Title:
NON-FOULING OR SUPER STEALTH VESICLE
Document Type and Number:
WIPO Patent Application WO/2024/085242
Kind Code:
A2
Abstract:
The disclosure provides non-fouling or super stealth vesicle that can be used for a drug delivery. The non-fouling or super stealth vesicle comprises polycation and polyanion, wherein the polycation and polyanion are neutralized in charge, and crosslinked to have a crosslinking degree over a certain level, and has a half-life (T1/2) over 24 hours in a blood or serum of the subject.
Inventors:
KATAOKA KAZUNORI (JP)
LI JUNJIE (JP)
LI JUNJIE (JP)
Application Number:
PCT/JP2023/037954
Publication Date:
April 25, 2024
Filing Date:
October 20, 2023
Export Citation:
Assignee:
KAWASAKI INST OF INDUSTRIAL PROMOTION (JP)
Domestic Patent References:
| WO1996040210A1 | 1996-12-19 | |||
| WO1998050433A2 | 1998-11-12 | |||
| WO1998014451A1 | 1998-04-09 | |||
| WO1998050038A1 | 1998-11-12 | |||
| WO1999009016A1 | 1999-02-25 | |||
| WO1999024037A1 | 1999-05-20 | |||
| WO1999009016A1 | 1999-02-25 | |||
| WO1998043960A1 | 1998-10-08 | |||
| WO1997038983A1 | 1997-10-23 | |||
| WO1999006378A1 | 1999-02-11 | |||
| WO1999006396A1 | 1999-02-11 | |||
| WO1996030347A1 | 1996-10-03 | |||
| WO1996033978A1 | 1996-10-31 | |||
| WO1996003397A3 | ||||
| WO1996033980A1 | 1996-10-31 |
Foreign References:
| US20210346472A1 | 2021-11-11 | |||
| US4943533A | 1990-07-24 | |||
| US5212290A | 1993-05-18 | |||
| US5891996A | 1999-04-06 | |||
| US6235883B1 | 2001-05-22 | |||
| EP0659439A2 | 1995-06-28 | |||
| US5616582A | 1997-04-01 | |||
| US5457105A | 1995-10-10 | |||
| US5475001A | 1995-12-12 | |||
| US5654307A | 1997-08-05 | |||
| US5679683A | 1997-10-21 | |||
| US6084095A | 2000-07-04 | |||
| US6265410B1 | 2001-07-24 | |||
| US6455534B2 | 2002-09-24 | |||
| US6521620B1 | 2003-02-18 | |||
| US6596726B1 | 2003-07-22 | |||
| US6713484B2 | 2004-03-30 | |||
| US5770599A | 1998-06-23 | |||
| US6140332A | 2000-10-31 | |||
| US5866572A | 1999-02-02 | |||
| US6399602B1 | 2002-06-04 | |||
| US6344459B1 | 2002-02-05 | |||
| US6602863B1 | 2003-08-05 | |||
| US6391874B1 | 2002-05-21 | |||
| US6344455B1 | 2002-02-05 | |||
| US5760041A | 1998-06-02 | |||
| US6002008A | 1999-12-14 | |||
| US5747498A | 1998-05-05 | |||
| US5804396A | 1998-09-08 |
Other References:
ANGEW CHEM. INTL. ED. ENGL., vol. 33, 1994, pages 183 - 186
STRAGLIOTTO ET AL., EUR. J. CANCER, vol. 32A, 1996, pages 636 - 640
KLOTZ, I. M.: "Ligand-receptor complexes: origin and development of the concept", J. BIOL. CHEM., vol. 279, no. 29, 2004, pages 30375 - 30384
YAMADA ET AL., CANCER SCI, vol. 104, 2013, pages 14 - 21
NEL, A. E. ET AL.: "Understanding biophysicochemical interactions at the nano-bio interface", NAT. MATER., vol. 8, 2009, pages 543 - 557
MONOPOLI, M. P.ABERG, C.SALVATI, A.DAWSON, K. A.: "Biomolecular coronas provide the biological identity of nanosized materials", NAT. NANOTECHNOL., vol. 7, 2012, pages 779 - 786
CHEN, S.LI, L.ZHAO, C.ZHENG, J.: "Surface hydration: Principles and applications toward low-fouling/nonfouling biomaterials", POLYMER, vol. 51, 2010, pages 5283 - 5293, XP027437364
MCPHERSON, T. B.LEE, S. J.PARK, K.: "Analysis of the prevention of protein adsorption by steric repulsion theory", ACS SYMP. SER., vol. 602, 1995, pages 395 - 404
OTSUKA, H.NAGASAKI, Y.KATAOKA, K.: "PEGylated nanoparticles for biological and pharmaceutical applications", ADV. DRUG DELIV. REV., vol. 55, 2003, pages 403 - 419, XP008082599, DOI: 10.1016/S0169-409X(02)00226-0
KEEFE, A. J.JIANG, S.: "Poly(zwitterionic)protein conjugates offer increased stability without sacrificing binding affinity or bioactivity", NAT. CHEM., vol. 4, 2011, pages 59 - 63, XP055791287, DOI: 10.1038/nchem.1213
LU, Y. ET AL.: "Micelles with ultralow critical micelle concentration as carriers for drug delivery", NAT. BIOMED. ENG., vol. 2, 2018, pages 318 - 325, XP036513434, DOI: 10.1038/s41551-018-0234-x
CHEN, S. ET AL.: "Enhanced tumour penetration and prolonged circulation in blood of polyzwitterion-drug conjugates with cell-membrane affinity", NAT. BIOMED. ENG., vol. 5, 2021, pages 1019 - 1037, XP037581302, DOI: 10.1038/s41551-021-00701-4
WALKEY, C. D.OLSEN, J. B.GUO, H.EMILI, A.CHAN, W. C.: "Nanoparticle size and surface chemistry determine serum protein adsorption and macrophage uptake", J. AM. CHEM. SOC., vol. 134, 2012, pages 2139 - 2147, XP002714556, DOI: 10.1021/ja2084338
BERTRAND, N. ET AL.: "Mechanistic understanding of in vivo protein corona formation on polymeric nanoparticles and impact on pharmacokinetics", NAT. COMMUN., vol. 8, 2017, pages 777
FOX, M. E.SZOKA, F. C.FRECHET, J. M. J.: "Soluble polymer carriers for the treatment of cancer: the importance of molecular architecture", ACC. CHEM. RES., vol. 42, 2009, pages 1141 - 1151
PERRY, J. L. ET AL.: "PEGylated PRINT nanoparticles: the impact of PEG density on protein binding, macrophage association, biodistribution, and pharmacokinetics", NANO LETT, vol. 12, 2012, pages 5304 - 5310, XP055192989, DOI: 10.1021/nl302638g
YANG, Q. ET AL.: "Evading immune cell uptake and clearance requires PEG grafting at densities substantially exceeding the minimum for brush conformation", MOL. PHARM., vol. 11, 2014, pages 1250 - 1258, XP055675707, DOI: 10.1021/mp400703d
TOCKARY, T. A. ET AL.: "Tethered PEG crowdedness determining shape and blood circulation profile of polyplex micelle gene carriers", MACROMOLECULES, vol. 46, 2013, pages 6585 - 6592
ZHOU, H. ET AL.: "Dense and dynamic polyethylene glycol shells cloak nanoparticles from uptake by liver endothelial cells for long blood circulation", ACS NANO, vol. 12, 2018, pages 10130 - 10141
KOIDE, A. ET AL.: "Semipermeable polymer vesicle (PICsome) self-assembled in aqueous medium from a pair of oppositely charged block copolymers: physiologically stable micro-/nanocontainers of water-soluble macromolecules", J. AM. CHEM. SOC., vol. 128, 2006, pages 5988 - 5989, XP002786287
ROCKER, C.POTZL, M.ZHANG, F.PARAK, W. J.NIENHAUS, G. U.: "A quantitative fluorescence study of protein monolayer formation on colloidal nanoparticles", NAT. NANOTECHNOL., vol. 4, 2009, pages 577 - 580
CEDERVALL, T. ET AL.: "Understanding the nanoparticle-protein corona using methods to quantify exchange rates and affinities of proteins for nanoparticles", PROC. NATL. ACAD. SCI. USA, vol. 104, 2007, pages 2050 - 2055
ACHAZI, K. ET AL.: "Understanding the interaction of polyelectrolyte architectures with proteins and biosystems", ANGEW. CHEM. INT. ED., vol. 60, 2021, pages 3882 - 3904
ABDELWAHED, W.DEGOBERT, G.STAINMESSE, S.FESSI, H.: "Freeze-drying of nanoparticles: formulation, process and storage considerations", ADV. DRUG DELIV. REV., vol. 58, 2006, pages 1688 - 1713, XP005788419, DOI: 10.1016/j.addr.2006.09.017
KATAOKA, K.TSURUTA, T.AKAIKE, T.SAKURAI, Y.: "Biomedical behavior of synthetic polyion complexes toward blood platelets", MAKROMOL. CHEM., vol. 181, 1980, pages 1363 - 1373
WADA, A.NAKAMURA, H.: "Nature of the charge distribution in proteins", NATURE, vol. 293, 1981, pages 757 - 758
NAKAMURA, H: "Roles of electrostatic interaction in proteins", Q. REV. BIOPHYSICS, vol. 29, 1996, pages 1 - 90
LAI, S. K.WANG, Y. Y.HANES, J.: "Mucus-penetrating nanoparticles for drug and gene delivery to mucosal tissues", ADV. DRUG DELIV. REV., vol. 61, 2009, pages 158 - 171, XP025950272, DOI: 10.1016/j.addr.2008.11.002
KUMAR, R.FREDRICKSON, G. H.: "Theory of polyzwitterion conformations", J. CHEM. PHYS., vol. 131, 2009, pages 104901
DELGADO, J. D.SCHLENOFF, J. B.: "Static and dynamic solution behavior of a polyzwitterion using a hofmeister salt series", MACROMOLECULES, vol. 50, 2017, pages 4454 - 4464
HUANG, C.MASON, J. T.: "Geometric packing constraints in egg phosphatidylcholine vesicles", PROC. NATL. ACAD. SCI. USA, vol. 75, 1978, pages 308 - 310
ALLEN, C. ET AL.: "Controlling the physical behavior and biological performance of liposome formulations through use of surface grafted poly (ethylene glycol", BIOSCI. REP., vol. 22, 2002, pages 225 - 250, XP055211237, DOI: 10.1023/A:1020186505848
TIROSH, O.BARENHOLZ, Y.KATZHENDLER, J.PRIEV, A.: "Hydration of polyethylene glycol-grafted liposomes", BIOPHYS. J., vol. 74, 1998, pages 1371 - 1379
GARBUZENKO, O.BARENHOLZ, Y.PRIEV, A.: "Effect of grafted PEG on liposome size and on compressibility and packing of lipid bilayer", CHEM. PHYS. LIPIDS, vol. 135, 2005, pages 117 - 129, XP004910906, DOI: 10.1016/j.chemphyslip.2005.02.003
ARNOLD, K.HERRMANN, A.PRATSCH, L.GAWRISCH, K.: "The dielectric properties of aqueous solutions of poly(ethylene glycol) and their influence on membrane structure", BIOCHIM. BIOPHYS. ACTA, vol. 815, 1985, pages 515 - 518, XP023504267, DOI: 10.1016/0005-2736(85)90381-5
SORENSEN, K. K.SIMON-SANTAMARIA, J.MCCUSKEY, R. S.SMEDSROD, B.: "Liver sinusoidal endothelial cells", COMPR. PHYSIOL., vol. 5, 2015, pages 1751 - 1774
DIRISALA, A. ET AL.: "Transient stealth coating of liver sinusoidal wall by anchoring two-armed PEG for retargeting nanomedicines", SCI. ADV., vol. 6, 2020, pages eabb8133
LI, J.ANRAKU, Y.KATAOKA, K.: "Self-boosting catalytic nanoreactors integrated with triggerable crosslinking membrane networks for initiation of immunogenic cell death by pyroptosis", ANGEW. CHEM. INT. ED., vol. 59, 2020, pages 13526 - 13530
ANRAKU, Y. ET AL.: "Systemically injectable enzyme-loaded polyion complex vesicles as in vivo nanoreactors functioning in tumors", ANGEW. CHEM. INT. ED., vol. 55, 2016, pages 560 - 565, XP002786288
LOHR, M. ET AL.: "Transforming growth factor-(31 induces desmoplasia in an experimental model of human pancreatic carcinoma", CANCER RES, vol. 61, 2001, pages 550 - 555
KRALL, A. S.XU, S.GRAEBER, T. G.BRAAS, D.CHRISTOFK, H. R.: "Asparagine promotes cancer cell proliferation through use as an amino acid exchange factor", NAT. COMMUN., vol. 7, 2016, pages 11457
RASSOLIAN, M.CHASS, G. A.SETIADI, D. H.CSIZMADIA, I. G.: "Asparagine-ab initio structural analyses", J. MOL. STRUCT.: THEOCHEM, vol. 666-667, 2003, pages 273 - 278, XP027133869
KNOTT, S. R. V. ET AL.: "Asparagine bioavailability governs metastasis in a model of breast cancer", NATURE, vol. 554, 2018, pages 378 - 381
HAMMEL, P. ET AL.: "Erythrocyte-encapsulated asparaginase (eryaspase) combined with chemotherapy in second-line treatment of advanced pancreatic cancer: An open-label, randomized Phase IIb trial", EUR. J. CANCER, vol. 124, 2020, pages 91 - 101, XP085966104, DOI: 10.1016/j.ejca.2019.10.020
STRAGLIOTTO ET AL., EUR. J. CANCER, vol. 32A, 1996, pages 636 - 640
KLOTZ, I. M.: "Ligand-receptor complexes: origin and development of the concept", J. BIOL. CHEM., vol. 279, no. 29, 2004, pages 30375 - 30384
YAMADA ET AL., CANCER SCI, vol. 104, 2013, pages 14 - 21
NEL, A. E. ET AL.: "Understanding biophysicochemical interactions at the nano-bio interface", NAT. MATER., vol. 8, 2009, pages 543 - 557
MONOPOLI, M. P.ABERG, C.SALVATI, A.DAWSON, K. A.: "Biomolecular coronas provide the biological identity of nanosized materials", NAT. NANOTECHNOL., vol. 7, 2012, pages 779 - 786
CHEN, S.LI, L.ZHAO, C.ZHENG, J.: "Surface hydration: Principles and applications toward low-fouling/nonfouling biomaterials", POLYMER, vol. 51, 2010, pages 5283 - 5293, XP027437364
MCPHERSON, T. B.LEE, S. J.PARK, K.: "Analysis of the prevention of protein adsorption by steric repulsion theory", ACS SYMP. SER., vol. 602, 1995, pages 395 - 404
OTSUKA, H.NAGASAKI, Y.KATAOKA, K.: "PEGylated nanoparticles for biological and pharmaceutical applications", ADV. DRUG DELIV. REV., vol. 55, 2003, pages 403 - 419, XP008082599, DOI: 10.1016/S0169-409X(02)00226-0
KEEFE, A. J.JIANG, S.: "Poly(zwitterionic)protein conjugates offer increased stability without sacrificing binding affinity or bioactivity", NAT. CHEM., vol. 4, 2011, pages 59 - 63, XP055791287, DOI: 10.1038/nchem.1213
LU, Y. ET AL.: "Micelles with ultralow critical micelle concentration as carriers for drug delivery", NAT. BIOMED. ENG., vol. 2, 2018, pages 318 - 325, XP036513434, DOI: 10.1038/s41551-018-0234-x
CHEN, S. ET AL.: "Enhanced tumour penetration and prolonged circulation in blood of polyzwitterion-drug conjugates with cell-membrane affinity", NAT. BIOMED. ENG., vol. 5, 2021, pages 1019 - 1037, XP037581302, DOI: 10.1038/s41551-021-00701-4
WALKEY, C. D.OLSEN, J. B.GUO, H.EMILI, A.CHAN, W. C.: "Nanoparticle size and surface chemistry determine serum protein adsorption and macrophage uptake", J. AM. CHEM. SOC., vol. 134, 2012, pages 2139 - 2147, XP002714556, DOI: 10.1021/ja2084338
BERTRAND, N. ET AL.: "Mechanistic understanding of in vivo protein corona formation on polymeric nanoparticles and impact on pharmacokinetics", NAT. COMMUN., vol. 8, 2017, pages 777
FOX, M. E.SZOKA, F. C.FRECHET, J. M. J.: "Soluble polymer carriers for the treatment of cancer: the importance of molecular architecture", ACC. CHEM. RES., vol. 42, 2009, pages 1141 - 1151
PERRY, J. L. ET AL.: "PEGylated PRINT nanoparticles: the impact of PEG density on protein binding, macrophage association, biodistribution, and pharmacokinetics", NANO LETT, vol. 12, 2012, pages 5304 - 5310, XP055192989, DOI: 10.1021/nl302638g
YANG, Q. ET AL.: "Evading immune cell uptake and clearance requires PEG grafting at densities substantially exceeding the minimum for brush conformation", MOL. PHARM., vol. 11, 2014, pages 1250 - 1258, XP055675707, DOI: 10.1021/mp400703d
TOCKARY, T. A. ET AL.: "Tethered PEG crowdedness determining shape and blood circulation profile of polyplex micelle gene carriers", MACROMOLECULES, vol. 46, 2013, pages 6585 - 6592
ZHOU, H. ET AL.: "Dense and dynamic polyethylene glycol shells cloak nanoparticles from uptake by liver endothelial cells for long blood circulation", ACS NANO, vol. 12, 2018, pages 10130 - 10141
KOIDE, A. ET AL.: "Semipermeable polymer vesicle (PICsome) self-assembled in aqueous medium from a pair of oppositely charged block copolymers: physiologically stable micro-/nanocontainers of water-soluble macromolecules", J. AM. CHEM. SOC., vol. 128, 2006, pages 5988 - 5989, XP002786287
ROCKER, C.POTZL, M.ZHANG, F.PARAK, W. J.NIENHAUS, G. U.: "A quantitative fluorescence study of protein monolayer formation on colloidal nanoparticles", NAT. NANOTECHNOL., vol. 4, 2009, pages 577 - 580
CEDERVALL, T. ET AL.: "Understanding the nanoparticle-protein corona using methods to quantify exchange rates and affinities of proteins for nanoparticles", PROC. NATL. ACAD. SCI. USA, vol. 104, 2007, pages 2050 - 2055
ACHAZI, K. ET AL.: "Understanding the interaction of polyelectrolyte architectures with proteins and biosystems", ANGEW. CHEM. INT. ED., vol. 60, 2021, pages 3882 - 3904
ABDELWAHED, W.DEGOBERT, G.STAINMESSE, S.FESSI, H.: "Freeze-drying of nanoparticles: formulation, process and storage considerations", ADV. DRUG DELIV. REV., vol. 58, 2006, pages 1688 - 1713, XP005788419, DOI: 10.1016/j.addr.2006.09.017
KATAOKA, K.TSURUTA, T.AKAIKE, T.SAKURAI, Y.: "Biomedical behavior of synthetic polyion complexes toward blood platelets", MAKROMOL. CHEM., vol. 181, 1980, pages 1363 - 1373
WADA, A.NAKAMURA, H.: "Nature of the charge distribution in proteins", NATURE, vol. 293, 1981, pages 757 - 758
NAKAMURA, H: "Roles of electrostatic interaction in proteins", Q. REV. BIOPHYSICS, vol. 29, 1996, pages 1 - 90
LAI, S. K.WANG, Y. Y.HANES, J.: "Mucus-penetrating nanoparticles for drug and gene delivery to mucosal tissues", ADV. DRUG DELIV. REV., vol. 61, 2009, pages 158 - 171, XP025950272, DOI: 10.1016/j.addr.2008.11.002
KUMAR, R.FREDRICKSON, G. H.: "Theory of polyzwitterion conformations", J. CHEM. PHYS., vol. 131, 2009, pages 104901
DELGADO, J. D.SCHLENOFF, J. B.: "Static and dynamic solution behavior of a polyzwitterion using a hofmeister salt series", MACROMOLECULES, vol. 50, 2017, pages 4454 - 4464
HUANG, C.MASON, J. T.: "Geometric packing constraints in egg phosphatidylcholine vesicles", PROC. NATL. ACAD. SCI. USA, vol. 75, 1978, pages 308 - 310
ALLEN, C. ET AL.: "Controlling the physical behavior and biological performance of liposome formulations through use of surface grafted poly (ethylene glycol", BIOSCI. REP., vol. 22, 2002, pages 225 - 250, XP055211237, DOI: 10.1023/A:1020186505848
TIROSH, O.BARENHOLZ, Y.KATZHENDLER, J.PRIEV, A.: "Hydration of polyethylene glycol-grafted liposomes", BIOPHYS. J., vol. 74, 1998, pages 1371 - 1379
GARBUZENKO, O.BARENHOLZ, Y.PRIEV, A.: "Effect of grafted PEG on liposome size and on compressibility and packing of lipid bilayer", CHEM. PHYS. LIPIDS, vol. 135, 2005, pages 117 - 129, XP004910906, DOI: 10.1016/j.chemphyslip.2005.02.003
ARNOLD, K.HERRMANN, A.PRATSCH, L.GAWRISCH, K.: "The dielectric properties of aqueous solutions of poly(ethylene glycol) and their influence on membrane structure", BIOCHIM. BIOPHYS. ACTA, vol. 815, 1985, pages 515 - 518, XP023504267, DOI: 10.1016/0005-2736(85)90381-5
SORENSEN, K. K.SIMON-SANTAMARIA, J.MCCUSKEY, R. S.SMEDSROD, B.: "Liver sinusoidal endothelial cells", COMPR. PHYSIOL., vol. 5, 2015, pages 1751 - 1774
DIRISALA, A. ET AL.: "Transient stealth coating of liver sinusoidal wall by anchoring two-armed PEG for retargeting nanomedicines", SCI. ADV., vol. 6, 2020, pages eabb8133
LI, J.ANRAKU, Y.KATAOKA, K.: "Self-boosting catalytic nanoreactors integrated with triggerable crosslinking membrane networks for initiation of immunogenic cell death by pyroptosis", ANGEW. CHEM. INT. ED., vol. 59, 2020, pages 13526 - 13530
ANRAKU, Y. ET AL.: "Systemically injectable enzyme-loaded polyion complex vesicles as in vivo nanoreactors functioning in tumors", ANGEW. CHEM. INT. ED., vol. 55, 2016, pages 560 - 565, XP002786288
LOHR, M. ET AL.: "Transforming growth factor-(31 induces desmoplasia in an experimental model of human pancreatic carcinoma", CANCER RES, vol. 61, 2001, pages 550 - 555
KRALL, A. S.XU, S.GRAEBER, T. G.BRAAS, D.CHRISTOFK, H. R.: "Asparagine promotes cancer cell proliferation through use as an amino acid exchange factor", NAT. COMMUN., vol. 7, 2016, pages 11457
RASSOLIAN, M.CHASS, G. A.SETIADI, D. H.CSIZMADIA, I. G.: "Asparagine-ab initio structural analyses", J. MOL. STRUCT.: THEOCHEM, vol. 666-667, 2003, pages 273 - 278, XP027133869
KNOTT, S. R. V. ET AL.: "Asparagine bioavailability governs metastasis in a model of breast cancer", NATURE, vol. 554, 2018, pages 378 - 381
HAMMEL, P. ET AL.: "Erythrocyte-encapsulated asparaginase (eryaspase) combined with chemotherapy in second-line treatment of advanced pancreatic cancer: An open-label, randomized Phase IIb trial", EUR. J. CANCER, vol. 124, 2020, pages 91 - 101, XP085966104, DOI: 10.1016/j.ejca.2019.10.020
Attorney, Agent or Firm:
MORITA Yutaka (JP)
Download PDF:
Previous Patent: BALL SCREW
Next Patent: SEMICONDUCTOR SUBSTRATE, TEMPLATE SUBSTRATE, AND METHOD AND DEVICE FOR PRODUCING TEMPLATE SUBSTRATE
Next Patent: SEMICONDUCTOR SUBSTRATE, TEMPLATE SUBSTRATE, AND METHOD AND DEVICE FOR PRODUCING TEMPLATE SUBSTRATE