Title:
CONJUGATE AND CANCER THERAPEUTIC AGENT
Document Type and Number:
WIPO Patent Application WO/2020/218390
Kind Code:
A1
Abstract:
A conjugate in which a deferoxamine compound, which is at least one member selected from the group consisting of deferoxamine, an ion thereof, a salt thereof and a derivative of the same, is conjugated to a biocompatible polymer, wherein the biocompatible polymer contains a first biocompatible polymer chain and a second biocompatible polymer chain being different from the first biocompatible polymer chain.
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Inventors:
NISHIYAMA NOBUHIRO (JP)
NOMOTO TAKAHIRO (JP)
KOHMOTO KANA (JP)
TAKEMOTO HIROYASU (JP)
MATSUI MAKOTO (JP)
NOMOTO TAKAHIRO (JP)
KOHMOTO KANA (JP)
TAKEMOTO HIROYASU (JP)
MATSUI MAKOTO (JP)
Application Number:
PCT/JP2020/017421
Publication Date:
October 29, 2020
Filing Date:
April 23, 2020
Export Citation:
Assignee:
TOKYO INST TECH (JP)
SBI PHARMACEUTICALS CO LTD (JP)
SBI PHARMACEUTICALS CO LTD (JP)
International Classes:
A61P35/00; A61K31/16; A61K47/64
Domestic Patent References:
| WO2017170845A1 | 2017-10-05 |
Foreign References:
| JP2011162569A | 2011-08-25 | |||
| JP2019083250A | 2019-05-30 |
Other References:
TAKAHIRO YAMASAKI , SHUJI TERAI , ISAO SAKAIDA: "Deferoxamine for Advanced Hepatocellular Carcinoma", NEW ENGLAND JOURNAL OF MEDECINE, vol. 365, no. 6, 11 August 2011 (2011-08-11), pages 576 - 578, XP055860223, DOI: 10.1056/NEJMc1105726
ALBERTO DONFRANCESCO, GIOVANNI DEB, CARLO DOMINICI, DOMENICO PILEGGI, MANUEL A. CASTELLO, LAWRENCE HELSON: "Effects of a Single Course of Deferoxamine in Neuroblastoma Patients1", CANCER RESEARCH, vol. 50, no. 16, 15 August 1990 (1990-08-15), pages 4929 - 4930, XP055758829
JASMINE L. HAMILTON MUHAMMAD IMRAN UL‐HAQ A. LOUISE CREAGH CHARLES A. HAYNES JAYACHANDRAN N. KIZHAKKEDATHU: "Iron Binding and Iron Removal Efficiency of Desferrioxamine Based Polymeric Iron Chelators: Influence of Molecular Size and Chelator Density", MACROMOLECULAR BIOSCIENCE, vol. 17, no. 3, 28 September 2017 (2017-09-28), pages 1 - 12, XP055758833, ISSN: 1616-5187, DOI: 10.1002/mabi.201600244
YOKOYAMA MASAYUKI: "Research summaries of 'polymer nanomedical' project", 26 February 2009 (2009-02-26), pages 1 - 110, XP055758841, Retrieved from the Internet
WILKS, M. Q. ET AL.: "Imaging PEG-Like Nanoprobes in Tumor , Transient Ischemia, and Inflammatory Disease Models", BIOCONJUGATE CHEMISTRY, vol. 26, 2015, pages 1061 - 1069, XP055283192, DOI: 10.1021/acs.bioconjchem.5b00213
BECTON DLBRYLES P: "Deferoxamine Inhibition of Human Neuroblastoma Viability and Proliferation", CANCER RESEARCH, vol. 48, 1988, pages 7189 - 7192
YANG Y.XU Y.SU A.YANG D.ZHANG X.: "Effects of Deferoxamine on Leukemia In Vitro and Its Related Mechanism", MED SCI MONIT, vol. 24, 2018, pages 6735 - 6741
BAJBOUJ K.SHAFARIN J.HAMAD M.: "High-Dose Deferoxamine Treatment Disrupts Intracellular Iron Homeostasis, Reduces Growth, and Induces Apoptosis in Metastatic and Nonmetastatic Breast Cancer Cell Lines", TECHNOL CANCER RES TREAT, vol. 17, 2018, pages 1 - 11
YAMASAKI T.TERAI S.SAKAIDA I.: "Deferoxamine for Advanced Hepatocellular Carcinoma", THE NEW ENGLAND JOURNAL OF MEDICINE, vol. 365, 2011, pages 576 - 578
DONFRANCESCO A.DEB G.DOMINICI C.PILEGGI D.CASTELLO MA.HELSON L.: "Effects of a Single Course of Deferoxamine in Neuroblastoma Patients", CANCER RESEARCH, vol. 50, 1990, pages 4929 - 4930, XP055758829
HAMILTON JLKIZHAKKEDATHU JN: "Polymeric nanocarriers for the treatment of systemic iron overload", MOL. CELL. THER., vol. 3, 2015, pages 3, XP021220024, DOI: 10.1186/s40591-015-0039-1
HALLAWAY PE.EATON JW.PANTER SS.HEDLUND BE.: "Modulation of deferoxamine toxicity and clearance by covalent attachment to biocompatible polymers", PROC NATL ACAD SCI USA, vol. 86, 1989, pages 10108 - 10112, XP002054495, DOI: 10.1073/pnas.86.24.10108
BLATT J.BOEGEL F.HEDLUND BE.ARENA VC.: "Shadduck RK. Failure to alter the course of acute myelogenous leukemia in the rat with subcutaneous deferoxamine", LEUKEMIA RESEARCH, vol. 15, 1991, pages 391 - 394, XP026298329, DOI: 10.1016/0145-2126(91)90015-L
WANG W.TABU K.HAGIYA Y.SUGIYAMA Y.KOKUBU Y.MUROTA Y.OGURA S.TAGA T.: "Enhancement of 5-aminolevulinic acid-based fluorescence detection of side population-defined glioma stem cells by iron chelation", SCIENTIFIC REPORTS, vol. 7, 2017, pages 42070
C. KRISHNAJ. B. MITCHELLC. P. CORPEG. R. BUETTNERE. SHACTERM. LEVINE: "Pharmacologic ascorbic acid concentrations selectively kill cancer cells: action as a prodrug to deliver hydrogen peroxide to tissues", PROC. NATL. ACAD. SCI. U. S. A., vol. 102, 2005, pages 13604 - 13609, XP008079305, DOI: 10.1073/pnas.0506390102
Q. CHENM. G. ESPEYA. Y. SUNJ. H. LEEM. C. KRISHNAE. SHACTERP. L. CHOYKEC. POOPUTK. L. KIRKG. R. BUETTNER: "Ascorbate in pharmacologic concentrations selectively generates ascorbate radical and hydrogen peroxide in extracellular fluid in vivo", PROC. NATL. ACAD. SCI. U. S. A., vol. 104, 2007, pages 8749 - 8754
Q. CHENM. G. ESPEYA. Y. SUNC. POOPUTK. L. KIRKM. C. KRISHNAD. S. KHOSHJ. DRISKOM. LEVINE: "Pharmacologic doses of ascorbate act as a prooxidant and decrease growth of aggressive tumor xenografts in mice", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, vol. 105, 2008, pages 11105 - 11109, XP055457771, DOI: 10.1073/pnas.0804226105
M. MOJICJ. BOGDANOVIC PRISTOVD. MAKSIMOVIC-LVANICD. R. JONESM. STANICS. MIJATOVIC1. SPASOJEVIC: "Extracellular iron diminishes anticancer effects of vitamin C: an in vitro study", SCI. REP., vol. 4, 2014, pages 5955
See also references of EP 3960242A4
ALBERTO DONFRANCESCO, GIOVANNI DEB, CARLO DOMINICI, DOMENICO PILEGGI, MANUEL A. CASTELLO, LAWRENCE HELSON: "Effects of a Single Course of Deferoxamine in Neuroblastoma Patients1", CANCER RESEARCH, vol. 50, no. 16, 15 August 1990 (1990-08-15), pages 4929 - 4930, XP055758829
JASMINE L. HAMILTON MUHAMMAD IMRAN UL‐HAQ A. LOUISE CREAGH CHARLES A. HAYNES JAYACHANDRAN N. KIZHAKKEDATHU: "Iron Binding and Iron Removal Efficiency of Desferrioxamine Based Polymeric Iron Chelators: Influence of Molecular Size and Chelator Density", MACROMOLECULAR BIOSCIENCE, vol. 17, no. 3, 28 September 2017 (2017-09-28), pages 1 - 12, XP055758833, ISSN: 1616-5187, DOI: 10.1002/mabi.201600244
YOKOYAMA MASAYUKI: "Research summaries of 'polymer nanomedical' project", 26 February 2009 (2009-02-26), pages 1 - 110, XP055758841, Retrieved from the Internet
WILKS, M. Q. ET AL.: "Imaging PEG-Like Nanoprobes in Tumor , Transient Ischemia, and Inflammatory Disease Models", BIOCONJUGATE CHEMISTRY, vol. 26, 2015, pages 1061 - 1069, XP055283192, DOI: 10.1021/acs.bioconjchem.5b00213
BECTON DLBRYLES P: "Deferoxamine Inhibition of Human Neuroblastoma Viability and Proliferation", CANCER RESEARCH, vol. 48, 1988, pages 7189 - 7192
YANG Y.XU Y.SU A.YANG D.ZHANG X.: "Effects of Deferoxamine on Leukemia In Vitro and Its Related Mechanism", MED SCI MONIT, vol. 24, 2018, pages 6735 - 6741
BAJBOUJ K.SHAFARIN J.HAMAD M.: "High-Dose Deferoxamine Treatment Disrupts Intracellular Iron Homeostasis, Reduces Growth, and Induces Apoptosis in Metastatic and Nonmetastatic Breast Cancer Cell Lines", TECHNOL CANCER RES TREAT, vol. 17, 2018, pages 1 - 11
YAMASAKI T.TERAI S.SAKAIDA I.: "Deferoxamine for Advanced Hepatocellular Carcinoma", THE NEW ENGLAND JOURNAL OF MEDICINE, vol. 365, 2011, pages 576 - 578
DONFRANCESCO A.DEB G.DOMINICI C.PILEGGI D.CASTELLO MA.HELSON L.: "Effects of a Single Course of Deferoxamine in Neuroblastoma Patients", CANCER RESEARCH, vol. 50, 1990, pages 4929 - 4930, XP055758829
HAMILTON JLKIZHAKKEDATHU JN: "Polymeric nanocarriers for the treatment of systemic iron overload", MOL. CELL. THER., vol. 3, 2015, pages 3, XP021220024, DOI: 10.1186/s40591-015-0039-1
HALLAWAY PE.EATON JW.PANTER SS.HEDLUND BE.: "Modulation of deferoxamine toxicity and clearance by covalent attachment to biocompatible polymers", PROC NATL ACAD SCI USA, vol. 86, 1989, pages 10108 - 10112, XP002054495, DOI: 10.1073/pnas.86.24.10108
BLATT J.BOEGEL F.HEDLUND BE.ARENA VC.: "Shadduck RK. Failure to alter the course of acute myelogenous leukemia in the rat with subcutaneous deferoxamine", LEUKEMIA RESEARCH, vol. 15, 1991, pages 391 - 394, XP026298329, DOI: 10.1016/0145-2126(91)90015-L
WANG W.TABU K.HAGIYA Y.SUGIYAMA Y.KOKUBU Y.MUROTA Y.OGURA S.TAGA T.: "Enhancement of 5-aminolevulinic acid-based fluorescence detection of side population-defined glioma stem cells by iron chelation", SCIENTIFIC REPORTS, vol. 7, 2017, pages 42070
C. KRISHNAJ. B. MITCHELLC. P. CORPEG. R. BUETTNERE. SHACTERM. LEVINE: "Pharmacologic ascorbic acid concentrations selectively kill cancer cells: action as a prodrug to deliver hydrogen peroxide to tissues", PROC. NATL. ACAD. SCI. U. S. A., vol. 102, 2005, pages 13604 - 13609, XP008079305, DOI: 10.1073/pnas.0506390102
Q. CHENM. G. ESPEYA. Y. SUNJ. H. LEEM. C. KRISHNAE. SHACTERP. L. CHOYKEC. POOPUTK. L. KIRKG. R. BUETTNER: "Ascorbate in pharmacologic concentrations selectively generates ascorbate radical and hydrogen peroxide in extracellular fluid in vivo", PROC. NATL. ACAD. SCI. U. S. A., vol. 104, 2007, pages 8749 - 8754
Q. CHENM. G. ESPEYA. Y. SUNC. POOPUTK. L. KIRKM. C. KRISHNAD. S. KHOSHJ. DRISKOM. LEVINE: "Pharmacologic doses of ascorbate act as a prooxidant and decrease growth of aggressive tumor xenografts in mice", PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, vol. 105, 2008, pages 11105 - 11109, XP055457771, DOI: 10.1073/pnas.0804226105
M. MOJICJ. BOGDANOVIC PRISTOVD. MAKSIMOVIC-LVANICD. R. JONESM. STANICS. MIJATOVIC1. SPASOJEVIC: "Extracellular iron diminishes anticancer effects of vitamin C: an in vitro study", SCI. REP., vol. 4, 2014, pages 5955
See also references of EP 3960242A4
Attorney, Agent or Firm:
TANAI Sumio et al. (JP)
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