JP2016519080A5 - - Google Patents
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- JP2016519080A5 JP2016519080A5 JP2016503019A JP2016503019A JP2016519080A5 JP 2016519080 A5 JP2016519080 A5 JP 2016519080A5 JP 2016503019 A JP2016503019 A JP 2016503019A JP 2016503019 A JP2016503019 A JP 2016503019A JP 2016519080 A5 JP2016519080 A5 JP 2016519080A5
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- independently
- alkyl
- halogen
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- compound
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- 150000001875 compounds Chemical class 0.000 claims description 93
- 125000000217 alkyl group Chemical group 0.000 claims description 69
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 66
- 229910052736 halogen Inorganic materials 0.000 claims description 66
- 150000002367 halogens Chemical class 0.000 claims description 61
- 229910052739 hydrogen Inorganic materials 0.000 claims description 56
- 239000001257 hydrogen Substances 0.000 claims description 50
- 239000003795 chemical substances by application Substances 0.000 claims description 38
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 31
- 150000002148 esters Chemical class 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 239000007850 fluorescent dye Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 19
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 16
- 229910052760 oxygen Inorganic materials 0.000 claims description 16
- 125000004429 atom Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 claims description 14
- 229920001223 polyethylene glycol Polymers 0.000 claims description 14
- PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 12
- 239000002202 Polyethylene glycol Substances 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 12
- 201000010099 disease Diseases 0.000 claims description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000000304 alkynyl group Chemical group 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004076 pyridyl group Chemical group 0.000 claims description 10
- 239000000523 sample Substances 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims description 10
- -1 N-hydroxysulfosuccinimide ester Chemical class 0.000 claims description 9
- 102000004169 proteins and genes Human genes 0.000 claims description 9
- 108090000623 proteins and genes Proteins 0.000 claims description 9
- 150000001540 azides Chemical class 0.000 claims description 8
- 229910052711 selenium Inorganic materials 0.000 claims description 8
- 238000002372 labelling Methods 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 238000003384 imaging method Methods 0.000 claims description 5
- 238000012634 optical imaging Methods 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- 150000001345 alkine derivatives Chemical class 0.000 claims description 4
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- PGLTVOMIXTUURA-UHFFFAOYSA-N iodoacetamide Chemical compound NC(=O)CI PGLTVOMIXTUURA-UHFFFAOYSA-N 0.000 claims description 4
- 239000012948 isocyanate Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- 150000002540 isothiocyanates Chemical class 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient 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
- 150000003573 thiols Chemical class 0.000 claims description 4
- 239000012472 biological sample Substances 0.000 claims description 3
- 238000011156 evaluation Methods 0.000 claims description 3
- 229910052740 iodine Inorganic materials 0.000 claims description 3
- 201000001320 Atherosclerosis Diseases 0.000 claims description 2
- 208000020084 Bone disease Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- 102000004190 Enzymes Human genes 0.000 claims description 2
- 108090000790 Enzymes Proteins 0.000 claims description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 2
- 208000026350 Inborn Genetic disease Diseases 0.000 claims description 2
- 206010061218 Inflammation Diseases 0.000 claims description 2
- 208000007201 Myocardial reperfusion injury Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 102000015636 Oligopeptides Human genes 0.000 claims description 2
- 108010038807 Oligopeptides Proteins 0.000 claims description 2
- 150000001413 amino acids Chemical class 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 150000001720 carbohydrates Chemical class 0.000 claims description 2
- 235000014633 carbohydrates Nutrition 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 238000001514 detection method Methods 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 claims description 2
- 208000030533 eye disease Diseases 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 239000000194 fatty acid Substances 0.000 claims description 2
- 150000004665 fatty acids Chemical class 0.000 claims description 2
- 208000016361 genetic disease Diseases 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 235000001727 glucose Nutrition 0.000 claims description 2
- 208000026278 immune system disease Diseases 0.000 claims description 2
- 238000001727 in vivo Methods 0.000 claims description 2
- 238000011503 in vivo imaging Methods 0.000 claims description 2
- 208000015181 infectious disease Diseases 0.000 claims description 2
- 230000004054 inflammatory process Effects 0.000 claims description 2
- 125000005647 linker group Chemical group 0.000 claims description 2
- 150000002632 lipids Chemical class 0.000 claims description 2
- 230000004807 localization Effects 0.000 claims description 2
- 208000030159 metabolic disease Diseases 0.000 claims description 2
- 208000031225 myocardial ischemia Diseases 0.000 claims description 2
- 230000004770 neurodegeneration Effects 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 102000039446 nucleic acids Human genes 0.000 claims description 2
- 108020004707 nucleic acids Proteins 0.000 claims description 2
- 150000007523 nucleic acids Chemical class 0.000 claims description 2
- 150000008300 phosphoramidites Chemical class 0.000 claims description 2
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 claims description 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
- 230000005855 radiation Effects 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 208000037803 restenosis Diseases 0.000 claims description 2
- 208000017520 skin disease Diseases 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 150000008163 sugars Chemical class 0.000 claims description 2
- 238000003325 tomography Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 32
- BFMYDTVEBKDAKJ-UHFFFAOYSA-L disodium;(2',7'-dibromo-3',6'-dioxido-3-oxospiro[2-benzofuran-1,9'-xanthene]-4'-yl)mercury;hydrate Chemical compound O.[Na+].[Na+].O1C(=O)C2=CC=CC=C2C21C1=CC(Br)=C([O-])C([Hg])=C1OC1=C2C=C(Br)C([O-])=C1 BFMYDTVEBKDAKJ-UHFFFAOYSA-L 0.000 claims 1
- NMHMNPHRMNGLLB-UHFFFAOYSA-N phloretic acid Chemical class OC(=O)CCC1=CC=C(O)C=C1 NMHMNPHRMNGLLB-UHFFFAOYSA-N 0.000 claims 1
- 238000000338 in vitro Methods 0.000 description 2
- GVJXGCIPWAVXJP-UHFFFAOYSA-N 2,5-dioxo-1-oxoniopyrrolidine-3-sulfonate Chemical class ON1C(=O)CC(S(O)(=O)=O)C1=O GVJXGCIPWAVXJP-UHFFFAOYSA-N 0.000 description 1
- HFHFGHLXUCOHLN-UHFFFAOYSA-N 2-fluorophenol Chemical class OC1=CC=CC=C1F HFHFGHLXUCOHLN-UHFFFAOYSA-N 0.000 description 1
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical class ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000005670 electromagnetic radiation Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361798562P | 2013-03-15 | 2013-03-15 | |
| US61/798,562 | 2013-03-15 | ||
| PCT/US2014/029224 WO2014144702A2 (en) | 2013-03-15 | 2014-03-14 | 4,4-disubstituted cyclohexyl bridged heptamethine cyanine dyes and uses thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019103596A Division JP7018913B2 (ja) | 2013-03-15 | 2019-06-03 | ４，４－二置換シクロヘキシル架橋ヘプタメチンシアニン色素およびその使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016519080A JP2016519080A (ja) | 2016-06-30 |
| JP2016519080A5 true JP2016519080A5 (https=) | 2017-04-20 |
| JP6580552B2 JP6580552B2 (ja) | 2019-09-25 |
Family
ID=50631078
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016503019A Active JP6580552B2 (ja) | 2013-03-15 | 2014-03-14 | ４，４−二置換シクロヘキシル架橋ヘプタメチンシアニン色素およびその使用 |
| JP2019103596A Active JP7018913B2 (ja) | 2013-03-15 | 2019-06-03 | ４，４－二置換シクロヘキシル架橋ヘプタメチンシアニン色素およびその使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019103596A Active JP7018913B2 (ja) | 2013-03-15 | 2019-06-03 | ４，４－二置換シクロヘキシル架橋ヘプタメチンシアニン色素およびその使用 |
Country Status (7)
| Country | Link |
|---|---|
| US (5) | US9897604B2 (https=) |
| EP (2) | EP2970674B1 (https=) |
| JP (2) | JP6580552B2 (https=) |
| CN (1) | CN105339436B (https=) |
| AU (1) | AU2014228808C1 (https=) |
| CA (1) | CA2901000C (https=) |
| WO (1) | WO2014144702A2 (https=) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2621137C (en) | 2005-09-02 | 2014-07-29 | Visen Medical, Inc. | Biocompatible n,n-disubstituted sulfonamide-containing fluorescent dye labels |
| WO2007136413A2 (en) | 2005-12-22 | 2007-11-29 | Visen Medical, Inc. | Biocompatible fluorescent metal oxide nanoparticles |
| US8815214B2 (en) | 2008-01-18 | 2014-08-26 | Visen Medical, Inc. | Fluorescent imaging agents |
| CN103687854A (zh) | 2011-05-09 | 2014-03-26 | 文森医学公司 | 碳酸酐酶靶向剂及其使用方法 |
| WO2014144702A2 (en) * | 2013-03-15 | 2014-09-18 | Visen Medical, Inc. | 4,4-disubstituted cyclohexyl bridged heptamethine cyanine dyes and uses thereof |
| CA2901379C (en) | 2013-03-15 | 2023-05-16 | Visen Medical, Inc. | Substituted silaxanthenium red to near-infrared fluorochromes for in vitro and in vivo imaging and detection |
| WO2018031448A1 (en) | 2016-08-11 | 2018-02-15 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Near-ir light-cleavable conjugates and conjugate precursors |
| CN107400080B (zh) * | 2017-07-27 | 2020-03-31 | 中国科学院烟台海岸带研究所 | 一种基于花菁的有机化合物及其中间体的应用 |
| JP2020050610A (ja) * | 2018-09-27 | 2020-04-02 | 国立研究開発法人理化学研究所 | バイオイメージング剤 |
| CN109985252A (zh) * | 2019-05-10 | 2019-07-09 | 南京鼓楼医院 | 一种新型双模态小分子造影剂及其制备方法与应用 |
| CN110642839B (zh) * | 2019-08-14 | 2022-04-01 | 深圳大学 | 一种纳米探针及其制备方法与应用 |
| CN113045563A (zh) * | 2019-12-27 | 2021-06-29 | 上海泓博智源医药股份有限公司 | 一种感蓝光谱增感剂的制备方法 |
| CN112920171A (zh) * | 2021-01-29 | 2021-06-08 | 南京邮电大学 | 一种含四嗪单元的花菁化合物及其制备方法和应用 |
| CN113350336B (zh) * | 2021-07-01 | 2022-06-10 | 中国人民解放军陆军军医大学 | 一种七甲川吲哚花菁或其衍生物的用途 |
| CN115403503B (zh) * | 2022-09-02 | 2023-05-26 | 中国药科大学 | 七甲川花菁素类染料偶联物、制法、药物组合物和应用 |
| CN117169182B (zh) * | 2023-08-30 | 2024-03-15 | 广州沙艾生物科技有限公司 | 一种干细胞治疗制剂体外效力检测方法及其应用 |
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-
2014
- 2014-03-14 WO PCT/US2014/029224 patent/WO2014144702A2/en not_active Ceased
- 2014-03-14 CN CN201480016214.6A patent/CN105339436B/zh active Active
- 2014-03-14 JP JP2016503019A patent/JP6580552B2/ja active Active
- 2014-03-14 EP EP14721134.6A patent/EP2970674B1/en active Active
- 2014-03-14 EP EP18211794.5A patent/EP3489309A1/en active Pending
- 2014-03-14 AU AU2014228808A patent/AU2014228808C1/en active Active
- 2014-03-14 CA CA2901000A patent/CA2901000C/en active Active
- 2014-03-17 US US14/215,930 patent/US9897604B2/en active Active
-
2018
- 2018-02-07 US US15/890,646 patent/US10473658B2/en active Active
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2019
- 2019-06-03 JP JP2019103596A patent/JP7018913B2/ja active Active
- 2019-10-16 US US16/654,305 patent/US11193932B2/en active Active
-
2021
- 2021-11-10 US US17/454,300 patent/US20220178921A1/en not_active Abandoned
-
2024
- 2024-05-28 US US18/675,875 patent/US20240393330A1/en active Pending
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