JP2019516812A5 - - Google Patents
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- JP2019516812A5 JP2019516812A5 JP2018549448A JP2018549448A JP2019516812A5 JP 2019516812 A5 JP2019516812 A5 JP 2019516812A5 JP 2018549448 A JP2018549448 A JP 2018549448A JP 2018549448 A JP2018549448 A JP 2018549448A JP 2019516812 A5 JP2019516812 A5 JP 2019516812A5
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- 150000001875 compounds Chemical class 0.000 claims description 130
- 125000005647 linker group Chemical group 0.000 claims description 38
- 239000012491 analyte Substances 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 23
- -1 Alkoxyalkyl ether Chemical compound 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 20
- 230000000295 complement effect Effects 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 14
- 125000002947 alkylene group Chemical group 0.000 claims description 13
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000000975 dye Substances 0.000 claims description 12
- 125000004474 heteroalkylene group Chemical group 0.000 claims description 11
- 125000000524 functional group Chemical group 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 8
- 125000004450 alkenylene group Chemical group 0.000 claims description 8
- 150000005215 alkyl ethers Chemical class 0.000 claims description 8
- 125000004419 alkynylene group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 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 7
- 239000011324 bead Substances 0.000 claims description 6
- 125000002837 carbocyclic group Chemical group 0.000 claims description 5
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 5
- 230000021615 conjugation Effects 0.000 claims description 5
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 claims description 5
- 229910019142 PO4 Inorganic materials 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
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 4
- 239000010452 phosphate Substances 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
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 4
- 125000000464 thioxo group Chemical group S=* 0.000 claims description 4
- 108091023037 Aptamer Proteins 0.000 claims description 3
- 108090000790 Enzymes Proteins 0.000 claims description 3
- 102000004190 Enzymes Human genes 0.000 claims description 3
- 102000003886 Glycoproteins Human genes 0.000 claims description 3
- 108090000288 Glycoproteins Proteins 0.000 claims description 3
- 108091000054 Prion Proteins 0.000 claims description 3
- 102000029797 Prion Human genes 0.000 claims description 3
- 150000001413 amino acids Chemical class 0.000 claims description 3
- 239000003446 ligand Substances 0.000 claims description 3
- 108020004707 nucleic acids Proteins 0.000 claims description 3
- 150000007523 nucleic acids Chemical class 0.000 claims description 3
- 102000039446 nucleic acids Human genes 0.000 claims description 3
- 230000000007 visual effect Effects 0.000 claims description 3
- 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
- IHXWECHPYNPJRR-UHFFFAOYSA-N 3-hydroxycyclobut-2-en-1-one Chemical compound OC1=CC(=O)C1 IHXWECHPYNPJRR-UHFFFAOYSA-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
- 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
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 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
- DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims description 2
- 229960000956 coumarin Drugs 0.000 claims description 2
- 235000001671 coumarin Nutrition 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
- 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 description 2
- 239000001048 orange dye Substances 0.000 claims description 2
- 229930184652 p-Terphenyl Natural products 0.000 claims description 2
- 239000005020 polyethylene terephthalate Substances 0.000 claims description 2
- 150000004032 porphyrins Chemical class 0.000 claims description 2
- HSSLDCABUXLXKM-UHFFFAOYSA-N resorufin Chemical compound C1=CC(=O)C=C2OC3=CC(O)=CC=C3N=C21 HSSLDCABUXLXKM-UHFFFAOYSA-N 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
- 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
- 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 1
- 229920001897 terpolymer Polymers 0.000 claims 1
- ANRHNWWPFJCPAZ-UHFFFAOYSA-M thionine Chemical compound [Cl-].C1=CC(N)=CC2=[S+]C3=CC(N)=CC=C3N=C21 ANRHNWWPFJCPAZ-UHFFFAOYSA-M 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 11
- 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 description 8
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 8
- 150000001345 alkine derivatives Chemical class 0.000 description 8
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 150000001540 azides Chemical class 0.000 description 5
- 229960002685 biotin Drugs 0.000 description 4
- 235000020958 biotin Nutrition 0.000 description 4
- 239000011616 biotin Substances 0.000 description 4
- 125000001072 heteroaryl group Chemical group 0.000 description 4
- 150000002540 isothiocyanates Chemical class 0.000 description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 4
- 150000003461 sulfonyl halides Chemical class 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 125000001425 triazolyl group Chemical group 0.000 description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 2
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 2
- AVPPAALOLZNNKT-UHFFFAOYSA-N C[n]1nnc(I)c1 Chemical compound C[n]1nnc(I)c1 AVPPAALOLZNNKT-UHFFFAOYSA-N 0.000 description 2
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 2
- DPOPAJRDYZGTIR-UHFFFAOYSA-N Tetrazine Chemical compound C1=CN=NN=N1 DPOPAJRDYZGTIR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 238000006352 cycloaddition reaction Methods 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 150000007857 hydrazones Chemical class 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 238000002372 labelling Methods 0.000 description 2
- 125000005439 maleimidyl group Chemical group C1(C=CC(N1*)=O)=O 0.000 description 2
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 230000000269 nucleophilic effect Effects 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 229960002317 succinimide Drugs 0.000 description 2
- 150000003536 tetrazoles Chemical class 0.000 description 2
- 125000001730 thiiranyl group Chemical group 0.000 description 2
- 150000007970 thio esters Chemical class 0.000 description 2
- 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 1
- 125000001054 5 membered carbocyclic group Chemical group 0.000 description 1
- 125000004008 6 membered carbocyclic group Chemical group 0.000 description 1
- 125000001960 7 membered carbocyclic group Chemical group 0.000 description 1
- DXCLQRUFEMNWAP-UHFFFAOYSA-N CCCCNC([I](C)C)=O Chemical compound CCCCNC([I](C)C)=O DXCLQRUFEMNWAP-UHFFFAOYSA-N 0.000 description 1
- JVQALPFABFBUJW-UHFFFAOYSA-N CCCOCCNC(C)=O Chemical compound CCCOCCNC(C)=O JVQALPFABFBUJW-UHFFFAOYSA-N 0.000 description 1
- ANVKXLWNHRSJSH-UHFFFAOYSA-N CCOCCCNC(OCC)=O Chemical compound CCOCCCNC(OCC)=O ANVKXLWNHRSJSH-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 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
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000000684 flow cytometry Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662316836P | 2016-04-01 | 2016-04-01 | |
| US62/316,836 | 2016-04-01 | ||
| PCT/US2017/025513 WO2017173348A1 (en) | 2016-04-01 | 2017-03-31 | Ultra bright dimeric or polymeric dyes with rigid spacing groups |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019516812A JP2019516812A (ja) | 2019-06-20 |
| JP2019516812A5 true JP2019516812A5 (enExample) | 2020-05-07 |
| JP7145079B2 JP7145079B2 (ja) | 2022-09-30 |
Family
ID=58609994
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018549448A Active JP7145079B2 (ja) | 2016-04-01 | 2017-03-31 | 剛性のスペーシング基を有する超明色ダイマーまたはポリマー染料 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US11434377B2 (enExample) |
| EP (1) | EP3436528B1 (enExample) |
| JP (1) | JP7145079B2 (enExample) |
| KR (1) | KR102525252B1 (enExample) |
| CN (1) | CN109415574B (enExample) |
| WO (1) | WO2017173348A1 (enExample) |
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3019559A4 (en) | 2013-08-22 | 2017-04-05 | Sony Corporation | Water soluble fluorescent or colored dyes and methods for their use |
| WO2016138457A1 (en) | 2015-02-26 | 2016-09-01 | Sony Corporation | Phenylethynylnaphthalene dyes and methods for their use |
| KR102676814B1 (ko) | 2015-02-26 | 2024-06-21 | 소니그룹주식회사 | 접합 그룹을 포함하는 수용성 형광 또는 착색 염료 |
| JP6849599B2 (ja) | 2015-05-11 | 2021-03-24 | ソニー株式会社 | 超明色ダイマーまたはポリマー染料 |
| KR102530707B1 (ko) | 2016-04-01 | 2023-05-11 | 소니그룹주식회사 | 초휘도 이량체성 또는 중합체성 염료 |
| US11434377B2 (en) | 2016-04-01 | 2022-09-06 | Sony Corporation | Ultra bright dimeric or polymeric dyes with rigid spacing groups |
| KR20180133890A (ko) | 2016-04-06 | 2018-12-17 | 소니 주식회사 | 스페이싱 링커 그룹을 포함하는 초고명도 이량체성 또는 중합체성 염료 |
| WO2017197014A2 (en) | 2016-05-10 | 2017-11-16 | Sony Corporation | Compositions comprising a polymeric dye and a cyclodextrin and uses thereof |
| WO2017196954A1 (en) | 2016-05-10 | 2017-11-16 | Sony Corporation | Ultra bright polymeric dyes with peptide backbones |
| EP3455300A1 (en) | 2016-05-11 | 2019-03-20 | Sony Corporation | Ultra bright dimeric or polymeric dyes |
| 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 |
| AU2018282868B2 (en) | 2017-06-16 | 2023-10-19 | Duke University | Resonator networks for improved label detection, computation, analyte sensing, and tunable random number generation |
| EP3691689A1 (en) | 2017-10-05 | 2020-08-12 | Sony Corporation | Programmable dendritic drugs |
| JP7551056B2 (ja) | 2017-10-05 | 2024-09-17 | ソニーグループ株式会社 | プログラマブルなポリマー薬物 |
| CN111836645A (zh) | 2017-11-16 | 2020-10-27 | 索尼公司 | 可编程的聚合药物 |
| EP4616912A3 (en) | 2018-01-12 | 2025-11-19 | Sony Group Corporation | Phosphoalkyl ribose polymers comprising biologically active compounds |
| WO2019140301A1 (en) | 2018-01-12 | 2019-07-18 | Sony Corporation | Polymers with rigid spacing groups comprising biologically active compounds |
| KR102742386B1 (ko) | 2018-03-19 | 2024-12-16 | 소니그룹주식회사 | 형광 신호 향상을 위한 2가 금속의 사용 |
| WO2019182766A1 (en) | 2018-03-21 | 2019-09-26 | Sony 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 |
| KR102854332B1 (ko) | 2018-06-27 | 2025-09-03 | 소니그룹주식회사 | 디옥시리보오스를 포함하는 링커 군을 갖는 중합체성 염료 |
| EP3952916A1 (en) * | 2019-04-11 | 2022-02-16 | Sony Group Corporation | Programmable polymeric drugs |
| KR102486779B1 (ko) | 2019-09-26 | 2023-01-12 | 소니그룹주식회사 | 링커 그룹을 갖는 중합체성 탠덤 염료 |
| CN111103761B (zh) * | 2019-12-27 | 2023-10-17 | Tcl华星光电技术有限公司 | 一种染料色阻及其制备方法、彩膜基板 |
| EP4256078A1 (en) | 2020-12-07 | 2023-10-11 | 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 |
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- 2017-03-31 KR KR1020187031703A patent/KR102525252B1/ko active Active
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- 2017-03-31 JP JP2018549448A patent/JP7145079B2/ja active Active
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