JP2016521254A5 - - Google Patents
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- JP2016521254A5 JP2016521254A5 JP2016503068A JP2016503068A JP2016521254A5 JP 2016521254 A5 JP2016521254 A5 JP 2016521254A5 JP 2016503068 A JP2016503068 A JP 2016503068A JP 2016503068 A JP2016503068 A JP 2016503068A JP 2016521254 A5 JP2016521254 A5 JP 2016521254A5
- Authority
- JP
- Japan
- Prior art keywords
- alkylene
- alkyl
- optionally substituted
- compound
- optionally
- 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.)
- Granted
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- 150000001875 compounds Chemical class 0.000 claims description 166
- 125000000217 alkyl group Chemical group 0.000 claims description 116
- -1 succinimidyl ester Chemical class 0.000 claims description 93
- 125000000623 heterocyclic group Chemical group 0.000 claims description 92
- 229910052739 hydrogen Inorganic materials 0.000 claims description 84
- 239000001257 hydrogen Substances 0.000 claims description 74
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 72
- 150000002431 hydrogen Chemical class 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 45
- 229910052757 nitrogen Inorganic materials 0.000 claims description 44
- 150000003839 salts Chemical class 0.000 claims description 40
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 32
- 125000001188 haloalkyl group Chemical group 0.000 claims description 30
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 30
- 229910052736 halogen Inorganic materials 0.000 claims description 28
- 150000002367 halogens Chemical class 0.000 claims description 28
- 125000001424 substituent group Chemical group 0.000 claims description 28
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 125000002619 bicyclic group Chemical group 0.000 claims description 24
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 24
- 150000002148 esters Chemical class 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 24
- 125000002950 monocyclic group Chemical group 0.000 claims description 24
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 22
- 150000001540 azides Chemical class 0.000 claims description 20
- 125000005335 azido alkyl group Chemical group 0.000 claims description 20
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 18
- 150000003857 carboxamides Chemical class 0.000 claims description 18
- 210000004027 cell Anatomy 0.000 claims description 18
- 150000002540 isothiocyanates Chemical class 0.000 claims description 18
- 150000008300 phosphoramidites Chemical class 0.000 claims description 18
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 claims description 18
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 16
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 16
- 125000001072 heteroaryl group Chemical group 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 239000000523 sample Substances 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 15
- 238000003384 imaging method Methods 0.000 claims description 14
- 238000010521 absorption reaction Methods 0.000 claims description 12
- 239000012491 analyte Substances 0.000 claims description 12
- 230000027455 binding Effects 0.000 claims description 12
- 229910052799 carbon Inorganic materials 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
- 150000001345 alkine derivatives Chemical class 0.000 claims description 10
- 125000000524 functional group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 150000001408 amides Chemical class 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000005647 linker group Chemical group 0.000 claims description 8
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 238000004458 analytical method Methods 0.000 claims description 7
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 6
- 102000004190 Enzymes Human genes 0.000 claims description 6
- 108090000790 Enzymes Proteins 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 102000039446 nucleic acids Human genes 0.000 claims description 6
- 108020004707 nucleic acids Proteins 0.000 claims description 6
- 150000007523 nucleic acids Chemical class 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 5
- 239000007850 fluorescent dye Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001413 amino acids Chemical class 0.000 claims description 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000012472 biological sample Substances 0.000 claims description 4
- 150000007942 carboxylates Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000004122 cyclic group Chemical group 0.000 claims description 4
- 238000011156 evaluation Methods 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 238000012634 optical imaging Methods 0.000 claims description 4
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 229920001184 polypeptide Polymers 0.000 claims description 4
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 239000010703 silicon Substances 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 230000002123 temporal effect Effects 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
- 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
- 238000009825 accumulation Methods 0.000 claims description 2
- 230000004913 activation Effects 0.000 claims description 2
- 238000003556 assay Methods 0.000 claims description 2
- 239000000090 biomarker Substances 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 210000000170 cell membrane Anatomy 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 230000007613 environmental effect Effects 0.000 claims description 2
- 208000030533 eye disease Diseases 0.000 claims description 2
- 238000002866 fluorescence resonance energy transfer Methods 0.000 claims description 2
- 208000016361 genetic disease Diseases 0.000 claims description 2
- 238000007424 high content screening assay Methods 0.000 claims description 2
- 208000026278 immune system disease Diseases 0.000 claims description 2
- 238000000338 in vitro Methods 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
- 230000004807 localization Effects 0.000 claims description 2
- 238000005259 measurement Methods 0.000 claims description 2
- 208000030159 metabolic disease Diseases 0.000 claims description 2
- 238000007837 multiplex assay Methods 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
- 230000000149 penetrating effect Effects 0.000 claims description 2
- 102000004169 proteins and genes Human genes 0.000 claims description 2
- 108090000623 proteins and genes 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
- 230000009870 specific binding Effects 0.000 claims description 2
- 210000001519 tissue Anatomy 0.000 claims description 2
- 238000003325 tomography Methods 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 30
- 239000000203 mixture Substances 0.000 claims 23
- 150000002989 phenols Chemical class 0.000 claims 4
- 125000001207 fluorophenyl group Chemical group 0.000 claims 3
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims 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 claims 1
- 150000004010 onium ions Chemical class 0.000 claims 1
- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 description 3
- 238000002659 cell therapy Methods 0.000 description 1
- 230000004656 cell transport Effects 0.000 description 1
- 230000007762 localization of cell Effects 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 230000032258 transport Effects 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201361794188P | 2013-03-15 | 2013-03-15 | |
| US61/794,188 | 2013-03-15 | ||
| PCT/US2014/029350 WO2014144793A1 (en) | 2013-03-15 | 2014-03-14 | Substituted silaxanthenium red to near-infrared fluorochromes for in vitro and in vivo imaging and detection |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2016521254A JP2016521254A (ja) | 2016-07-21 |
| JP2016521254A5 true JP2016521254A5 (enExample) | 2017-04-20 |
| JP6606487B2 JP6606487B2 (ja) | 2019-11-13 |
Family
ID=50721890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016503068A Active JP6606487B2 (ja) | 2013-03-15 | 2014-03-14 | ｉｎｖｉｔｒｏおよびｉｎｖｉｖｏイメージングおよび検出のための置換シラキサンテニウム赤色〜近赤外蛍光色素 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US9649389B2 (enExample) |
| EP (1) | EP2970342B1 (enExample) |
| JP (1) | JP6606487B2 (enExample) |
| CN (1) | CN105073761B (enExample) |
| AU (1) | AU2014228504C1 (enExample) |
| CA (1) | CA2901379C (enExample) |
| WO (1) | WO2014144793A1 (enExample) |
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- 2014-03-14 AU AU2014228504A patent/AU2014228504C1/en active Active
- 2014-03-14 JP JP2016503068A patent/JP6606487B2/ja active Active
- 2014-03-17 US US14/215,979 patent/US9649389B2/en active Active
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