CA2131455A1 - Selective Crosslinking of Hemoglobin by Oxidized, Ring-Opened Saccharides - Google Patents

Selective Crosslinking of Hemoglobin by Oxidized, Ring-Opened Saccharides

Info

Publication number
CA2131455A1
CA2131455A1 CA2131455A CA2131455A CA2131455A1 CA 2131455 A1 CA2131455 A1 CA 2131455A1 CA 2131455 A CA2131455 A CA 2131455A CA 2131455 A CA2131455 A CA 2131455A CA 2131455 A1 CA2131455 A1 CA 2131455A1
Authority
CA
Canada
Prior art keywords
hemoglobin
saccharide
tri
reaction
ring
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA2131455A
Other languages
French (fr)
Other versions
CA2131455C (en
Inventor
Diana Pliura
Lawrence T. Wong
Song S. Er
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Therapure Biopharma Inc
Original Assignee
Diana Pliura
Lawrence T. Wong
Song S. Er
Hemosol Inc.
Hemosol Lp
2140304 Ontario Inc.
Hemosol Biopharma Inc.
Therapure Biopharma Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Diana Pliura, Lawrence T. Wong, Song S. Er, Hemosol Inc., Hemosol Lp, 2140304 Ontario Inc., Hemosol Biopharma Inc., Therapure Biopharma Inc. filed Critical Diana Pliura
Publication of CA2131455A1 publication Critical patent/CA2131455A1/en
Application granted granted Critical
Publication of CA2131455C publication Critical patent/CA2131455C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/795—Porphyrin- or corrin-ring-containing peptides
    • C07K14/805—Haemoglobins; Myoglobins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/08—Plasma substitutes; Perfusion solutions; Dialytics or haemodialytics; Drugs for electrolytic or acid-base disorders, e.g. hypovolemic shock

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Medicinal Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Biochemistry (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • General Chemical & Material Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Hematology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Diabetes (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Polysaccharides And Polysaccharide Derivatives (AREA)
  • Saccharide Compounds (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)

Abstract

Hemoglobin for forming the basis of blood substitute is modified by crosslinking it by reaction with a polyaldehyde produced by ring opening oxidation of a di/tri-saccharide such as raffinose, wherein the o-saccharide solutions are maintained and the reaction is conducted at a pH from about 5.0-7.0, and at a stoichiometry from about 1:1-4:1 based upon the molar ratio of di/tri-saccharide to hemoglobin tetramers, followed by appropriate reduction of the Schiff base linkages so formed to stabilize them. Careful control of the pH of ring opening of the di/tri-saccharide ensures consistent production of the polyaldehyde without unwanted side products and reaction of this product with the hemoglobin at the specified stoichiometry leads to high yields of stabilized, tetrameric hemoglobin and oligomers thereof of predetermined composition and beneficial properties.
CA002131455A 1993-03-16 1994-03-11 Selective crosslinking of hemoglobin by oxidized, ring-opened saccharides Expired - Fee Related CA2131455C (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US3183093A 1993-03-16 1993-03-16
US08/031,830 1993-03-16

Publications (2)

Publication Number Publication Date
CA2131455A1 true CA2131455A1 (en) 1994-09-29
CA2131455C CA2131455C (en) 1998-08-18

Family

ID=21861634

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002131455A Expired - Fee Related CA2131455C (en) 1993-03-16 1994-03-11 Selective crosslinking of hemoglobin by oxidized, ring-opened saccharides

Country Status (13)

Country Link
US (2) US5532352A (en)
EP (1) EP0646130B1 (en)
JP (1) JP2594241B2 (en)
KR (1) KR100306000B1 (en)
CN (1) CN1046292C (en)
AT (1) ATE146189T1 (en)
AU (1) AU668294B2 (en)
CA (1) CA2131455C (en)
DE (1) DE69401109T2 (en)
DK (1) DK0646130T3 (en)
ES (1) ES2095751T3 (en)
NZ (1) NZ262349A (en)
WO (1) WO1994021682A1 (en)

Families Citing this family (29)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE503711C2 (en) * 1994-12-14 1996-08-12 Medicarb Ab Multistage procedure for coating an intraocular lens
US5952470A (en) * 1995-06-07 1999-09-14 Biopure Corporation Method for separating unmodified hemoglobin from cross-linked hemoglobin
US5891506A (en) * 1996-08-09 1999-04-06 Medtronic, Inc. Oxidative method for attachment of glycoproteins or glycopeptides to surfaces of medical devices
EP0939644B1 (en) * 1996-08-27 2004-01-14 Hemosol Inc. Enhanced stimulation of erythropoiesis
US5917020A (en) * 1997-01-15 1999-06-29 Kluger; Ronald H. Bis-tetrameric hemoglobin and reagents for its production
US6054427A (en) * 1997-02-28 2000-04-25 The Regents Of The University Of California Methods and compositions for optimization of oxygen transport by cell-free systems
US5814601A (en) * 1997-02-28 1998-09-29 The Regents Of The University Of California Methods and compositions for optimization of oxygen transport by cell-free systems
CA2233725A1 (en) 1998-03-31 1999-09-30 Hemosol Inc. Hemoglobin-hydroxyethyl starch complexes
CA2266174A1 (en) 1999-03-18 2000-09-18 Hemosol Inc. Hemoglobin-antioxidant conjugates
DE19933275A1 (en) * 1999-07-14 2001-01-18 Fresenius Ag Use of hemoglobin derivatives to determine the plasma and / or blood volume
US6894150B1 (en) 1999-10-01 2005-05-17 Ross Walden Tye Non-pyrogenic, endotoxin-free, stroma-free tetrameric hemoglobin
US6500809B1 (en) 1999-11-12 2002-12-31 Neuron Therapeutics, Inc. Hyperoncotic artificial cerebrospinal fluid and method of treating neural tissue edema therewith
DE10031742A1 (en) * 2000-06-29 2002-01-17 Sanguibio Tech Ag Production of cross-linked hemoglobin useful as artificial oxygen carrier comprises cross-linkage of hemoglobin in presence of a chemically inert effector of the hemoglobin oxygen affinity
DE10112825A1 (en) 2001-03-16 2002-10-02 Fresenius Kabi De Gmbh HESylation of active ingredients in aqueous solution
US20050164915A1 (en) * 2002-04-01 2005-07-28 Sangart, Inc. Compositions for oxygen transport comprising a high oxygen affinity modified hemoglobin
US20030153491A1 (en) * 2002-01-11 2003-08-14 Winslow Robert M. Methods and compositions for oxygen transport comprising a high oxygen affinity modified hemoglobin
DE10209821A1 (en) 2002-03-06 2003-09-25 Biotechnologie Ges Mittelhesse Coupling of proteins to a modified polysaccharide
DE10209822A1 (en) 2002-03-06 2003-09-25 Biotechnologie Ges Mittelhesse Coupling of low molecular weight substances to a modified polysaccharide
JP3912206B2 (en) * 2002-07-05 2007-05-09 株式会社日立製作所 Fuel pump for in-cylinder direct fuel injection system
BR0314107A (en) 2002-09-11 2005-07-19 Fresenius Kabi De Gmbh Production method of hydroxyalkyl starch derivatives
DE60323756D1 (en) 2002-10-08 2008-11-06 Fresenius Kabi De Gmbh Pharmaceutically active oligosaccharide conjugates
WO2005014655A2 (en) 2003-08-08 2005-02-17 Fresenius Kabi Deutschland Gmbh Conjugates of hydroxyalkyl starch and a protein
US7135554B1 (en) 2004-01-27 2006-11-14 Biopure Corporation Method of forming a polymerized hemoglobin solution from stabilized hemoglobin
WO2005092928A1 (en) 2004-03-11 2005-10-06 Fresenius Kabi Deutschland Gmbh Conjugates of hydroxyalkyl starch and a protein, prepared by reductive amination
WO2006108047A2 (en) * 2005-04-05 2006-10-12 Biopure Corporation Oxygenated polymerized hemoglobin solutions and their uses for tissue visualization
US7504377B2 (en) * 2006-10-23 2009-03-17 Ikor, Inc. Nitric oxide-blocked cross-linked tetrameric hemoglobin
US7494974B2 (en) * 2006-10-24 2009-02-24 Ikor, Inc. Carboxymethylated cross-linked tetrameric hemoglobin
EP2070950A1 (en) 2007-12-14 2009-06-17 Fresenius Kabi Deutschland GmbH Hydroxyalkyl starch derivatives and process for their preparation
US20140260586A1 (en) * 2013-03-14 2014-09-18 Schlumberger Technology Corporation Method to perform rapid formation fluid analysis

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4529719A (en) * 1983-05-04 1985-07-16 Tye Ross W Modified crosslinked stroma-free tetrameric hemoglobin
JPH0645681B2 (en) * 1986-02-05 1994-06-15 美浜 久春 Modified hem
DE3636590A1 (en) * 1986-10-28 1988-05-26 Braun Melsungen Ag BLOOD REPLACEMENT
GB8710598D0 (en) * 1987-05-05 1987-06-10 Star Medical Diagnostics Ltd Hemoglobin based blood substitute
FR2640141B1 (en) * 1988-12-14 1993-04-16 Merieux Inst MACROMOLECULAR CONJUGATES OF HEMOGLOBIN, THEIR PREPARATION PROCESS AND THEIR APPLICATIONS
US5234903A (en) * 1989-11-22 1993-08-10 Enzon, Inc. Chemically modified hemoglobin as an effective, stable non-immunogenic red blood cell substitute
DK0559655T3 (en) * 1990-11-29 1995-07-24 Upjohn Co With imidoester crosslinked hemoglobin preparations
FR2680369B1 (en) * 1991-08-14 1993-11-05 Pasteur Merieux Serums Vaccins HUMAN HEMOGLOBIN DERIVATIVES, THEIR PREPARATION PROCESS, DERIVATIVES THEREOF, AND THE USE THEREOF.
US5399671A (en) * 1992-11-18 1995-03-21 Kluger; Ronald Specifically crosslinked hemoglobin with free functionality

Also Published As

Publication number Publication date
AU668294B2 (en) 1996-04-26
DE69401109T2 (en) 1997-05-28
US5532352A (en) 1996-07-02
JP2594241B2 (en) 1997-03-26
ATE146189T1 (en) 1996-12-15
EP0646130A1 (en) 1995-04-05
JPH07506123A (en) 1995-07-06
DK0646130T3 (en) 1997-06-02
US5770727A (en) 1998-06-23
AU6179394A (en) 1994-10-11
CN1105800A (en) 1995-07-26
WO1994021682A1 (en) 1994-09-29
CA2131455C (en) 1998-08-18
NZ262349A (en) 1996-05-28
DE69401109D1 (en) 1997-01-23
EP0646130B1 (en) 1996-12-11
ES2095751T3 (en) 1997-02-16
KR100306000B1 (en) 2001-12-01
CN1046292C (en) 1999-11-10

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