Title:
PROTEIN-ENCLOSING POLYMERIC MICELLE
Document Type and Number:
WIPO Patent Application WO/2020/262550
Kind Code:
A1
Abstract:
According to the present invention, a polymeric complex includes a protein and a block copolymer represented by formula (1).
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Inventors:
CABRAL HORACIO (JP)
TAO ANQI (JP)
IGARASHI KAZUNORI (JP)
MIYAZAKI TAKUYA (JP)
HUANG GEORGE (JP)
CHEN PENGWEN (JP)
TAO ANQI (JP)
IGARASHI KAZUNORI (JP)
MIYAZAKI TAKUYA (JP)
HUANG GEORGE (JP)
CHEN PENGWEN (JP)
Application Number:
PCT/JP2020/025086
Publication Date:
December 30, 2020
Filing Date:
June 25, 2020
Export Citation:
Assignee:
UNIV TOKYO (JP)
International Classes:
C08G73/02; C07K17/04
Foreign References:
| JP2005529931A | 2005-10-06 | |||
| US20040162235A1 | 2004-08-19 |
Other References:
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XU CHEN, SONG RI-JIN, LU PEI, CHEN JIAN-CHUN, ZHOU YONG-QIANG, SHEN GANG, JIANG MIN-JUN, ZHANG WEI: "pH-triggered charge-reversal and redox-sensitive drug-release polymer micelles codeliver doxorubicin and triptolide for prostate tumor therapy", INTERNATIONAL JOURNAL OF NANOMEDICINE, vol. 13, 2018, pages 7229 - 7249, XP009525395, DOI: 10.2147/1JN.S182197
QI, YIZHI ET AL.: "Protein-polymer conjugation- moving beyond PEGylation", CURRENT OPINION IN CHEMICAL BIOLOGY, vol. 28, 2015, pages 181 - 193, XP055409460, DOI: 10.1016/j.cbpa. 2015.08.00 9
TANGSANGASAKSRI, MONTIRA ET AL.: "siRNA-Loaded Polyion Complex Micelle Decorated with Charge- Conversional Polymer Tuned to Undergo Stepwise Response to Intra-Tumoral and Intra-Endosomal pHs for Exerting Enhanced RNAi Efficacy", BIOMACROMOLECULES, vol. 17, 2016, pages 246 - 255, XP055495444, DOI: 10.1021/acs.niomac.5b01334
R. LANGERD. A. TIRRELL, NATURE, vol. 428, 2004, pages 487 - 492
B. ROMBERGW. E. HENNINKG. STORM, PHARM. RES., vol. 25, 2008, pages 55 - 71
V. TORCHILIN, ADV. DRUG DELIV. REV., vol. 63, 2011, pages 131 - 135
H. CABRALK. MIYATAK. OSADAK. KATAOKA, CHEM. REV., vol. 118, 2018, pages 6844 - 6892
Y. QIA. CHILKOTI, CURR. OPIN. CHEM. BIOL., vol. 28, 2015, pages 181 - 193
S. N. S. ALCONCELA. S. BAASH. D. MAYNARD, POLYM. CHEM., vol. 2, 2011, pages 1442 - 1448
F. M. VERONESEG. PASUT, DRUG DISCOV. TODAY, vol. 10, 2005, pages 1451 - 1458
F. F. ABUCHOWSKIA., MCCOYJ. R., PALCZUKN. C., VAN EST., DAVIS, J. BIOL. CHEM., vol. 252, 1977, pages 3582 - 3586
J. L. KAARK. MATYJASZEWSKIA. J. RUSSELLC. M. COLINAA. SIMAKOVAB. S. SUMERLINC. A. FIGGS. L. BAKER, AICHE J, vol. 64, 2018, pages 3230 - 3245
Y. LUW. SUNZ. GU, J. CONTROL, vol. 194, 2014, pages 1 - 19
S. MURAJ. NICOLASP. COUVREUR, NAT. MATER., vol. 12, 2013, pages 991
L. E. GERWECKK. SEETHARAMAN, CANCER RES., vol. 56, 1996
G. HELMLINGERF. YUANM. DELLIANR. K. JAIN, NAT. MED., vol. 3, 1997, pages 177 - 182
Y. LEET. ISHIIH. CABRALH. J. KIMJ. H. SEON. NISHIYAMAH. OSHIMAK. OSADAK. KATAOKA, ANGEW. CHEMIE, vol. 48, 2009, pages 5309 - 5312
Y. LEET. ISHIIH. J. KIMN. NISHIYAMAY. HAYAKAWAK. ITAKAK. KATAOKA, ANGEW. CHEMIE, vol. 122, 2010, pages 2606 - 2609
A. KIMY. MIURAT. ISHIIO. F. MUTAFN. NISHIYAMAH. CABRALK. KATAOKA, BIOMACROMOLECULES, vol. 17, 2016, pages 446 - 453
P. J. G. BUTLERJ. I. HARRISB. S. HARTLEYR. LEBERMAN, BIOCHEM. J., vol. 112, 1969, pages 679 - 689
K. MAIERE. WAGNER, J. AM. CHEM. SOC., vol. 134, 2012, pages 10169 - 10173
Y. LIUJ. DUC. SUNC. XUZ. CAOJ. WANG, ANGEW. CHEMIE, vol. 55, 2015, pages 1010 - 1014
H. C. YENH. CABRALP. MIK. TOHY. MATSUMOTOX. LIUH. KOORIA. KIMK. MIYAZAKIY. MIURA ET AL., ACS NANO, vol. 8, 2014, pages 11591 - 11602
D. B. ROZEMAD. L. LEWISD. H. WAKEFIELDS. C. WONGJ. J. KLEINP. L. ROESCHS. L. BERTINT. W. REPPENQ. CHUA. V. BLOKHIN ET AL., PROC. NATL. ACAD. SCI., vol. 104, 2007, pages 12982 - 12987
A. KISHIMURAA. KOIDEK. OSADAY. YAMASAKIK. KATAOKA, ANGEW. CHEMIE, vol. 46, 2007, pages 6085 - 6088
K. MATSUMOTO, Y.NOMOTO, T.CABRAL, H.MATSUMOTO, Y.WATANABE, S.CHRISTIE, R. J.MIYATA, K.OBA, M.OGURA, T.YAMASAKI, Y., KATAOKA, BIOMED. OPT. EXPRESS, vol. 1, 2010, pages 1209
F. CHENR. RAVEENDRANC. CAOR. CHAPMANM. H. STENZEL, POLYM. CHEM., vol. 10, 2019, pages 1221 - 1230
H. TAKEMOTOA. ISHIIK. MIYATAM. NAKANISHIM. OBAT. ISHIIY. YAMASAKIN. NISHIYAMAK. KATAOKA, BIOMATERIALS, vol. 31, 2010, pages 8097 - 8105
M. HARADA-SHIBAK. YAMAUCHIA. HARADAI. TAKAMISAWAK. SHIMOKADOK. KATAOKA, GENE THER, vol. 9, 2002, pages 407
Y. WANGK. KIMURAQ. HUANGP. L. DUBINW. JAEGER, MACROMOLECULES, vol. 32, 1999, pages 7128 - 7134
Q. C. LIP. A. MABROUK, J. BIOL. INORG. CHEM., vol. 8, 2003, pages 83 - 94
M. C. HSUR. W. WOODY, J. AM. CHEM. SOC., vol. 93, 1971, pages 3515 - 3525
R. M. ESQUERRAR. A. GOLDBECKD. B. KIM-SHAPIROD. S. KLIGER, BIOCHEMISTRY, vol. 37, 1998, pages 17527 - 17536
F. M. VERONESEA. MERO, BIODRUGS, vol. 22, 2008, pages 315 - 329
T. ARVINTEC. PALAISE. GREEN-TREXLERS. GREGORYH. MACHC. NARASIMHANM. SHAMEEM: "MAbs", 2013, TAYLOR & FRANCIS, pages: 491 - 500
L. J. KAGENA. BUTT, CLIN. CHEM., vol. 23, 1977, pages 1813 - 1818
R. VANHOLDERM. S. SEVERE. EREKN. LAMEIRE, J. AM. SOC. NEPHROL., vol. 11, 2000, pages 1553 - 1561
L. R. WETTERH. F. DEUTSCH, J. BIOL. CHEM., vol. 192, 1951, pages 237 - 42
R. E. CANFIELD, J. BIOL. CHEM., vol. 238, 1963, pages 2698 - 2707
Q. SHIY. ZHOUY. SUN, BIOTECHNOL. PROG., vol. 21, 2005, pages 516 - 523
K. HIRAYAMAS. AKASHIM. FURUYAK.FUKUHARA, BIOCHEM. BIOPHYS. RES. COMMUN., vol. 173, 1990, pages 639 - 646
B. J. RADOLA, BIOCHIM. BIOPHYS. ACTA - PROTEIN STRUCT., vol. 295, 1973, pages 412 - 428
P. D. DARBREA. E. ROMERO-HERRERAH. LEHMANN, BIOCHIM. BIOPHYS. ACTA - PROTEIN STRUCT., vol. 393, 1975, pages 201 - 204
See also references of EP 3992229A4
XU CHEN, SONG RI-JIN, LU PEI, CHEN JIAN-CHUN, ZHOU YONG-QIANG, SHEN GANG, JIANG MIN-JUN, ZHANG WEI: "pH-triggered charge-reversal and redox-sensitive drug-release polymer micelles codeliver doxorubicin and triptolide for prostate tumor therapy", INTERNATIONAL JOURNAL OF NANOMEDICINE, vol. 13, 2018, pages 7229 - 7249, XP009525395, DOI: 10.2147/1JN.S182197
QI, YIZHI ET AL.: "Protein-polymer conjugation- moving beyond PEGylation", CURRENT OPINION IN CHEMICAL BIOLOGY, vol. 28, 2015, pages 181 - 193, XP055409460, DOI: 10.1016/j.cbpa. 2015.08.00 9
TANGSANGASAKSRI, MONTIRA ET AL.: "siRNA-Loaded Polyion Complex Micelle Decorated with Charge- Conversional Polymer Tuned to Undergo Stepwise Response to Intra-Tumoral and Intra-Endosomal pHs for Exerting Enhanced RNAi Efficacy", BIOMACROMOLECULES, vol. 17, 2016, pages 246 - 255, XP055495444, DOI: 10.1021/acs.niomac.5b01334
R. LANGERD. A. TIRRELL, NATURE, vol. 428, 2004, pages 487 - 492
B. ROMBERGW. E. HENNINKG. STORM, PHARM. RES., vol. 25, 2008, pages 55 - 71
V. TORCHILIN, ADV. DRUG DELIV. REV., vol. 63, 2011, pages 131 - 135
H. CABRALK. MIYATAK. OSADAK. KATAOKA, CHEM. REV., vol. 118, 2018, pages 6844 - 6892
Y. QIA. CHILKOTI, CURR. OPIN. CHEM. BIOL., vol. 28, 2015, pages 181 - 193
S. N. S. ALCONCELA. S. BAASH. D. MAYNARD, POLYM. CHEM., vol. 2, 2011, pages 1442 - 1448
F. M. VERONESEG. PASUT, DRUG DISCOV. TODAY, vol. 10, 2005, pages 1451 - 1458
F. F. ABUCHOWSKIA., MCCOYJ. R., PALCZUKN. C., VAN EST., DAVIS, J. BIOL. CHEM., vol. 252, 1977, pages 3582 - 3586
J. L. KAARK. MATYJASZEWSKIA. J. RUSSELLC. M. COLINAA. SIMAKOVAB. S. SUMERLINC. A. FIGGS. L. BAKER, AICHE J, vol. 64, 2018, pages 3230 - 3245
Y. LUW. SUNZ. GU, J. CONTROL, vol. 194, 2014, pages 1 - 19
S. MURAJ. NICOLASP. COUVREUR, NAT. MATER., vol. 12, 2013, pages 991
L. E. GERWECKK. SEETHARAMAN, CANCER RES., vol. 56, 1996
G. HELMLINGERF. YUANM. DELLIANR. K. JAIN, NAT. MED., vol. 3, 1997, pages 177 - 182
Y. LEET. ISHIIH. CABRALH. J. KIMJ. H. SEON. NISHIYAMAH. OSHIMAK. OSADAK. KATAOKA, ANGEW. CHEMIE, vol. 48, 2009, pages 5309 - 5312
Y. LEET. ISHIIH. J. KIMN. NISHIYAMAY. HAYAKAWAK. ITAKAK. KATAOKA, ANGEW. CHEMIE, vol. 122, 2010, pages 2606 - 2609
A. KIMY. MIURAT. ISHIIO. F. MUTAFN. NISHIYAMAH. CABRALK. KATAOKA, BIOMACROMOLECULES, vol. 17, 2016, pages 446 - 453
P. J. G. BUTLERJ. I. HARRISB. S. HARTLEYR. LEBERMAN, BIOCHEM. J., vol. 112, 1969, pages 679 - 689
K. MAIERE. WAGNER, J. AM. CHEM. SOC., vol. 134, 2012, pages 10169 - 10173
Y. LIUJ. DUC. SUNC. XUZ. CAOJ. WANG, ANGEW. CHEMIE, vol. 55, 2015, pages 1010 - 1014
H. C. YENH. CABRALP. MIK. TOHY. MATSUMOTOX. LIUH. KOORIA. KIMK. MIYAZAKIY. MIURA ET AL., ACS NANO, vol. 8, 2014, pages 11591 - 11602
D. B. ROZEMAD. L. LEWISD. H. WAKEFIELDS. C. WONGJ. J. KLEINP. L. ROESCHS. L. BERTINT. W. REPPENQ. CHUA. V. BLOKHIN ET AL., PROC. NATL. ACAD. SCI., vol. 104, 2007, pages 12982 - 12987
A. KISHIMURAA. KOIDEK. OSADAY. YAMASAKIK. KATAOKA, ANGEW. CHEMIE, vol. 46, 2007, pages 6085 - 6088
K. MATSUMOTO, Y.NOMOTO, T.CABRAL, H.MATSUMOTO, Y.WATANABE, S.CHRISTIE, R. J.MIYATA, K.OBA, M.OGURA, T.YAMASAKI, Y., KATAOKA, BIOMED. OPT. EXPRESS, vol. 1, 2010, pages 1209
F. CHENR. RAVEENDRANC. CAOR. CHAPMANM. H. STENZEL, POLYM. CHEM., vol. 10, 2019, pages 1221 - 1230
H. TAKEMOTOA. ISHIIK. MIYATAM. NAKANISHIM. OBAT. ISHIIY. YAMASAKIN. NISHIYAMAK. KATAOKA, BIOMATERIALS, vol. 31, 2010, pages 8097 - 8105
M. HARADA-SHIBAK. YAMAUCHIA. HARADAI. TAKAMISAWAK. SHIMOKADOK. KATAOKA, GENE THER, vol. 9, 2002, pages 407
Y. WANGK. KIMURAQ. HUANGP. L. DUBINW. JAEGER, MACROMOLECULES, vol. 32, 1999, pages 7128 - 7134
Q. C. LIP. A. MABROUK, J. BIOL. INORG. CHEM., vol. 8, 2003, pages 83 - 94
M. C. HSUR. W. WOODY, J. AM. CHEM. SOC., vol. 93, 1971, pages 3515 - 3525
R. M. ESQUERRAR. A. GOLDBECKD. B. KIM-SHAPIROD. S. KLIGER, BIOCHEMISTRY, vol. 37, 1998, pages 17527 - 17536
F. M. VERONESEA. MERO, BIODRUGS, vol. 22, 2008, pages 315 - 329
T. ARVINTEC. PALAISE. GREEN-TREXLERS. GREGORYH. MACHC. NARASIMHANM. SHAMEEM: "MAbs", 2013, TAYLOR & FRANCIS, pages: 491 - 500
L. J. KAGENA. BUTT, CLIN. CHEM., vol. 23, 1977, pages 1813 - 1818
R. VANHOLDERM. S. SEVERE. EREKN. LAMEIRE, J. AM. SOC. NEPHROL., vol. 11, 2000, pages 1553 - 1561
L. R. WETTERH. F. DEUTSCH, J. BIOL. CHEM., vol. 192, 1951, pages 237 - 42
R. E. CANFIELD, J. BIOL. CHEM., vol. 238, 1963, pages 2698 - 2707
Q. SHIY. ZHOUY. SUN, BIOTECHNOL. PROG., vol. 21, 2005, pages 516 - 523
K. HIRAYAMAS. AKASHIM. FURUYAK.FUKUHARA, BIOCHEM. BIOPHYS. RES. COMMUN., vol. 173, 1990, pages 639 - 646
B. J. RADOLA, BIOCHIM. BIOPHYS. ACTA - PROTEIN STRUCT., vol. 295, 1973, pages 412 - 428
P. D. DARBREA. E. ROMERO-HERRERAH. LEHMANN, BIOCHIM. BIOPHYS. ACTA - PROTEIN STRUCT., vol. 393, 1975, pages 201 - 204
See also references of EP 3992229A4
Attorney, Agent or Firm:
KOBAYASHI Hiroshi et al. (JP)
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