Title:
CARBOXYLIC ACID-TYPE LIPID, AND LIPID PARTICLE AND LIPID MEMBRANE CONTAINING CARBOXYLIC ACID-TYPE LIPID
Document Type and Number:
WIPO Patent Application WO/2020/080495
Kind Code:
A1
Abstract:
The purpose of the present invention is to provide: a carboxylic acid-type lipid which can promote adhesion and coagulation of platelets without carrying a protein or peptide (e.g., GPIb or H12) which is involved in adhesion or coagulation of platelets; lipid particles containing the carboxylic acid-type lipid; a lipid membrane containing the carboxylic acid-type lipid; and a platelet coagulation promoting agent, a platelet adhesion promoting agent, a hemostatic agent, and a platelet alternative which contain the carboxylic acid-type lipid, the lipid particles, or the lipid membrane. To achieve the purpose, the present invention provides: a carboxylic acid-type lipid selected from carboxylic acid-type lipids represented by formulae (I) to (VI); lipid particles containing the carboxylic acid-type lipid; a lipid membrane containing the carboxylic acid-type lipid; and a platelet coagulation promoting agent, a platelet adhesion promoting agent, a hemostatic agent, and a platelet alternative which contain the carboxylic acid-type lipid, the lipid particles, or the lipid membrane.
Inventors:
TAKEOKA SHINJI (JP)
NAKAHARA KEIKO (JP)
NISHIURA MAMORU (JP)
OTSUBO SHINYA (JP)
KURUMATANI HAJIMU (JP)
ARAKANE TORU (JP)
NAKAHARA KEIKO (JP)
NISHIURA MAMORU (JP)
OTSUBO SHINYA (JP)
KURUMATANI HAJIMU (JP)
ARAKANE TORU (JP)
Application Number:
PCT/JP2019/040984
Publication Date:
April 23, 2020
Filing Date:
October 17, 2019
Export Citation:
Assignee:
TORAY INDUSTRIES (JP)
NANOTHETA CO LTD (JP)
NANOTHETA CO LTD (JP)
International Classes:
C07C233/05; A61K31/225; A61P7/04; C07K5/00; C07K7/00
Domestic Patent References:
| WO2008062911A1 | 2008-05-29 | |||
| WO2008008523A1 | 2008-01-17 | |||
| WO1998007752A1 | 1998-02-26 | |||
| WO2001064743A1 | 2001-09-07 |
Foreign References:
| CN104356196A | 2015-02-18 | |||
| JP2005239549A | 2005-09-08 |
Other References:
SUN, QIONG: "A Collaborative Assembly Strategy for Tumor-Targeted siRNA Delivery", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 137, no. 18, 15 April 2015 (2015-04-15), pages 6000 - 6010, XP055703245
WAYBRANT, BRETT: "Effect of Polyethylene Glycol, Alkyl, and Oligonucleotide Spacers on the Binding, Secondary Structure, and Self-Assembly of Fractalkine Binding FKN-S2 Aptamer-Amphiphiles", LANGMUIR, vol. 30, no. 25, 17 June 2014 (2014-06-17), pages 7465 - 7474, XP055422967
SHROFF, KAMLESH: "Enhanced Integrin Mediated Signaling and Cell Cycle Progression on Fibronectin Mimetic Peptide Amphiphile Monolayers", LANGMUIR, vol. 28, no. 3, 24 January 2012 (2012-01-24), pages 1858 - 1865, XP055703248
ANANTHANARAYANAN, BADRIPRASAD: "Neural stem cell adhesion and proliferation on phospholipid bilayersfunctionalized with RGD peptides", BIOMATERIALS, vol. 31, no. 33, 21 August 2010 (2010-08-21), pages 8706 - 8715, XP027381030
OBATA, YOSUKE: "Plasmid DNA-encapsulating liposomes: Effect of a spacer between the cationic headgroup and hydrophobic moieties of the lipids on gene expression efficiency", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1788, no. 5, 26 February 2009 (2009-02-26), pages 1148 - 1158, XP026023992
GARG, ASHISH: "Targeting colon cancer cells using PEGylated liposomes modified with a fibronectin-mimetic peptide", INTERNATIONAL JOURNAL OF PHARMACEUTICS, vol. 366, no. 1-2, 21 January 2009 (2009-01-21), pages 201 - 210, XP025839917
CRAIG, JENNIFER A.: "Effect of linker and spacer on the design of a fibronectin-mimetic peptide evaluated via cell studies and AFM adhesion forces", LANGMUIR, vol. 24, no. 18, 12 August 2008 (2008-08-12), pages 10282 - 10292, XP009119284
WANG, KEWEI: "Synthesis and in vitro Behavior of Multivalent Cationic Lipopeptide for DNA Delivery and Release in HeLa Cells", BIOCONJUGATE CHEM., vol. 18, no. 6, 1 November 2007 (2007-11-01), pages 1735 - 1738, XP055606197
OCHSENHIRT, SARAH E.: "Effect of RGD secondary structure and the synergy site PHSRN on cell adhesion, spreading and specific integrin engagement", BIOMATERIALS, vol. 27, no. 20, 1 July 2006 (2006-07-01), pages 3863 - 3874, XP005388077
MARQUES, BRUNO F.: "Sequence-Specific Binding of DNA to Liposomes Containing Di-Alkyl Peptide Nucleic Acid (PNA) Amphiphiles", LANGMUIR, vol. 21, no. 6, March 2005 (2005-03-01), pages 2488 - 2494, XP055703257
SCHNEIDER, JAMES: "Surface Force Measurements of Electrostatic and Hydrogen-Bonding Interactions between Bilayers of Glycine Amphiphiles", LANGMUIR, vol. 18, no. 10, 1 May 2002 (2002-05-01), pages 3923 - 3931, XP055703261
GORE, TUSHAR: "Self-Assembly of Model Collagen Peptide Amphiphiles", LANGMUIR, vol. 17, no. 17, 10 February 2001 (2001-02-10), pages 5352 - 5360, XP05570326
PAKALNS, TEIKA: "Cellular recognition of synthetic peptide amphiphiles in self-assembled monolayer "lms", BIOMATERIALS, vol. 20, no. 23, December 1999 (1999-12-01), pages 2265 - 2279, XP055703271
HABERMANN, JORG: "Fragment Condensation on Solid-Phase in the Synthesis of an Amphiphilic Glycopeptide from the Homophilic Recognition Domain of Epithelial Cadherin", TETRAHEDRON LETTERS, vol. 39, no. 27, 2 July 1998 (1998-07-02), pages 4797 - 4800, XP004120760
BERNDT, PETER: "Synthetic lipidation of peptides and amino acids: monolayer structure and properties", J. AM. CHEM. SOC., vol. 117, no. 37, 20 September 1995 (1995-09-20), pages 9515 - 9522, XP002030763
KALBER TAMMY L; SMITH CHRISTOPHER J; HOWE FRANKLYN A; GRIFFITHS JOHN R; RYAN ANDERSON J; WATERTON JOHN C; ROBINSON SIMON P: "A longitudinal study of R2* and R2 magnetic resonance imaging relaxation rate measurements in murine liver after a single administration of 3 different iron oxide-based contrast agents", POLYMERIC MATERIALS SCIENCE AND ENGINEERING, vol. 77, 1997, pages 584 - 585, XP009119273, ISSN: 0743-0515
PROCEEDINGS OF THE 32ND ANNUAL MEETING OF THE JAPANESE SOCIETY FOR BIOMATERIALS, pages 324
PROCEEDINGS OF THE 33RD ANNUAL MEETING OF THE JAPANESE SOCIETY FOR BIOMATERIALS, pages 319
See also references of EP 3868740A4
WAYBRANT, BRETT: "Effect of Polyethylene Glycol, Alkyl, and Oligonucleotide Spacers on the Binding, Secondary Structure, and Self-Assembly of Fractalkine Binding FKN-S2 Aptamer-Amphiphiles", LANGMUIR, vol. 30, no. 25, 17 June 2014 (2014-06-17), pages 7465 - 7474, XP055422967
SHROFF, KAMLESH: "Enhanced Integrin Mediated Signaling and Cell Cycle Progression on Fibronectin Mimetic Peptide Amphiphile Monolayers", LANGMUIR, vol. 28, no. 3, 24 January 2012 (2012-01-24), pages 1858 - 1865, XP055703248
ANANTHANARAYANAN, BADRIPRASAD: "Neural stem cell adhesion and proliferation on phospholipid bilayersfunctionalized with RGD peptides", BIOMATERIALS, vol. 31, no. 33, 21 August 2010 (2010-08-21), pages 8706 - 8715, XP027381030
OBATA, YOSUKE: "Plasmid DNA-encapsulating liposomes: Effect of a spacer between the cationic headgroup and hydrophobic moieties of the lipids on gene expression efficiency", BIOCHIMICA ET BIOPHYSICA ACTA, vol. 1788, no. 5, 26 February 2009 (2009-02-26), pages 1148 - 1158, XP026023992
GARG, ASHISH: "Targeting colon cancer cells using PEGylated liposomes modified with a fibronectin-mimetic peptide", INTERNATIONAL JOURNAL OF PHARMACEUTICS, vol. 366, no. 1-2, 21 January 2009 (2009-01-21), pages 201 - 210, XP025839917
CRAIG, JENNIFER A.: "Effect of linker and spacer on the design of a fibronectin-mimetic peptide evaluated via cell studies and AFM adhesion forces", LANGMUIR, vol. 24, no. 18, 12 August 2008 (2008-08-12), pages 10282 - 10292, XP009119284
WANG, KEWEI: "Synthesis and in vitro Behavior of Multivalent Cationic Lipopeptide for DNA Delivery and Release in HeLa Cells", BIOCONJUGATE CHEM., vol. 18, no. 6, 1 November 2007 (2007-11-01), pages 1735 - 1738, XP055606197
OCHSENHIRT, SARAH E.: "Effect of RGD secondary structure and the synergy site PHSRN on cell adhesion, spreading and specific integrin engagement", BIOMATERIALS, vol. 27, no. 20, 1 July 2006 (2006-07-01), pages 3863 - 3874, XP005388077
MARQUES, BRUNO F.: "Sequence-Specific Binding of DNA to Liposomes Containing Di-Alkyl Peptide Nucleic Acid (PNA) Amphiphiles", LANGMUIR, vol. 21, no. 6, March 2005 (2005-03-01), pages 2488 - 2494, XP055703257
SCHNEIDER, JAMES: "Surface Force Measurements of Electrostatic and Hydrogen-Bonding Interactions between Bilayers of Glycine Amphiphiles", LANGMUIR, vol. 18, no. 10, 1 May 2002 (2002-05-01), pages 3923 - 3931, XP055703261
GORE, TUSHAR: "Self-Assembly of Model Collagen Peptide Amphiphiles", LANGMUIR, vol. 17, no. 17, 10 February 2001 (2001-02-10), pages 5352 - 5360, XP05570326
PAKALNS, TEIKA: "Cellular recognition of synthetic peptide amphiphiles in self-assembled monolayer "lms", BIOMATERIALS, vol. 20, no. 23, December 1999 (1999-12-01), pages 2265 - 2279, XP055703271
HABERMANN, JORG: "Fragment Condensation on Solid-Phase in the Synthesis of an Amphiphilic Glycopeptide from the Homophilic Recognition Domain of Epithelial Cadherin", TETRAHEDRON LETTERS, vol. 39, no. 27, 2 July 1998 (1998-07-02), pages 4797 - 4800, XP004120760
BERNDT, PETER: "Synthetic lipidation of peptides and amino acids: monolayer structure and properties", J. AM. CHEM. SOC., vol. 117, no. 37, 20 September 1995 (1995-09-20), pages 9515 - 9522, XP002030763
KALBER TAMMY L; SMITH CHRISTOPHER J; HOWE FRANKLYN A; GRIFFITHS JOHN R; RYAN ANDERSON J; WATERTON JOHN C; ROBINSON SIMON P: "A longitudinal study of R2* and R2 magnetic resonance imaging relaxation rate measurements in murine liver after a single administration of 3 different iron oxide-based contrast agents", POLYMERIC MATERIALS SCIENCE AND ENGINEERING, vol. 77, 1997, pages 584 - 585, XP009119273, ISSN: 0743-0515
PROCEEDINGS OF THE 32ND ANNUAL MEETING OF THE JAPANESE SOCIETY FOR BIOMATERIALS, pages 324
PROCEEDINGS OF THE 33RD ANNUAL MEETING OF THE JAPANESE SOCIETY FOR BIOMATERIALS, pages 319
See also references of EP 3868740A4
Attorney, Agent or Firm:
NAGAI Hiroshi et al. (JP)
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