JP3984475B2 - 蛍光検出法および試薬 - Google Patents
蛍光検出法および試薬 Download PDFInfo
- Publication number
- JP3984475B2 JP3984475B2 JP2001558049A JP2001558049A JP3984475B2 JP 3984475 B2 JP3984475 B2 JP 3984475B2 JP 2001558049 A JP2001558049 A JP 2001558049A JP 2001558049 A JP2001558049 A JP 2001558049A JP 3984475 B2 JP3984475 B2 JP 3984475B2
- Authority
- JP
- Japan
- Prior art keywords
- nitroreductase
- fluorescence
- group
- cyanine dye
- dye molecule
- 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 33
- 239000003153 chemical reaction reagent Substances 0.000 title description 4
- 238000001917 fluorescence detection Methods 0.000 title description 2
- 108020001162 nitroreductase Proteins 0.000 claims abstract description 112
- 102000004459 Nitroreductase Human genes 0.000 claims abstract description 109
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims abstract description 47
- 230000014509 gene expression Effects 0.000 claims abstract description 25
- 230000001965 increasing effect Effects 0.000 claims abstract description 11
- 230000009467 reduction Effects 0.000 claims abstract description 6
- 210000004027 cell Anatomy 0.000 claims description 63
- 150000001875 compounds Chemical class 0.000 claims description 36
- 238000003556 assay Methods 0.000 claims description 28
- -1 amino, hydroxyl Chemical group 0.000 claims description 20
- 238000004458 analytical method Methods 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 150000007523 nucleic acids Chemical class 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 108020004707 nucleic acids Proteins 0.000 claims description 11
- 102000039446 nucleic acids Human genes 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 6
- 230000001580 bacterial effect Effects 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 6
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 5
- 239000000284 extract Substances 0.000 claims description 5
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 4
- 125000001475 halogen functional group Chemical group 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003140 primary amides Chemical class 0.000 claims description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 239000002202 Polyethylene glycol Substances 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000001721 carbon Chemical group 0.000 claims description 3
- 229920001223 polyethylene glycol Polymers 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- 239000011593 sulfur Substances 0.000 claims description 3
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical class [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 claims description 2
- 125000004442 acylamino group Chemical group 0.000 claims description 2
- 230000001935 permeabilising effect Effects 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 2
- 229910052711 selenium Inorganic materials 0.000 claims description 2
- 239000011669 selenium Chemical class 0.000 claims description 2
- 230000008823 permeabilization Effects 0.000 claims 1
- 238000003571 reporter gene assay Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 239000000758 substrate Substances 0.000 abstract description 35
- 230000000694 effects Effects 0.000 abstract description 29
- 238000009739 binding Methods 0.000 abstract description 18
- 238000001514 detection method Methods 0.000 abstract description 10
- 239000000203 mixture Substances 0.000 abstract description 5
- 230000009471 action Effects 0.000 abstract description 3
- 239000000975 dye Substances 0.000 description 65
- 108090000790 Enzymes Proteins 0.000 description 32
- 102000004190 Enzymes Human genes 0.000 description 31
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 230000005284 excitation Effects 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 20
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- 230000027455 binding Effects 0.000 description 17
- 238000005259 measurement Methods 0.000 description 17
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 16
- 238000004128 high performance liquid chromatography Methods 0.000 description 13
- 239000000126 substance Substances 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 12
- 239000002953 phosphate buffered saline Substances 0.000 description 12
- 108700008625 Reporter Genes Proteins 0.000 description 11
- 108090000623 proteins and genes Proteins 0.000 description 11
- 230000001413 cellular effect Effects 0.000 description 10
- 238000002866 fluorescence resonance energy transfer Methods 0.000 description 10
- 238000011534 incubation Methods 0.000 description 10
- 230000002829 reductive effect Effects 0.000 description 10
- 241001522878 Escherichia coli B Species 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000007850 fluorescent dye Substances 0.000 description 9
- 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 8
- 238000002189 fluorescence spectrum Methods 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 239000013592 cell lysate Substances 0.000 description 7
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 238000000338 in vitro Methods 0.000 description 6
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 6
- 238000001228 spectrum Methods 0.000 description 6
- BOSJTWUNDWDFAT-UHFFFAOYSA-N 2-(1,2,3,3-tetramethylindol-1-ium-5-yl)acetate Chemical compound C1=C(CC([O-])=O)C=C2C(C)(C)C(C)=[N+](C)C2=C1 BOSJTWUNDWDFAT-UHFFFAOYSA-N 0.000 description 5
- 108020004774 Alkaline Phosphatase Proteins 0.000 description 5
- 102000002260 Alkaline Phosphatase Human genes 0.000 description 5
- 102100026189 Beta-galactosidase Human genes 0.000 description 5
- 108020004414 DNA Proteins 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 239000012491 analyte Substances 0.000 description 5
- 108010005774 beta-Galactosidase Proteins 0.000 description 5
- 230000002255 enzymatic effect Effects 0.000 description 5
- 238000000684 flow cytometry Methods 0.000 description 5
- 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 description 5
- 238000003018 immunoassay Methods 0.000 description 5
- 125000005647 linker group Chemical group 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 5
- 230000001105 regulatory effect Effects 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- OBJOZRVSMLPASY-UHFFFAOYSA-N 8-hydroxypyrene-1,3,6-trisulfonic acid Chemical compound C1=C2C(O)=CC(S(O)(=O)=O)=C(C=C3)C2=C2C3=C(S(O)(=O)=O)C=C(S(O)(=O)=O)C2=C1 OBJOZRVSMLPASY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000427 antigen Substances 0.000 description 4
- 102000036639 antigens Human genes 0.000 description 4
- 108091007433 antigens Proteins 0.000 description 4
- 229960002685 biotin Drugs 0.000 description 4
- 235000020958 biotin Nutrition 0.000 description 4
- 239000011616 biotin Substances 0.000 description 4
- 238000003776 cleavage reaction Methods 0.000 description 4
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 4
- 239000003480 eluent Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000003834 intracellular effect Effects 0.000 description 4
- 238000010369 molecular cloning Methods 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 238000006722 reduction reaction Methods 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000010183 spectrum analysis Methods 0.000 description 4
- KSPMXOLMFBUXDT-UHFFFAOYSA-N 1-[(3,5-dinitrophenyl)methyl]-3,3-dimethylindol-1-ium Chemical class CC1(C)[CH+]N(CC2=CC(=CC(=C2)[N+]([O-])=O)[N+]([O-])=O)C2=CC=CC=C12 KSPMXOLMFBUXDT-UHFFFAOYSA-N 0.000 description 3
- JINXFUDPGIICQE-UHFFFAOYSA-N 2-[1-[(3,5-dinitrophenyl)methyl]-3h-indol-1-ium-5-yl]acetic acid;bromide Chemical compound [Br-].C=1C(CC(=O)O)=CC=C2C=1CC=[N+]2CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 JINXFUDPGIICQE-UHFFFAOYSA-N 0.000 description 3
- 108090000204 Dipeptidase 1 Proteins 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 108010090804 Streptavidin Proteins 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 102000006635 beta-lactamase Human genes 0.000 description 3
- 231100000433 cytotoxic Toxicity 0.000 description 3
- 230000001472 cytotoxic effect Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- FVTCRASFADXXNN-SCRDCRAPSA-N flavin mononucleotide Chemical compound OP(=O)(O)OC[C@@H](O)[C@@H](O)[C@@H](O)CN1C=2C=C(C)C(C)=CC=2N=C2C1=NC(=O)NC2=O FVTCRASFADXXNN-SCRDCRAPSA-N 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 239000006166 lysate Substances 0.000 description 3
- 210000004962 mammalian cell Anatomy 0.000 description 3
- 238000007899 nucleic acid hybridization Methods 0.000 description 3
- 108090000765 processed proteins & peptides Proteins 0.000 description 3
- 229940002612 prodrug Drugs 0.000 description 3
- 239000000651 prodrug Substances 0.000 description 3
- 238000000159 protein binding assay Methods 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 3
- 230000009870 specific binding Effects 0.000 description 3
- 238000013518 transcription Methods 0.000 description 3
- 230000035897 transcription Effects 0.000 description 3
- 210000004881 tumor cell Anatomy 0.000 description 3
- HCYIOKVZAATOEW-UHFFFAOYSA-M 1,2,3,3-tetramethylindol-1-ium;iodide Chemical compound [I-].C1=CC=C2C(C)(C)C(C)=[N+](C)C2=C1 HCYIOKVZAATOEW-UHFFFAOYSA-M 0.000 description 2
- QUBPDPHWANFEJB-UHFFFAOYSA-N 2-(2,3,3-trimethylindol-5-yl)acetic acid Chemical compound C1=C(CC(O)=O)C=C2C(C)(C)C(C)=NC2=C1 QUBPDPHWANFEJB-UHFFFAOYSA-N 0.000 description 2
- 230000005778 DNA damage Effects 0.000 description 2
- 231100000277 DNA damage Toxicity 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 206010056740 Genital discharge Diseases 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-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
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000000862 absorption spectrum Methods 0.000 description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 238000000423 cell based assay Methods 0.000 description 2
- 210000000170 cell membrane Anatomy 0.000 description 2
- 230000033077 cellular process Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000003271 compound fluorescence assay Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 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
- 229940079593 drug Drugs 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 2
- 238000000799 fluorescence microscopy Methods 0.000 description 2
- 239000000383 hazardous chemical Substances 0.000 description 2
- 238000013537 high throughput screening Methods 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 238000000099 in vitro assay Methods 0.000 description 2
- 238000005462 in vivo assay Methods 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 230000000670 limiting effect Effects 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000000873 masking effect Effects 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003068 molecular probe Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 230000007030 peptide scission Effects 0.000 description 2
- 238000003752 polymerase chain reaction Methods 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 230000011664 signaling Effects 0.000 description 2
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical class [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical class C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 239000003104 tissue culture media Substances 0.000 description 2
- 238000001890 transfection Methods 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- IMZBXSAKACGTPH-UHFFFAOYSA-N (3-oxo-6'-phosphonooxyspiro[2-benzofuran-1,9'-xanthene]-3'-yl) dihydrogen phosphate Chemical compound O1C(=O)C2=CC=CC=C2C21C1=CC=C(OP(O)(O)=O)C=C1OC1=CC(OP(O)(=O)O)=CC=C21 IMZBXSAKACGTPH-UHFFFAOYSA-N 0.000 description 1
- BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 1
- SMJODKZAFKWUJG-UHFFFAOYSA-N 1-(chloromethyl)-3,5-dinitrobenzene Chemical compound [O-][N+](=O)C1=CC(CCl)=CC([N+]([O-])=O)=C1 SMJODKZAFKWUJG-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- SPSSULHKWOKEEL-UHFFFAOYSA-N 2,4,6-trinitrotoluene Chemical compound CC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O SPSSULHKWOKEEL-UHFFFAOYSA-N 0.000 description 1
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
- ZXVONLUNISGICL-UHFFFAOYSA-N 4,6-dinitro-o-cresol Chemical group CC1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O ZXVONLUNISGICL-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- AYXZIZMZXAORLO-UFLZEWODSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid;1-hydroxypyrrolidine-2,5-dione Chemical compound ON1C(=O)CCC1=O.N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 AYXZIZMZXAORLO-UFLZEWODSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 108010001857 Cell Surface Receptors Proteins 0.000 description 1
- 102100025064 Cellular tumor antigen p53 Human genes 0.000 description 1
- 101710150820 Cellular tumor antigen p53 Proteins 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 102000011724 DNA Repair Enzymes Human genes 0.000 description 1
- 108010076525 DNA Repair Enzymes Proteins 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 108090000371 Esterases Proteins 0.000 description 1
- 108010074122 Ferredoxins Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 108700039691 Genetic Promoter Regions Proteins 0.000 description 1
- 108010063907 Glutathione Reductase Proteins 0.000 description 1
- 102100036442 Glutathione reductase, mitochondrial Human genes 0.000 description 1
- 102000003886 Glycoproteins Human genes 0.000 description 1
- 108090000288 Glycoproteins Proteins 0.000 description 1
- 108010001336 Horseradish Peroxidase Proteins 0.000 description 1
- 102000004856 Lectins Human genes 0.000 description 1
- 108090001090 Lectins Proteins 0.000 description 1
- 102000043136 MAP kinase family Human genes 0.000 description 1
- 108091054455 MAP kinase family Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- 102000004316 Oxidoreductases Human genes 0.000 description 1
- 108090000854 Oxidoreductases Proteins 0.000 description 1
- 108091005804 Peptidases Proteins 0.000 description 1
- 239000004365 Protease Substances 0.000 description 1
- 108091027981 Response element Proteins 0.000 description 1
- 102100037486 Reverse transcriptase/ribonuclease H Human genes 0.000 description 1
- 229910006069 SO3H Inorganic materials 0.000 description 1
- 102100033220 Xanthine oxidase Human genes 0.000 description 1
- 108010093894 Xanthine oxidase Proteins 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 102000023732 binding proteins Human genes 0.000 description 1
- 108091008324 binding proteins Proteins 0.000 description 1
- 238000010256 biochemical assay Methods 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 150000001615 biotins Chemical class 0.000 description 1
- NHYXMAKLBXBVEO-UHFFFAOYSA-N bromomethyl acetate Chemical compound CC(=O)OCBr NHYXMAKLBXBVEO-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 230000005779 cell damage Effects 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 208000037887 cell injury Diseases 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 125000003636 chemical group Chemical group 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 239000002299 complementary DNA Substances 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 230000001268 conjugating effect Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000013613 expression plasmid Substances 0.000 description 1
- 239000013604 expression vector Substances 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 238000003818 flash chromatography Methods 0.000 description 1
- 238000003633 gene expression assay Methods 0.000 description 1
- 231100000206 health hazard Toxicity 0.000 description 1
- 238000009396 hybridization Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N hydroxylamine group Chemical group NO AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000012623 in vivo measurement Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052747 lanthanoid Inorganic materials 0.000 description 1
- 239000002523 lectin Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- ZQUVDXMUKIVNOW-UHFFFAOYSA-N n,n'-diphenylmethanimidamide Chemical compound C=1C=CC=CC=1NC=NC1=CC=CC=C1 ZQUVDXMUKIVNOW-UHFFFAOYSA-N 0.000 description 1
- FLMLOZWXXPLHIE-UHFFFAOYSA-N n,n'-diphenylpropane-1,3-diimine;hydrochloride Chemical compound Cl.C=1C=CC=CC=1N=CCC=NC1=CC=CC=C1 FLMLOZWXXPLHIE-UHFFFAOYSA-N 0.000 description 1
- XUZLXCQFXTZASF-UHFFFAOYSA-N nitro(phenyl)methanol Chemical compound [O-][N+](=O)C(O)C1=CC=CC=C1 XUZLXCQFXTZASF-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 150000004713 phosphodiesters Chemical class 0.000 description 1
- 230000002186 photoactivation Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 102000005962 receptors Human genes 0.000 description 1
- 108020003175 receptors Proteins 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 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 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000036962 time dependent Effects 0.000 description 1
- 239000012096 transfection reagent Substances 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000000015 trinitrotoluene Substances 0.000 description 1
- 230000005909 tumor killing Effects 0.000 description 1
- 239000013598 vector Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Images
Classifications
-
- 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
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/08—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups more than three >CH- groups, e.g. polycarbocyanines
-
- 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
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
-
- 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
- G01N33/84—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving inorganic compounds or pH
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Hematology (AREA)
- Organic Chemistry (AREA)
- Biomedical Technology (AREA)
- Molecular Biology (AREA)
- Immunology (AREA)
- Physics & Mathematics (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Analytical Chemistry (AREA)
- Cell Biology (AREA)
- General Health & Medical Sciences (AREA)
- General Physics & Mathematics (AREA)
- Pathology (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Materials By The Use Of Optical Means Adapted For Particular Applications (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0002261.6 | 2000-02-02 | ||
| GBGB0002261.6A GB0002261D0 (en) | 2000-02-02 | 2000-02-02 | Fluorescent detection method & reagent |
| PCT/GB2001/000396 WO2001057237A2 (en) | 2000-02-02 | 2001-02-01 | Methods employing increased dye-fluorescence upon nitroreduction |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007023109A Division JP2007183284A (ja) | 2000-02-02 | 2007-02-01 | 蛍光検出法および試薬 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2003522333A JP2003522333A (ja) | 2003-07-22 |
| JP2003522333A5 JP2003522333A5 (enExample) | 2007-04-12 |
| JP3984475B2 true JP3984475B2 (ja) | 2007-10-03 |
Family
ID=9884728
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001558049A Expired - Fee Related JP3984475B2 (ja) | 2000-02-02 | 2001-02-01 | 蛍光検出法および試薬 |
| JP2007023109A Pending JP2007183284A (ja) | 2000-02-02 | 2007-02-01 | 蛍光検出法および試薬 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007023109A Pending JP2007183284A (ja) | 2000-02-02 | 2007-02-01 | 蛍光検出法および試薬 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US7662973B2 (enExample) |
| EP (2) | EP1252520B1 (enExample) |
| JP (2) | JP3984475B2 (enExample) |
| AT (1) | ATE306669T1 (enExample) |
| AU (2) | AU782381B2 (enExample) |
| CA (1) | CA2399368C (enExample) |
| DE (1) | DE60115205T2 (enExample) |
| DK (1) | DK1252520T3 (enExample) |
| ES (1) | ES2250349T3 (enExample) |
| GB (1) | GB0002261D0 (enExample) |
| IL (1) | IL150947A0 (enExample) |
| WO (1) | WO2001057237A2 (enExample) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1437386A4 (en) * | 2001-09-27 | 2005-01-26 | Fuji Photo Film Co Ltd | ASYMMETRIC CYANINE DYE |
| GB0123856D0 (en) * | 2001-10-05 | 2001-11-28 | Amersham Pharm Biotech Uk Ltd | Method for determining cell cycle position |
| WO2003082988A1 (en) * | 2002-03-29 | 2003-10-09 | The General Hospital Corporation | Nir-fluorescent cyanine dyes, their synthesis and biological use |
| WO2004043417A2 (en) * | 2002-11-14 | 2004-05-27 | L'oreal | Composition for dyeing keratin fibres containing a dye precursor and an enzyme with nitroreductase activity |
| FR2847161B1 (fr) * | 2002-11-14 | 2005-01-07 | Oreal | Composition de teinture des fibres keratiniques contenant un precurseur de colorant et une enzyme a activite nitroreductase et procede mettant en oeuvre cette composition |
| US20070166695A1 (en) * | 2004-02-09 | 2007-07-19 | Novozymes A/S | Method for testing or screening for an enzyme of interest |
| JP4965434B2 (ja) * | 2004-04-23 | 2012-07-04 | ジーイー・ヘルスケア・アクスイェ・セルスカプ | 蛍光共鳴エネルギー移動酵素基質 |
| GB0411993D0 (en) * | 2004-05-28 | 2004-06-30 | Amersham Biosciences Uk Ltd | Method and reagent for measuring nitroreductase enzyme activity |
| US7671218B2 (en) * | 2004-08-13 | 2010-03-02 | Elitech Holdings B.V. | Phosphonate fluorescent dyes and conjugates |
| US7767834B2 (en) * | 2004-08-13 | 2010-08-03 | Elitech Holding B.V. | Phosphonylated fluorescent dyes and conjugates |
| US7445902B2 (en) * | 2004-09-30 | 2008-11-04 | Ge Healthcare Uk Limited | Fluorescent nucleotide analogues |
| GB0505777D0 (en) * | 2005-03-22 | 2005-04-27 | Amersham Biosciences Uk Ltd | Enzyme detection method and reagent |
| EP1954763B1 (en) * | 2005-11-28 | 2016-11-16 | Dako Denmark A/S | Cyanine dyes and methods for detecting a target using said dyes |
| US20100173332A1 (en) * | 2006-09-07 | 2010-07-08 | Auckland Uniservices Limited | Method for the Fluorescent Detection of Nitroreductase Activity Using Nitro-Substituted Aromatic Compounds |
| US20080226160A1 (en) * | 2007-03-12 | 2008-09-18 | Conversion Works, Inc. | Systems and methods for filling light in frames during 2-d to 3-d image conversion |
| US7906106B2 (en) * | 2007-06-27 | 2011-03-15 | General Electric Company | In vivo cell trafficking |
| US8021647B2 (en) * | 2007-06-29 | 2011-09-20 | General Electric Company | In vivo optical imaging |
| JP2013530699A (ja) | 2010-06-15 | 2013-08-01 | セルラー ダイナミクス インターナショナル， インコーポレイテッド | 生物学的応答の調査のための既製の幹細胞モデルの概要 |
| US8828678B2 (en) | 2010-11-16 | 2014-09-09 | Enzo Life Sciences, Inc. | Self-immolative probes for enzyme activity detection |
| EP2732029B1 (en) | 2011-07-11 | 2019-01-16 | FUJIFILM Cellular Dynamics, Inc. | Methods for cell reprogramming and genome engineering |
| CN102516793B (zh) * | 2011-11-22 | 2014-02-05 | 大连理工大学 | 一类双苄基五甲川菁荧光染料、其制备方法及应用 |
| WO2014132137A2 (en) | 2013-03-01 | 2014-09-04 | Université De Genève | Transgenic cell selection |
| US11662312B2 (en) * | 2017-06-27 | 2023-05-30 | Coriolis Pharma Research GmbH | Polysorbate quantification assay |
| JPWO2025211296A1 (enExample) * | 2024-04-05 | 2025-10-09 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1004428A1 (ru) * | 1981-12-30 | 1983-03-15 | Предприятие П/Я Р-6496 | 4-Амино-N-пиразолилнафталимиды в качестве органических люминофоров желто-зеленого свечени |
| US5633158A (en) * | 1991-10-23 | 1997-05-27 | Cancer Research Campaign Technology Limited | Bacterial nitroreductase for the reduction of CB 1954 and analogues thereof to a cytotoxic form |
| US5658751A (en) * | 1993-04-13 | 1997-08-19 | Molecular Probes, Inc. | Substituted unsymmetrical cyanine dyes with selected permeability |
| US5534416A (en) * | 1993-04-13 | 1996-07-09 | Molecular Probes, Inc. | Fluorescent viability assay using cyclic-substituted unsymmetrical cyanine dyes |
| DE69821289T2 (de) * | 1997-06-24 | 2004-11-25 | Eastman Kodak Co. | Sensibilisierungsfarbstoffe für verbesserte Lichtabsorption |
| CA2325050A1 (en) * | 1998-04-06 | 1999-10-14 | Dalhousie University | A novel nitroreductase and therapeutic uses therefor |
| GB9812596D0 (en) * | 1998-06-11 | 1998-08-12 | Amersham Pharm Biotech Uk Ltd | Energy transfer assay method |
-
2000
- 2000-02-02 GB GBGB0002261.6A patent/GB0002261D0/en not_active Ceased
-
2001
- 2001-02-01 WO PCT/GB2001/000396 patent/WO2001057237A2/en not_active Ceased
- 2001-02-01 ES ES01902521T patent/ES2250349T3/es not_active Expired - Lifetime
- 2001-02-01 AU AU30376/01A patent/AU782381B2/en not_active Ceased
- 2001-02-01 AT AT01902521T patent/ATE306669T1/de not_active IP Right Cessation
- 2001-02-01 DK DK01902521T patent/DK1252520T3/da active
- 2001-02-01 IL IL15094701A patent/IL150947A0/xx unknown
- 2001-02-01 JP JP2001558049A patent/JP3984475B2/ja not_active Expired - Fee Related
- 2001-02-01 EP EP01902521A patent/EP1252520B1/en not_active Expired - Lifetime
- 2001-02-01 US US10/182,996 patent/US7662973B2/en not_active Expired - Fee Related
- 2001-02-01 EP EP05021689A patent/EP1698900A1/en not_active Withdrawn
- 2001-02-01 CA CA002399368A patent/CA2399368C/en not_active Expired - Fee Related
- 2001-02-01 DE DE60115205T patent/DE60115205T2/de not_active Expired - Lifetime
-
2005
- 2005-10-14 AU AU2005222569A patent/AU2005222569A1/en not_active Abandoned
-
2007
- 2007-02-01 JP JP2007023109A patent/JP2007183284A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE60115205D1 (de) | 2005-12-29 |
| EP1252520A2 (en) | 2002-10-30 |
| US7662973B2 (en) | 2010-02-16 |
| WO2001057237A2 (en) | 2001-08-09 |
| AU3037601A (en) | 2001-08-14 |
| EP1698900A1 (en) | 2006-09-06 |
| DK1252520T3 (da) | 2006-02-06 |
| JP2003522333A (ja) | 2003-07-22 |
| AU782381B2 (en) | 2005-07-21 |
| CA2399368A1 (en) | 2001-08-09 |
| IL150947A0 (en) | 2003-02-12 |
| AU2005222569A1 (en) | 2005-11-10 |
| WO2001057237A3 (en) | 2002-05-16 |
| JP2007183284A (ja) | 2007-07-19 |
| GB0002261D0 (en) | 2000-03-22 |
| EP1252520B1 (en) | 2005-10-12 |
| DE60115205T2 (de) | 2006-07-20 |
| CA2399368C (en) | 2007-04-10 |
| US20030186348A1 (en) | 2003-10-02 |
| ATE306669T1 (de) | 2005-10-15 |
| ES2250349T3 (es) | 2006-04-16 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP3984475B2 (ja) | 蛍光検出法および試薬 | |
| JP5008044B2 (ja) | エネルギー伝達アッセイ法および試薬 | |
| US8034558B2 (en) | Acridone derivatives as labels for fluorescence detection of target materials | |
| US7964361B2 (en) | Rigidized trimethine cyanine dyes | |
| US6686145B1 (en) | Rigidized trimethine cyanine dyes | |
| Lakowicz | Fluorophores | |
| EP2577309B1 (en) | Targeted probes of cellular physiology | |
| US7335771B2 (en) | Quinacridone derivatives as labelling reagents for fluorescence detection of biological materials | |
| AU2002314302A1 (en) | Quinacridone labelling reagents for fluorescence detection of biological materials | |
| US20030211454A1 (en) | Detection reagent | |
| WO2006100417A1 (en) | Enzyme detection method and reagent | |
| AU2002257963A1 (en) | Acridone derivatives as labels for fluorescence detection of target materials |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20060801 |
|
| A601 | Written request for extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A601 Effective date: 20061101 |
|
| A602 | Written permission of extension of time |
Free format text: JAPANESE INTERMEDIATE CODE: A602 Effective date: 20061109 |
|
| A524 | Written submission of copy of amendment under article 19 pct |
Free format text: JAPANESE INTERMEDIATE CODE: A524 Effective date: 20070201 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20070201 |
|
| A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20070327 |
|
| A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20070522 |
|
| 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: 20070626 |
|
| A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20070706 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20100713 Year of fee payment: 3 |
|
| R150 | Certificate of patent or registration of utility model |
Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110713 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20110713 Year of fee payment: 4 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120713 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20120713 Year of fee payment: 5 |
|
| FPAY | Renewal fee payment (event date is renewal date of database) |
Free format text: PAYMENT UNTIL: 20130713 Year of fee payment: 6 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
| LAPS | Cancellation because of no payment of annual fees |