JPH08505121A - 分子プローブとしての４，７−ジクロロフルオレセイン染料 - Google Patents
分子プローブとしての４，７−ジクロロフルオレセイン染料Info
- Publication number
- JPH08505121A JPH08505121A JP6507415A JP50741594A JPH08505121A JP H08505121 A JPH08505121 A JP H08505121A JP 6507415 A JP6507415 A JP 6507415A JP 50741594 A JP50741594 A JP 50741594A JP H08505121 A JPH08505121 A JP H08505121A
- Authority
- JP
- Japan
- Prior art keywords
- dye
- dichlorofluorescein
- group
- dichloro
- dyes
- 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.)
- Withdrawn
Links
- 239000003068 molecular probe Substances 0.000 title description 4
- 125000000524 functional group Chemical group 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 12
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 150000002540 isothiocyanates Chemical class 0.000 claims description 5
- 150000008300 phosphoramidites Chemical class 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- CQYYGCVORGQMEQ-UHFFFAOYSA-N 2,5-dioxopyrrolidine-1-carboxylic acid Chemical compound OC(=O)N1C(=O)CCC1=O CQYYGCVORGQMEQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 28
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- 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 abstract description 6
- 239000000975 dye Substances 0.000 description 69
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- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- 230000000295 complement effect Effects 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
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- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
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- 125000001424 substituent group Chemical group 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
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- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/78—Ring systems having three or more relevant rings
- C07D311/80—Dibenzopyrans; Hydrogenated dibenzopyrans
- C07D311/82—Xanthenes
-
- 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
- C09B11/06—Hydroxy derivatives of triarylmethanes in which at least one OH group is bound to an aryl nucleus and their ethers or esters
- C09B11/08—Phthaleins; Phenolphthaleins; Fluorescein
-
- 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
- C12Q1/6869—Methods for sequencing
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biochemistry (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Zoology (AREA)
- Analytical Chemistry (AREA)
- Immunology (AREA)
- Microbiology (AREA)
- Biophysics (AREA)
- Physics & Mathematics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Pyrane Compounds (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93981392A | 1992-09-03 | 1992-09-03 | |
| US939,813 | 1992-09-03 | ||
| PCT/US1993/008227 WO1994005688A1 (en) | 1992-09-03 | 1993-09-01 | 4,7-dichlorofluorescein dyes as molecular probes |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| JP2004024814A Division JP4554224B2 (ja) | 1992-09-03 | 2004-01-30 | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH08505121A true JPH08505121A (ja) | 1996-06-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP6507415A Withdrawn JPH08505121A (ja) | 1992-09-03 | 1993-09-01 | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
| JP2004024814A Expired - Lifetime JP4554224B2 (ja) | 1992-09-03 | 2004-01-30 | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
| JP2008177253A Withdrawn JP2009000119A (ja) | 1992-09-03 | 2008-07-07 | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
| JP2011054840A Withdrawn JP2011162548A (ja) | 1992-09-03 | 2011-03-11 | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004024814A Expired - Lifetime JP4554224B2 (ja) | 1992-09-03 | 2004-01-30 | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
| JP2008177253A Withdrawn JP2009000119A (ja) | 1992-09-03 | 2008-07-07 | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
| JP2011054840A Withdrawn JP2011162548A (ja) | 1992-09-03 | 2011-03-11 | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
Country Status (4)
| Country | Link |
|---|---|
| EP (1) | EP0658167B1 (enExample) |
| JP (4) | JPH08505121A (enExample) |
| DE (1) | DE69324494T2 (enExample) |
| WO (1) | WO1994005688A1 (enExample) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2001508494A (ja) * | 1997-09-23 | 2001-06-26 | モレキュラー プローブス インコーポレーテッド | スルホン化キサンテン誘導体 |
| JP2004043819A (ja) * | 1996-05-03 | 2004-02-12 | Applera Corp | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2004225049A (ja) * | 1992-09-03 | 2004-08-12 | Applera Corp | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5658751A (en) * | 1993-04-13 | 1997-08-19 | Molecular Probes, Inc. | Substituted unsymmetrical cyanine dyes with selected permeability |
| US6020481A (en) | 1996-04-01 | 2000-02-01 | The Perkin-Elmer Corporation | Asymmetric benzoxanthene dyes |
| US6162931A (en) * | 1996-04-12 | 2000-12-19 | Molecular Probes, Inc. | Fluorinated xanthene derivatives |
| WO1997040033A1 (en) * | 1996-04-19 | 1997-10-30 | Lexigen Pharmaceuticals Corp. | Inhibition of the binding of human ige to its receptor by tetracyclic compounds for the alleviation of ige-mediated immune response |
| US7825237B2 (en) | 1996-05-03 | 2010-11-02 | Applied Biosystems, Llc | Oligonucleotides and analogs labeled with energy transfer dyes |
| US7388092B2 (en) | 1996-05-03 | 2008-06-17 | Applera Corporation | Oligonucleotides and analogs labeled with energy transfer dyes |
| US5945526A (en) | 1996-05-03 | 1999-08-31 | Perkin-Elmer Corporation | Energy transfer dyes with enhanced fluorescence |
| US5847162A (en) * | 1996-06-27 | 1998-12-08 | The Perkin Elmer Corporation | 4, 7-Dichlororhodamine dyes |
| US6080852A (en) | 1996-06-27 | 2000-06-27 | The Perkin-Elmer Corporation | 4,7-dichlororhodamine dyes |
| US6017712A (en) * | 1996-06-27 | 2000-01-25 | Lee; Linda | 4,7-dichlororhodamine dyes |
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-
1993
- 1993-09-01 WO PCT/US1993/008227 patent/WO1994005688A1/en not_active Ceased
- 1993-09-01 JP JP6507415A patent/JPH08505121A/ja not_active Withdrawn
- 1993-09-01 DE DE69324494T patent/DE69324494T2/de not_active Expired - Lifetime
- 1993-09-01 EP EP93920447A patent/EP0658167B1/en not_active Expired - Lifetime
-
2004
- 2004-01-30 JP JP2004024814A patent/JP4554224B2/ja not_active Expired - Lifetime
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2008
- 2008-07-07 JP JP2008177253A patent/JP2009000119A/ja not_active Withdrawn
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2011
- 2011-03-11 JP JP2011054840A patent/JP2011162548A/ja not_active Withdrawn
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2004225049A (ja) * | 1992-09-03 | 2004-08-12 | Applera Corp | 分子プローブとしての４，７−ジクロロフルオレセイン染料 |
| JP2004043819A (ja) * | 1996-05-03 | 2004-02-12 | Applera Corp | 硬質リンカ―を有するエネルギ―転移色素 |
| JP2001508494A (ja) * | 1997-09-23 | 2001-06-26 | モレキュラー プローブス インコーポレーテッド | スルホン化キサンテン誘導体 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE69324494D1 (de) | 1999-05-20 |
| JP2004225049A (ja) | 2004-08-12 |
| EP0658167B1 (en) | 1999-04-14 |
| DE69324494T2 (de) | 1999-09-23 |
| JP2011162548A (ja) | 2011-08-25 |
| JP2009000119A (ja) | 2009-01-08 |
| EP0658167A1 (en) | 1995-06-21 |
| JP4554224B2 (ja) | 2010-09-29 |
| WO1994005688A1 (en) | 1994-03-17 |
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