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WO2011069523A1 - Composition de marquage et de visualisation de greffe en i.r.m. et en fluoroscopie, et ses applications - Google Patents

Composition de marquage et de visualisation de greffe en i.r.m. et en fluoroscopie, et ses applications Download PDF

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Publication number
WO2011069523A1
WO2011069523A1 PCT/EP2009/008789 EP2009008789W WO2011069523A1 WO 2011069523 A1 WO2011069523 A1 WO 2011069523A1 EP 2009008789 W EP2009008789 W EP 2009008789W WO 2011069523 A1 WO2011069523 A1 WO 2011069523A1
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composition according
nanoparticles
composition
acid
group
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Ceased
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PCT/EP2009/008789
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English (en)
Inventor
Paul J. A. Borm
Viorel Rusu
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MagnaMedics GmbH
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MagnaMedics GmbH
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Priority to PCT/EP2009/008789 priority Critical patent/WO2011069523A1/fr
Publication of WO2011069523A1 publication Critical patent/WO2011069523A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/04—X-ray contrast preparations
    • A61K49/0409—Physical forms of mixtures of two different X-ray contrast-enhancing agents, containing at least one X-ray contrast-enhancing agent which is not a halogenated organic compound
    • A61K49/0414—Particles, beads, capsules or spheres
    • A61K49/0423—Nanoparticles, nanobeads, nanospheres, nanocapsules, i.e. having a size or diameter smaller than 1 micrometer
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K49/00—Preparations for testing in vivo
    • A61K49/0002—General or multifunctional contrast agents, e.g. chelated agents
    • 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
    • A61K49/183—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 inorganic material or being composed of an inorganic material entrapping the MRI-active nucleus, e.g. silica core doped with a MRI-active nucleus
    • 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
    • A61K49/1857—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 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. PLGA
    • 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
    • A61K49/1875—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 coated or functionalised with an antibody
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery

Definitions

  • composition for labeling and visualizing grafts in magnetic MRI and X-ray fluoroscopy and use thereof
  • the present invention concerns compositions and methods for labeling or marking grafts such as tissues, organs, blood vessels or vasculature (veins, arteries, capillaries) and the like such that the labeled entity becomes visible in magnetic resonance imaging (MRI) and/or in X-ray fluoroscopy.
  • the present invention further comprises the use of the nanoparticle compositions for labeling tissue grafts, organs, blood vessels, vein grafts, artery grafts, capillaries or tissues for rendering them visible in MRI and X-ray fluoroscopy.
  • Medical imaging techniques such as X-ray fluoroscopic imaging, computed tomography (CT), magnetic resonance imaging (MRI) and positron emission tomography (PET) are among the most important and versatile methods which are used by clinicians today for diagnostic purposes. Beyond that, physicians also use medical imaging techniques in visualizing the guidance and placement of medical devices such as guidewires, catheters, stents, biopsy needles or the like within a patient's body.
  • CT computed tomography
  • MRI magnetic resonance imaging
  • PET positron emission tomography
  • X-ray fluoroscopy is the preferred imaging modality for cardiovascular interventional procedures because of its temporal and spatial resolution.
  • X-ray fluoroscopy has some drawbacks such as the patient's exposure to ionizing radiation.
  • MRI is a medical imaging modality which does not use ionizing radiation and has the potential to supplant X-ray fluoroscopy. Moreover, MRI has greater soft tissue contrast than X-ray based imaging techniques. Beyond mere diagnostic purposes, interventional magnetic resonance (iMR) angiography as well as stent placements under MRI have been performed to demonstrate feasibility of MRI.
  • iMR interventional magnetic resonance
  • X-ray fluoroscopy is an imaging modality which utilizes ionizing X-ray radiation. Visualization and tracking of medical devices under X-ray fluoroscopy is accomplished either by the devices inherent absorption of X-rays or by securing radiopaque markers to the medical device, intermittent injection of radiopaque material in the veins. Radiopaque material absorbes X-rays and thereby creates contrast within the image, and thus is visible.
  • MRI Magnetic resonance Imaging
  • T1 longitudinal relaxation time
  • T2 transverse relaxation time
  • proton density and flow proton density and flow.
  • MRIs provide a distribution map of protons and their properties in organs and tissues.
  • MRI contrast agents usually shorten either the T1 relaxation time or the T2 relaxation time.
  • CABG coronary artery bypass graft
  • CABG is often done to supply the cardiac muscle with the necessary blood flow and reduce the risk of having a myocardial infarction.
  • CABG can be carried out more than once and repeated in the future if necessary, for example, if a bypass graft has become blocked. Due to this reason there a clear demand to label the bypass grafts and to provide them with a marking system for different medical imaging modalities, especially for X-ray fluoroscopic imaging and for magnetic resonance imaging (MRI). It was an object of the present invention to provide a marking system for labeling tissue grafts, organs, vasculature, tissues and the like for in-vivo permanent visualization in X-ray fluoroscopy and MRI.
  • a MRI and X-ray responsive composition comprises metal oxide nanoparticles and colloidal metallic nanoparticles in a pre-dispersion combined with an aqueous carrier composition, wherein the preferred metal oxide pre-dispersion contains iron oxide nanoparticles as MRI contrast agent and wherein the preferred colloidal metallic consists of colloidal gold as X-ray contrast agent.
  • the hybrid magnetic MRI and X-ray responsive ink contains at least one adjuvant, preferably as surfactant to aid the dispersion and the stabilization of the metal oxide/metal nanoparticles.
  • the ink composition contains at least one responsive material as nanoparticles dispersed within a carrier and at most both type of nanoparticles thus as a result a hybrid responsive ink is created.
  • the present invention comprises magnetic MRI and X- ray responsive ink compositions for permanent visualization and positioning of any tissue-graft or vasculature (vein, artery, capillary) using magnetic resonance imaging and X-ray fluoroscopic imaging.
  • the present invention concerns an imprinting MRI and X-ray responsive ink composition containing colloidal gold as attached onto glass beads, gold nanoparticles coated iron oxide nanoparticles as dispersed within an aqueous sterile carrier.
  • the ink compositions of the present invention contain at least one either MRI or X-ray responsive material as nanoparticles dispersed within a carrier and at most both type of nanoparticles and as a result a hybrid responsive ink is created. In some cases, in order to improve the stability of these systems, some dispersant compounds are needed to be added.
  • the U.S. Patent No. 5,656,071 patent discloses an ink composition including a polymeric dispersant to maintain a metal oxide in solution and a co-solvent mixture of 1 ,3-propanediol or 1 ,4-butanediol with a second solvent selected from polyethylene glycol-type materials and polyol/polyalkylene oxide condensates.
  • U.S. Patent No. 5,240,626 discloses an ink including colloidally dispersed magnetite particles coated with a carboxy compound-type anti-agglomeration agent and a dispersing aid.
  • the composition of the present invention for labeling grafts to render the graft visible in MRI and X-ray fluoroscopy comprises magnetic metal oxide nanoparticles and radiopaque nanoparticles.
  • the metal oxide of the magnetic metal oxide nanoparticles is selected from the group consisting of gadolinium oxide, dysprosium oxide, terbium oxide, nickel oxide, iron oxide, magnesium oxide, cobalt oxide and mixtures thereof.
  • the magnetic metal oxide of the most preferred metal oxide nanoparticles is magnetite (Fe30 4 ).
  • the term "magnetic" also refers to particles comprising paramagnetic material.
  • Paramagnetic material possesses magnetism only in the presence of an externally applied magnetic field, and does not retain any magnetization in the absence of an externally applied magnetic field. However, paramagnetic materials are attracted to magnetic fields and hence have a relative magnetic permeability of greater than one, i. e. a positive magnetic susceptibility.
  • Suitable paramagnetic iron oxides include FeO, Fe203 and Fe30 4 .
  • the magnetic metal oxide nanoparticles have a diameter of at least 100 nm, preferably at least 200 nm, more preferably at least 400 nm, and most preferably at least 500 nm. The diameter of the magnetic metal oxide nanoparticles is less than 2,000 nm, preferably less than 1 ,000 nm and more preferably less than 800 nm.
  • the radiopaque nanoparticles of the composition comprise or consist of a material that is selected from the group consisting of gold, platinum, tungsten, tantalum, rhenium, bismuth, silver, iridium, and mixtures thereof.
  • the preferred material is colloidal gold.
  • the radiopaque nanoparticles have a diameter of at least 5 nm, preferably at least 10 nm and more preferably at least 20 nm.
  • the diameter of the radiopaque nanoparticles is less than 100 nm, preferably less than 50 nm, and more preferably less than 40 nm.
  • the composition of the present invention further comprises a carrier which is selected from the group comprising water and water-soluble organic solvents, wherein the preferred water-soluble organic solvents are selected from the group comprising saline solutions, glycerol, propylenglycol and polypropylenglycol.
  • the saline solution may contain a salt selected from the group comprising sodium chloride, sodium phosphate, sodium dihydrogen phosphate, disodium hydrogen phosphate, potassium chloride, potassium phosphate, potassium dihydrogen phosphate, dipotassium hydrogenphosphate, calcium chloride and magnesium chloride, or mixtures thereof.
  • composition of the present invention further comprises an adjuvant, preferably selected from the group comprising biodegradable polymers, ionic surfactants and non-ionic surfactants.
  • the biodegradable polymer may be selected from the group comprising alginates, polylactic acid, polyvinyl alcohols, poly glycolic acids, gelatin, and mixtures thereof.
  • the non-ionic surfactant may be selected from the group comprising monoalkyl glycerol ester, dialkyi glycerol ester, trialkyi glycerol ester, and mixtures thereof, and wherein the fatty acid residues of the preferred monoalkyl glycerol esters, dialkyi glycerol esters and trialkyi glycerol esters are selected from the group comprising lauric acid, myrisitc acid, palmitic acid, palmitoleic acid, stearic acid, oleic acid, linoleic acid, gamma-linolenic acid, arachidic acid, arachidonic acid, and mixtures thereof.
  • the ionic surfactant is selected from the group comprising sorbitan monolaurate (Polysorbate 20, Span® 20, Tween® 20), sorbitan monopalmitate (Polysorbate 40, Span® 40), sorbitan monostearate (Polysorbate 60, Span® 60), sorbitan monooleate (Polysorbate 80, Span® 80, Tween® 80), and mixtures thereof.
  • the magnetic nanoparticles further comprise a polymer coating, preferably a polymer coating wherein the polymer comprises or consists of polyvinylpyrrolidone.
  • the radiopaque nanoparticles are embedded within the shell of the magnetic nanoparticles in a preferred embodiment of the composition.
  • the magnetic nanoparticles and/or the radiopaque nanoparticles comprise antibodies, preferably antibodies against collagen, which are conjugated to the nanoparticles.
  • the composition of the present invention is understood as at least one suspension of nanoparticles in a carrier fluid or embedded in a film such that the composition can be applied as an "ink” or "film” into the site or tissue graft to be marked.
  • the composition of the present invention consists of a single suspension comprising the magnetic metal oxide nanoparticles and the radiopaque nanoparticles.
  • This ink composition is designated multi-functional ink, because it provides visualization in both X-ray fluoroscopy and MRI. In the multi-functional ink it is preferred that the amount of magnetic metal oxide nanoparticles is equal to or greater than tha amount of radiopaque nanoparticles.
  • the composition of the present invention comprises two suspensions, wherein the magnetic metal oxide nanoparticles are present in one suspension, and the radiopaque nanoparticles are provided in a separate suspension.
  • the composition may comprise two types of suspension.
  • the first suspension comprises radiopaque nanoparticles but no magnetic metal oxide nanoparticles
  • the second suspension comprises magnetic metal oxide nanoparticles, but no radiopaque nanoparticles.
  • composition of the present invention shall be sterile. It can be sterilized by methods known to the skilled artisan.
  • the ink composition of the present invention can be incorporated into the structure of a graft prior to transplantation or implantation, and is intended to remain in the application area for long term.
  • the graft may be any organ or tissue that was or is intended to be explanted from a human or animal body to be implanted into another human or animal body.
  • the term “graft” also comprises blood vessels such as arteries, veins and capillaries.
  • the term “graft” also refers to tissues, organs and blood vessels that were not explanted from a human or animal body, but grown in vitro only. "Grown in vitro only” refers to tissue engineering wherein cells are propagated and differentiated in culture such that a desired tissue can be obtained without the need of surgical intervention prior to implantation of the graft.
  • the grafts and blood vessels which are provided with the composition of the present invention can be visualized in X-ray fluoroscopy and/of MRI due to their labeling with the composition.
  • the labeled graft can be easily tracked and visualized "in vivo" in a patient's body. Therefore, the present invention also pertains to methods of labeling or marking grafts for their visualization in MRI and X-ray fluoroscopy.
  • the method of labeling or marking grafts comprises application of the composition of the present invention to the site or tissue graft to be marked. Using the multifunctional ink composition, a single marking element is sufficient to render the labeled organ, tissue or graft visible in MRI and X-ray fluoroscopy.
  • a composition which comprises two suspension, the first suspension first suspension comprising radiopaque nanoparticles but no magnetic metal oxide nanoparticles, and the second suspension comprising magnetic metal oxide nanoparticles, but no radiopaque nanoparticles

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Nanotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Radiology & Medical Imaging (AREA)
  • Immunology (AREA)
  • Molecular Biology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biophysics (AREA)
  • Biotechnology (AREA)
  • General Engineering & Computer Science (AREA)
  • Medical Informatics (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)

Abstract

La présente invention concerne une composition de marquage et de visualisation de tissus, de greffes, d'organes ou de vaisseaux en I.R.M. et/ou en fluoroscopie, ladite composition comprenant des nanoparticules d'oxyde métallique magnétique et des nanoparticules opaques aux rayons X, ainsi que les emplois de ladite composition.
PCT/EP2009/008789 2009-12-09 2009-12-09 Composition de marquage et de visualisation de greffe en i.r.m. et en fluoroscopie, et ses applications Ceased WO2011069523A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
PCT/EP2009/008789 WO2011069523A1 (fr) 2009-12-09 2009-12-09 Composition de marquage et de visualisation de greffe en i.r.m. et en fluoroscopie, et ses applications

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/EP2009/008789 WO2011069523A1 (fr) 2009-12-09 2009-12-09 Composition de marquage et de visualisation de greffe en i.r.m. et en fluoroscopie, et ses applications

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WO2011069523A1 true WO2011069523A1 (fr) 2011-06-16

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015051186A3 (fr) * 2013-10-02 2015-05-28 The Regents Of The University Of Colorado, A Body Corporate Matériaux nanocomposites photoactifs et radio-opaques à base de polymère à mémoire de forme-or pour dispositifs médicaux de type transcathéters
CN118516016A (zh) * 2024-05-27 2024-08-20 西安交通大学 一种磁性荧光复合隐性标记墨水和制备方法及其应用

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US5240626A (en) 1990-09-21 1993-08-31 Minnesota Mining And Manufacturing Company Aqueous ferrofluid
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015051186A3 (fr) * 2013-10-02 2015-05-28 The Regents Of The University Of Colorado, A Body Corporate Matériaux nanocomposites photoactifs et radio-opaques à base de polymère à mémoire de forme-or pour dispositifs médicaux de type transcathéters
CN118516016A (zh) * 2024-05-27 2024-08-20 西安交通大学 一种磁性荧光复合隐性标记墨水和制备方法及其应用

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