Title:
SUBSTANCE HAVING AFFINITY FOR ANTIBODY, AND COMPOUND OR SALT THEREOF HAVING BIOORTHOGONAL FUNCTIONAL GROUP
Document Type and Number:
WIPO Patent Application WO/2019/240288
Kind Code:
A1
Abstract:
The present invention provides art that enables modification of an antibody, particularly regioselective modification of an antibody. More specifically, the present invention provides a substance having affinity for an antibody, and a compound or salt thereof having a bioorthogonal functional group, which are represented by formula (I): A-L-E-B (where, A is a substance having affinity for an antibody, L is a divalent group containing a leaving group, E is a divalent group containing an electrophilic group that (i) is linked to the leaving group and (ii) has a capacity for reacting with a nucleophilic group in the antibody, B is a bioorthogonal functional group, and the leaving group has a capacity for separating from and leaving E due to a reaction between the nucleophilic group and the electrophilic group).
Inventors:
MATSUDA YUTAKA (JP)
HATADA NORIKO (JP)
YAMADA KEI (JP)
SHIKIDA NATSUKI (JP)
SHIMBO KAZUTAKA (JP)
FUJII TOMOHIRO (JP)
HIRASAWA SHIGEO (JP)
HATADA NORIKO (JP)
YAMADA KEI (JP)
SHIKIDA NATSUKI (JP)
SHIMBO KAZUTAKA (JP)
FUJII TOMOHIRO (JP)
HIRASAWA SHIGEO (JP)
Application Number:
PCT/JP2019/023779
Publication Date:
December 19, 2019
Filing Date:
June 14, 2019
Export Citation:
Assignee:
AJINOMOTO KK (JP)
International Classes:
A61K47/64; A61K39/395; A61P35/00; C07K2/00; C07K4/00; C07K14/00; C07K16/00
Domestic Patent References:
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| WO2017217347A1 | 2017-12-21 | |||
| WO2018199337A1 | 2018-11-01 | |||
| WO2018230257A1 | 2018-12-20 | |||
| WO2017191817A1 | 2017-11-09 | |||
| WO2016186206A1 | 2016-11-24 | |||
| WO2013027796A1 | 2013-02-28 | |||
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WARREN L. DELANO ET AL., SCIENCE, vol. 287, 2000, pages 1279 - 1283
BIOCHEMICAL ENGINEERING JOURNAL, vol. 79, 2013, pages 33 - 40
NOMURA Y ET AL., NUCLEIC ACIDS RES., vol. 38, no. 21, November 2010 (2010-11-01), pages 7822 - 9
MIYAKAWA S ET AL., RNA., vol. 14, no. 6, June 2008 (2008-06-01), pages 1154 - 63
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CHEM. SCI., 2015, pages 3217 - 3224
NATURE CHEMISTRY, vol. 8, 2016, pages 542 - 548
TSUKIJI ET AL., NATURE CHEMICAL BIOLOGY, vol. 5, no. 5, May 2009 (2009-05-01)
SHARPLESS K. B. ET AL., ANGEW. CHEM. INT. ED., vol. 40, 2015, pages 2004
BERTOZZI C. R. ET AL., SCIENCE, vol. 291, 2001, pages 2357
BERTOZZI C. R. ET AL., NATURE CHEMICAL BIOLOGY, vol. 1, 2005, pages 13
G. J. L. BERNARDES ET AL., CHEM. REV., vol. 115, 2015, pages 2174 - 2195
G. J. L. BERNARDES ET AL., CHEM. ASIAN. J., vol. 4, 2009, pages 630
B. G. DAVIES ET AL., NAT. COMMUN., vol. 5, 2014, pages 4740
A. WAGNER ET AL., BIOCONJUGATE. CHEM., vol. 25, 2014, pages 825
DUBOWCHIK ET AL., PHARM. THERAPEUTICS, vol. 83, 1999, pages 67 - 123
E. J. RAZUMIENKO, D. A. SCOLLARD, R. M. REILLY: "Small-Animal SPECT/CT of HER2 and HER3 Expression in Tumor Xenografts in Athymic Mice Using Trastuzumab Fab-Heregulin Bispecific Radioimmunoconjugates", THE JOURNAL OF NUCLEAR MEDICINE, SOCIETY OF NUCLEAR MEDICINE, US, vol. 53, no. 12, 1 December 2012 (2012-12-01), US , pages 1943 - 1950, XP055404561, ISSN: 0161-5505, DOI: 10.2967/jnumed.112.106906
MATULIS DAUMANTAS, LOVRIEN REX: "1-Anilino-8-Naphthalene Sulfonate Anion-Protein Binding Depends Primarily on Ion Pair Formation", BIOPHYSICAL JOURNAL, ELSEVIER, AMSTERDAM, NL, vol. 74, no. 1, 1 January 1998 (1998-01-01), AMSTERDAM, NL, pages 422 - 429, XP055861158, ISSN: 0006-3495, DOI: 10.1016/S0006-3495(98)77799-9
SHAW BRYAN F., SCHNEIDER GRÉGORY F., ARTHANARI HARIBABU, NAROVLYANSKY MAX, MOUSTAKAS DEMETRI, DURAZO ARMANDO, WAGNER GERHARD, WHIT: "Complexes of Native Ubiquitin and Dodecyl Sulfate Illustrate the Nature of Hydrophobic and Electrostatic Interactions in the Binding of Proteins and Surfactants", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 133, no. 44, 9 November 2011 (2011-11-09), pages 17681 - 17695, XP055861160, ISSN: 0002-7863, DOI: 10.1021/ja205735q
CHAN, C. ET AL.: "Trastazumab Labeled to High Specific Activity with In by Conjugation to G4 PAMAM Dendrimers Derivatized with Multiple DTPA Chelators Exhibits Increased Cytotoxic Potency on HER2-Positive Breast Cancer Cells", PHARM. RES., vol. 30, no. 8, August 2013 (2013-08-01), pages 1999 - 2009, XP055861163
TAMURA, T. ET AL.: "Rapid labelling and covalent inhibition of intracellular native proteins using ligand-directed N-acy-N-alkyl sulfonamide", NATURE COMMUNICATIONS, vol. 9, 2018, pages 1870, XP055850044, DOI: 10.1038/s41467-018-04343-0
TAMURA, T. ET AL.: "Affinity-Guided Oxime Chemistry for Selective Protein Acylation in Live Tissue Systems", J. AM. CHEM. SOC., vol. 139, 2017, pages 14181 - 14191, XP055429449, DOI: 10.1021/jacs.7b07339
TSUKIJI, S. ET AL.: "Ligand-directed tosyl chemistry for protein labeling in vivo", NATURE CHEM. BIOL., vol. 5, 2009, pages 341 - 343, XP055121566, DOI: 10.1038/nchembio.157
FUJISHIMA, S.-H. ET AL.: "Ligand-Directed Acyl Imidazole Chemistry for Labeling of Membrane-Bound Proteins on Live Cells", J. AM. CHEM. SOC., vol. 134, 2012, pages 3961 - 3964, XP055221548, DOI: 10.1021/ja2108855
See also references of EP 3811978A4
R AZUMIENKO EVA J. ET AL.: "Small-Animal SPECT/CT of HER2and HER3 Expression in Tumor Xenografts in Athymic Mice Using Trastuzumab Fab-Heregulin Bispecific Radioimmunoconjugates", THE JOURNAL OF NUCLEAR MEDICINE, vol. 53, no. 12, 2012, pages 1943 - 1950, XP055404561, DOI: 10.2967/jnumed.112.106906
REICHERT JM ET AL., NAT BIOTECHNOL, vol. 23, 2005, pages 1137 - 46
KUBOTA T ET AL., CANCER SCI, vol. 100, 2009, pages 1566 - 72
JUNUTULA JR ET AL., NAT BIOTECHNOL, vol. 26, 2008, pages 925 - 32
SHEN BQ ET AL., NAT BIOTECHNOL, vol. 30, 2012, pages 184 - 9
HOFER T ET AL., BIOCHEMISTRY, vol. 48, 2009, pages 12047 - 57
LIU W ET AL., NAT METHODS, vol. 4, 2007, pages 239 - 44
S. T. LAUGHLIN ET AL., SCIENCE, vol. 320, 2008, pages 664
A. E. SPEERS ET AL., CHEMBIOCHEM, vol. 5, 2004, pages 41
Y. TAKAOKA ET AL., ANGEW. CHEM. INT. ED., vol. 52, 2013, pages 4088
FUJISHIMA, S. ET AL., J. AM. CHEM. SOC, vol. 134, 2012, pages 3961 - 3964
FASSINA G ET AL., JOURNAL OF MOLECULAR RECOGNITION, vol. 6, 1996, pages 564 - 569
EHRLICH G. K ET AL., J. BIOCHEM. BIOPHYS. METHODS, vol. 49, 2001, pages 443 - 454
RUVO M ET AL., CHEMBIOCHEM, vol. 6, 2005, pages 1242 - 1253
KROOK M ET AL., JOURNAL OF IMMUNOLOGICAL METHODS, vol. 221, 1998, pages 151 - 157
JACOBS J. M. ET AL., BIO. TECHNIQUES, vol. 34, 2003, pages 132 - 141
CARBONELL R. G. ET AL., JOURNAL OF CHROMATOGRAPHY A, vol. 1216, 2009, pages 910 - 918
LUND L. N. ET AL., JOURNAL OF CHROMATOGRAPHY A, vol. 1225, 2012, pages 158 - 167
WARREN L. DELANO ET AL., SCIENCE, vol. 287, 2000, pages 1279 - 1283
BIOCHEMICAL ENGINEERING JOURNAL, vol. 79, 2013, pages 33 - 40
NOMURA Y ET AL., NUCLEIC ACIDS RES., vol. 38, no. 21, November 2010 (2010-11-01), pages 7822 - 9
MIYAKAWA S ET AL., RNA., vol. 14, no. 6, June 2008 (2008-06-01), pages 1154 - 63
STAROVASNIK, M. A. ET AL.: "Structural mimicry of a native protein by a minimized binding domain.", PROC. NATL. ACAD. SCI. USA., vol. 94, 1997, pages 10080 - 10085, XP055563260, DOI: 10.1073/pnas.94.19.10080
CHEM. SCI., 2015, pages 3217 - 3224
NATURE CHEMISTRY, vol. 8, 2016, pages 542 - 548
TSUKIJI ET AL., NATURE CHEMICAL BIOLOGY, vol. 5, no. 5, May 2009 (2009-05-01)
SHARPLESS K. B. ET AL., ANGEW. CHEM. INT. ED., vol. 40, 2015, pages 2004
BERTOZZI C. R. ET AL., SCIENCE, vol. 291, 2001, pages 2357
BERTOZZI C. R. ET AL., NATURE CHEMICAL BIOLOGY, vol. 1, 2005, pages 13
G. J. L. BERNARDES ET AL., CHEM. REV., vol. 115, 2015, pages 2174 - 2195
G. J. L. BERNARDES ET AL., CHEM. ASIAN. J., vol. 4, 2009, pages 630
B. G. DAVIES ET AL., NAT. COMMUN., vol. 5, 2014, pages 4740
A. WAGNER ET AL., BIOCONJUGATE. CHEM., vol. 25, 2014, pages 825
DUBOWCHIK ET AL., PHARM. THERAPEUTICS, vol. 83, 1999, pages 67 - 123
E. J. RAZUMIENKO, D. A. SCOLLARD, R. M. REILLY: "Small-Animal SPECT/CT of HER2 and HER3 Expression in Tumor Xenografts in Athymic Mice Using Trastuzumab Fab-Heregulin Bispecific Radioimmunoconjugates", THE JOURNAL OF NUCLEAR MEDICINE, SOCIETY OF NUCLEAR MEDICINE, US, vol. 53, no. 12, 1 December 2012 (2012-12-01), US , pages 1943 - 1950, XP055404561, ISSN: 0161-5505, DOI: 10.2967/jnumed.112.106906
MATULIS DAUMANTAS, LOVRIEN REX: "1-Anilino-8-Naphthalene Sulfonate Anion-Protein Binding Depends Primarily on Ion Pair Formation", BIOPHYSICAL JOURNAL, ELSEVIER, AMSTERDAM, NL, vol. 74, no. 1, 1 January 1998 (1998-01-01), AMSTERDAM, NL, pages 422 - 429, XP055861158, ISSN: 0006-3495, DOI: 10.1016/S0006-3495(98)77799-9
SHAW BRYAN F., SCHNEIDER GRÉGORY F., ARTHANARI HARIBABU, NAROVLYANSKY MAX, MOUSTAKAS DEMETRI, DURAZO ARMANDO, WAGNER GERHARD, WHIT: "Complexes of Native Ubiquitin and Dodecyl Sulfate Illustrate the Nature of Hydrophobic and Electrostatic Interactions in the Binding of Proteins and Surfactants", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, vol. 133, no. 44, 9 November 2011 (2011-11-09), pages 17681 - 17695, XP055861160, ISSN: 0002-7863, DOI: 10.1021/ja205735q
CHAN, C. ET AL.: "Trastazumab Labeled to High Specific Activity with In by Conjugation to G4 PAMAM Dendrimers Derivatized with Multiple DTPA Chelators Exhibits Increased Cytotoxic Potency on HER2-Positive Breast Cancer Cells", PHARM. RES., vol. 30, no. 8, August 2013 (2013-08-01), pages 1999 - 2009, XP055861163
TAMURA, T. ET AL.: "Rapid labelling and covalent inhibition of intracellular native proteins using ligand-directed N-acy-N-alkyl sulfonamide", NATURE COMMUNICATIONS, vol. 9, 2018, pages 1870, XP055850044, DOI: 10.1038/s41467-018-04343-0
TAMURA, T. ET AL.: "Affinity-Guided Oxime Chemistry for Selective Protein Acylation in Live Tissue Systems", J. AM. CHEM. SOC., vol. 139, 2017, pages 14181 - 14191, XP055429449, DOI: 10.1021/jacs.7b07339
TSUKIJI, S. ET AL.: "Ligand-directed tosyl chemistry for protein labeling in vivo", NATURE CHEM. BIOL., vol. 5, 2009, pages 341 - 343, XP055121566, DOI: 10.1038/nchembio.157
FUJISHIMA, S.-H. ET AL.: "Ligand-Directed Acyl Imidazole Chemistry for Labeling of Membrane-Bound Proteins on Live Cells", J. AM. CHEM. SOC., vol. 134, 2012, pages 3961 - 3964, XP055221548, DOI: 10.1021/ja2108855
See also references of EP 3811978A4
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SAKAI INTERNATIONAL PATENT OFFICE (JP)
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