CN103110963A - Dual-mode synergistically-enhanced magnetic-resonance contrast agent and method for synthesizing same - Google Patents
Dual-mode synergistically-enhanced magnetic-resonance contrast agent and method for synthesizing same Download PDFInfo
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- CN103110963A CN103110963A CN2013100576952A CN201310057695A CN103110963A CN 103110963 A CN103110963 A CN 103110963A CN 2013100576952 A CN2013100576952 A CN 2013100576952A CN 201310057695 A CN201310057695 A CN 201310057695A CN 103110963 A CN103110963 A CN 103110963A
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- gadolinium
- magnetic resonance
- resonance contrast
- oleic acid
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Abstract
The invention relates to a contrast agent and particularly relates to a dual-mode synergistically-enhanced magnetic-resonance contrast agent and a method for synthesizing the same. The dual-mode synergistically-enhanced magnetic-resonance contrast agent is synthesized in one pot by taking the compound of a contrasting material T1 and a contrasting material T2 as a reaction precursor. The method comprises the following steps of: dissolving gadolinium oleate or gadolinium acetylacetone and ferric oleate or ferric acetylacetonate into octadecene or benzyl ether, adding oleic acid, heating an obtained solution, carrying out reflux reaction to obtain a reaction solution, cooling to room temperature, adding a first solvent to precipitate a product of reaction, centrifuging, removing a supernate, and dissolving a precipitate into a second solvent. The method is simple in steps, is convenient to operate, ensures high yield and is suitable for large-scale preparation. The idea of doping and synthesizing ensures that the field directions of the contrasting material T1 and the contrasting material T2 are parallel and same in the external magnetic field. The dual-mode contrast agent synthesized from the contrasting material T1 and the contrasting material T2 has the capacity of making two imaging modes complementary to each other and can obtain two imaging results nearly at the same time in the same place under the same resolution.
Description
Technical field
The present invention relates to a kind of contrast agent, particularly relate to a kind of double mode collaborative enhancing magnetic resonance contrast agent and synthetic method thereof.
Background technology
The development that develops into each field of scientific studies such as chemistry, physics, biology, medical science and the energy of nanotechnology has brought huge change.Such as, the paramagnetic of magnetic Nano material or ferromagnetic property can be used as the contrast agent of good nuclear magnetic resonance, can effectively improve and utilize clinically mr imaging technique to the accuracy of medical diagnosis on disease.The magnetic resonance radiography material Feridex that has gone on the market is a kind of ferroferric oxide nano granules of glucosan parcel, and it can (be designated hereinafter simply as T as good transverse relaxation imaging
2Imaging) contrast agent improves the bright contrast between pathological tissues and normal structure, thereby improves the reliability of clinical diagnosis.In addition, has paramagnetic material (as: Gd
3+, Mn
2+, Cu
2+Deng) also can be used as good longitudinal relaxation imaging and (be designated hereinafter simply as T
1Imaging) radiography material.
At present, for single imaging (T
1Or T
2Weighted imaging) contrast agent used can show good magnetic resonance radiography effect separately.Yet socioeconomic development and progress makes people have higher requirement to accuracy, accuracy and the reliability of medical diagnosis on disease.Therefore, development is a kind of can realize T on a nuclear magnetic resonance instrument
1-T
2It is extremely urgent that the radiography material of Double-mode imaging is used for medical diagnosis on disease.Existing mentality of designing is with T
2Radiography material is core, T
1Radiography material is that shell forms nucleocapsid structure establishment T
1-T
2The Double-mode imaging contrast agent.Yet, T in this method
1The radiography material direction of magnetization just in time is in T
2The opposite direction of radiography material magnetization vector line, both weaken mutually, and therefore, the Double-mode imaging effect is undesirable ([1] J.S.Choi, J.H.Lee, T.H.Shin, H.T.Song, E.Y.Kim, J.Cheon, J.Am.Chem.Soc.2010,132,11015 also; [2] H.Yang, Y.M.Zhuang, Y.Sun, A.T.Dai, X.Y.Shi, D.M.Wu, F.Y.Li, H.Hu, S.P.Yang, Biomaterials2011,32,4584.).
Summary of the invention
The object of the present invention is to provide a kind of double mode collaborative enhancing magnetic resonance contrast agent and synthetic method thereof.
Described double mode collaborative enhancing magnetic resonance contrast agent is (to be designated hereinafter simply as T by the longitudinal relaxation imaging
1) and the transverse relaxation imaging (be designated hereinafter simply as T
2) compound of radiography material is synthetic as reaction precursor one kettle way, particle diameter is 2～50nm, T in product
1Radiography material and T
2Element ratio between radiography material is 1: (1～20).
The compound of described radiography material can be selected from oleate or acetylacetonate etc.
Described T
1Radiography material can adopt paramagnet, and described paramagnet can be selected from Gd, Mn, Cu, Eu, Sm or its compound; Described T
2Radiography material can adopt superparamagnetism or ferromagnetic material, and described superparamagnetism or ferromagnetic material can be selected from Fe, Co, Ni or its compound.
The synthetic method of described double mode collaborative enhancing magnetic resonance contrast agent comprises the following steps:
1) in atmosphere of inert gases, oleic acid gadolinium or acetylacetone,2,4-pentanedione gadolinium and iron oleate or ferric acetyl acetonade are dissolved in octadecylene or Bian ether simultaneously, add oleic acid, the reaction of gained vlil gets reactant liquor;
2) reactant liquor with the step 1) gained is cooled to room temperature, and adds the 1st solvent to make the product precipitation, then carries out centrifugal treating, and abandoning supernatant also will precipitate and again be dissolved in the 2nd solvent.
In step 1), the mass ratio of described oleic acid gadolinium or acetylacetone,2,4-pentanedione gadolinium and iron oleate or ferric acetyl acetonade can be (0.1～500): (10～1000), the proportioning of the addition of described oleic acid and oleic acid gadolinium or acetylacetone,2,4-pentanedione gadolinium can be (0.01～10) mL: (0.1～500) mg, wherein oleic acid is calculated by volume, and oleic acid gadolinium or acetylacetone,2,4-pentanedione gadolinium are calculated in mass.
In step 2) in, described the 1st solvent can be selected from a kind of in ethanol, isopropyl alcohol, acetone etc., and described the 2nd solvent can be selected from a kind of in normal hexane, chloroform, toluene etc.
The characteristics of combining nano technology of the present invention and the principle of nuclear magnetic resonance have proposed a kind of mentality of designing of novelty and have synthesized to have T
1-T
2The nano-particle of double-mode magnetic resonance radiography performance.Basic ideas combine paramagnetic material and superparamagnetic or ferrimagnet for by regulation and control chemosynthesis means, form a nanometer entity by blend.Under extraneous magnetic field condition, two kinds of radiography material magnetization vectors in this nano-particle in the same way, and T
1Radiography material magnetization vector and T
2The local magnetic direction of radiography material is also consistent, thereby at T
1And T
2Play the collaborative double-mode magnetic resonance radiography effect that strengthens in two kinds of imaging patterns.
With traditional employing with T
2Radiography material is as carrier, and then carries out finishing and connect T
1The method for designing of radiography material is compared, and the present invention proposes embedded synthetic mentality of designing, and one kettle way namely obtains nano material of the present invention, and the later stage only need be carried out simple surface-functionalized can directly the application, and therefore, the present invention has following outstanding advantages:
(1) step is simple and easy, and is easy to operate, and output is higher, is easy to the amplificationization preparation;
(2) the synthetic thinking of doping has guaranteed T
1And T
2Two kinds of radiography materials are under extraneous magnetic field condition, and magnetic direction is in the same way parallel, and that has avoided that above-mentioned traditional method causes weakens mutually, shows the collaborative effect that strengthens;
(3) T
1-T
2The Double-mode imaging contrast agent itself has the ability that two kinds of imaging patterns are proved mutually, obtain two kinds of imaging results under can be almost simultaneously, with ground, with the resolution condition, thereby may provide higher accuracy, accuracy and reliability for nuclear magnetic resonance clinical research and even the clinical diagnosis of disease.
Description of drawings
Fig. 1 is T of the present invention
1-T
2The design principle schematic diagram of double-mode magnetic resonance contrast agent.
Fig. 2 is the low resolution of ferric oxide nanometer particle of Gadolinia. doping of diameter 14nm of embodiment 1 preparation and the transmission electron microscope picture of high-resolution (top right plot).Scale is 20nm.
Fig. 3 is the low resolution of ferric oxide nanometer particle of Gadolinia. doping of diameter 3nm of embodiment 2 preparation and the transmission electron microscope picture of high-resolution (top right plot).Scale is 10nm.
Fig. 4 is the angle of elevation details in a play not acted out on stage, but told through dialogues scanning transmission electron microscope face scanned picture as an example of the ferric oxide nanometer particle of the Gadolinia. of diameter 14nm doping example.In Fig. 4, A is the ferrum element face scanogram of many nano-particle, and B is the first vegetarian noodles scanogram of the gadolinium of many nano-particle, and C is the merging superimposed images of two kinds of elements.
Fig. 5 is the angle of elevation details in a play not acted out on stage, but told through dialogues scanning transmission electron microscope line sweep picture as an example of the ferric oxide nanometer particle of the Gadolinia. of diameter 14nm doping example.In Fig. 5, be the wherein ferrum element of a nano-particle and the line sweep image of gadolinium element; Abscissa is diameter Distance (nm), and vertical coordinate is intensity I ntensity; Curve a is Fe (K), and curve b is Gd (L).
Fig. 6 is the magnetic hysteresis regression curve picture of ferric oxide nanometer particle of the Gadolinia. doping of diameter 14nm, comprises two temperature conditions of 300K and 5K.In Fig. 6, abscissa is H (kOe), and vertical coordinate is M (emu/g); Curve a is 5K, and curve b is 300K.
Fig. 7 is the magnetic hysteresis regression curve picture of ferric oxide nanometer particle of the Gadolinia. doping of diameter 3nm, comprises two temperature conditions of 300K and 5K.In Fig. 7, abscissa is H (kOe), and vertical coordinate is M (emu/g); Curve a is 5K, and curve b is 300K.
Fig. 8 is the T of ferric oxide nanometer particle of the Gadolinia. doping of diameter 14nm
1-T
2Double-mode magnetic resonance imaging picture.T
1Under imaging pattern from low concentration to the high concentration image by secretly brightening; T
2Just opposite under imaging pattern.
Fig. 9 is the T of ferric oxide nanometer particle of the Gadolinia. doping of diameter 3nm
1Pattern nuclear magnetic resonance picture.
The specific embodiment
Below by embodiment, the present invention is specifically described; the present embodiment is only for the present invention is further illustrated; can not be interpreted as limiting the scope of the invention; some nonessential improvement and adjustment that those skilled in the art makes according to design principle and the preparation method of foregoing invention all belong to protection domain of the present invention.
Fig. 1 provides T of the present invention
1-T
2The design principle schematic diagram of double-mode magnetic resonance contrast agent.Than traditional T
1And T
2The combination of radiography material, i.e. T
1Radiography material is connected to T
2Therefore the radiography material surface will be in T under extraneous magnetic field condition
2The opposite direction of radiography material magnetic field line weakens mutually.The T that the present invention proposes
1-T
2The mentality of designing of double-mode magnetic resonance contrast agent is with T
1Radiography material is embedded in T
2The radiography material the inside forms the nanometer entity; Therefore both magnetic directions are in cocurrent and parallel under extraneous magnetic field condition, the collaborative enhancing.
Embodiment 1: diameter is the Gadolinia. doped ferric oxide nano-particle (Gd: Fe=1: preparation 10) of 14nm
In the 50mL there-necked flask, add 0.9g iron oleate and 0.1g oleic acid gadolinium (Gd: Fe=1: 10), and with the dissolving of 15mL octadecylene, add simultaneously 0.2mL oleic acid.Air displacement in reaction bulb is become nitrogen, repeat 3 times.Then be heated to reflux temperature and keep 1 hour afterreaction to stop, reactant liquor naturally cools to room temperature.The isopropyl alcohol that adds 40mL in reactant liquor, the centrifugal 10min abandoning supernatant of 6000rpm.The gained precipitation is dissolved in the 10mL normal hexane again, namely gets the gadolinium doped ferric oxide nano-particle that diameter is about 14nm.Fig. 2 provides the low resolution of ferric oxide nanometer particle of Gadolinia. doping of diameter 14nm of embodiment 1 preparation and the transmission electron microscope picture of high-resolution (top right plot).
Embodiment 2: diameter is the Gadolinia. doped ferric oxide nano-particle (Gd: Fe=1: preparation 20) of 3nm
In the 50mL there-necked flask, add 0.176g ferric acetyl acetonade and 0.16g oleic acid gadolinium (Gd: Fe=1: 20), be dissolved in 15mL Bian ether, add simultaneously 0.6mL oleic acid, 1 of 0.6mL oleyl amine and 0.39g, 2-cetyl glycol.Air displacement in reaction bulb is become nitrogen, repeat 3 times.Then be heated to reflux temperature and keep 0.5 hour afterreaction to stop, reactant liquor naturally cools to room temperature.The ethanol that adds 40mL in reactant liquor, the centrifugal 10min abandoning supernatant of 6000rpm.The gained precipitation is dissolved in the 10mL normal hexane again, namely gets the gadolinium doped ferric oxide nano-particle that diameter is about 3nm.
Fig. 3 provides the low resolution of ferric oxide nanometer particle of Gadolinia. doping of diameter 3nm of embodiment 2 preparation and the transmission electron microscope picture of high-resolution (top right plot).
Fig. 4 provides the angle of elevation details in a play not acted out on stage, but told through dialogues scanning transmission electron microscope face scanned picture as an example of the ferric oxide nanometer particle of the Gadolinia. of diameter 14nm doping example.In Fig. 4, A is the ferrum element face scanogram of many nano-particle, and B is the first vegetarian noodles scanogram of the gadolinium of many nano-particle, and C is the merging superimposed images of two kinds of elements.
Fig. 5 provides the angle of elevation details in a play not acted out on stage, but told through dialogues scanning transmission electron microscope line sweep picture as an example of the ferric oxide nanometer particle of the Gadolinia. of diameter 14nm doping example.In Fig. 5, be the wherein ferrum element of a nano-particle and the line sweep image of gadolinium element.
Result by Figure 4 and 5 shows, the gadolinium Uniform Doped is in ferric oxide nanometer particle.
Fig. 6 provides the magnetic hysteresis regression curve picture of ferric oxide nanometer particle of the Gadolinia. doping of diameter 14nm, comprises two temperature conditions of 300K and 5K.Curve shows as shown in Figure 6, and nano-particle magnetic is between superparamagnetic and paramagnetism.
Fig. 7 provides the magnetic hysteresis regression curve picture of ferric oxide nanometer particle of the Gadolinia. doping of diameter 3nm, comprises two temperature conditions of 300K and 5K.Curve shows as shown in Figure 7, and due to the spin of small-size magnetic nano-particle-oblique effect, this nano-particle shows obvious paramagnetism.
Fig. 8 provides the T of ferric oxide nanometer particle of the Gadolinia. doping of diameter 14nm
1-T
2Double-mode magnetic resonance imaging picture.T
1Under imaging pattern from low concentration to the high concentration image by secretly brightening; T
2Just opposite under imaging pattern.Result shows, this nano-particle has obvious T
1-T
2Double-mode imaging radiography effect.
Fig. 9 provides the T of ferric oxide nanometer particle of the Gadolinia. doping of diameter 3nm
1Pattern nuclear magnetic resonance picture.Result obviously goes out obvious T
1Imaging radiography effect.
Claims (8)
1. double mode collaborative enhancing magnetic resonance contrast agent, it is characterized in that by the compound of longitudinal relaxation imaging and transverse relaxation imaging radiography material synthetic as reaction precursor one kettle way, particle diameter is 2～50nm, and the element ratio in product between longitudinal relaxation imaging and transverse relaxation imaging radiography material is 1: 1～20.
2. a kind of double mode collaborative enhancing magnetic resonance contrast agent as claimed in claim 1, is characterized in that the compound of described radiography material is selected from oleate or acetylacetonate.
3. a kind of double mode collaborative enhancing magnetic resonance contrast agent as claimed in claim 1, is characterized in that described longitudinal relaxation imaging radiography material adopts paramagnet; Described transverse relaxation imaging radiography material adopts superparamagnetism or ferromagnetic material.
4. a kind of double mode collaborative enhancing magnetic resonance contrast agent as claimed in claim 3, is characterized in that described paramagnet is selected from Gd, Mn, Cu, Eu, Sm or its compound; Described superparamagnetism or ferromagnetic material are selected from Fe, Co, Ni or its compound.
5. a kind of synthetic method of double mode collaborative enhancing magnetic resonance contrast agent as claimed in claim 1 is characterized in that comprising the following steps:
1) in atmosphere of inert gases, oleic acid gadolinium or acetylacetone,2,4-pentanedione gadolinium and iron oleate or ferric acetyl acetonade are dissolved in octadecylene or Bian ether simultaneously, add oleic acid, the reaction of gained vlil gets reactant liquor;
2) reactant liquor with the step 1) gained is cooled to room temperature, and adds the 1st solvent to make the product precipitation, then carries out centrifugal treating, and abandoning supernatant also will precipitate and again be dissolved in the 2nd solvent.
6. a kind of synthetic method of double mode collaborative enhancing magnetic resonance contrast agent as claimed in claim 5, it is characterized in that in step 1), the mass ratio of described oleic acid gadolinium or acetylacetone,2,4-pentanedione gadolinium and iron oleate or ferric acetyl acetonade is (0.1～500): (10～1000), the proportioning of the addition of described oleic acid and oleic acid gadolinium or acetylacetone,2,4-pentanedione gadolinium is (0.01～10) mL: (0.1～500) mg, wherein oleic acid is calculated by volume, and oleic acid gadolinium or acetylacetone,2,4-pentanedione gadolinium are calculated in mass.
7. a kind of synthetic method of double mode collaborative enhancing magnetic resonance contrast agent as claimed in claim 5, is characterized in that in step 2) in, described the 1st solvent is selected from a kind of in ethanol, isopropyl alcohol, acetone.
8. a kind of synthetic method of double mode collaborative enhancing magnetic resonance contrast agent as claimed in claim 5, is characterized in that in step 2) in, described the 2nd solvent is selected from a kind of in normal hexane, chloroform, toluene.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103405792A (en) * | 2013-08-14 | 2013-11-27 | 东华大学 | Preparation of PEI-coated bimodal contrast agent ferriferrous oxide-gadolinium hydroxide magnetic nanoparticle |
| CN104174037A (en) * | 2013-05-28 | 2014-12-03 | 中国科学院大连化学物理研究所 | Preparation method for blending type contrast agent with T1 and T2 contrast functions |
| CN108030933A (en) * | 2017-12-13 | 2018-05-15 | 北京工商大学 | A kind of high sensitivity bimodal magnetic resonance contrast agent and preparation method thereof |
| CN108245689A (en) * | 2016-12-29 | 2018-07-06 | 国家纳米科学中心 | For improving the contrast agent of magnetic resonance detection accuracy, preparation method and application |
| CN109106955A (en) * | 2018-10-16 | 2019-01-01 | 福州大学 | A kind of magnetic resonance imaging contrast and preparation method thereof of acid environment response |
| CN111634951A (en) * | 2020-06-09 | 2020-09-08 | 太原理工大学 | Preparation method of iron oxide/gadolinium oxide composite nanoparticles with uniformly distributed elements |
-
2013
- 2013-02-22 CN CN2013100576952A patent/CN103110963A/en active Pending
Non-Patent Citations (1)
| Title |
|---|
| ZIJIAN ZHOU，ETAL，: "A Synergistically Enhanced T 1 – T 2 Dual-Modal Contrast Agent", 《ADVANCED MATERIALS》 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104174037A (en) * | 2013-05-28 | 2014-12-03 | 中国科学院大连化学物理研究所 | Preparation method for blending type contrast agent with T1 and T2 contrast functions |
| CN104174037B (en) * | 2013-05-28 | 2017-02-08 | 中国科学院大连化学物理研究所 | Preparation method for blending type contrast agent with T1 and T2 contrast functions |
| CN103405792A (en) * | 2013-08-14 | 2013-11-27 | 东华大学 | Preparation of PEI-coated bimodal contrast agent ferriferrous oxide-gadolinium hydroxide magnetic nanoparticle |
| CN108245689A (en) * | 2016-12-29 | 2018-07-06 | 国家纳米科学中心 | For improving the contrast agent of magnetic resonance detection accuracy, preparation method and application |
| CN108030933A (en) * | 2017-12-13 | 2018-05-15 | 北京工商大学 | A kind of high sensitivity bimodal magnetic resonance contrast agent and preparation method thereof |
| CN108030933B (en) * | 2017-12-13 | 2020-06-19 | 北京工商大学 | High-sensitivity bimodal magnetic resonance contrast agent and preparation method thereof |
| CN109106955A (en) * | 2018-10-16 | 2019-01-01 | 福州大学 | A kind of magnetic resonance imaging contrast and preparation method thereof of acid environment response |
| CN109106955B (en) * | 2018-10-16 | 2020-12-25 | 福州大学 | Magnetic resonance imaging contrast agent with acid environment response and preparation method thereof |
| CN111634951A (en) * | 2020-06-09 | 2020-09-08 | 太原理工大学 | Preparation method of iron oxide/gadolinium oxide composite nanoparticles with uniformly distributed elements |
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Application publication date: 20130522 |