JP2020520981A5 - - Google Patents
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- JP2020520981A5 JP2020520981A5 JP2019565169A JP2019565169A JP2020520981A5 JP 2020520981 A5 JP2020520981 A5 JP 2020520981A5 JP 2019565169 A JP2019565169 A JP 2019565169A JP 2019565169 A JP2019565169 A JP 2019565169A JP 2020520981 A5 JP2020520981 A5 JP 2020520981A5
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- JP
- Japan
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- pep
- gly
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- 150000001875 compounds Chemical class 0.000 claims description 27
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 18
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 17
- -1 4-pyridinyl Chemical group 0.000 claims description 15
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 14
- AGGWFDNPHKLBBV-YUMQZZPRSA-N (2s)-2-[[(2s)-2-amino-3-methylbutanoyl]amino]-5-(carbamoylamino)pentanoic acid Chemical compound CC(C)[C@H](N)C(=O)N[C@H](C(O)=O)CCCNC(N)=O AGGWFDNPHKLBBV-YUMQZZPRSA-N 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 9
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 claims description 8
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 claims description 8
- ZDXPYRJPNDTMRX-UHFFFAOYSA-N glutamine Natural products OC(=O)C(N)CCC(N)=O ZDXPYRJPNDTMRX-UHFFFAOYSA-N 0.000 claims description 8
- 239000004474 valine Substances 0.000 claims description 8
- 108010088535 Pep-1 peptide Proteins 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 5
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 4
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 17
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 239000004471 Glycine Substances 0.000 claims 8
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 claims 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 7
- 102000035195 Peptidases Human genes 0.000 claims 6
- 108091005804 Peptidases Proteins 0.000 claims 6
- 239000002202 Polyethylene glycol Substances 0.000 claims 6
- 239000004365 Protease Substances 0.000 claims 6
- 238000000034 method Methods 0.000 claims 6
- 229920001223 polyethylene glycol Polymers 0.000 claims 6
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims 5
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims 5
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 150000002367 halogens Chemical class 0.000 claims 5
- WEZDRVHTDXTVLT-GJZGRUSLSA-N 2-[[(2s)-2-[[(2s)-2-[(2-aminoacetyl)amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]acetic acid Chemical compound OC(=O)CNC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)CN)CC1=CC=CC=C1 WEZDRVHTDXTVLT-GJZGRUSLSA-N 0.000 claims 4
- AAQGRPOPTAUUBM-ZLUOBGJFSA-N Ala-Ala-Asn Chemical compound [H]N[C@@H](C)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(N)=O)C(O)=O AAQGRPOPTAUUBM-ZLUOBGJFSA-N 0.000 claims 4
- WQVFQXXBNHHPLX-ZKWXMUAHSA-N Ala-Ala-His Chemical compound C[C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](Cc1cnc[nH]1)C(O)=O WQVFQXXBNHHPLX-ZKWXMUAHSA-N 0.000 claims 4
- DCXYFEDJOCDNAF-UHFFFAOYSA-N Asparagine Natural products OC(=O)C(N)CC(N)=O DCXYFEDJOCDNAF-UHFFFAOYSA-N 0.000 claims 4
- 108010009504 Gly-Phe-Leu-Gly Proteins 0.000 claims 4
- FADYJNXDPBKVCA-UHFFFAOYSA-N L-Phenylalanyl-L-lysin Natural products NCCCCC(C(O)=O)NC(=O)C(N)CC1=CC=CC=C1 FADYJNXDPBKVCA-UHFFFAOYSA-N 0.000 claims 4
- DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical compound OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims 4
- LRQKBLKVPFOOQJ-YFKPBYRVSA-N L-norleucine Chemical compound CCCC[C@H]([NH3+])C([O-])=O LRQKBLKVPFOOQJ-YFKPBYRVSA-N 0.000 claims 4
- 239000004472 Lysine Substances 0.000 claims 4
- FADYJNXDPBKVCA-STQMWFEESA-N Phe-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@@H](N)CC1=CC=CC=C1 FADYJNXDPBKVCA-STQMWFEESA-N 0.000 claims 4
- 235000009582 asparagine Nutrition 0.000 claims 4
- 229960001230 asparagine Drugs 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- 125000003367 polycyclic group Chemical group 0.000 claims 4
- 239000000523 sample Substances 0.000 claims 4
- 125000003003 spiro group Chemical group 0.000 claims 4
- RHGKLRLOHDJJDR-BYPYZUCNSA-N L-citrulline Chemical compound NC(=O)NCCC[C@H]([NH3+])C([O-])=O RHGKLRLOHDJJDR-BYPYZUCNSA-N 0.000 claims 3
- RHGKLRLOHDJJDR-UHFFFAOYSA-N Ndelta-carbamoyl-DL-ornithine Natural products OC(=O)C(N)CCCNC(N)=O RHGKLRLOHDJJDR-UHFFFAOYSA-N 0.000 claims 3
- 150000001413 amino acids Chemical group 0.000 claims 3
- 235000013477 citrulline Nutrition 0.000 claims 3
- 229960002173 citrulline Drugs 0.000 claims 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 2
- 102100024940 Cathepsin K Human genes 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
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims 2
- 108010072866 Prostate-Specific Antigen Proteins 0.000 claims 2
- 102100038358 Prostate-specific antigen Human genes 0.000 claims 2
- 235000004279 alanine Nutrition 0.000 claims 2
- 125000000539 amino acid group Chemical group 0.000 claims 2
- 210000001124 body fluid Anatomy 0.000 claims 2
- 239000010839 body fluid Substances 0.000 claims 2
- 150000001721 carbon Chemical group 0.000 claims 2
- 125000005647 linker group Chemical group 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
- 241000894007 species Species 0.000 claims 2
- KRXXWINWRGUIBJ-UHFFFAOYSA-N 1,3,3-trimethyl-2h-indole Chemical compound C1=CC=C2N(C)CC(C)(C)C2=C1 KRXXWINWRGUIBJ-UHFFFAOYSA-N 0.000 claims 1
- 102000030431 Asparaginyl endopeptidase Human genes 0.000 claims 1
- 108010059081 Cathepsin A Proteins 0.000 claims 1
- 102000005572 Cathepsin A Human genes 0.000 claims 1
- 108090000712 Cathepsin B Proteins 0.000 claims 1
- 102000004225 Cathepsin B Human genes 0.000 claims 1
- 102000003902 Cathepsin C Human genes 0.000 claims 1
- 108090000267 Cathepsin C Proteins 0.000 claims 1
- 102000003908 Cathepsin D Human genes 0.000 claims 1
- 108090000258 Cathepsin D Proteins 0.000 claims 1
- 102000004178 Cathepsin E Human genes 0.000 claims 1
- 108090000611 Cathepsin E Proteins 0.000 claims 1
- 108090000610 Cathepsin F Proteins 0.000 claims 1
- 102000004176 Cathepsin F Human genes 0.000 claims 1
- 108090000617 Cathepsin G Proteins 0.000 claims 1
- 102000004173 Cathepsin G Human genes 0.000 claims 1
- 108090000619 Cathepsin H Proteins 0.000 claims 1
- 102000004175 Cathepsin H Human genes 0.000 claims 1
- 108090000625 Cathepsin K Proteins 0.000 claims 1
- 102100026540 Cathepsin L2 Human genes 0.000 claims 1
- 101710169274 Cathepsin L2 Proteins 0.000 claims 1
- 101710177066 Cathepsin O Proteins 0.000 claims 1
- 108090000613 Cathepsin S Proteins 0.000 claims 1
- 102100035654 Cathepsin S Human genes 0.000 claims 1
- 108010061112 Cathepsin W Proteins 0.000 claims 1
- 102000011933 Cathepsin W Human genes 0.000 claims 1
- 108010061117 Cathepsin Z Proteins 0.000 claims 1
- 102000011937 Cathepsin Z Human genes 0.000 claims 1
- 102000005600 Cathepsins Human genes 0.000 claims 1
- 108010084457 Cathepsins Proteins 0.000 claims 1
- 241001125840 Coryphaenidae Species 0.000 claims 1
- 102000005741 Metalloproteases Human genes 0.000 claims 1
- 108010006035 Metalloproteases Proteins 0.000 claims 1
- 102100026534 Procathepsin L Human genes 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 108010055066 asparaginylendopeptidase Proteins 0.000 claims 1
- 239000012472 biological sample Substances 0.000 claims 1
- 238000001574 biopsy Methods 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 238000003745 diagnosis Methods 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 238000003384 imaging method Methods 0.000 claims 1
- 238000000338 in vitro Methods 0.000 claims 1
- 238000001727 in vivo Methods 0.000 claims 1
- 238000004020 luminiscence type Methods 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 108010028075 procathepsin L Proteins 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 210000001519 tissue Anatomy 0.000 claims 1
- 229910052721 tungsten Inorganic materials 0.000 claims 1
- PNMBYMBIFJJMIF-UHFFFAOYSA-N CCc(cc1)ccc1NI Chemical compound CCc(cc1)ccc1NI PNMBYMBIFJJMIF-UHFFFAOYSA-N 0.000 description 1
- JYOAXOMPIXKMKK-YUMQZZPRSA-N Leu-Gln Chemical compound CC(C)C[C@H]([NH3+])C(=O)N[C@H](C([O-])=O)CCC(N)=O JYOAXOMPIXKMKK-YUMQZZPRSA-N 0.000 description 1
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2023000803A JP7553615B2 (ja) | 2017-05-24 | 2023-01-06 | プロテアーゼのイメージング／検出のための化学発光プローブ |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201762510370P | 2017-05-24 | 2017-05-24 | |
| US62/510,370 | 2017-05-24 | ||
| US201762557881P | 2017-09-13 | 2017-09-13 | |
| US62/557,881 | 2017-09-13 | ||
| PCT/IL2018/050557 WO2018216012A1 (en) | 2017-05-24 | 2018-05-23 | Chemiluminescent probes for imaging/detection of proteases |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023000803A Division JP7553615B2 (ja) | 2017-05-24 | 2023-01-06 | プロテアーゼのイメージング／検出のための化学発光プローブ |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2020520981A JP2020520981A (ja) | 2020-07-16 |
| JP2020520981A5 true JP2020520981A5 (https=) | 2021-05-06 |
Family
ID=64396284
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2019565169A Pending JP2020520981A (ja) | 2017-05-24 | 2018-05-23 | プロテアーゼのイメージング／検出のための化学発光プローブ |
| JP2023000803A Active JP7553615B2 (ja) | 2017-05-24 | 2023-01-06 | プロテアーゼのイメージング／検出のための化学発光プローブ |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2023000803A Active JP7553615B2 (ja) | 2017-05-24 | 2023-01-06 | プロテアーゼのイメージング／検出のための化学発光プローブ |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US12173350B2 (https=) |
| EP (1) | EP3630742B1 (https=) |
| JP (2) | JP2020520981A (https=) |
| CN (1) | CN110944985B (https=) |
| ES (1) | ES2963606T3 (https=) |
| PL (1) | PL3630742T3 (https=) |
| WO (1) | WO2018216012A1 (https=) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3802511A1 (en) * | 2018-05-25 | 2021-04-14 | Nemis Technologies AG | Dioxetane compounds and their use for the detection of microorganisms |
| US20230094870A1 (en) * | 2020-02-19 | 2023-03-30 | Ramot At Tel-Aviv University Ltd. | Chemiluminescence probes for tuberculosis |
| US20240277873A1 (en) * | 2021-08-11 | 2024-08-22 | Nanyang Technological University | Ultrabright chemiluminescent probes for detection and imaging |
| CN114315791B (zh) * | 2021-12-22 | 2023-12-08 | 东南大学 | 用于实现手术导航和微小转移瘤成像的小分子化学发光探针及其制备方法和用途 |
| CN114380786B (zh) * | 2021-12-23 | 2023-03-24 | 苏州大学 | 基于氨基肽酶激活型化学发光探针及其在恶性肿瘤的活体检测与手术导航方面的应用 |
| CN114716407A (zh) * | 2022-03-16 | 2022-07-08 | 大连理工大学 | 一种检测泛酰巯基乙胺酶活性的化学发光探针、制备方法及其生物应用 |
| CN115819416B (zh) * | 2022-11-29 | 2024-06-25 | 遵义医科大学 | 一种用于检测和区分的多模态化学发光分子及其应用 |
| WO2024147125A1 (en) * | 2023-01-04 | 2024-07-11 | Ramot At Tel-Aviv University Ltd. | Cyclobutyl-substituted phenoxy-dioxetanes and uses thereof |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6083486A (en) | 1998-05-14 | 2000-07-04 | The General Hospital Corporation | Intramolecularly-quenched near infrared fluorescent probes |
| PE20011267A1 (es) * | 2000-03-29 | 2001-12-15 | Vertex Pharma | Carbamato como inhibidores de caspasa |
| UA75093C2 (en) * | 2000-10-06 | 2006-03-15 | Dimensional Pharm Inc | Aminopyridinyl-,aminoguanidinyl-, and alkoxyguanidinesubstituted phenylsubstituted phenylacetamides as protease inhibitors |
| US9695251B2 (en) * | 2003-10-31 | 2017-07-04 | The Regents Of The University Of California | Activatable cell penetrating peptides with quenched fluorophores |
| US20100278745A1 (en) * | 2006-12-21 | 2010-11-04 | Norbert Lange | Compounds for fluorescence imaging |
| WO2009019115A1 (en) * | 2007-08-03 | 2009-02-12 | Sanofi-Aventis | Caspase imaging probes |
| ES2658852T3 (es) * | 2008-01-18 | 2018-03-12 | Visen Medical, Inc. | Agentes de imaginología fluorescentes |
| NZ611656A (en) | 2010-12-29 | 2014-10-31 | Arrowhead Res Corp | In vivo polynucleotide delivery conjugates having enzyme sensitive linkages |
| WO2012123916A2 (en) * | 2011-03-15 | 2012-09-20 | Ramot At Tel-Aviv University Ltd. | Activatable fluorogenic compounds and uses thereof as near infrared probes |
| FR3022784B1 (fr) * | 2014-06-26 | 2017-09-08 | Ecole Normale Superieure Lyon | Sondes moleculaires activables hydrosolubles, intermediaires pour leur synthese et procedes de detection associes |
| EP3408349B1 (en) * | 2016-01-26 | 2021-03-31 | Ramot at Tel-Aviv University Ltd. | Chemiluminescent fluorophor-linked adamantylene-dioxetane probes as diagnostics or in-vivo imaging sensors |
| EP3802511A1 (en) * | 2018-05-25 | 2021-04-14 | Nemis Technologies AG | Dioxetane compounds and their use for the detection of microorganisms |
-
2018
- 2018-05-23 CN CN201880047726.7A patent/CN110944985B/zh active Active
- 2018-05-23 WO PCT/IL2018/050557 patent/WO2018216012A1/en not_active Ceased
- 2018-05-23 ES ES18804980T patent/ES2963606T3/es active Active
- 2018-05-23 EP EP18804980.3A patent/EP3630742B1/en active Active
- 2018-05-23 US US16/616,356 patent/US12173350B2/en active Active
- 2018-05-23 JP JP2019565169A patent/JP2020520981A/ja active Pending
- 2018-05-23 PL PL18804980.3T patent/PL3630742T3/pl unknown
-
2023
- 2023-01-06 JP JP2023000803A patent/JP7553615B2/ja active Active
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