JP2004508448A - オキサジン誘導体 - Google Patents
オキサジン誘導体 Download PDFInfo
- Publication number
- JP2004508448A JP2004508448A JP2002525681A JP2002525681A JP2004508448A JP 2004508448 A JP2004508448 A JP 2004508448A JP 2002525681 A JP2002525681 A JP 2002525681A JP 2002525681 A JP2002525681 A JP 2002525681A JP 2004508448 A JP2004508448 A JP 2004508448A
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- JP
- Japan
- Prior art keywords
- oxazine derivative
- oxazine
- derivative according
- derivative
- studied
- 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.)
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- 150000004893 oxazines Chemical class 0.000 title claims abstract description 89
- 239000000463 material Substances 0.000 claims abstract description 31
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- -1 aryldiazo Chemical group 0.000 claims description 70
- 150000002148 esters Chemical class 0.000 claims description 28
- 238000002372 labelling Methods 0.000 claims description 21
- 108090000623 proteins and genes Proteins 0.000 claims description 21
- 102000004169 proteins and genes Human genes 0.000 claims description 21
- 239000000126 substance Substances 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 20
- 239000003550 marker Substances 0.000 claims description 17
- 239000002253 acid Substances 0.000 claims description 16
- 229910052736 halogen Inorganic materials 0.000 claims description 15
- 239000012620 biological material Substances 0.000 claims description 14
- 150000008300 phosphoramidites Chemical class 0.000 claims description 14
- 150000001412 amines Chemical class 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 11
- 239000011859 microparticle Substances 0.000 claims description 11
- 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 claims description 10
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- 150000003839 salts Chemical class 0.000 claims description 9
- 150000008065 acid anhydrides Chemical class 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 150000004820 halides Chemical class 0.000 claims description 8
- 150000003949 imides Chemical class 0.000 claims description 8
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- 150000002500 ions Chemical class 0.000 claims description 7
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- XSYUPRQVAHJETO-WPMUBMLPSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-3-(1h-imidazol-5-yl)propanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]amino]-3-(1h-imidazol-5-yl)propanoyl]amino]-3-(1h-imidaz Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1NC=NC=1)C(O)=O)C1=CN=CN1 XSYUPRQVAHJETO-WPMUBMLPSA-N 0.000 claims description 3
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- BGRWYRAHAFMIBJ-UHFFFAOYSA-N diisopropylcarbodiimide Natural products CC(C)NC(=O)NC(C)C BGRWYRAHAFMIBJ-UHFFFAOYSA-N 0.000 claims description 2
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- 125000002723 alicyclic group Chemical group 0.000 claims 1
- 210000000170 cell membrane Anatomy 0.000 claims 1
- XFMJUIKWKVJNDY-UHFFFAOYSA-N diethoxyphosphorylsulfanylmethylbenzene Chemical compound CCOP(=O)(OCC)SCC1=CC=CC=C1 XFMJUIKWKVJNDY-UHFFFAOYSA-N 0.000 claims 1
- 238000011835 investigation Methods 0.000 claims 1
- UQRSIYQDOPDZHV-UHFFFAOYSA-N oxido-oxo-thiocyanatophosphanium Chemical compound C(#N)SP(=O)=O UQRSIYQDOPDZHV-UHFFFAOYSA-N 0.000 claims 1
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
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- BCHZICNRHXRCHY-UHFFFAOYSA-N 2h-oxazine Chemical compound N1OC=CC=C1 BCHZICNRHXRCHY-UHFFFAOYSA-N 0.000 description 9
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- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
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- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 229910000906 Bronze Inorganic materials 0.000 description 1
- CQTKUEOHELQPQK-UHFFFAOYSA-N C(=O)(OC(C)(C)C)NCCCCCN.C(C)(C)(C)OC(=O)C(CCN)CCN Chemical compound C(=O)(OC(C)(C)C)NCCCCCN.C(C)(C)(C)OC(=O)C(CCN)CCN CQTKUEOHELQPQK-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- LEVWYRKDKASIDU-IMJSIDKUSA-N L-cystine Chemical compound [O-]C(=O)[C@@H]([NH3+])CSSC[C@H]([NH3+])C([O-])=O LEVWYRKDKASIDU-IMJSIDKUSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000003875 Wang resin Substances 0.000 description 1
- NERFNHBZJXXFGY-UHFFFAOYSA-N [4-[(4-methylphenyl)methoxy]phenyl]methanol Chemical compound C1=CC(C)=CC=C1COC1=CC=C(CO)C=C1 NERFNHBZJXXFGY-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 150000001449 anionic compounds Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000010974 bronze Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000005591 charge neutralization Effects 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- KUNSUQLRTQLHQQ-UHFFFAOYSA-N copper tin Chemical compound [Cu].[Sn] KUNSUQLRTQLHQQ-UHFFFAOYSA-N 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
- 229960003067 cystine Drugs 0.000 description 1
- 239000000412 dendrimer Substances 0.000 description 1
- 229920000736 dendritic polymer Polymers 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- INBXHFRQITUXGJ-UHFFFAOYSA-N diazidoazaniumylideneazanide Chemical group [N-]=[N+]=N[N+](=[N-])N=[N+]=[N-] INBXHFRQITUXGJ-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000004043 dyeing Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 230000009881 electrostatic interaction Effects 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 230000005496 eutectics Effects 0.000 description 1
- 238000002270 exclusion chromatography Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 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 1
- 238000001917 fluorescence detection Methods 0.000 description 1
- 238000002875 fluorescence polarization Methods 0.000 description 1
- 238000001506 fluorescence spectroscopy Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229920000578 graft copolymer Polymers 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 238000013537 high throughput screening Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000007901 in situ hybridization Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 229910001412 inorganic anion Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 210000004379 membrane Anatomy 0.000 description 1
- BWWSSJKXSQGUGW-UHFFFAOYSA-N methyl 2-(3-hydroxy-n-methylanilino)propanoate Chemical compound COC(=O)C(C)N(C)C1=CC=CC(O)=C1 BWWSSJKXSQGUGW-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- CMWYAOXYQATXSI-UHFFFAOYSA-N n,n-dimethylformamide;piperidine Chemical compound CN(C)C=O.C1CCNCC1 CMWYAOXYQATXSI-UHFFFAOYSA-N 0.000 description 1
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
- AYGYHGXUJBFUJU-UHFFFAOYSA-N n-[2-(prop-2-enoylamino)ethyl]prop-2-enamide Chemical compound C=CC(=O)NCCNC(=O)C=C AYGYHGXUJBFUJU-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- SXADIBFZNXBEGI-UHFFFAOYSA-N phosphoramidous acid Chemical group NP(O)O SXADIBFZNXBEGI-UHFFFAOYSA-N 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
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- 230000008092 positive effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011160 research 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
- 238000004621 scanning probe microscopy Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
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- 241000894007 species Species 0.000 description 1
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- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 150000003732 xanthenes Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
-
- 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
- C09B19/00—Oxazine dyes
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—Immunoassay; Biospecific binding assay; Materials therefor
- G01N33/531—Production of immunochemical test materials
- G01N33/532—Production of labelled immunochemicals
- G01N33/533—Production of labelled immunochemicals with fluorescent label
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Immunology (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Urology & Nephrology (AREA)
- Molecular Biology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Biochemistry (AREA)
- General Physics & Mathematics (AREA)
- Cell Biology (AREA)
- Food Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Physics & Mathematics (AREA)
- Analytical Chemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Microbiology (AREA)
- Pathology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Plural Heterocyclic Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Flanged Joints, Insulating Joints, And Other Joints (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP00119292 | 2000-09-06 | ||
| EP00127005A EP1213328A1 (de) | 2000-12-08 | 2000-12-08 | Oxazinderivate |
| PCT/EP2001/010236 WO2002020670A1 (de) | 2000-09-06 | 2001-09-05 | Oxazinderivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2004508448A true JP2004508448A (ja) | 2004-03-18 |
| JP2004508448A5 JP2004508448A5 (enExample) | 2008-10-09 |
Family
ID=26071369
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002525681A Pending JP2004508448A (ja) | 2000-09-06 | 2001-09-05 | オキサジン誘導体 |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US7101999B2 (enExample) |
| EP (2) | EP1317511B1 (enExample) |
| JP (1) | JP2004508448A (enExample) |
| AT (2) | ATE287430T1 (enExample) |
| DE (1) | DE50105139D1 (enExample) |
| WO (1) | WO2002020670A1 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009107448A1 (ja) * | 2008-02-29 | 2009-09-03 | 独立行政法人理化学研究所 | チオールの検出方法 |
| JP7023604B2 (ja) | 2013-10-31 | 2022-02-22 | ベス・イスラエル・ディーコネス・メディカル・センター，インコーポレイテッド | 近赤外蛍光造影バイオイメージング剤及びその使用方法 |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE287430T1 (de) | 2000-09-06 | 2005-02-15 | Evotec Ag | Oxazinderivate |
| DE10212960A1 (de) * | 2002-03-22 | 2003-10-23 | Gnothis Holding Sa Ecublens | Verwendung von Oxazin-Farbstoffen als Markierungsgruppen für die Einzelmolekülanalyse |
| MXPA06001891A (es) * | 2003-08-18 | 2006-05-17 | Novartis Ag | Derivados de 3h-fenoxazina adecuados como agentes para la formacion de imagenes casi-infrarrojas, preparacion y uso de los mismos. |
| US7326258B2 (en) | 2004-06-18 | 2008-02-05 | L'oreal S.A. | Compositions comprising hydroxyalkyl direct dyes, implementation processes and uses thereof |
| EP1607393A1 (fr) * | 2004-06-18 | 2005-12-21 | L'oreal | Compositions comprenant des colorants directs hydroxyalkyles, procédés de mise en oeuvre et utilisations. |
| US20120010404A1 (en) * | 2008-06-10 | 2012-01-12 | Sigma-Aldrich Co. | Oxazine dyes with improved aqueous solubility |
| GB0903348D0 (en) * | 2009-02-27 | 2009-04-08 | Pharmalucia Ltd | Compounds and methods relating thereto |
| CN103044947B (zh) * | 2013-01-09 | 2014-05-21 | 大连理工大学 | 一类尼罗蓝荧光染料，其制备方法及应用 |
| WO2015066296A1 (en) | 2013-10-31 | 2015-05-07 | Beth Israel Deaconess Medical Center | Near-infrared fluorescent nerve contrast agents and methods of use thereof |
| US12440585B2 (en) | 2023-09-12 | 2025-10-14 | Curadel Surgical Innovations, Inc. | Zwitterionic metal chelators |
Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS493928A (enExample) * | 1972-04-25 | 1974-01-14 | ||
| JPS50123133A (enExample) * | 1974-03-12 | 1975-09-27 | ||
| GB1410815A (en) * | 1972-12-20 | 1975-10-22 | Ici Ltd | Oxazine dyestuffs |
| US4622395A (en) * | 1984-10-01 | 1986-11-11 | Minnesota Mining And Manufacturing Company | Phenoxazine and phenothiazine dyes and leuco forms thereof |
| US4714763A (en) * | 1985-07-11 | 1987-12-22 | Viomedics Inc. | Novel oxazine-ureas and thiazine urea chromophors as fluorescent labels |
| US4780535A (en) * | 1986-11-21 | 1988-10-25 | Spyros Theodoropulos | Maleic and phthalic diamides |
| JPH02796A (ja) * | 1987-12-24 | 1990-01-05 | Applied Biosystems Inc | 固体支持体上にアンモニアに不安定な基で標識化されたオリゴヌクレオチド類の合成方法 |
| US4962197A (en) * | 1988-02-12 | 1990-10-09 | Rowland Institute For Science | Photo-inactivation of cancer cells |
| DE4023212A1 (de) * | 1989-07-28 | 1991-02-07 | Fzb Biotechnik Berlin Gmbh | Neue fluorophorderivate, verfahren zu ihrer herstellung und deren verwendung zur herstellung neuartiger fluoreszenzmarkierter nucleoside, nucleotide und oligonucleotide |
| JPH05170752A (ja) * | 1991-04-26 | 1993-07-09 | Takeda Chem Ind Ltd | ３，７−ビス（ジ置換アミノ）フェノチアジン誘導体およびその製造法 |
| JPH093343A (ja) * | 1995-06-10 | 1997-01-07 | Boehringer Mannheim Gmbh | 新規なオキサジン染料およびその染料の蛍光マーカーとしての使用 |
| WO1999007793A1 (en) * | 1997-08-04 | 1999-02-18 | Nycomed Amersham Plc | Dye intermediate and method to manufacture dyes |
| JP2000504755A (ja) * | 1996-02-05 | 2000-04-18 | アマーシャム・ファーマシア・バイオテック・ユーケイ・リミテッド | ベンゾフェノキサジン染料 |
| US6140500A (en) * | 1999-09-03 | 2000-10-31 | Pe Corporation | Red-emitting [8,9]benzophenoxazine nucleic acid dyes and methods for their use |
| JP2003531946A (ja) * | 2000-05-02 | 2003-10-28 | アプレラ コーポレイション | スルホン化［８，９］ベンゾフェノキサジン色素およびそれらの標識結合体の使用 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE287040C (enExample) | ||||
| US1488609A (en) * | 1924-04-01 | murphy | ||
| IL91673A0 (en) | 1988-09-20 | 1990-04-29 | Us Health | Method for tagging an oligodeoxynucleotide |
| GB9024775D0 (en) * | 1990-11-14 | 1991-01-02 | Axis Research | Chemical compounds |
| US5344928A (en) * | 1991-04-26 | 1994-09-06 | Takeda Chemical Industries, Ltd. | Phenothiazine derivatives, their production and use |
| DE59309805D1 (de) | 1992-12-15 | 1999-11-04 | Ciba Sc Holding Ag | Oxazinfarbstoffe, Verfahren zu deren Herstellung und deren Verwendung |
| US5656759A (en) | 1993-07-22 | 1997-08-12 | Sony Corporation | Hydrophobic cationic dye compounds |
| US5792389A (en) * | 1993-10-27 | 1998-08-11 | United States Of America | Water soluble laser dyes |
| US5620842A (en) * | 1995-03-29 | 1997-04-15 | Becton Dickinson And Company | Determination of the number of fluorescent molecules on calibration beads for flow cytometry |
| FR2780791B1 (fr) | 1998-07-03 | 2000-09-01 | Bio Merieux | Methode de depistage ou de diagnostic d'un adenocarcinome ou d'une pathologie benigne de la prostate et procede de mise en oeuvre |
| US6727356B1 (en) | 1999-12-08 | 2004-04-27 | Epoch Pharmaceuticals, Inc. | Fluorescent quenching detection reagents and methods |
| ATE287430T1 (de) | 2000-09-06 | 2005-02-15 | Evotec Ag | Oxazinderivate |
| ES2245995T3 (es) * | 2000-11-16 | 2006-02-01 | F. Hoffmann-La Roche Ag | Pares de colorantes para mediciones de transferencia de energia de fluorescencia-resonancia (fret). |
-
2001
- 2001-09-05 AT AT01978341T patent/ATE287430T1/de not_active IP Right Cessation
- 2001-09-05 JP JP2002525681A patent/JP2004508448A/ja active Pending
- 2001-09-05 EP EP01978341A patent/EP1317511B1/de not_active Expired - Lifetime
- 2001-09-05 EP EP05000174A patent/EP1535967B1/de not_active Expired - Lifetime
- 2001-09-05 WO PCT/EP2001/010236 patent/WO2002020670A1/de not_active Ceased
- 2001-09-05 US US10/363,813 patent/US7101999B2/en not_active Expired - Fee Related
- 2001-09-05 DE DE50105139T patent/DE50105139D1/de not_active Expired - Lifetime
- 2001-09-05 AT AT05000174T patent/ATE518913T1/de active
-
2006
- 2006-04-20 US US11/379,433 patent/US20060240455A1/en not_active Abandoned
Patent Citations (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS493928A (enExample) * | 1972-04-25 | 1974-01-14 | ||
| GB1410815A (en) * | 1972-12-20 | 1975-10-22 | Ici Ltd | Oxazine dyestuffs |
| JPS50123133A (enExample) * | 1974-03-12 | 1975-09-27 | ||
| US4622395A (en) * | 1984-10-01 | 1986-11-11 | Minnesota Mining And Manufacturing Company | Phenoxazine and phenothiazine dyes and leuco forms thereof |
| US4714763A (en) * | 1985-07-11 | 1987-12-22 | Viomedics Inc. | Novel oxazine-ureas and thiazine urea chromophors as fluorescent labels |
| US4780535A (en) * | 1986-11-21 | 1988-10-25 | Spyros Theodoropulos | Maleic and phthalic diamides |
| JPH02796A (ja) * | 1987-12-24 | 1990-01-05 | Applied Biosystems Inc | 固体支持体上にアンモニアに不安定な基で標識化されたオリゴヌクレオチド類の合成方法 |
| US4962197A (en) * | 1988-02-12 | 1990-10-09 | Rowland Institute For Science | Photo-inactivation of cancer cells |
| DE4023212A1 (de) * | 1989-07-28 | 1991-02-07 | Fzb Biotechnik Berlin Gmbh | Neue fluorophorderivate, verfahren zu ihrer herstellung und deren verwendung zur herstellung neuartiger fluoreszenzmarkierter nucleoside, nucleotide und oligonucleotide |
| JPH05170752A (ja) * | 1991-04-26 | 1993-07-09 | Takeda Chem Ind Ltd | ３，７−ビス（ジ置換アミノ）フェノチアジン誘導体およびその製造法 |
| JPH093343A (ja) * | 1995-06-10 | 1997-01-07 | Boehringer Mannheim Gmbh | 新規なオキサジン染料およびその染料の蛍光マーカーとしての使用 |
| JP2000504755A (ja) * | 1996-02-05 | 2000-04-18 | アマーシャム・ファーマシア・バイオテック・ユーケイ・リミテッド | ベンゾフェノキサジン染料 |
| WO1999007793A1 (en) * | 1997-08-04 | 1999-02-18 | Nycomed Amersham Plc | Dye intermediate and method to manufacture dyes |
| US6140500A (en) * | 1999-09-03 | 2000-10-31 | Pe Corporation | Red-emitting [8,9]benzophenoxazine nucleic acid dyes and methods for their use |
| JP2003531946A (ja) * | 2000-05-02 | 2003-10-28 | アプレラ コーポレイション | スルホン化［８，９］ベンゾフェノキサジン色素およびそれらの標識結合体の使用 |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009107448A1 (ja) * | 2008-02-29 | 2009-09-03 | 独立行政法人理化学研究所 | チオールの検出方法 |
| US8187825B2 (en) | 2008-02-29 | 2012-05-29 | Riken | Thiol detection method |
| JP5585960B2 (ja) * | 2008-02-29 | 2014-09-10 | 独立行政法人理化学研究所 | チオールの検出方法 |
| JP7023604B2 (ja) | 2013-10-31 | 2022-02-22 | ベス・イスラエル・ディーコネス・メディカル・センター，インコーポレイテッド | 近赤外蛍光造影バイオイメージング剤及びその使用方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP1317511B1 (de) | 2005-01-19 |
| ATE518913T1 (de) | 2011-08-15 |
| ATE287430T1 (de) | 2005-02-15 |
| US20060240455A1 (en) | 2006-10-26 |
| DE50105139D1 (en) | 2005-02-24 |
| EP1317511A1 (de) | 2003-06-11 |
| EP1535967A1 (de) | 2005-06-01 |
| EP1535967B1 (de) | 2011-08-03 |
| US7101999B2 (en) | 2006-09-05 |
| US20040029837A1 (en) | 2004-02-12 |
| WO2002020670A1 (de) | 2002-03-14 |
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