Title:
SULFOXONIUM YLIDE DERIVATIVES AS PROBES FOR CYSTEINE PROTEASE
Document Type and Number:
WIPO Patent Application WO/2020/130152
Kind Code:
A1
Abstract:
The present invention relates to compounds of formula I bearing a sulfoxonium ylide moiety as warhead, or salts thereof. Such compounds can be used as activity-based probes for cysteine proteases such as cathepsin X, in methods of detecting cysteine protease activity and in related diagnostic or therapeutic methods.
Inventors:
EDGINGTON-MITCHELL LAURA (AU)
MOUNTFORD SIMON (AU)
ANDERSON BETHANY M (AU)
SZABO MONIKA (AU)
AURELIO LUIGI (AU)
THOMPSON PHILIP (AU)
MOUNTFORD SIMON (AU)
ANDERSON BETHANY M (AU)
SZABO MONIKA (AU)
AURELIO LUIGI (AU)
THOMPSON PHILIP (AU)
Application Number:
PCT/JP2019/050228
Publication Date:
June 25, 2020
Filing Date:
December 20, 2019
Export Citation:
Assignee:
TAKEDA PHARMACEUTICALS CO (JP)
International Classes:
A61K49/00; C09B23/08; C07C381/00; C07D221/18; G01N33/58
Domestic Patent References:
| WO2010117796A2 | 2010-10-14 | |||
| WO2014145257A2 | 2014-09-18 | |||
| WO2012118715A2 | 2012-09-07 | |||
| WO2009124265A1 | 2009-10-08 | |||
| WO2018119476A1 | 2018-06-28 | |||
| WO2018119476A1 | 2018-06-28 |
Foreign References:
| US5223486A | 1993-06-29 |
Other References:
MARGOT G. PAULICK ET AL: "Development of Activity-Based Probes for Cathepsin X", ACS CHEMICAL BIOLOGY, vol. 6, no. 6, 28 February 2011 (2011-02-28), pages 563 - 572, XP055680043, ISSN: 1554-8929, DOI: 10.1021/cb100392r
LECHTENBERG ET AL., ACS CHEM. BIOL., vol. 10, 2015, pages 945 - 951
DEU, E.VERDOES, M.BOGYO, M.: "New approaches for dissecting protease functions to improve probe development and drug discovery", NAT. STRUCT. MOL. BIOL., vol. 19, 2012, pages 9 - 16
DEU ET AL., NAT. STRUCT. MOL. BIOL., vol. 19, 2012, pages 9 - 16
MARTELL ET AL.: "Applications of Copper-Catalyzed Click Chemistry in Activity-Based Protein Profiling", MOLECULES, vol. 19, 2014, pages 1378 - 1393, XP055612888, DOI: 10.3390/molecules19021378
WILLEMS ET AL.: "Bioorthogonal chemistry: Applications in activity-based protein profiling", ACC. CHEM. RES., vol. 44, 2011, pages 718 - 729
CHANG, X.-Z.LI, D.-Q.HOU, Y.-FWU, J.LU, J.-S.DI, G.-H.JIN, W.OU, Z.-L.SHEN, Z.-Z.SHAO, Z.-M: "Identification of the functional role of AF1Q in the progression of breast cancer", BREAST CANCER RES. TREAT., vol. 111, 2007, pages 65 - 78, XP019600726
P. KOCIENSKI, THIEME, 2005
"Mechanisms, and Structure", 2013, WILEY, article "March 's Advanced Organic Chemistry: Reactions"
CAREYSUNDBERG: "Advanced Organic Chemistry", vol. A; B, 2000, PLENUM
EDGINGTON, L.E.BOGYO, M.: "In vivo imaging and biochemical characterization of protease function using fluorescent activity-based probes", CURR. PROTOC. CHEM. BIOL., vol. 1 -27, 2013, pages 25 - 44
"Larock's Comprehensive Organic Transformations", vol. 1-5, 1989, ELSEVIER SCIENCE PUBLISHERS
MARTELL ET AL., MOLECULES, vol. 19, 2014, pages 1378 - 1393
EDGINGTON-MITCHELL, L.E.AND BOGYO, M.: "Detection of Active Caspases During Apoptosis Using Fluorescent Activity-Based Probes", METHODS MOL BIOL., vol. 1419, 2016, pages 27 - 39
EDGINGTON-MITCHELL, L.E.BOGYO, M.VERDOES, M.: "Live Cell Imaging and Profiling of Cysteine Cathepsin Activity Using a Quenched Activity-Based Probe", METHODS MOL BIOL., vol. 1491, 2017, pages 145 - 159
AKKARI, L.GOCHEVA, V.KESTER, J.C.HUNTER, K.E.QUICK, M.L.SEVENICH, L.WANG, H.-W.PETERS, C.TANG, L.H.KLIMSTRA, D.S.: "Distinct functions of macrophage-derived and cancer cell-derived cathepsin Z combine to promote tumor malignancy via interactions with the extracellular matrix", GENES DEV., vol. 28, 2014, pages 2134 - 2150
ALLAN, E.R.O.CAMPDEN, R.I.EWANCHUK, B.W.TAILOR, P.BALCE, D.R.MCKENNA, N.T.GREENE, C.J.WARREN, A.L.REINHECKEL, T.YATES, R.M.: "A role for cathepsin Z in neuroinflammation provides mechanistic support for an epigenetic risk factor in multiple sclerosis", J NEUROINFLAMMATION, vol. 14, 2017, pages 1 - 11
BERNHARDT, A.KUESTER, D.ROESSNER, A.REINHECKEL, T.KRUEGER, S.: "Cathepsin X-deficient Gastric Epithelial Cells in Co-culture with Macrophages: Characterization of cytokine response and migration capability after Helicobacter pylori infection", J. BIOL. CHEM., vol. 285, 2010, pages 33691 - 33700
DUIVENVOORDEN, H.M.RAUTELA, JEDGINGTON-MITCHELL, L.E.SPURLING, A.GREENING, D.W.NOWELL, C.J.MOLLOY, T.J.ROBBINS, E.BROCKWELL, N.KLE: "Myoepithelial cell-specific expression of stefin A as a suppressor of early breast cancer invasion", J. PATHOL, vol. 243, 2017, pages 496 - 509
EDGINGTON, L.E.BERGER, A.B.BLUM, G.ALBROW, V.E.PAULICK, M.G.LINEBERRY, N.BOGYO, M.: "Noninvasive optical imaging of apoptosis by caspase-targeted activity-based probes", NAT. MED., vol. 15, 2009, pages 967 - 973
EDGINGTON, L.E.VAN RAAM, B.J.VERDOES, M.WIERSCHEM, C.SALVESEN, G.S.BOGYO, M.: "An Optimized Activity-Based Probe for the Study of Caspase-6 Activation", CHEM. BIOL., vol. 19, 2012, pages 340 - 352, XP028475180, DOI: 10.1016/j.chembiol.2011.12.021
EDGINGTON, L.E.VERDOES, M.BOGYO, M.: "Functional imaging of proteases: recent advances in the design and application of substrate-based and activity-based probes", CURR. OP. CHEM. BIOL., vol. 15, 2011, pages 798 - 805, XP028338677, DOI: 10.1016/j.cbpa.2011.10.012
EDGINGTON, L.EVERDOES, M.ORTEGA, A.WITHANA, N.P.LEE, J.SYED, S.BACHMANN, M.H.BLUM, G.BOGYO, M.: "Functional Imaging of Legumain in Cancer Using a New Quenched Activity-Based Probe", J. AM. CHEM. SOC., vol. 135, 2013, pages 174 - 182
EDGINGTON-MITCHELL, L.E.RAUTELA, J.DUIVENVOORDEN, H.M.JAYATILLEKE, K.MVAN DER LINDEN, W.A.VERDOES, M.BOGYO, M.PARKER, B.S.: "Cysteine cathepsin activity suppresses osteoclastogenesis of myeloid-derived suppressor cells in breast cancer", ONCOTARGET, vol. 6, 2015, pages 27008 - 27022
HAFNER, A.GLAVAN, G.OBERMAJER, N.ZIVIN, M.SCHLIEBS, R.KOS, J.: "Neuroprotective role of y-enolase in microglia in a mouse model of Alzheimer's disease is regulated by cathepsin X", AGING CELL, vol. 12, 2013, pages 604 - 614
HUYNH, J.L.GARG, P.THIN, T.H.YOO, S.DUTTA, R.TRAPP, B.D.HAROUTUNIAN, V.ZHU, J.DONOVAN, M.J.SHARP, A.J.: "Epigenome-wide dif ferences in pathology-free regions of multiple sclerosis-affected brains", NAT. NEUROSCI., vol. 17, 2013, pages 121 - 130
KRUEGER, S.KALINSKI, T.HUNDERTMARK, T.WEX, T.KüSTER, D.PEITZ, U.EBERT, M.NAGLER, D.K.KELLNER, U.MALFERTHEINER, P.: "Up-regulation of cathepsin X inHelicobacter pylori gastritis and gastric cancer", J. PATHOL., vol. 207, 2005, pages 32 - 42
LEICHSENRING, A.BäCKERI., WENDTW., ANDRISKEM.SCHMITZ, B.STICHEL, C.C.LüBBERT, H.: "Differential expression of Cathepsin S and X in the spinal cord of a rat neuropathic pain model", BMC NEUROSCI., vol. 9, 2008, pages 80 - 13
MEARA, J.P.RICH, D.H.: "Mechanistic studies on the inactivation of papain by epoxysuccinyl inhibitors", J. MED. CHEM., vol. 39, 1996, pages 3357 - 3366
NAGLER, D.K.KRAUS, S.FEIERLER, J.MENTELE, R.LOTTSPEICH, F.JOCHUM, M.FAUSSNER, A.: "A cysteine-type carboxypeptidase, cathepsin X, generates peptide receptor agonists", INT. IMMUNOPHARMACO, vol. 10, 2010, pages 134 - 139, XP026826384
NAGLER, D.K.KRUGER, S.KELLNER, AZIOMEK, EMENARD, R.BUHTZ, P.KRAMS, M.ROESSNER, A.KELLNER, U.: "Up-regulation of cathepsin X in prostate cancer and prostatic intraepithelial neoplasia", PROSTATE, vol. 60, 2004, pages 109 - 119
NAGLER, D.K.ZHANG, R.TARN, W.SULEA, T.PURISIMA, E.O.MENARD, R.: "Human Cathepsin X: A Cysteine Protease with Unique Carboxypeptidase Activity", BIOCHEM., vol. 38, 1999, pages 12648 - 12654
OBERMAJER, N.DOLJAK, B.JAMNIK, P.FONOVIC, U.P.KOS, J: "Cathepsin X cleaves the C-terminal dipeptide of alpha- and gamma-enolase and impairs survival and neuritogenesis of neuronal cells", INT. J. BIOCHEM. CELL BIOL., vol. 41, 2009, pages 1685 - 1696, XP026101484, DOI: 10.1016/j.biocel.2009.02.019
OBERMAJER, N.SVAJGER, U.BOGYO, M.JERAS, M.KOS, J.: "Maturation of dendritic cells depends on proteolytic cleavage by cathepsin X", J. LEUKOCYTE BIOL., vol. 84, 2008, pages 1306 - 1315
ORESIC BENDER, KOFORI, L.VAN DER LINDEN, W.A.MOCK, E.D.DATTA, G.K.CHOWDHURY, SLI, H.SEGAL, E.SANCHEZ LOPEZ, M.ELLMAN, J.A.: "Design of a Highly Selective Quenched Activity-Based Probe and Its Application in Dual Color Imaging Studies of Cathepsin S Activity Localization", J. AM. CHEM. SOC., vol. 137, 2015, pages 4771 - 4777
ORLOWSKI, G.MCOLBERT, J.D.SHARMA, S.BOGYO, M.ROBERTSON, S.A.ROCK, K.L.: "Multiple Cathepsins Promote Pro-IL-Iβ Synthesis and NLRP3-Mediated IL-Iβ Activation", J. IMMUNOL., vol. 195, 2015, pages 1685 - 1697
PAULICK, M.G.BOGYO, M.: "Development of Activity-Based Probes for Cathepsin X", ACS CHEM. BIOL., vol. 6, 2011, pages 563 - 572
PECAR FONOVIC, U.KOS, J.: "Cathepsin X Cleaves Profilin 1 C-Terminal Tyr139 and Influences Clathrin-Mediated Endocytosis", PLOS ONE, vol. 10, 2015, pages e0137217 - 13
SANMAN, L.E.BOGYO, M.: "Activity-Based Profiling of Proteases", ANNU. REV. BIOCHEM., vol. 83, 2014, pages 249 - 273, XP055403896, DOI: 10.1146/annurev-biochem-060713-035352
SEVENICH, L.SCHURIGT, U.SACHSE, K.GAJDA, M.WERNER, F.MULLER, S.VASILJEVA, O.SCHWINDE, A.KLEMM, N.DEUSSING, J.: "Synergistic antitumor effects of combined cathepsin B and cathepsin Z deficiencies on breast cancer progression and metastasis in mice", PROC. NAT. ACAD. SCI., vol. 107, 2010, pages 2497 - 2502, XP055151096, DOI: 10.1073/pnas.0907240107
SHAW, E.: "Peptidyl sulfonium salts. A new class of protease inhibitors", J. BIOL. CHEM., vol. 263, 1988, pages 2768 - 2772, XP001034096
VERDOES, M.EDGINGTON, L.E.SCHEEREN, F.A.LEYVA, M.BLUM, G.WEISKOPF, K.BACHMANN, M.H.ELLMAN, J.A.BOGYO, M.: "A Nonpeptidic Cathepsin S Activity-Based Probe for Noninvasive Optical Imaging of Tumor-Associated Macrophages", CHEM. BIOL., vol. 19, 2012, pages 619 - 628, XP055287983, DOI: 10.1016/j.chembiol.2012.03.012
VERDOES, M.ORESIC BENDER, K.SEGAL, E.VAN DER LINDEN, W.A.SYED, S.WITHANA, N.P.SANMAN, L.E.BOGYO, M.: "Improved Quenched Fluorescent Probe for Imaging of Cysteine Cathepsin Activity", J. AM. CHEM. SOC., vol. 135, 2013, pages 14726 - 14730, XP055287988, DOI: 10.1021/ja4056068
WENDT, W., ZHU, X.-R., LüBBERT, H., AND STICHEL, C.C.: "Differential expression of cathepsin X in aging and pathological central nervous system of mice", EXP. NEUROL., vol. 204, 2007, pages 525 - 540, XP022005830, DOI: 10.1016/j.expneurol.2007.01.007
LECHTENBERG ET AL., ACS CHEM. BIOL., vol. 10, 2015, pages 945 - 951
DEU, E.VERDOES, M.BOGYO, M.: "New approaches for dissecting protease functions to improve probe development and drug discovery", NAT. STRUCT. MOL. BIOL., vol. 19, 2012, pages 9 - 16
DEU ET AL., NAT. STRUCT. MOL. BIOL., vol. 19, 2012, pages 9 - 16
MARTELL ET AL.: "Applications of Copper-Catalyzed Click Chemistry in Activity-Based Protein Profiling", MOLECULES, vol. 19, 2014, pages 1378 - 1393, XP055612888, DOI: 10.3390/molecules19021378
WILLEMS ET AL.: "Bioorthogonal chemistry: Applications in activity-based protein profiling", ACC. CHEM. RES., vol. 44, 2011, pages 718 - 729
CHANG, X.-Z.LI, D.-Q.HOU, Y.-FWU, J.LU, J.-S.DI, G.-H.JIN, W.OU, Z.-L.SHEN, Z.-Z.SHAO, Z.-M: "Identification of the functional role of AF1Q in the progression of breast cancer", BREAST CANCER RES. TREAT., vol. 111, 2007, pages 65 - 78, XP019600726
P. KOCIENSKI, THIEME, 2005
"Mechanisms, and Structure", 2013, WILEY, article "March 's Advanced Organic Chemistry: Reactions"
CAREYSUNDBERG: "Advanced Organic Chemistry", vol. A; B, 2000, PLENUM
EDGINGTON, L.E.BOGYO, M.: "In vivo imaging and biochemical characterization of protease function using fluorescent activity-based probes", CURR. PROTOC. CHEM. BIOL., vol. 1 -27, 2013, pages 25 - 44
"Larock's Comprehensive Organic Transformations", vol. 1-5, 1989, ELSEVIER SCIENCE PUBLISHERS
MARTELL ET AL., MOLECULES, vol. 19, 2014, pages 1378 - 1393
EDGINGTON-MITCHELL, L.E.AND BOGYO, M.: "Detection of Active Caspases During Apoptosis Using Fluorescent Activity-Based Probes", METHODS MOL BIOL., vol. 1419, 2016, pages 27 - 39
EDGINGTON-MITCHELL, L.E.BOGYO, M.VERDOES, M.: "Live Cell Imaging and Profiling of Cysteine Cathepsin Activity Using a Quenched Activity-Based Probe", METHODS MOL BIOL., vol. 1491, 2017, pages 145 - 159
AKKARI, L.GOCHEVA, V.KESTER, J.C.HUNTER, K.E.QUICK, M.L.SEVENICH, L.WANG, H.-W.PETERS, C.TANG, L.H.KLIMSTRA, D.S.: "Distinct functions of macrophage-derived and cancer cell-derived cathepsin Z combine to promote tumor malignancy via interactions with the extracellular matrix", GENES DEV., vol. 28, 2014, pages 2134 - 2150
ALLAN, E.R.O.CAMPDEN, R.I.EWANCHUK, B.W.TAILOR, P.BALCE, D.R.MCKENNA, N.T.GREENE, C.J.WARREN, A.L.REINHECKEL, T.YATES, R.M.: "A role for cathepsin Z in neuroinflammation provides mechanistic support for an epigenetic risk factor in multiple sclerosis", J NEUROINFLAMMATION, vol. 14, 2017, pages 1 - 11
BERNHARDT, A.KUESTER, D.ROESSNER, A.REINHECKEL, T.KRUEGER, S.: "Cathepsin X-deficient Gastric Epithelial Cells in Co-culture with Macrophages: Characterization of cytokine response and migration capability after Helicobacter pylori infection", J. BIOL. CHEM., vol. 285, 2010, pages 33691 - 33700
DUIVENVOORDEN, H.M.RAUTELA, JEDGINGTON-MITCHELL, L.E.SPURLING, A.GREENING, D.W.NOWELL, C.J.MOLLOY, T.J.ROBBINS, E.BROCKWELL, N.KLE: "Myoepithelial cell-specific expression of stefin A as a suppressor of early breast cancer invasion", J. PATHOL, vol. 243, 2017, pages 496 - 509
EDGINGTON, L.E.BERGER, A.B.BLUM, G.ALBROW, V.E.PAULICK, M.G.LINEBERRY, N.BOGYO, M.: "Noninvasive optical imaging of apoptosis by caspase-targeted activity-based probes", NAT. MED., vol. 15, 2009, pages 967 - 973
EDGINGTON, L.E.VAN RAAM, B.J.VERDOES, M.WIERSCHEM, C.SALVESEN, G.S.BOGYO, M.: "An Optimized Activity-Based Probe for the Study of Caspase-6 Activation", CHEM. BIOL., vol. 19, 2012, pages 340 - 352, XP028475180, DOI: 10.1016/j.chembiol.2011.12.021
EDGINGTON, L.E.VERDOES, M.BOGYO, M.: "Functional imaging of proteases: recent advances in the design and application of substrate-based and activity-based probes", CURR. OP. CHEM. BIOL., vol. 15, 2011, pages 798 - 805, XP028338677, DOI: 10.1016/j.cbpa.2011.10.012
EDGINGTON, L.EVERDOES, M.ORTEGA, A.WITHANA, N.P.LEE, J.SYED, S.BACHMANN, M.H.BLUM, G.BOGYO, M.: "Functional Imaging of Legumain in Cancer Using a New Quenched Activity-Based Probe", J. AM. CHEM. SOC., vol. 135, 2013, pages 174 - 182
EDGINGTON-MITCHELL, L.E.RAUTELA, J.DUIVENVOORDEN, H.M.JAYATILLEKE, K.MVAN DER LINDEN, W.A.VERDOES, M.BOGYO, M.PARKER, B.S.: "Cysteine cathepsin activity suppresses osteoclastogenesis of myeloid-derived suppressor cells in breast cancer", ONCOTARGET, vol. 6, 2015, pages 27008 - 27022
HAFNER, A.GLAVAN, G.OBERMAJER, N.ZIVIN, M.SCHLIEBS, R.KOS, J.: "Neuroprotective role of y-enolase in microglia in a mouse model of Alzheimer's disease is regulated by cathepsin X", AGING CELL, vol. 12, 2013, pages 604 - 614
HUYNH, J.L.GARG, P.THIN, T.H.YOO, S.DUTTA, R.TRAPP, B.D.HAROUTUNIAN, V.ZHU, J.DONOVAN, M.J.SHARP, A.J.: "Epigenome-wide dif ferences in pathology-free regions of multiple sclerosis-affected brains", NAT. NEUROSCI., vol. 17, 2013, pages 121 - 130
KRUEGER, S.KALINSKI, T.HUNDERTMARK, T.WEX, T.KüSTER, D.PEITZ, U.EBERT, M.NAGLER, D.K.KELLNER, U.MALFERTHEINER, P.: "Up-regulation of cathepsin X inHelicobacter pylori gastritis and gastric cancer", J. PATHOL., vol. 207, 2005, pages 32 - 42
LEICHSENRING, A.BäCKERI., WENDTW., ANDRISKEM.SCHMITZ, B.STICHEL, C.C.LüBBERT, H.: "Differential expression of Cathepsin S and X in the spinal cord of a rat neuropathic pain model", BMC NEUROSCI., vol. 9, 2008, pages 80 - 13
MEARA, J.P.RICH, D.H.: "Mechanistic studies on the inactivation of papain by epoxysuccinyl inhibitors", J. MED. CHEM., vol. 39, 1996, pages 3357 - 3366
NAGLER, D.K.KRAUS, S.FEIERLER, J.MENTELE, R.LOTTSPEICH, F.JOCHUM, M.FAUSSNER, A.: "A cysteine-type carboxypeptidase, cathepsin X, generates peptide receptor agonists", INT. IMMUNOPHARMACO, vol. 10, 2010, pages 134 - 139, XP026826384
NAGLER, D.K.KRUGER, S.KELLNER, AZIOMEK, EMENARD, R.BUHTZ, P.KRAMS, M.ROESSNER, A.KELLNER, U.: "Up-regulation of cathepsin X in prostate cancer and prostatic intraepithelial neoplasia", PROSTATE, vol. 60, 2004, pages 109 - 119
NAGLER, D.K.ZHANG, R.TARN, W.SULEA, T.PURISIMA, E.O.MENARD, R.: "Human Cathepsin X: A Cysteine Protease with Unique Carboxypeptidase Activity", BIOCHEM., vol. 38, 1999, pages 12648 - 12654
OBERMAJER, N.DOLJAK, B.JAMNIK, P.FONOVIC, U.P.KOS, J: "Cathepsin X cleaves the C-terminal dipeptide of alpha- and gamma-enolase and impairs survival and neuritogenesis of neuronal cells", INT. J. BIOCHEM. CELL BIOL., vol. 41, 2009, pages 1685 - 1696, XP026101484, DOI: 10.1016/j.biocel.2009.02.019
OBERMAJER, N.SVAJGER, U.BOGYO, M.JERAS, M.KOS, J.: "Maturation of dendritic cells depends on proteolytic cleavage by cathepsin X", J. LEUKOCYTE BIOL., vol. 84, 2008, pages 1306 - 1315
ORESIC BENDER, KOFORI, L.VAN DER LINDEN, W.A.MOCK, E.D.DATTA, G.K.CHOWDHURY, SLI, H.SEGAL, E.SANCHEZ LOPEZ, M.ELLMAN, J.A.: "Design of a Highly Selective Quenched Activity-Based Probe and Its Application in Dual Color Imaging Studies of Cathepsin S Activity Localization", J. AM. CHEM. SOC., vol. 137, 2015, pages 4771 - 4777
ORLOWSKI, G.MCOLBERT, J.D.SHARMA, S.BOGYO, M.ROBERTSON, S.A.ROCK, K.L.: "Multiple Cathepsins Promote Pro-IL-Iβ Synthesis and NLRP3-Mediated IL-Iβ Activation", J. IMMUNOL., vol. 195, 2015, pages 1685 - 1697
PAULICK, M.G.BOGYO, M.: "Development of Activity-Based Probes for Cathepsin X", ACS CHEM. BIOL., vol. 6, 2011, pages 563 - 572
PECAR FONOVIC, U.KOS, J.: "Cathepsin X Cleaves Profilin 1 C-Terminal Tyr139 and Influences Clathrin-Mediated Endocytosis", PLOS ONE, vol. 10, 2015, pages e0137217 - 13
SANMAN, L.E.BOGYO, M.: "Activity-Based Profiling of Proteases", ANNU. REV. BIOCHEM., vol. 83, 2014, pages 249 - 273, XP055403896, DOI: 10.1146/annurev-biochem-060713-035352
SEVENICH, L.SCHURIGT, U.SACHSE, K.GAJDA, M.WERNER, F.MULLER, S.VASILJEVA, O.SCHWINDE, A.KLEMM, N.DEUSSING, J.: "Synergistic antitumor effects of combined cathepsin B and cathepsin Z deficiencies on breast cancer progression and metastasis in mice", PROC. NAT. ACAD. SCI., vol. 107, 2010, pages 2497 - 2502, XP055151096, DOI: 10.1073/pnas.0907240107
SHAW, E.: "Peptidyl sulfonium salts. A new class of protease inhibitors", J. BIOL. CHEM., vol. 263, 1988, pages 2768 - 2772, XP001034096
VERDOES, M.EDGINGTON, L.E.SCHEEREN, F.A.LEYVA, M.BLUM, G.WEISKOPF, K.BACHMANN, M.H.ELLMAN, J.A.BOGYO, M.: "A Nonpeptidic Cathepsin S Activity-Based Probe for Noninvasive Optical Imaging of Tumor-Associated Macrophages", CHEM. BIOL., vol. 19, 2012, pages 619 - 628, XP055287983, DOI: 10.1016/j.chembiol.2012.03.012
VERDOES, M.ORESIC BENDER, K.SEGAL, E.VAN DER LINDEN, W.A.SYED, S.WITHANA, N.P.SANMAN, L.E.BOGYO, M.: "Improved Quenched Fluorescent Probe for Imaging of Cysteine Cathepsin Activity", J. AM. CHEM. SOC., vol. 135, 2013, pages 14726 - 14730, XP055287988, DOI: 10.1021/ja4056068
WENDT, W., ZHU, X.-R., LüBBERT, H., AND STICHEL, C.C.: "Differential expression of cathepsin X in aging and pathological central nervous system of mice", EXP. NEUROL., vol. 204, 2007, pages 525 - 540, XP022005830, DOI: 10.1016/j.expneurol.2007.01.007
Attorney, Agent or Firm:
TAKASHIMA, Hajime (JP)
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