JP2018515628A5 - - Google Patents
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- JP2018515628A5 JP2018515628A5 JP2017537266A JP2017537266A JP2018515628A5 JP 2018515628 A5 JP2018515628 A5 JP 2018515628A5 JP 2017537266 A JP2017537266 A JP 2017537266A JP 2017537266 A JP2017537266 A JP 2017537266A JP 2018515628 A5 JP2018515628 A5 JP 2018515628A5
- Authority
- JP
- Japan
- Prior art keywords
- compound according
- water
- soluble compound
- independently
- covalent bond
- 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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- 150000001875 compounds Chemical class 0.000 claims description 104
- 238000000034 method Methods 0.000 claims description 33
- 125000005647 linker group Chemical group 0.000 claims description 29
- -1 alquinylene Chemical group 0.000 claims description 18
- 239000012491 analyte Substances 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000975 dye Substances 0.000 claims description 12
- 239000007787 solid Substances 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 10
- 238000004458 analytical method Methods 0.000 claims description 10
- 125000002947 alkylene group Chemical group 0.000 claims description 9
- 125000004450 alkenylene group Chemical group 0.000 claims description 7
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 7
- 150000005215 alkyl ethers Chemical class 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 150000002170 ethers Chemical class 0.000 claims description 6
- 230000003287 optical effect Effects 0.000 claims description 6
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 6
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 claims description 6
- 229920000642 polymer Polymers 0.000 claims description 6
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 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 4
- 229910019142 PO4 Inorganic materials 0.000 claims description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 4
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 4
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 239000011324 bead Substances 0.000 claims description 4
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 claims description 4
- VPUGDVKSAQVFFS-UHFFFAOYSA-N coronene Chemical compound C1=C(C2=C34)C=CC3=CC=C(C=C3)C4=C4C3=CC=C(C=C3)C4=C2C3=C1 VPUGDVKSAQVFFS-UHFFFAOYSA-N 0.000 claims description 4
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 claims description 4
- 238000000684 flow cytometry Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 235000021317 phosphate Nutrition 0.000 claims description 4
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 claims description 4
- 230000000007 visual effect Effects 0.000 claims description 4
- 230000000295 complement effect Effects 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- XJKSTNDFUHDPQJ-UHFFFAOYSA-N 1,4-diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=C(C=2C=CC=CC=2)C=C1 XJKSTNDFUHDPQJ-UHFFFAOYSA-N 0.000 claims description 2
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 claims description 2
- BZTDTCNHAFUJOG-UHFFFAOYSA-N 6-carboxyfluorescein Chemical compound C12=CC=C(O)C=C2OC2=CC(O)=CC=C2C11OC(=O)C2=CC=C(C(=O)O)C=C21 BZTDTCNHAFUJOG-UHFFFAOYSA-N 0.000 claims description 2
- WSZBYXQREMPYLP-UHFFFAOYSA-N 9-ethynylanthracene Chemical compound C1=CC=C2C(C#C)=C(C=CC=C3)C3=CC2=C1 WSZBYXQREMPYLP-UHFFFAOYSA-N 0.000 claims description 2
- 108091023037 Aptamer Proteins 0.000 claims description 2
- FMMWHPNWAFZXNH-UHFFFAOYSA-N Benz[a]pyrene Chemical compound C1=C2C3=CC=CC=C3C=C(C=C3)C2=C2C3=CC=CC2=C1 FMMWHPNWAFZXNH-UHFFFAOYSA-N 0.000 claims description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 102000003886 Glycoproteins Human genes 0.000 claims description 2
- 108090000288 Glycoproteins Proteins 0.000 claims description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
- 102000029797 Prion Human genes 0.000 claims description 2
- 108091000054 Prion Proteins 0.000 claims description 2
- NRCMAYZCPIVABH-UHFFFAOYSA-N Quinacridone Chemical compound N1C2=CC=CC=C2C(=O)C2=C1C=C1C(=O)C3=CC=CC=C3NC1=C2 NRCMAYZCPIVABH-UHFFFAOYSA-N 0.000 claims description 2
- 229920004933 Terylene® Polymers 0.000 claims description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 150000001336 alkenes Chemical class 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims description 2
- 229960002685 biotin Drugs 0.000 claims description 2
- 235000020958 biotin Nutrition 0.000 claims description 2
- 239000011616 biotin Substances 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 235000001671 coumarin Nutrition 0.000 claims description 2
- 238000006352 cycloaddition reaction Methods 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims description 2
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 150000002540 isothiocyanates Chemical class 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 claims description 2
- 108020004707 nucleic acids Proteins 0.000 claims description 2
- 150000007523 nucleic acids Chemical class 0.000 claims description 2
- 102000039446 nucleic acids Human genes 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 239000001048 orange dye Substances 0.000 claims description 2
- 229930184652 p-Terphenyl Natural products 0.000 claims description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 150000004032 porphyrins Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052707 ruthenium Inorganic materials 0.000 claims description 2
- 238000010186 staining Methods 0.000 claims description 2
- 229960002317 succinimide Drugs 0.000 claims description 2
- 150000003461 sulfonyl halides Chemical class 0.000 claims description 2
- ACOJCCLIDPZYJC-UHFFFAOYSA-M thiazole orange Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=CC=C2C(C=C3N(C4=CC=CC=C4S3)C)=CC=[N+](C)C2=C1 ACOJCCLIDPZYJC-UHFFFAOYSA-M 0.000 claims description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 2
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- WZYNTGFFWDNWGG-UHFFFAOYSA-N n,n-dimethyl-2-(2-phenylethenyl)aniline Chemical compound CN(C)C1=CC=CC=C1C=CC1=CC=CC=C1 WZYNTGFFWDNWGG-UHFFFAOYSA-N 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 1
- XJHABGPPCLHLLV-UHFFFAOYSA-N benzo[de]isoquinoline-1,3-dione Chemical compound C1=CC(C(=O)NC2=O)=C3C2=CC=CC3=C1 XJHABGPPCLHLLV-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201562159771P | 2015-05-11 | 2015-05-11 | |
| US62/159,771 | 2015-05-11 | ||
| PCT/US2016/031831 WO2016183185A1 (en) | 2015-05-11 | 2016-05-11 | Ultra bright dimeric or polymeric dyes |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2018515628A JP2018515628A (ja) | 2018-06-14 |
| JP2018515628A5 true JP2018515628A5 (enExample) | 2020-11-05 |
| JP6849599B2 JP6849599B2 (ja) | 2021-03-24 |
Family
ID=57248385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017537266A Active JP6849599B2 (ja) | 2015-05-11 | 2016-05-11 | 超明色ダイマーまたはポリマー染料 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US10865310B2 (enExample) |
| EP (1) | EP3294811B1 (enExample) |
| JP (1) | JP6849599B2 (enExample) |
| KR (1) | KR102765335B1 (enExample) |
| CN (1) | CN107709470B (enExample) |
| WO (1) | WO2016183185A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP3019559A4 (en) | 2013-08-22 | 2017-04-05 | Sony Corporation | Water soluble fluorescent or colored dyes and methods for their use |
| WO2015109136A2 (en) | 2014-01-16 | 2015-07-23 | Sony Corporation | Water soluble fluorescent or colored dyes and methods for their use |
| KR102676814B1 (ko) | 2015-02-26 | 2024-06-21 | 소니그룹주식회사 | 접합 그룹을 포함하는 수용성 형광 또는 착색 염료 |
| CN107406353A (zh) | 2015-02-26 | 2017-11-28 | 索尼公司 | 苯基乙炔基萘染料和用于它们用途的方法 |
| WO2016183185A1 (en) | 2015-05-11 | 2016-11-17 | Sony Corporation | Ultra bright dimeric or polymeric dyes |
| KR102525252B1 (ko) | 2016-04-01 | 2023-04-26 | 소니그룹주식회사 | 강성 공간군을 갖는 매우 밝은 이량체성 또는 중합체성 염료 |
| KR20250029292A (ko) * | 2016-04-01 | 2025-03-04 | 소니그룹주식회사 | 초휘도 이량체성 또는 중합체성 염료 |
| RU2753706C2 (ru) * | 2016-04-06 | 2021-08-20 | Сони Корпорейшн | Ультраяркие димерные или полимерные красители со спейсерными линкерными группами |
| US11370922B2 (en) | 2016-05-10 | 2022-06-28 | Sony Corporation | Ultra bright polymeric dyes with peptide backbones |
| WO2017197014A2 (en) | 2016-05-10 | 2017-11-16 | Sony Corporation | Compositions comprising a polymeric dye and a cyclodextrin and uses thereof |
| RU2018143594A (ru) | 2016-05-11 | 2020-06-11 | Сони Корпорейшн | Ультраяркие димерные или полимерные красители |
| JP7068191B2 (ja) | 2016-06-06 | 2022-05-16 | ソニーグループ株式会社 | 蛍光または有色レポーター基を含むイオン性ポリマー |
| US12018159B2 (en) | 2016-07-29 | 2024-06-25 | Sony Group Corporation | Ultra bright dimeric or polymeric dyes and methods for preparation of the same |
| CN116519642A (zh) | 2017-06-16 | 2023-08-01 | 杜克大学 | 用于改善标记检测、计算、分析物感应和可调随机数生成的谐振器网络和方法 |
| US12145956B2 (en) | 2017-10-05 | 2024-11-19 | Sony Group Corporation | Programmable polymeric drugs |
| US12290571B2 (en) | 2017-10-05 | 2025-05-06 | Sony Group Corporation | Programmable dendritic drugs |
| CN111836645A (zh) * | 2017-11-16 | 2020-10-27 | 索尼公司 | 可编程的聚合药物 |
| CN111565757A (zh) * | 2018-01-12 | 2020-08-21 | 索尼公司 | 包含生物活性化合物的磷酸烷基聚合物 |
| US12194104B2 (en) | 2018-01-12 | 2025-01-14 | Sony Group Corporation | Phosphoalkyl ribose polymers comprising biologically active compounds |
| EP3737418B1 (en) | 2018-01-12 | 2024-02-28 | Sony Group Corporation | Polymers with rigid spacing groups comprising biologically active compounds |
| EP4137818B1 (en) | 2018-03-19 | 2025-12-10 | Sony Group Corporation | Use of divalent metals for enhancement of fluorescent signals |
| US12319817B2 (en) | 2018-03-21 | 2025-06-03 | Sony Group Corporation | Polymeric tandem dyes with linker groups |
| WO2019191482A1 (en) | 2018-03-30 | 2019-10-03 | Becton, Dickinson And Company | Water-soluble polymeric dyes having pendant chromophores |
| JP7580689B2 (ja) * | 2018-06-27 | 2024-11-12 | ソニーグループ株式会社 | デオキシリボースを含むリンカー基を有するポリマー色素 |
| CN112399996A (zh) * | 2018-07-13 | 2021-02-23 | 索尼公司 | 具有包含有机磷酸酯单元的主链的聚合的染料 |
| JP7551060B2 (ja) * | 2019-04-11 | 2024-09-17 | ソニーグループ株式会社 | プログラム可能なポリマー薬 |
| JP7603918B2 (ja) * | 2019-04-11 | 2024-12-23 | ソニーグループ株式会社 | プログラム可能なポリマー薬 |
| KR20210152524A (ko) | 2019-04-11 | 2021-12-15 | 소니그룹주식회사 | 프로그램 가능한 중합체성 약물 |
| JP7239904B2 (ja) * | 2019-09-26 | 2023-03-15 | ソニーグループ株式会社 | リンカー基を有するポリマータンデム色素 |
| KR20220075399A (ko) | 2019-09-30 | 2022-06-08 | 소니그룹주식회사 | 뉴클레오티드 프로브 |
| CN116615557A (zh) * | 2020-11-25 | 2023-08-18 | 索尼集团公司 | 聚合物染料 |
| US20240132725A1 (en) | 2020-12-07 | 2024-04-25 | Sony Group Corporation | Spacing linker group design for brightness enhancement in dimeric or polymeric dyes |
| US12180401B2 (en) | 2021-04-07 | 2024-12-31 | Becton, Dickinson And Company | Water-soluble fluorescent polymeric dyes |
| EP4540323A2 (en) | 2022-06-15 | 2025-04-23 | Sony Group Corporation | Polymeric tandem dyes with spacing linker groups |
| KR20250023375A (ko) | 2022-06-15 | 2025-02-18 | 소니그룹주식회사 | 스페이싱 링커 그룹을 갖는 중합체성 탄뎀 염료 |
| WO2025047293A1 (ja) * | 2023-08-30 | 2025-03-06 | ソニーグループ株式会社 | 化合物、検出システムおよび測定装置 |
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-
2016
- 2016-05-11 WO PCT/US2016/031831 patent/WO2016183185A1/en not_active Ceased
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- 2016-05-11 JP JP2017537266A patent/JP6849599B2/ja active Active
- 2016-05-11 CN CN201680006600.6A patent/CN107709470B/zh active Active
- 2016-05-11 EP EP16793440.5A patent/EP3294811B1/en active Active
- 2016-05-11 US US15/543,827 patent/US10865310B2/en active Active
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