JP2019512500A5 - - Google Patents
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- JP2019512500A5 JP2019512500A5 JP2018548414A JP2018548414A JP2019512500A5 JP 2019512500 A5 JP2019512500 A5 JP 2019512500A5 JP 2018548414 A JP2018548414 A JP 2018548414A JP 2018548414 A JP2018548414 A JP 2018548414A JP 2019512500 A5 JP2019512500 A5 JP 2019512500A5
- Authority
- JP
- Japan
- Prior art keywords
- compound
- group
- amino acid
- tyrosine
- atoms
- 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 19
- 235000001014 amino acid Nutrition 0.000 claims 13
- 229940024606 amino acid Drugs 0.000 claims 13
- 125000004429 atom Chemical group 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 7
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 5
- 239000002202 Polyethylene glycol Substances 0.000 claims 5
- 150000001413 amino acids Chemical class 0.000 claims 5
- -1 aromatic amino acid Chemical class 0.000 claims 5
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 230000002209 hydrophobic effect Effects 0.000 claims 5
- 229920001223 polyethylene glycol Polymers 0.000 claims 5
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 5
- 235000002374 tyrosine Nutrition 0.000 claims 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 4
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 4
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims 4
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims 4
- AGPKZVBTJJNPAG-WHFBIAKZSA-N L-isoleucine Chemical compound CC[C@H](C)[C@H](N)C(O)=O AGPKZVBTJJNPAG-WHFBIAKZSA-N 0.000 claims 4
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 4
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 4
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 4
- 229920002873 Polyethylenimine Polymers 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 3
- 239000011593 sulfur Substances 0.000 claims 3
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 claims 2
- 239000004475 Arginine Substances 0.000 claims 2
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- 108700012439 CA9 Proteins 0.000 claims 2
- 102100024423 Carbonic anhydrase 9 Human genes 0.000 claims 2
- 239000004471 Glycine Substances 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- XUJNEKJLAYXESH-REOHCLBHSA-N L-Cysteine Chemical compound SC[C@H](N)C(O)=O XUJNEKJLAYXESH-REOHCLBHSA-N 0.000 claims 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 claims 2
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 claims 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims 2
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims 2
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 claims 2
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 claims 2
- 125000000510 L-tryptophano group Chemical group [H]C1=C([H])C([H])=C2N([H])C([H])=C(C([H])([H])[C@@]([H])(C(O[H])=O)N([H])[*])C2=C1[H] 0.000 claims 2
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 claims 2
- 239000004472 Lysine Substances 0.000 claims 2
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 2
- AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 claims 2
- 239000004473 Threonine Substances 0.000 claims 2
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 claims 2
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 150000007513 acids Chemical class 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims 2
- 235000009697 arginine Nutrition 0.000 claims 2
- 235000009582 asparagine Nutrition 0.000 claims 2
- 229960001230 asparagine Drugs 0.000 claims 2
- 235000003704 aspartic acid Nutrition 0.000 claims 2
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims 2
- 125000002091 cationic group Chemical group 0.000 claims 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 claims 2
- 235000018417 cysteine Nutrition 0.000 claims 2
- 235000013922 glutamic acid Nutrition 0.000 claims 2
- 239000004220 glutamic acid Substances 0.000 claims 2
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims 2
- 235000014304 histidine Nutrition 0.000 claims 2
- AGPKZVBTJJNPAG-UHFFFAOYSA-N isoleucine Natural products CCC(C)C(N)C(O)=O AGPKZVBTJJNPAG-UHFFFAOYSA-N 0.000 claims 2
- 229960000310 isoleucine Drugs 0.000 claims 2
- 235000018977 lysine Nutrition 0.000 claims 2
- 229930182817 methionine Natural products 0.000 claims 2
- 230000007935 neutral effect Effects 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims 2
- 108090000765 processed proteins & peptides Proteins 0.000 claims 2
- 235000004400 serine Nutrition 0.000 claims 2
- 125000006850 spacer group Chemical group 0.000 claims 2
- 230000008685 targeting Effects 0.000 claims 2
- 235000008521 threonine Nutrition 0.000 claims 2
- 239000004474 valine Substances 0.000 claims 2
- BEJKOYIMCGMNRB-GRHHLOCNSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-amino-3-phenylpropanoic acid Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 BEJKOYIMCGMNRB-GRHHLOCNSA-N 0.000 claims 1
- FTDJMHFEPHDWJS-CWRCKCRTSA-N (2s)-2-amino-5-(diaminomethylideneamino)pentanoic acid;(2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-amino-3-phenylpropanoic acid Chemical compound OC(=O)[C@@H](N)CCCNC(N)=N.OC(=O)[C@@H](N)CC1=CC=CC=C1.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 FTDJMHFEPHDWJS-CWRCKCRTSA-N 0.000 claims 1
- IVQXRAXDXYPHBU-UHFFFAOYSA-N 2-aminohectanoic acid Chemical class NC(C(=O)O)CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCC IVQXRAXDXYPHBU-UHFFFAOYSA-N 0.000 claims 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 1
- 229910006069 SO3H Inorganic materials 0.000 claims 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims 1
- 238000010521 absorption reaction Methods 0.000 claims 1
- 150000001412 amines Chemical group 0.000 claims 1
- 125000000129 anionic group Chemical group 0.000 claims 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
- 210000004027 cell Anatomy 0.000 claims 1
- 229910052798 chalcogen Inorganic materials 0.000 claims 1
- 150000001787 chalcogens Chemical class 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
- 230000005284 excitation Effects 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000001165 hydrophobic group Chemical group 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 239000001301 oxygen Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000003595 spectral effect Effects 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical group SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims 1
- 210000004881 tumor cell Anatomy 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201662309412P | 2016-03-16 | 2016-03-16 | |
| US62/309,412 | 2016-03-16 | ||
| PCT/US2017/022824 WO2017161197A1 (en) | 2016-03-16 | 2017-03-16 | Ca ix-target nir dyes and their uses |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2019512500A JP2019512500A (ja) | 2019-05-16 |
| JP2019512500A5 true JP2019512500A5 (https=) | 2020-04-23 |
| JP7285537B2 JP7285537B2 (ja) | 2023-06-02 |
Family
ID=59851675
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2018548414A Active JP7285537B2 (ja) | 2016-03-16 | 2017-03-16 | Ｃａ ｉｘ標的ｎｉｒ色素及びそれらの使用 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US10557854B2 (https=) |
| EP (1) | EP3430383B1 (https=) |
| JP (1) | JP7285537B2 (https=) |
| KR (1) | KR102342319B1 (https=) |
| CN (1) | CN109791107B (https=) |
| AU (1) | AU2017234681B2 (https=) |
| BR (1) | BR112018068142B1 (https=) |
| ES (1) | ES2989466T3 (https=) |
| IL (1) | IL261470B (https=) |
| MX (1) | MX2018011130A (https=) |
| WO (2) | WO2017161197A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11555821B2 (en) | 2016-03-16 | 2023-01-17 | On Target Laboratories, Inc. | CA IX-NIR dyes and their uses |
| CN111225688B (zh) * | 2017-08-22 | 2025-06-17 | 普渡研究基金会 | 靶向碳酸酐酶阳性癌症的基于fbsa的治疗和放射性成像缀合物 |
| WO2019133914A1 (en) * | 2017-12-29 | 2019-07-04 | Wayne State University | Method of treatment for solid tumors containing hypoxia and/or stroma features |
| WO2020131980A1 (en) * | 2018-12-19 | 2020-06-25 | Purdue Research Foundation | Carbonic anhydrase inhibitors and antibiotics against multidrug resistant bacteria |
| CN110790724B (zh) * | 2019-09-20 | 2023-01-31 | 中山大学 | 一种选择性碳酸酐酶抑制剂及其合成方法和应用 |
| US20210353151A1 (en) * | 2020-05-12 | 2021-11-18 | On Target Laboratories, LLC | Targeted fluorescent markers in combination with a flexible probe |
| EP4247436A4 (en) * | 2020-11-18 | 2024-10-16 | On Target Laboratories, LLC | NEAR-INFRARED II PROBES AS HIGH-AFFINE TARGETING IMAGING AGENTS AND USES THEREOF |
| US20240000946A1 (en) * | 2020-12-03 | 2024-01-04 | Vilnius University | Carbonic anhydrase inhibitors synthesized on interconnecting linker chains |
| CA3217981A1 (en) * | 2021-05-14 | 2022-11-17 | Philip Low | Folate receptor-targeted conjugates with brush border membrane enzyme-cleavable linkers and methods of use in imaging and treating cancer |
| WO2023081301A1 (en) * | 2021-11-05 | 2023-05-11 | On Target Laboratories, LLC | Fibroblast activation protein targeted dyes their related uses |
| CA3243979A1 (en) * | 2022-02-11 | 2025-04-30 | C-Biomex Co., Ltd. | Peptide ligand targeting carbonic anhydrase IX, peptide construction comprising it, and associated uses |
| EP4562099A1 (en) | 2022-07-28 | 2025-06-04 | Bracco Imaging SPA | Ca-ix targeting fluorescent probes |
| CN119325492A (zh) | 2022-07-28 | 2025-01-17 | 伯拉考成像股份公司 | 靶向ca-ix的荧光探针 |
| CN119490505A (zh) * | 2023-08-16 | 2025-02-21 | 新斗生物科技(苏州)有限公司 | 一种含叶酸类化合物的组合物及近红外荧光捕获系统 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7833734B2 (en) | 2002-11-26 | 2010-11-16 | Institute Of Virology Of The Slovak Academy Of Sciences | CA IX-specific inhibitors |
| WO2006137092A1 (en) * | 2005-06-23 | 2006-12-28 | Supuran Claudiu T | Fluorescent sulfonamide derivatives having carbonic anhydrase inhibiting activity and their use as theapeutic and diagnostic agents |
| US11077212B2 (en) * | 2010-08-24 | 2021-08-03 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Molecular imaging of cancer cells in vivo |
| WO2012154884A2 (en) | 2011-05-09 | 2012-11-15 | The Regents Of The University Of California | Method and compositions to promote plant growth in metal contaminated environments |
| 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 |
| WO2013036543A2 (en) * | 2011-09-10 | 2013-03-14 | H. Lee Moffitt Cancer Center And Research Institute, Inc. | Molecular imaging of cancer cells in vivo |
| EP2855520B1 (en) | 2012-06-04 | 2018-09-26 | Novartis AG | Site-specific labeling methods and molecules produced thereby |
| LT6064B (lt) * | 2012-10-15 | 2014-08-25 | Vilniaus Universitetas | Fluorinti benzensulfonamidai kaip karboanhidrazės inhibitoriai |
| ITRM20130138A1 (it) | 2013-03-07 | 2014-09-08 | Consiglio Nazionale Ricerche | Assemblato comprendente un assorbitore della luce nel vicino infrarosso legato covalentemente ad un inibitore dell'anidrasi carbonica |
| WO2014149069A1 (en) * | 2013-03-15 | 2014-09-25 | Purdue Research Foundation | Synthesis and composition of amino acid linking groups conjugated to compounds used for the targeted imaging of tumors |
| ES2735348T3 (es) * | 2014-02-03 | 2019-12-18 | Eidgenoessiche Technische Hochschule Zuerich | Conjugados de fármaco de molécula pequeña |
| US9808538B2 (en) | 2015-09-09 | 2017-11-07 | On Target Laboratories, LLC | PSMA-targeted NIR dyes and their uses |
-
2017
- 2017-03-16 EP EP17767580.8A patent/EP3430383B1/en active Active
- 2017-03-16 WO PCT/US2017/022824 patent/WO2017161197A1/en not_active Ceased
- 2017-03-16 KR KR1020187027616A patent/KR102342319B1/ko active Active
- 2017-03-16 US US15/461,361 patent/US10557854B2/en active Active
- 2017-03-16 BR BR112018068142-3A patent/BR112018068142B1/pt active IP Right Grant
- 2017-03-16 AU AU2017234681A patent/AU2017234681B2/en active Active
- 2017-03-16 JP JP2018548414A patent/JP7285537B2/ja active Active
- 2017-03-16 WO PCT/US2017/022822 patent/WO2017161195A1/en not_active Ceased
- 2017-03-16 CN CN201780017435.9A patent/CN109791107B/zh active Active
- 2017-03-16 MX MX2018011130A patent/MX2018011130A/es unknown
- 2017-03-16 ES ES17767580T patent/ES2989466T3/es active Active
-
2018
- 2018-08-29 IL IL261470A patent/IL261470B/en unknown
-
2019
- 2019-12-20 US US16/723,319 patent/US10746741B2/en active Active
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