CA2244768C - Fluorophores polymeres ameliores par des fractions creant un microenvironnement hydrophobe et a restriction conformationnelle - Google Patents
Fluorophores polymeres ameliores par des fractions creant un microenvironnement hydrophobe et a restriction conformationnelle Download PDFInfo
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- CA2244768C CA2244768C CA002244768A CA2244768A CA2244768C CA 2244768 C CA2244768 C CA 2244768C CA 002244768 A CA002244768 A CA 002244768A CA 2244768 A CA2244768 A CA 2244768A CA 2244768 C CA2244768 C CA 2244768C
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- Prior art keywords
- polymeric
- dye
- anilino
- polymeric dye
- signal
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- 230000002209 hydrophobic effect Effects 0.000 title claims abstract description 26
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 108
- PVVYECWIEUSSDK-UHFFFAOYSA-O 1-(2-phenylethenyl)pyridin-1-ium-2-amine Chemical compound NC1=CC=CC=[N+]1C=CC1=CC=CC=C1 PVVYECWIEUSSDK-UHFFFAOYSA-O 0.000 claims abstract description 7
- 238000000034 method Methods 0.000 claims description 70
- -1 anilino, carboxy Chemical group 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 26
- 238000012360 testing method Methods 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 230000027455 binding Effects 0.000 claims description 22
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 19
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 229940097362 cyclodextrins Drugs 0.000 claims description 10
- 230000000269 nucleophilic effect Effects 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000002500 ions Chemical class 0.000 claims description 6
- 125000005647 linker group Chemical group 0.000 claims description 5
- 230000002934 lysing effect Effects 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 238000013394 immunophenotyping Methods 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 abstract description 74
- 238000000684 flow cytometry Methods 0.000 abstract description 19
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- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 58
- 239000011541 reaction mixture Substances 0.000 description 50
- 239000000243 solution Substances 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 36
- 239000000543 intermediate Substances 0.000 description 35
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- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 27
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- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical class CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
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- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 10
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 239000012506 Sephacryl® Substances 0.000 description 8
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 7
- 239000000908 ammonium hydroxide Substances 0.000 description 7
- YJXGADCZMLHGLV-UHFFFAOYSA-N aniline;pyridine Chemical compound C1=CC=NC=C1.NC1=CC=CC=C1 YJXGADCZMLHGLV-UHFFFAOYSA-N 0.000 description 7
- 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 7
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- QWXYZCJEXYQNEI-OSZHWHEXSA-N intermediate I Chemical compound COC(=O)[C@@]1(C=O)[C@H]2CC=[N+](C\C2=C\C)CCc2c1[nH]c1ccccc21 QWXYZCJEXYQNEI-OSZHWHEXSA-N 0.000 description 7
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- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 6
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
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Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Investigating, Analyzing Materials By Fluorescence Or Luminescence (AREA)
- Investigating Or Analysing Materials By The Use Of Chemical Reactions (AREA)
Abstract
Cette invention se rapporte à des conjugués fluorescents se prêtant à une utilisation en cytométrie en flux et dans d'autres applications biologiques. Ces conjugués fluorescents comprennent un anticorps auquel est lié un colorant polymère. Ce colorant polymère est de préférence amélioré par une fraction hydrophobe et à restriction conformationnelle qui est soit liée au colorant soit étroitement associée à lui. Cette fraction hydrophobe et à restriction conformationnelle est de préférence dérivée d'une cyclodextrine. Ledit colorant polymère contient une entité polymère à laquelle sont fixés des groupes générateurs de signaux, tels que des restes de colorant aminostyrylpyridinium. Ces conjugués fluorescents possèdent des caractéristiques de stabilité exceptionnelles et permettent d'éviter les nombreux problèmes de transfert d'énergie, de bioconjugabilité et de solubilité.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US08/595,092 US5994143A (en) | 1996-02-01 | 1996-02-01 | Polymeric fluorophores enhanced by moieties providing a hydrophobic and conformationally restrictive microenvironment |
| US08/595,092 | 1996-02-01 | ||
| PCT/US1997/001429 WO1997028447A1 (fr) | 1996-02-01 | 1997-01-30 | Fluorophores polymeres ameliores par des fractions creant un microenvironnement hydrophobe et a restriction conformationnelle |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2244768A1 CA2244768A1 (fr) | 1997-08-07 |
| CA2244768C true CA2244768C (fr) | 2006-04-18 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002244768A Expired - Fee Related CA2244768C (fr) | 1996-02-01 | 1997-01-30 | Fluorophores polymeres ameliores par des fractions creant un microenvironnement hydrophobe et a restriction conformationnelle |
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| Country | Link |
|---|---|
| CA (1) | CA2244768C (fr) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN119667140B (zh) * | 2025-02-20 | 2025-08-01 | 杭州聚拓生物科技有限公司 | 一种防止荧光外泄的免疫检测液、试剂盒及其应用 |
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- 1997-01-30 CA CA002244768A patent/CA2244768C/fr not_active Expired - Fee Related
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| Publication number | Publication date |
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| CA2244768A1 (fr) | 1997-08-07 |
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