SE519116C2 - Syntes och utvärdering av nya cyaninfärgämnen som binder till minor groove - Google Patents
Syntes och utvärdering av nya cyaninfärgämnen som binder till minor grooveInfo
- Publication number
- SE519116C2 SE519116C2 SE0101651A SE0101651A SE519116C2 SE 519116 C2 SE519116 C2 SE 519116C2 SE 0101651 A SE0101651 A SE 0101651A SE 0101651 A SE0101651 A SE 0101651A SE 519116 C2 SE519116 C2 SE 519116C2
- Authority
- SE
- Sweden
- Prior art keywords
- bind
- dna
- cyanine dyes
- synthesis
- binding
- Prior art date
Links
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 title claims abstract 5
- 239000000975 dye Substances 0.000 title abstract description 28
- 230000015572 biosynthetic process Effects 0.000 title description 7
- 238000003786 synthesis reaction Methods 0.000 title description 6
- 238000011156 evaluation Methods 0.000 title 1
- 239000000523 sample Substances 0.000 claims description 11
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 3
- 238000007899 nucleic acid hybridization Methods 0.000 claims 1
- 150000001720 carbohydrates Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 108020004414 DNA Proteins 0.000 description 21
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical compound [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 13
- 239000000126 substance Substances 0.000 description 9
- 102000053602 DNA Human genes 0.000 description 6
- FWBHETKCLVMNFS-UHFFFAOYSA-N 4',6-Diamino-2-phenylindol Chemical compound C1=CC(C(=N)N)=CC=C1C1=CC2=CC=C(C(N)=N)C=C2N1 FWBHETKCLVMNFS-UHFFFAOYSA-N 0.000 description 4
- 108020004682 Single-Stranded DNA Proteins 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 238000009396 hybridization Methods 0.000 description 4
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000013461 design Methods 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- 230000002687 intercalation Effects 0.000 description 3
- 238000009830 intercalation Methods 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- -1 BODIPY Chemical compound 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 230000000295 complement effect Effects 0.000 description 2
- 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 2
- 239000000138 intercalating agent Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 150000003248 quinolines Chemical class 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- VYFQTZSQRZCAGR-UHFFFAOYSA-N 3-methyl-1,3-benzothiazol-2-imine Chemical compound C1=CC=C2SC(=N)N(C)C2=C1 VYFQTZSQRZCAGR-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 108020004711 Nucleic Acid Probes Proteins 0.000 description 1
- 108091028043 Nucleic acid sequence Proteins 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- MZZINWWGSYUHGU-UHFFFAOYSA-J ToTo-1 Chemical compound [I-].[I-].[I-].[I-].C12=CC=CC=C2C(C=C2N(C3=CC=CC=C3S2)C)=CC=[N+]1CCC[N+](C)(C)CCC[N+](C)(C)CCC[N+](C1=CC=CC=C11)=CC=C1C=C1N(C)C2=CC=CC=C2S1 MZZINWWGSYUHGU-UHFFFAOYSA-J 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 description 1
- 229940027991 antiseptic and disinfectant quinoline derivative Drugs 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 244000309466 calf Species 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000001413 cellular effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 230000005595 deprotonation Effects 0.000 description 1
- 238000010537 deprotonation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005421 electrostatic potential Methods 0.000 description 1
- 238000000295 emission spectrum Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000002372 labelling Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002853 nucleic acid probe Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000004853 protein function Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 210000001541 thymus gland Anatomy 0.000 description 1
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
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
-
- 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
- C12Q1/6844—Nucleic acid amplification reactions
- C12Q1/686—Polymerase chain reaction [PCR]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Molecular Biology (AREA)
- Physics & Mathematics (AREA)
- Biotechnology (AREA)
- Biophysics (AREA)
- Analytical Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Plural Heterocyclic Compounds (AREA)
- Thermal Transfer Or Thermal Recording In General (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Polyesters Or Polycarbonates (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0101651A SE519116C2 (sv) | 2001-05-10 | 2001-05-10 | Syntes och utvärdering av nya cyaninfärgämnen som binder till minor groove |
| DE60203005T DE60203005T2 (de) | 2001-05-10 | 2002-05-10 | Synthese und ausprüfung von neuen cyaninfarbstoffen als an die kleine furche von poly(dadt)2 bindende stoffe |
| AT02731046T ATE289337T1 (de) | 2001-05-10 | 2002-05-10 | Synthese und ausprüfung von neuen cyaninfarbstoffen als an die kleine furche von poly(da-dt)2 bindende stoffe |
| PCT/SE2002/000860 WO2002090443A1 (en) | 2001-05-10 | 2002-05-10 | Synthesis and evaluation of new cyanine dyes as minor groove of [poly(da-dt)]2 binders |
| JP2002587511A JP2004536900A (ja) | 2001-05-10 | 2002-05-10 | ［ポリ（ｄＡ−ｄＴ）］２バインダーの小溝としての新規なシアニン染料の合成と評価 |
| HK04103781.3A HK1060895B (en) | 2001-05-10 | 2002-05-10 | Synthesis and evaluation of new cyanine dyes as minor groove of poly(da-dt)) 2 binders |
| CA002446982A CA2446982C (en) | 2001-05-10 | 2002-05-10 | Synthesis and evaluation of new cyanine dyes as minor groove of [poly(da-dt)]2 binders |
| EP02731046A EP1390433B1 (en) | 2001-05-10 | 2002-05-10 | Synthesis and evaluation of new cyanine dyes as minor groove of poly(da-dt)] 2 binders |
| AU2002303054A AU2002303054B2 (en) | 2001-05-10 | 2002-05-10 | Synthesis and evaluation of new cyanine dyes as minor groove of [POLY(DA-DT)]2 binders |
| US10/605,961 US7378240B2 (en) | 2001-05-10 | 2003-11-10 | Synthesis and evaluation of new cyanine dyes as minor groove of [POLY(dA-dT)]2 binders |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0101651A SE519116C2 (sv) | 2001-05-10 | 2001-05-10 | Syntes och utvärdering av nya cyaninfärgämnen som binder till minor groove |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| SE0101651D0 SE0101651D0 (sv) | 2001-05-10 |
| SE0101651L SE0101651L (sv) | 2002-11-11 |
| SE519116C2 true SE519116C2 (sv) | 2003-01-14 |
Family
ID=20284061
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE0101651A SE519116C2 (sv) | 2001-05-10 | 2001-05-10 | Syntes och utvärdering av nya cyaninfärgämnen som binder till minor groove |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US7378240B2 (https=) |
| EP (1) | EP1390433B1 (https=) |
| JP (1) | JP2004536900A (https=) |
| AT (1) | ATE289337T1 (https=) |
| AU (1) | AU2002303054B2 (https=) |
| CA (1) | CA2446982C (https=) |
| DE (1) | DE60203005T2 (https=) |
| SE (1) | SE519116C2 (https=) |
| WO (1) | WO2002090443A1 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE519116C2 (sv) | 2001-05-10 | 2003-01-14 | Lightup Technologies Ab | Syntes och utvärdering av nya cyaninfärgämnen som binder till minor groove |
| US7776567B2 (en) | 2005-03-17 | 2010-08-17 | Biotium, Inc. | Dimeric and trimeric nucleic acid dyes, and associated systems and methods |
| US7601498B2 (en) * | 2005-03-17 | 2009-10-13 | Biotium, Inc. | Methods of using dyes in association with nucleic acid staining or detection and associated technology |
| JP5306811B2 (ja) * | 2005-05-11 | 2013-10-02 | ライフ テクノロジーズ コーポレーション | ２本鎖ｄｎａへの高い選択性を有する蛍光化学物質及びそれらの使用 |
| US9433700B2 (en) | 2009-04-27 | 2016-09-06 | Medibeacon Inc. | Tissue sealant compositions, vascular closure devices, and uses thereof |
| US8877437B1 (en) | 2009-12-23 | 2014-11-04 | Biotium, Inc. | Methods of using dyes in association with nucleic acid staining or detection |
| CN105765066B (zh) * | 2013-11-29 | 2018-12-14 | 宝生物工程株式会社 | 用于定量腺伴随病毒的方法 |
| CN108165045B (zh) * | 2018-01-15 | 2021-03-16 | 广东工业大学 | 核酸染料化合物及其制备方法和应用 |
| WO2023086970A2 (en) | 2021-11-12 | 2023-05-19 | Arna Genomics Us Incorporated | Methods and compositions for analyzing nucleic acids and nucleases in a body fluid as indicators of disease |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5656449A (en) * | 1995-03-06 | 1997-08-12 | Molecular Probes, Inc. | Neutral unsymmetrical cyanine dyes |
| SE519172C2 (sv) | 2000-06-07 | 2003-01-21 | Lightup Technologies Ab | Fastfas syntes av cyaninfärgämnen |
| SE519116C2 (sv) | 2001-05-10 | 2003-01-14 | Lightup Technologies Ab | Syntes och utvärdering av nya cyaninfärgämnen som binder till minor groove |
-
2001
- 2001-05-10 SE SE0101651A patent/SE519116C2/sv unknown
-
2002
- 2002-05-10 AU AU2002303054A patent/AU2002303054B2/en not_active Ceased
- 2002-05-10 CA CA002446982A patent/CA2446982C/en not_active Expired - Fee Related
- 2002-05-10 EP EP02731046A patent/EP1390433B1/en not_active Expired - Lifetime
- 2002-05-10 JP JP2002587511A patent/JP2004536900A/ja not_active Ceased
- 2002-05-10 WO PCT/SE2002/000860 patent/WO2002090443A1/en not_active Ceased
- 2002-05-10 DE DE60203005T patent/DE60203005T2/de not_active Expired - Fee Related
- 2002-05-10 AT AT02731046T patent/ATE289337T1/de not_active IP Right Cessation
-
2003
- 2003-11-10 US US10/605,961 patent/US7378240B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2446982C (en) | 2009-01-13 |
| WO2002090443A1 (en) | 2002-11-14 |
| CA2446982A1 (en) | 2002-11-14 |
| SE0101651L (sv) | 2002-11-11 |
| HK1060895A1 (en) | 2004-08-27 |
| DE60203005T2 (de) | 2006-05-11 |
| AU2002303054B2 (en) | 2006-12-07 |
| JP2004536900A (ja) | 2004-12-09 |
| DE60203005D1 (de) | 2005-03-24 |
| SE0101651D0 (sv) | 2001-05-10 |
| US7378240B2 (en) | 2008-05-27 |
| EP1390433A1 (en) | 2004-02-25 |
| EP1390433B1 (en) | 2005-02-16 |
| ATE289337T1 (de) | 2005-03-15 |
| US20040132046A1 (en) | 2004-07-08 |
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