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WO1989003675A1 - Particules superparamagnetiques, moyen de production de telles particules et leur utilisation - Google Patents

Particules superparamagnetiques, moyen de production de telles particules et leur utilisation Download PDF

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Publication number
WO1989003675A1
WO1989003675A1 PCT/SE1988/000561 SE8800561W WO8903675A1 WO 1989003675 A1 WO1989003675 A1 WO 1989003675A1 SE 8800561 W SE8800561 W SE 8800561W WO 8903675 A1 WO8903675 A1 WO 8903675A1
Authority
WO
WIPO (PCT)
Prior art keywords
particles
superparamagnetic particles
superparamagnetic
particles according
solution
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.)
Ceased
Application number
PCT/SE1988/000561
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English (en)
Inventor
Ulf SCHRÖDER
Gunilla Nyberg
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.)
CARBOMATRIX AB
Original Assignee
CARBOMATRIX AB
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 CARBOMATRIX AB filed Critical CARBOMATRIX AB
Publication of WO1989003675A1 publication Critical patent/WO1989003675A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
    • B01J20/28016—Particle form
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/06—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations
    • A61K49/18—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes
    • A61K49/1818—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
    • A61K49/1821—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles
    • A61K49/1824—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles
    • A61K49/1827—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle
    • A61K49/1851—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule
    • A61K49/1863—Nuclear magnetic resonance [NMR] contrast preparations; Magnetic resonance imaging [MRI] contrast preparations characterised by a special physical form, e.g. emulsions, microcapsules, liposomes particles, e.g. uncoated or non-functionalised microparticles or nanoparticles coated or functionalised microparticles or nanoparticles coated or functionalised nanoparticles having a (super)(para)magnetic core, being a solid MRI-active material, e.g. magnetite, or composed of a plurality of MRI-active, organic agents, e.g. Gd-chelates, or nuclei, e.g. Eu3+, encapsulated or entrapped in the core of the coated or functionalised nanoparticle having a (super)(para)magnetic core coated or functionalised with an organic macromolecular compound, i.e. oligomeric, polymeric, dendrimeric organic molecule the organic macromolecular compound being a polysaccharide or derivative thereof, e.g. chitosan, chitin, cellulose, pectin, starch
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5094—Microcapsules containing magnetic carrier material, e.g. ferrite for drug targeting
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
    • B01J20/28004—Sorbent size or size distribution, e.g. particle size
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
    • B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
    • B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
    • B01J20/28009—Magnetic properties
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2400/00—Assays, e.g. immunoassays or enzyme assays, involving carbohydrates
    • G01N2400/10—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
    • G01N2400/12—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar
    • G01N2400/14—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar alpha-D-Glucans, i.e. having alpha 1,n (n=3,4,6) linkages between saccharide units, e.g. pullulan
    • G01N2400/16—Starch, amylose, amylopectin
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2446/00—Magnetic particle immunoreagent carriers
    • G01N2446/20—Magnetic particle immunoreagent carriers the magnetic material being present in the particle core
    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N2446/00—Magnetic particle immunoreagent carriers
    • G01N2446/30—Magnetic particle immunoreagent carriers the magnetic material being dispersed in the polymer composition before their conversion into particulate form

Definitions

  • This invention relates to magnetically responsive superparam agnetic particles, away of producing said particles and their use.
  • the invention describes a method for the production of superparamagnetic particles which are made of a metal oxide surrounded by a surface layer of a biologically acceptable polymer.
  • the particles may be used as a contrast agent in medical diagnostics in particular in Magnetic Resonance Imaging (MRI). They may also be used as a matrix for biological molecules, thus functioning as a separation device.
  • Another area for their use is by combining said particles with a drug which after injection into the blood stream is stopped in an predetermined area using an external magnet,
  • the invention is based on magnetically responsive particles which are superparamagnetie, indicating that they are not permanently magnetized when subjected to a magnetic field. This means that the particles, after withdrawing of the magnetic field, are easily resuspended, Using magnetically responsive particles within the areas mentioned above, it is of utmost importance that the particles are superparamagnetic m order to avoid permanent aggregation,
  • Magnetic particles has for long times been discussed as a extremely effective separation device (Hirschbein et al. Chemtech . March 1982 , 172- 179).
  • prior art regarding magnetic particles lack one or several of the demands needed in order for the technology to obtain general acceptance,
  • Avrameas & G ⁇ esdon (USTatent 4,241,176, Dec , 28, 19801 describes magnetic polymer particles where magnetite has been entrapped in a polyacrylamide-agarose polymer in an emulsion process, The sue of the spheres is 50-500 ⁇ m, Widder et al (US Patent 4,230,686. Oct. 28, 1980) describes away of producing magnetic particles where the magnetite is entrapped into albumin/protein-A with subsequent covalent stabilization of the polymer mixture.
  • Ugelstad et al (PCT/HO83/00014) describes away of producing particles where the magnetic material is precipitated within prefabricated polymer particles of a defined size.
  • Molday (US Patent 4,462,773. Jun.6, 1984) described sway of producing magnetite particles with a size of 10-70 nm, which are surface coated with a dextran polymer. Dextran has a high molecular weight and is not degraded in the body, thus particles produced in this way are less suitable for medical applications. After production these particles are further processed by centrifugation at 2S.000 rpm, alternatively the particles are allowed to pass a gel chromatography column in connection with the couphng of affinity ligands. Both of these methods may be used in laboratory scale production, however, the technologies are not suitable in the production of particles to be used in large scale separation of fermentation suspensions or the production of superparamagnetic particles for the use as a contrast agent, as discussed in this invention.
  • the particles may not be separated with conventional magnets. This is also seen in the examples presented, where only examples referring to the separation of cells or cell organells are described.
  • a large, number of magnetic particles are associated to the surface of one cell, whereby the total amount of magnetic material attached to a cell makes it responsive to the magnetic field obtained by conventional cobalt-samarium magnets.
  • Schroder & Borrebaeck (EPC 83901116.0) describes the entrappment of magnetite particles within a carbohydrate matrix by an emulsion process with subsequent stabilization try crystallization of the carbohydrate polymer.
  • Chagnon et al (EP 0 126 995) describes a process for the production of magnetic particles in a two step procedure: in the first step the magnetic particles are produced, and in step two, these particles are, after extensive washing, subjected to a surface coating with one or several silicone polymers. Two steps in the process of Chagnon thus differs significantly from the present invention:
  • an contrast agent for the liver and the spleen there is primarily a wish to obtain an contrast agent for the liver and the spleen. This can be accomplished using injection of particles into the blood stream having a size of 0.4-1.0 ⁇ m, since particles having this size are eliminated from the blood stream by these organs.
  • the size should, however , not be below 0.3 ⁇ m , since the magnetically responsive particle thus contains too small amounts of magnetic material to be attracted be a magnetic field. Furthermore, particles having a size below 0.3 ⁇ m possess particle/liquid interactions resulting in a suspension behaving more like a magnetic fluid and not as a suspension where the particles easily can be retrieved.
  • the superparamagnetic particles will aggregate, however, due to the superparamagnetic property, the particles will be resuspended as soon as the magnetic field is switched off, thereby allowing for the affinity attached protein to be recovered.
  • the structure of the particle renders a system where the affinity ligand is associated only to the surface of the particle.
  • the final product is economically advantageous as compared to macroporous particles since the amount of affinity ligand (e.g. a monoclonal antibody) used can be reduced.
  • the surface association of the monoclonal antibody renders rapid adsorption of the substance of interest due to the lack of the diffusion barriers.
  • the present invention relates to superparamagnetic particles, made of a core of magnetite, surrounded by a pharmacologically acceptable carbohydrate polymer, the superparamagnetic particle having a size of 0.1- 2.0 ⁇ m produced by precipitation of iron salts dissolved in a starch solution,
  • the process for fabrication of the superparamagnetic particles according to the present invention is based on optimization of parameters resulting in particles which all fulfills the demands mentioned above.
  • the process renders a high yield where further secondary purification steps in order to obtain optimal superparamagnetie particles having the adequate size and magnetic properties are not needed.
  • the process is based on the well known technology of precipitating iron salts in alkali, whereby the metal oxide is formed, However , this precipitation is performed in a way that both the starch and the iron salts simultaneously are added to the alkali solution (e.g, MaOH) while sonicating, The obtained solution is neutralized to pH 7.
  • the suspension containing a monodispers suspension of superparamagnetic particles in a solution of carbohydrates in an alkali or neutral environment, directly or after a concentration step, can be emulsified in an organic solvent, a crosslinker may added to the emulsion or the water solution of superparamagnetic particles, whereafter these ere stabilized into a water-insoluble three dimensional crosslinked superparamagnetic microsphere.
  • the size of the obtained monodisperse suspension of superparamagnetic particles is measured in an Coulter Counter Multisizer with the following result:
  • Average size 0.775 ⁇ m.
  • Dry weight 25 mg/ml, where 85% is magnetite.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nanotechnology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Radiology & Medical Imaging (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

La présente invention se rapporte à des particules superparamagnétiques, à un moyen de production de telles particules et à leur utilisation. La présente invention décrit plus particulièrement un procédé de fabrication de telles particules, qui permet de produire ces particules avec un grand pouvoir de régénération selon unprocessus simple en une seule étape.
PCT/SE1988/000561 1987-10-26 1988-10-24 Particules superparamagnetiques, moyen de production de telles particules et leur utilisation Ceased WO1989003675A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE8704157-0 1987-10-26
SE8704157A SE8704157L (sv) 1987-10-26 1987-10-26 Superparamagnetiska partiklar och foerfarande foer framstaellning daerav samt anvaendning

Publications (1)

Publication Number Publication Date
WO1989003675A1 true WO1989003675A1 (fr) 1989-05-05

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/SE1988/000561 Ceased WO1989003675A1 (fr) 1987-10-26 1988-10-24 Particules superparamagnetiques, moyen de production de telles particules et leur utilisation

Country Status (3)

Country Link
AU (1) AU2612188A (fr)
SE (1) SE8704157L (fr)
WO (1) WO1989003675A1 (fr)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001148A1 (fr) 1989-07-21 1991-02-07 Nycomed As Composition de substance de contraste
EP0517740A4 (en) * 1990-02-06 1993-02-03 Advanced Magnetics Incorporated Low molecular weight carbohydrates as additives to stabilize metal oxide compositions
WO1993005815A1 (fr) * 1991-09-16 1993-04-01 Syngenix Limited Vecteurs de transfection synthetiques
EP0525199A4 (en) * 1991-01-19 1994-08-17 Meito Sangyo Kk Composition containing ultrafine particles of magnetic metal oxide
WO1995031220A1 (fr) * 1994-05-12 1995-11-23 Otsuka Pharmaceutical Co., Ltd. Agent de contraste pour imagerie par resonance magnetique
EP0928611A4 (fr) * 1996-06-10 1999-12-15 Nittetsu Mining Co Ltd Poudre medicale
US6123920A (en) * 1996-01-10 2000-09-26 Nycomed Imaging As Superparamagnetic contrast media coated with starch and polyalkylene oxides
US6423296B1 (en) 1996-01-10 2002-07-23 Amersham Health As Constrast media
US6849400B1 (en) 1997-07-23 2005-02-01 Gen-Probe Incorporated Methods for detecting and measuring spliced nucleic acids
AU2001294068B2 (en) * 2000-10-16 2005-12-22 Consejo Superior De Investigaciones Cientificas Nanoparticles
WO2006069677A3 (fr) * 2004-12-30 2006-12-07 Blue Membranes Gmbh Ensemble comprenant un agent produisant un signal, un implant et un medicament
EP1683572A4 (fr) * 2003-10-14 2008-04-02 Mikhail Vladimirovich Kutushov Sorbant a commande magnetique et son procede de preparation
EP2277181A4 (fr) * 2008-04-16 2016-03-09 Stemcell Technologies Inc Particules magnétiques

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988000060A1 (fr) * 1986-07-03 1988-01-14 Advanced Magnetics, Inc. Materiau super paramagnetique biodegradable utilise dans des applications cliniques

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1988000060A1 (fr) * 1986-07-03 1988-01-14 Advanced Magnetics, Inc. Materiau super paramagnetique biodegradable utilise dans des applications cliniques

Cited By (22)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1991001148A1 (fr) 1989-07-21 1991-02-07 Nycomed As Composition de substance de contraste
EP0517740A4 (en) * 1990-02-06 1993-02-03 Advanced Magnetics Incorporated Low molecular weight carbohydrates as additives to stabilize metal oxide compositions
EP0525199A4 (en) * 1991-01-19 1994-08-17 Meito Sangyo Kk Composition containing ultrafine particles of magnetic metal oxide
US6153598A (en) * 1991-09-16 2000-11-28 Syngenix Limited Synthetic transfection vectors
WO1993005815A1 (fr) * 1991-09-16 1993-04-01 Syngenix Limited Vecteurs de transfection synthetiques
EP0640350A3 (fr) * 1991-09-16 1995-12-13 Syngenix Ltd Particules de céramique et leur préparation.
US6809082B2 (en) 1991-09-16 2004-10-26 Molecular Synthetics, Ltd. Synthetic transfection vectors
WO1995031220A1 (fr) * 1994-05-12 1995-11-23 Otsuka Pharmaceutical Co., Ltd. Agent de contraste pour imagerie par resonance magnetique
US6423296B1 (en) 1996-01-10 2002-07-23 Amersham Health As Constrast media
US6123920A (en) * 1996-01-10 2000-09-26 Nycomed Imaging As Superparamagnetic contrast media coated with starch and polyalkylene oxides
US6162469A (en) * 1996-06-10 2000-12-19 Nittetsu Mining Co., Ltd. Medical powder
EP0928611A4 (fr) * 1996-06-10 1999-12-15 Nittetsu Mining Co Ltd Poudre medicale
US6849400B1 (en) 1997-07-23 2005-02-01 Gen-Probe Incorporated Methods for detecting and measuring spliced nucleic acids
US8080431B2 (en) 2000-10-16 2011-12-20 Midatech Limited Nanoparticles
US7364919B2 (en) 2000-10-16 2008-04-29 Midatech Limited Nanoparticles
AU2001294068B2 (en) * 2000-10-16 2005-12-22 Consejo Superior De Investigaciones Cientificas Nanoparticles
US8790934B2 (en) 2000-10-16 2014-07-29 Consejo Superior De Investigaciones Cientificas Nanoparticles
EP1683572A4 (fr) * 2003-10-14 2008-04-02 Mikhail Vladimirovich Kutushov Sorbant a commande magnetique et son procede de preparation
WO2006069677A3 (fr) * 2004-12-30 2006-12-07 Blue Membranes Gmbh Ensemble comprenant un agent produisant un signal, un implant et un medicament
EA011594B1 (ru) * 2004-12-30 2009-04-28 Синвеншен Аг Композиция, включающая агент, обеспечивающий сигнал, имплантируемый материал и лекарство
EP2277181A4 (fr) * 2008-04-16 2016-03-09 Stemcell Technologies Inc Particules magnétiques
US9701935B2 (en) 2008-04-16 2017-07-11 Stemcell Technologies Inc. Magnetic particles

Also Published As

Publication number Publication date
SE8704157D0 (sv) 1987-10-26
AU2612188A (en) 1989-05-23
SE8704157L (sv) 1989-04-27

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