ES2209492T3 - Colorantes de transferencia energetica. - Google Patents
Colorantes de transferencia energetica.Info
- Publication number
- ES2209492T3 ES2209492T3 ES99943985T ES99943985T ES2209492T3 ES 2209492 T3 ES2209492 T3 ES 2209492T3 ES 99943985 T ES99943985 T ES 99943985T ES 99943985 T ES99943985 T ES 99943985T ES 2209492 T3 ES2209492 T3 ES 2209492T3
- Authority
- ES
- Spain
- Prior art keywords
- dye
- group
- fam
- phe
- energy transfer
- 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
- 238000012546 transfer Methods 0.000 title claims abstract description 131
- 239000003086 colorant Substances 0.000 title 1
- 239000000975 dye Substances 0.000 claims abstract description 249
- 125000004429 atom Chemical group 0.000 claims abstract description 70
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 22
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000000524 functional group Chemical group 0.000 claims abstract description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 21
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 16
- 239000012620 biological material Substances 0.000 claims abstract description 15
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 12
- 239000013077 target material Substances 0.000 claims abstract description 12
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 229910052698 phosphorus Inorganic materials 0.000 claims abstract description 10
- 239000011574 phosphorus Substances 0.000 claims abstract description 10
- 125000005647 linker group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 7
- 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
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
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- 238000000034 method Methods 0.000 claims description 39
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims description 34
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- 229960005190 phenylalanine Drugs 0.000 description 14
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- UFJPAQSLHAGEBL-RRKCRQDMSA-N dITP Chemical compound O1[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)C[C@@H]1N1C(N=CNC2=O)=C2N=C1 UFJPAQSLHAGEBL-RRKCRQDMSA-N 0.000 description 1
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- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
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- 239000005556 hormone Substances 0.000 description 1
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- 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
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- 244000005700 microbiome Species 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 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
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000001863 phosphorothioyl group Chemical group *P(*)(*)=S 0.000 description 1
- 230000001443 photoexcitation Effects 0.000 description 1
- 229920000642 polymer Polymers 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
- 125000006239 protecting group Chemical group 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011002 quantification Methods 0.000 description 1
- 238000003127 radioimmunoassay Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004007 reversed phase HPLC Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
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- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 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 description 1
- 229910052905 tridymite Inorganic materials 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
- 125000002264 triphosphate group Chemical class [H]OP(=O)(O[H])OP(=O)(O[H])OP(=O)(O[H])O* 0.000 description 1
- 238000012800 visualization Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000001834 xanthenyl group Chemical class C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
Classifications
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/53—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)
- Coloring (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Detergent Compositions (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9846998P | 1998-08-31 | 1998-08-31 | |
| US98469P | 1998-08-31 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2209492T3 true ES2209492T3 (es) | 2004-06-16 |
Family
ID=22269416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES99943985T Expired - Lifetime ES2209492T3 (es) | 1998-08-31 | 1999-08-30 | Colorantes de transferencia energetica. |
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) | DE69912139T2 (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 |
| CA2382063A1 (en) * | 1999-09-17 | 2001-03-22 | Shiv Kumar | 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 |
| CA2490961A1 (en) * | 2002-07-01 | 2004-01-08 | Guava Technologies, Inc. | Fluorescent dyes, energy transfer couples and methods |
| EP1439210B1 (en) | 2002-07-18 | 2007-09-05 | Protein Express Co., Ltd. | aminoacyl-tRNA bound to labelled p-aminophenylalanine or tyrosine |
| 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 |
| US7667024B2 (en) | 2003-11-19 | 2010-02-23 | Allelogic Biosciences Corp. | Oligonucleotides labeled with a plurality of fluorophores |
| CA2581174A1 (en) | 2004-09-16 | 2006-03-30 | Applera Corporation | Fluorescent dye compounds, conjugates and uses thereof |
| EP1886145A2 (en) | 2005-05-03 | 2008-02-13 | Applera Corporation | Fluorescent detection system and dye set for use therewith |
| JP2011506673A (ja) | 2007-12-14 | 2011-03-03 | バイオティウム， インコーポレイテッド | 蛍光性化合物 |
| 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 |
| WO2019002295A1 (en) * | 2017-06-27 | 2019-01-03 | Coriolis Pharma Research GmbH | QUANTITATIVE DETERMINATION OF POLYSORBATE |
| MX2023012081A (es) * | 2021-04-13 | 2023-10-25 | Somalogic Operating Co Inc | Nucleosidos modificados. |
| 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 AT AT99943985T patent/ATE252239T1/de not_active IP Right Cessation
- 1999-08-30 EP EP99943985A patent/EP1110088B1/en not_active Expired - Lifetime
- 1999-08-30 ES ES99943985T patent/ES2209492T3/es not_active Expired - Lifetime
- 1999-08-30 JP JP2000567958A patent/JP4659213B2/ja not_active Expired - Fee Related
- 1999-08-30 CA CA2341520A patent/CA2341520C/en not_active Expired - Fee Related
- 1999-08-30 DE DE69912139T patent/DE69912139T2/de not_active Expired - Lifetime
- 1999-08-30 AU AU56970/99A patent/AU767840B2/en not_active Ceased
- 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
Also Published As
| Publication number | Publication date |
|---|---|
| GB2341189B (en) | 2001-06-13 |
| WO2000013026A1 (en) | 2000-03-09 |
| DE69912139T2 (de) | 2004-07-22 |
| AU767840B2 (en) | 2003-11-27 |
| DE29915165U1 (de) | 2000-03-02 |
| WO2000013026A9 (en) | 2000-08-17 |
| GB9920022D0 (en) | 1999-10-27 |
| ATE252239T1 (de) | 2003-11-15 |
| GB2341189A (en) | 2000-03-08 |
| EP1110088B1 (en) | 2003-10-15 |
| JP4659213B2 (ja) | 2011-03-30 |
| CA2341520C (en) | 2010-11-02 |
| EP1110088A1 (en) | 2001-06-27 |
| JP2002523783A (ja) | 2002-07-30 |
| DE69912139D1 (de) | 2003-11-20 |
| AU5697099A (en) | 2000-03-21 |
| CA2341520A1 (en) | 2000-03-09 |
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