biosciences Corp | Energy transfer dyes |
| WO2001019841A1 (en) * | 1999-09-17 | 2001-03-22 | Amersham Pharmacia Biotech, Inc. | Charge-modified nucleic acid terminators |
| GB0024351D0 (en) * | 2000-10-04 | 2000-11-22 | Amersham Pharm Biotech Uk Ltd | Dye-labelled peptide and method |
| AT410601B (de) * | 2000-12-29 | 2003-06-25 | Hoffmann La Roche | Sensor zur lumineszenz-optischen bestimmung eines analyten sowie reagens, das nach dem fret-prinzip arbeitet |
| AU2003280470A1 (en) * | 2002-07-01 | 2004-01-19 | Guava Technologies, Inc. | Fluorescent dyes, energy transfer couples and methods |
| US7385038B2 (en) | 2002-07-18 | 2008-06-10 | Protein Express Co., Ltd. | Non-natural labeled amino acid and method of constructing amino acid/tRNA complex |
| ITPZ20030002A1 (it) | 2003-08-12 | 2005-02-13 | Giuseppe Caputo | Composti del tipo cianina aventi un braccio di legame alchinilico |
| US7417726B2 (en) | 2003-09-19 | 2008-08-26 | Applied Biosystems Inc. | Normalization of data using controls |
| JP2007534308A (ja) | 2003-11-19 | 2007-11-29 | アレロジック・バイオサイエンシズ・コーポレーション | 複数のフルオロフォアで標識したオリゴヌクレオチド |
| AU2005287078A1 (en) | 2004-09-16 | 2006-03-30 | Applied Biosystems, Llc. | Fluorescent dye compounds, conjugates and uses thereof |
| CN101189520A (zh) | 2005-05-03 | 2008-05-28 | 亚佩瑞股份有限公司 | 荧光检测系统和供其使用的染料组 |
| WO2009078970A1 (en) | 2007-12-14 | 2009-06-25 | Biotium, Inc. | Fluorescent compounds |
| US8658434B2 (en) | 2009-10-28 | 2014-02-25 | Biotium, Inc. | Fluorescent pyrene compounds |
| US9579402B2 (en) | 2009-12-04 | 2017-02-28 | Biotium, Inc. | Heterocycle-substituted xanthene dyes |
| JP5540867B2 (ja) * | 2010-04-26 | 2014-07-02 | コニカミノルタ株式会社 | 有機蛍光色素内包シリカナノ粒子、その製造方法、それを用いた生体物質標識剤 |
| WO2013056841A1 (en) | 2011-10-19 | 2013-04-25 | Inra (Institut National De La Recherche Agronomique) | A method for diagnosing tse |
| KR102587439B1 (ko) * | 2017-06-27 | 2023-10-10 | 코리올리스 파마 리서치 게엠베하 | 폴리소르베이트 정량 어세이 |
| KR20230170688A (ko) * | 2021-04-13 | 2023-12-19 | 소마로직 오퍼레이팅 컴퍼니, 인코포레이티드 | 변형된 뉴클레오사이드 |
| CN119462681B (zh) * | 2024-10-16 | 2025-09-30 | 聊城柏莱斯生物科技有限公司 | 一种荧光定量pcr参比染料及其制备方法与应用 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE397360B (sv) * | 1970-10-13 | 1977-10-31 | Kanzaki Paper Mfg Co Ltd | Fluoranforeningar, speciellt bensfluoranforeningar, till anvendning som fergmaterial i registrerings- och kopieringssystem och sett att framstella dessa nya foreningar |
| JP3260884B2 (ja) * | 1993-02-05 | 2002-02-25 | キヤノン株式会社 | 標識複合体、それを用いる分析法、生体関連物質の検出および定量の方法 |
| US6008373A (en) * | 1995-06-07 | 1999-12-28 | Carnegie Mellon University | Fluorescent labeling complexes with large stokes shift formed by coupling together cyanine and other fluorochromes capable of resonance energy transfer |
| US5728528A (en) * | 1995-09-20 | 1998-03-17 | The Regents Of The University Of California | Universal spacer/energy transfer dyes |
| US5800996A (en) * | 1996-05-03 | 1998-09-01 | The Perkin Elmer Corporation | Energy transfer dyes with enchanced fluorescence |
| US5853992A (en) * | 1996-10-04 | 1998-12-29 | The Regents Of The University Of California | Cyanine dyes with high-absorbance cross section as donor chromophores in energy transfer labels |
| US5804386A (en) * | 1997-01-15 | 1998-09-08 | Incyte Pharmaceuticals, Inc. | Sets of labeled energy transfer fluorescent primers and their use in multi component analysis |
| US6165800A (en) * | 1997-05-30 | 2000-12-26 | Bayer Corporation | Chemiluminescent energy transfer conjugates and their uses as labels in binding assays |
-
1999
- 1999-08-25 GB GB9920022A patent/GB2341189B/en not_active Revoked
- 1999-08-30 JP JP2000567958A patent/JP4659213B2/ja not_active Expired - Fee Related
- 1999-08-30 WO PCT/US1999/019739 patent/WO2000013026A1/en not_active Ceased
- 1999-08-30 DE DE29915165U patent/DE29915165U1/de not_active Expired - Lifetime
- 1999-08-30 DE DE69912139T patent/DE69912139T2/de not_active Expired - Lifetime
- 1999-08-30 CA CA2341520A patent/CA2341520C/en not_active Expired - Fee Related
- 1999-08-30 EP EP99943985A patent/EP1110088B1/en not_active Expired - Lifetime
- 1999-08-30 AU AU56970/99A patent/AU767840B2/en not_active Ceased
- 1999-08-30 AT AT99943985T patent/ATE252239T1/de not_active IP Right Cessation
- 1999-08-30 ES ES99943985T patent/ES2209492T3/es not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| EP1110088A1 (en) | 2001-06-27 |
| JP2002523783A (ja) | 2002-07-30 |
| AU5697099A (en) | 2000-03-21 |
| WO2000013026A1 (en) | 2000-03-09 |
| DE69912139T2 (de) | 2004-07-22 |
| CA2341520A1 (en) | 2000-03-09 |
| GB2341189A (en) | 2000-03-08 |
| ES2209492T3 (es) | 2004-06-16 |
| CA2341520C (en) | 2010-11-02 |
| JP4659213B2 (ja) | 2011-03-30 |
| AU767840B2 (en) | 2003-11-27 |
| EP1110088B1 (en) | 2003-10-15 |
| ATE252239T1 (de) | 2003-11-15 |
| DE69912139D1 (de) | 2003-11-20 |
| GB9920022D0 (en) | 1999-10-27 |
| WO2000013026A9 (en) | 2000-08-17 |
| GB2341189B (en) | 2001-06-13 |
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