ITRM20110022A1 - METHOD FOR THE PREPARATION OF MICROBULTS INCLUDING A CONTRAST AGENT - Google Patents
METHOD FOR THE PREPARATION OF MICROBULTS INCLUDING A CONTRAST AGENT Download PDFInfo
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- ITRM20110022A1 ITRM20110022A1 IT000022A ITRM20110022A ITRM20110022A1 IT RM20110022 A1 ITRM20110022 A1 IT RM20110022A1 IT 000022 A IT000022 A IT 000022A IT RM20110022 A ITRM20110022 A IT RM20110022A IT RM20110022 A1 ITRM20110022 A1 IT RM20110022A1
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- Prior art keywords
- microbubbles
- functionalized
- biocompatible
- hydroxylated
- polyamine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- 239000002872 contrast media Substances 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 229920000768 polyamine Polymers 0.000 claims description 11
- 230000002285 radioactive effect Effects 0.000 claims description 10
- 229920001661 Chitosan Polymers 0.000 claims description 7
- WTFXARWRTYJXII-UHFFFAOYSA-N iron(2+);iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[Fe+2].[Fe+3].[Fe+3] WTFXARWRTYJXII-UHFFFAOYSA-N 0.000 claims description 6
- 239000002082 metal nanoparticle Substances 0.000 claims description 6
- 230000005298 paramagnetic effect Effects 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 150000004676 glycans Chemical class 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 229920005862 polyol Polymers 0.000 claims description 5
- 150000003077 polyols Chemical class 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- 229910052713 technetium Inorganic materials 0.000 claims description 5
- GKLVYJBZJHMRIY-UHFFFAOYSA-N technetium atom Chemical group [Tc] GKLVYJBZJHMRIY-UHFFFAOYSA-N 0.000 claims description 5
- 239000004372 Polyvinyl alcohol Substances 0.000 claims description 4
- 229920002451 polyvinyl alcohol Polymers 0.000 claims description 4
- 239000004952 Polyamide Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 238000006359 acetalization reaction Methods 0.000 claims description 2
- 230000002829 reductive effect Effects 0.000 claims 1
- 229940031182 nanoparticles iron oxide Drugs 0.000 description 9
- 238000002604 ultrasonography Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 5
- 230000005291 magnetic effect Effects 0.000 description 3
- 238000012631 diagnostic technique Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- GKLVYJBZJHMRIY-OUBTZVSYSA-N Technetium-99 Chemical group [99Tc] GKLVYJBZJHMRIY-OUBTZVSYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012217 radiopharmaceutical Substances 0.000 description 1
- 229940121896 radiopharmaceutical Drugs 0.000 description 1
- 230000002799 radiopharmaceutical effect Effects 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 229940056501 technetium 99m Drugs 0.000 description 1
Classifications
-
- 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
- A61K49/1806—Suspensions, emulsions, colloids, dispersions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K49/00—Preparations for testing in vivo
- A61K49/22—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations
- A61K49/222—Echographic preparations; Ultrasound imaging preparations ; Optoacoustic imaging preparations characterised by a special physical form, e.g. emulsions, liposomes
- A61K49/223—Microbubbles, hollow microspheres, free gas bubbles, gas microspheres
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/12—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules
- A61K51/1241—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules particles, powders, lyophilizates, adsorbates, e.g. polymers or resins for adsorption or ion-exchange resins
- A61K51/1244—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules particles, powders, lyophilizates, adsorbates, e.g. polymers or resins for adsorption or ion-exchange resins microparticles or nanoparticles, e.g. polymeric nanoparticles
- A61K51/1251—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by a special physical form, e.g. emulsion, microcapsules, liposomes, characterized by a special physical form, e.g. emulsions, dispersions, microcapsules particles, powders, lyophilizates, adsorbates, e.g. polymers or resins for adsorption or ion-exchange resins microparticles or nanoparticles, e.g. polymeric nanoparticles micro- or nanospheres, micro- or nanobeads, micro- or nanocapsules
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Radiology & Medical Imaging (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Physics & Mathematics (AREA)
- Medicinal Chemistry (AREA)
- Optics & Photonics (AREA)
- Pharmacology & Pharmacy (AREA)
- Acoustics & Sound (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Description
DESCRIZIONE DESCRIPTION
del brevetto per invenzione industriale dal titolo: of the patent for industrial invention entitled:
"METODO PER LA PREPARAZIONE DI MICROBOLLE COMPRENDENTI UN AGENTE DI CONTRASTO" "METHOD FOR THE PREPARATION OF MICRO BUBBLES INCLUDING A CONTRAST AGENT"
La presente invenzione è relativa ad un metodo per la preparazione di microbolle comprendenti un agente di contrasto . The present invention relates to a method for the preparation of microbubbles comprising a contrast agent.
Qui e nel seguito per microbolle si intendono le microparticelle colloidali cave in grado di trattenere al loro interno gas. Here and in the following by microbubbles we mean the hollow colloidal microparticles capable of retaining gas inside them.
Nel campo medico sono note già da tempo le potenzialità che le microbolle presentano da un punto di vista sia diagnostico sia terapeutico. Ad esempio, le microbolle polimeriche hanno i vantaggi di presentare una elevata superficie di interfaccia, di essere stabili e di essere facilmente separabili dall'ambiente di reazione. In the medical field, the potential that microbubbles present from both a diagnostic and a therapeutic point of view have been known for some time. For example, polymeric microbubbles have the advantages of having a high interface surface, of being stable and of being easily separable from the reaction environment.
Fino ad oggi le microbolle sono utilizzate in particolare nella ecografia ad ultrasuoni. Until today, microbubbles are used in particular in ultrasound ultrasound.
È stato verificato che l'introduzione di un agente di contrasto per risonanaza magnetica, quali le nanoparticelle di ossido di ferro superparamagnetico, sulla parete delle microbolle consente di migliorare notevolmente il contrasto di immagine sia nella risonanza magnetica sia nell'ecografia ad ultrasuoni. It has been verified that the introduction of a contrast agent for magnetic resonance, such as superparamagnetic iron oxide nanoparticles, on the wall of the microbubbles allows to considerably improve the image contrast in both magnetic resonance and ultrasound ultrasound.
Era quindi sentita l'esigenza di disporre di un metodo efficace che garantisse la funzionalizzazione di microbolle con elementi di contrasto. The need was therefore felt to have an effective method that would guarantee the functionalization of microbubbles with contrasting elements.
Un'altra esigenza particolare nel settore della diagnostica medica è relativa al fatto di poter disporre di microbolle funzionalizzate in grado di poter essere utilizzate contemporaneamente per tecniche diagnostiche diverse. In questo modo, come risulta ovvio ad un tecnico del settore, si è in grado di realizzare delle analisi molto più accurate di quanto non siano quelle realizzate con le singole tecniche. Another particular requirement in the field of medical diagnostics relates to the fact that functionalized microbubbles can be used simultaneously for different diagnostic techniques. In this way, as is obvious to a person skilled in the art, it is possible to carry out much more accurate analyzes than those carried out with the individual techniques.
Oggetto della presente invenzione è un metodo per la realizzazione di microbolle funzionalizzate, in cui una poliammina idrossilata biocompatibile, legata a nanoparticelle metalliche paramagnetiche e/o isotopi radioattivi, viene fatta reagire con delle microbolle realizzate con polimeri polioli in maniera da realizzare dei legami covalenti tra la poliammina idrossilata e il polimero poliolo definente la microbolla. The object of the present invention is a method for the production of functionalized microbubbles, in which a biocompatible hydroxylated polyamine, linked to paramagnetic metal nanoparticles and / or radioactive isotopes, is reacted with microbubbles made with polyol polymers in order to create covalent bonds between the hydroxylated polyamine and the polyol polymer defining the microbubble.
Preferibilmente, la poliammide idrossilata biocompatibile è un polisaccaride, più preferibilmente è chitosano, ancora più preferibilmente il chitosano è funzionalizzato con -CH2COOH. Preferably, the biocompatible hydroxylated polyamide is a polysaccharide, more preferably it is chitosan, even more preferably the chitosan is functionalized with -CH2COOH.
Preferibilmente, dette nanoparticelle metalliche paramagnetiche sono ossido di ferro superparamagnetico. Preferably, said paramagnetic metal nanoparticles are superparamagnetic iron oxide.
Preferibilmente, detto isotopo radioattivo è il tecnezio99m (Tc99m). Preferably, said radioactive isotope is technetium 99m (Tc99m).
Preferibilmente, dette microbolle sono realizzate con alcol polivinilico. Preferably, said micro bubbles are made with polyvinyl alcohol.
Preferibilmente, la poliammina idrossilata biocompatibile viene fatta reagire con le microbolle mediante una reazione di amminazione riduttiva. Preferably, the biocompatible hydroxylated polyamine is reacted with the microbubbles by means of a reductive amination reaction.
Preferibilmente, la poliammina idrossilata biocompatibile viene fatta reagire con le microbolle mediante una reazione di acetalizzazione. Preferably, the biocompatible hydroxylated polyamine is reacted with the microbubbles by means of an acetalization reaction.
Preferibilmente, la reazione tra le microbolle e la poliammina idrossilata biocompatibile avviene in presenza di un eccesso in peso di quest'ultima. Preferably, the reaction between the microbubbles and the biocompatible hydroxylated polyamine takes place in the presence of an excess by weight of the latter.
Un ulteriore oggetto della presente invenzione sono delle microbolle realizzate secondo il metodo oggetto della presente invenzione. A further object of the present invention are micro bubbles made according to the method object of the present invention.
Per una migliore comprensione dell'invenzione sono riportate di seguito delle forme di realizzazione a puro titolo illustrativo e non limitativo. For a better understanding of the invention, some embodiments are reported hereinafter purely for illustrative and non-limiting purposes.
ESEMPI EXAMPLES
Esempio 1 Example 1
Del carbossimetilchitosano legato mediante legame amminico con nanoparticelle di ossido di ferro superparamagnetico, realizzate secondo quanto descritto in Zhilong Shi et al. Applied Material and Interfaces 2009, 1:328-335, è stato sottoposto a sonicazione per 30 minuti. Carboxymethylchitosan bound by amine bond with superparamagnetic iron oxide nanoparticles, made as described in Zhilong Shi et al. Applied Material and Interfaces 2009, 1: 328-335, was sonicated for 30 minutes.
Successivamente è stata aggiunta una sospensione di microbolle realizzate in alcol polivinilico tale da realizzare un rapporto in peso delle microbolle con carbossimetilchitosano legato alle nanoparticelle di ossido di ferro pari a 1:2. Subsequently, a suspension of microbubbles made of polyvinyl alcohol was added such as to achieve a weight ratio of the microbubbles with carboxymethylchitosan bound to the iron oxide nanoparticles equal to 1: 2.
Le microbolle sono state realizzate secondo gli insegnamenti della domanda di brevetto B02008A000224 qui incorporato per riferimento. The micro bubbles were made according to the teachings of the patent application B02008A000224 incorporated herein by reference.
Alla miscela formatasi è stato aggiunto NaBH3CN e il pH è stato aggiustato ad un valore pari circa a 5. NaBH3CN was added to the mixture formed and the pH was adjusted to a value of approximately 5.
La sospensione è stata mantenuta sotto agitazione per 5 giorni e successivamente le microbolle sono state lavate. The suspension was kept under stirring for 5 days and then the microbubbles were washed.
Esempio 2 Example 2
Del carbossimetilchitosano legato mediante legame amminico con nanoparticelle di ossido di ferro superparamagnetico come riportato nell'esempio 1, è stato sottoposto a sonicazione per 30 minuti. Carboxymethylchitosan bound by amine bond with superparamagnetic iron oxide nanoparticles as reported in Example 1, was subjected to sonication for 30 minutes.
A questo punto, il carbossimetilchitosano è stato fatto reagire con una quantità di NaICU pari alla metà del carbossimetilchitosano stesso. La reazione è durata un giorno. At this point, the carboxymethylchitosan was reacted with an amount of NaICU equal to half of the carboxymethylchitosan itself. The reaction lasted one day.
Successivamente, è stata aggiunta una sospensione di microbolle già descritte nell'esempio 1 tale da realizzare un rapporto in peso delle microbolle con carbossimetilchitosano legato alle nanoparticelle di ossido di ferro pari a 1:2, mentre il pH è stato aggiustato ad un valore pari circa a 3. Subsequently, a suspension of microbubbles already described in Example 1 was added such as to obtain a weight ratio of the microbubbles with carboxymethylchitosan bound to the iron oxide nanoparticles equal to 1: 2, while the pH was adjusted to a value of approximately to 3.
La sospensione è stata mantenuta sotto agitazione per 5 giorni e successivamente le microbolle sono state lavate. The suspension was kept under stirring for 5 days and then the microbubbles were washed.
Negli esempi 1 e 2 sono state ottenute delle microbolle ricoperte da uno strato di carbossimetilchitosano legato a nanoparticelle di ossido di ferro superparamegnatico. In Examples 1 and 2, microbubbles covered with a layer of carboxymethylchitosan bonded to superparamegnatic iron oxide nanoparticles were obtained.
Esempio 3 Example 3
Gli esempi 1 e 2 sono stati ripetuti con la differenza che il carbossimetilchitosano utilizzato non era legato a nanoparticelle di ossido di ferro superparamegnatico, ma comprendeva in forma complessata isotopi radioattivi quali il tecnezio. Examples 1 and 2 were repeated with the difference that the carboxymethylchitosan used was not bound to superparamegnatic iron oxide nanoparticles, but included radioactive isotopes such as technetium in complexed form.
Il TC99m nella forma di pertecnetato viene aggiunto alla sospensione contenente microbolle la cui superficie è ricoperta da carbossimetilchitosano o chitosano. TC99m in the form of pertechnetate is added to the suspension containing microbubbles whose surface is covered with carboxymethylchitosan or chitosan.
In questo modo, si è riusciti ad ottenere delle microbolle ricoperte di uno strato di carbossimetilchitosano o chitosano che comprendeva in forma complessata isotopi radioattivi quali il tecnezio. In this way, it was possible to obtain micro-bubbles covered with a layer of carboxymethylchitosan or chitosan which included in complexed form radioactive isotopes such as technetium.
Esempio 4 Example 4
Gli esempi 1 e 2 sono stati ripetuti con la differenza che il carbossimetilchitosano utilizzato non era soltanto legato a nanoparticelle di ossido di ferro superparamegnatico, ma comprendeva anche in forma complessata isotopi radioattivi quali il tecnezio. Examples 1 and 2 were repeated with the difference that the carboxymethylchitosan used was not only bound to superparamegnatic iron oxide nanoparticles, but also included radioactive isotopes such as technetium in complexed form.
In questo modo si è riusciti ad ottenere delle microbolle ricoperte da uno strato di carbossimetilchitosano il quale non solo era legato a nanoparticelle di ossido di ferro superparamegnatico ma comprendeva anche isotopi radioattivi, quali il tecnezio, in forma complessata. In this way it was possible to obtain micro bubbles covered with a layer of carboxymethylchitosan which was not only bound to superparamegnatic iron oxide nanoparticles but also included radioactive isotopes, such as technetium, in a complexed form.
Tali microbolle possono essere utilizzate per una analisi diagnostica che preveda il contemporaneo utilizzo delle tecniche di risonanza magnetica, ecografia ad ultrasuoni, radiodiagnostica quale ad esempio la scintigrafia e la tomografia computerizzata di emissione di fotone singolo (SPECT). These microbubbles can be used for a diagnostic analysis that involves the simultaneous use of magnetic resonance techniques, ultrasound ultrasound, radiodiagnostics such as scintigraphy and single photon emission computed tomography (SPECT).
La presente invenzione comprende, quindi, un metodo per la realizzazione di microbolle particolarmente versatili atte ad essere utilizzate per differenti tecniche diagnostiche, aumentando in questo modo l'efficienza della diagnosi nel suo complesso. The present invention therefore comprises a method for producing particularly versatile microbubbles suitable for use for different diagnostic techniques, thus increasing the efficiency of the diagnosis as a whole.
Inoltre, il metodo oggetto della presente invenzione risulta estremamente semplice ed in grado di realizzare microbolle funzionalizzate particolarmente stabili. Furthermore, the method object of the present invention is extremely simple and capable of producing particularly stable functionalized microbubbles.
Come può sembrare ovvio ad un tecnico del ramo, le microbolle oggetto della presente invenzione possono essere utilizzate non solo per finalità diagnostiche ma anche per finalità terapeutiche, si pensi ad esempio alle potenzialità che questo tipo di microbolle possono avere nella preparazione di radiofarmaci. As may seem obvious to a person skilled in the art, the microbubbles object of the present invention can be used not only for diagnostic purposes but also for therapeutic purposes, think for example of the potential that this type of microbubbles can have in the preparation of radiopharmaceuticals.
Claims (17)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT000022A ITRM20110022A1 (en) | 2011-01-21 | 2011-01-21 | METHOD FOR THE PREPARATION OF MICROBULTS INCLUDING A CONTRAST AGENT |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| IT000022A ITRM20110022A1 (en) | 2011-01-21 | 2011-01-21 | METHOD FOR THE PREPARATION OF MICROBULTS INCLUDING A CONTRAST AGENT |
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| ITRM20110022A1 true ITRM20110022A1 (en) | 2012-07-22 |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0467031A2 (en) * | 1990-07-10 | 1992-01-22 | Cavitation-Control Technology, Inc. | Medical-grade lipid-coated microbubbles, paramagnetic labelling thereof and their therapeutic use |
| WO1996028090A1 (en) * | 1995-03-09 | 1996-09-19 | Imarx Pharmaceutical Corp. | A method of magnetic resonance focused surgical and therapeutic ultrasound |
| WO1998017324A2 (en) * | 1996-10-21 | 1998-04-30 | Marsden, John, Christopher | Improvements in or relating to contrast agents |
| US20030216638A1 (en) * | 2002-05-16 | 2003-11-20 | Rohan Dharmakumar | Microbubble construct for sensitivity enhanced MR manometry |
| WO2010121153A2 (en) * | 2009-04-16 | 2010-10-21 | Arnsdorf Morton F | Biocompatible microbubbles to deliver radioactive compounds to tumors, atherosclerotic plaques, joints and other targeted sites |
| CN101912622A (en) * | 2010-08-11 | 2010-12-15 | 东南大学 | Targeted micro-bubble probe for magnetic resonance imaging and blood pressure monitoring and preparation method thereof |
-
2011
- 2011-01-21 IT IT000022A patent/ITRM20110022A1/en unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP0467031A2 (en) * | 1990-07-10 | 1992-01-22 | Cavitation-Control Technology, Inc. | Medical-grade lipid-coated microbubbles, paramagnetic labelling thereof and their therapeutic use |
| WO1996028090A1 (en) * | 1995-03-09 | 1996-09-19 | Imarx Pharmaceutical Corp. | A method of magnetic resonance focused surgical and therapeutic ultrasound |
| WO1998017324A2 (en) * | 1996-10-21 | 1998-04-30 | Marsden, John, Christopher | Improvements in or relating to contrast agents |
| US20030216638A1 (en) * | 2002-05-16 | 2003-11-20 | Rohan Dharmakumar | Microbubble construct for sensitivity enhanced MR manometry |
| WO2010121153A2 (en) * | 2009-04-16 | 2010-10-21 | Arnsdorf Morton F | Biocompatible microbubbles to deliver radioactive compounds to tumors, atherosclerotic plaques, joints and other targeted sites |
| CN101912622A (en) * | 2010-08-11 | 2010-12-15 | 东南大学 | Targeted micro-bubble probe for magnetic resonance imaging and blood pressure monitoring and preparation method thereof |
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| Title |
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| APRIL M. CHOW ET AL: "Enhancement of gas-filled microbubble R 2 * by iron oxide nanoparticles for MRI", MAGNETIC RESONANCE IN MEDICINE, 1 January 2009 (2009-01-01), pages 224 - 229, XP055001455, ISSN: 0740-3194, DOI: 10.1002/mrm.22184 * |
| CAVALIERI ET AL: "TETHERING FUNCTIONAL LIGANDS ONTO SHELL OF ULTRASOUND ACTIVE POLYMERIC MICROBUBBLES", BIOMACROMOLECULES, vol. 7, 19 January 2006 (2006-01-19), pages 607 - 611, XP002461357, ISSN: 1525-7797, DOI: 10.1021/BM050723G * |
| DATABASE CA [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 2010, YANG, FANG ET AL: "Method for preparing targeting microbubble probe for magnetic resonance imaging and blood pressure monitoring", XP002647417, retrieved from STN Database accession no. 154:73259 * |
| FANG YANG ET AL: "Superparamagnetic nanoparticle-inclusion microbubbles for ultrasound contrast agents; Superparamagnetic nanoparticle microbubbles for ultrasound", PHYSICS IN MEDICINE AND BIOLOGY, vol. 53, no. 21, 7 November 2008 (2008-11-07), pages 6129 - 6141, XP020141492, ISSN: 0031-9155, DOI: DOI:10.1088/0031-9155/53/21/016 * |
| SEO M ET AL: "Novel Generation of Nanoparticle-Incorporated Microbubbles as Multimodal Contrast Agent", PROCEEDINGS OF THE 2009 MOLECULAR IMAGING CONGRESS, J137, 3 November 2009 (2009-11-03), pages S70 - S71, XP007918971 * |
| YANG F ET AL: "Superparamagnetic iron oxide nanoparticle-embedded encapsulated microbubbles as dual contrast agents of magnetic resonance and ultrasound imaging", BIOMATERIALS, vol. 30, no. 23-24, 1 August 2009 (2009-08-01), pages 3882 - 3890, XP026149154, ISSN: 0142-9612, [retrieved on 20090422], DOI: DOI:10.1016/J.BIOMATERIALS.2009.03.051 * |
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