CN104511030A - Dual-modal nano imaging drug Dex-Rho-99mTc based on glucan - Google Patents
Dual-modal nano imaging drug Dex-Rho-99mTc based on glucan Download PDFInfo
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Abstract
The invention belongs to the field of molecular imaging probes and particularly relates to a preparation method of a dual-modal nano imaging drug Dex-Rho-99mTc based on glucan, and an application of the drug in imaging diagnosis. The general formula of the drug is Rho-Dex-PEG-DTPA-99mTc, wherein the Dex represents for the glucan of which the molecular weight is 10-100k, the PEG represents for polyethylene glycol of which the molecular weight is 1-10k, the Rho represents for a fluorescent group rhodamine, the DTPA is a chelating agent of an imaging nuclide and the 99mTc is a radioisotope Technetium-99 used for SPECT imaging. In the invention, the surface of the high-molecular material glucan is modified by a certain number of amino groups and the PEG, the fluorescent group and the SPECT imaging groups are connected to the glucan supporter through the amino groups and finally the drug is marked by the radioisotope [99mTc]. The drug is good in biocompatibility, is simple in the preparation method, is safe and convenient to use and can be employed in dual-modal imaging. The dual-modal nano imaging drug has wide application prospects in the biomedical fields of early diagnosis of cancer, medicine delivery under guide of imaging, noninvasive iconography curative effect evaluation and the like.
Description
Technical field
The invention belongs to molecular image probe field, relate to imaging medicine, be specifically related to a kind of preparation method of bimodal nano imaging medicine based on glucosan carrier and the application in diagnostic imaging thereof.
Background technology
Tumor is one of major disease threatening human health.Present stage causes cancer high mortality major reason to be the hysteresis quality of diagnosing tumor.Tumor is promptly and accurately diagnosed and takes corresponding treatment measure to improving the survival rate of cancer patient and improving its quality of life and have important scientific research and clinical meaning.
Single photon emission computerized tomography (SPECT) be by detection enter the radiopharmaceutical of Ti Nei particular organization organ launch the technology of gamma-rays and imaging.This technology has the advantages such as highly sensitive, imaging is rapid, required nucleic easily obtains, labelling is simple, is widely used in clinical nuclear medicine imaging.Optical imagery has highly sensitive as emerging molecular image technology, without ionizing radiation, easy and simple to handle, the advantages such as operating cost is low.Multiple optical image technology has applied to medical diagnosis on disease and curative effect evaluation.Such as means of optical coherence tomography (optical coherence tomography, OCT) has applied to the diagnosis of skin carcinoma.The bimodal image technology that SPECT and optical imagery combine can overcome single imaging technique inherent defect, by merging between different images pattern, comparing, obtains more single imaging pattern more horn of plenty and lesion information accurately.
Nano imaging probe has a wide range of applications potentiality in fields such as biomedicine, electronics and is subject to the extensive concern of Many researchers.By controlling composition, the shape and size of nano-probe, different diagnostic requirements can be met.In cancer target Diagnosis and Treat, nanoscale effect is one of major reason realizing nano-probe/drug on tumor passive targeting.Compared with normal vascular tissues, the neovascular tissue of tumor often presents immature property, the feature such as high osmosis and large aperture.Research shows that the tumor neovasculature tube wall aperture upper limit can reach 400nm-2 μm, and Normal tissue vascular cinclides footpath is less than 8nm.Therefore diameter often optionally can enter tumor tissues through tumor neogenetic blood vessels in the nanoparticle of 10-100nm, thus the tumor passive targeting reaching nanoscale effect and cause.
At some brain diseases as in the cerebral tumor, apoplexy, parkinson, Alzheimer, lesions position blood brain barrier is damaged in various degree, can demonstrate the feature that permeability increases.Identify change and the degree thereof of lesions position blood-brain barrier permeability, to for judging the brain diseases order of severity and taking suitable treatment means significant.At present, clinical shortage can identify and portray the medicine that blood-brain barrier permeability changes position and degree.Development different-grain diameter nano imaging medicine, enters brain position by following the trail of imaging medicine and enters the assessment that brain volume can realize blood brain barrier integrity.
Polysaccharide compound glucosan (Dextran) has good water solubility, the advantages such as nontoxic and biodegradability, and ratified as bio-safety material " Generally recognized as safe, GRAS " for medicine by FDA, the fields such as food additive.Glucosan is chosen as probe carrier and also has controllable molecular weight (5-2000kDa), the advantages such as numerous active group for modification and reasonable price.The features such as compared with Normal tissue vascular, tumor neogenetic blood vessels has immature, irregular and high-permeability.Macromole probe based on glucosan carrier can utilize permeability difference between tumor and normal blood vessels to realize tumor passive targeting (enhancedpermeability and retention effect, EPR effect).
Summary of the invention
The object of the present invention is to provide a kind of new imaging medicine, particularly relate to a kind of bimodal diagnostic nano imaging medicine based on glucosan and its production and use.
Bimodal diagnostic nano imaging medicine Dex-Rho-based on glucosan of the present invention
99mthe general formula of Tc is:
Rho-Dex-PEG-DTPA-
99mT
c
The wherein glucosan of Dex to be molecular weight be 10kDa-100kDa; The Polyethylene Glycol of PEG to be molecular weight be 1kDa-10kDa; Rho is fluoroscopic image group rhodamine B, and DTPA is the chelating agen diethyl pentetic acid of image nucleic,
99mt
cfor the radiosiotope for SPECT imaging
99mtechnetium.
The concrete structure formula of imaging medicine of the present invention is:
More specifically, bimodal diagnostic nano imaging medicine of the present invention is made up of following four funtion parts:
(1) as the glucosan of carrier material, there is good water solubility, nontoxic, the advantage such as degradability and good biocompatibility.Image group is carried by the amino residue of finishing.
(2) hydrophilic polyglycol chain, can further improve the biocompatibility of nano imaging medicine, and can extend the blood circulation time of imaging medicine, reduces imaging medicine by reticuloendothelial system phagocytic in liver and spleen.
(3) red fluorescence group rhodamine B has good water solubility, nontoxic, quantum yield advantages of higher, both may be used for live body and in vitro optical imagery, also may be used for the observation of microscope to tissue slice probe
(4) SPECT imaging group DTPA-
99mt
c.Radionuclide technetium has desirable nuclear physics performance, and the half-life is 6.02h, and launching the gamma-rays of 140keV, is the nucleic that clinical nuclear medicine can not be substituted.DTPA can efficiently complexation as chelating agen
99mtc, thus the labeling effciency and the body internal stability that improve nucleic.
The invention provides the preparation method of described bimodal diagnostic nano imaging medicine, comprise the following steps:
(1) synthesis of nano imaging medicine carrier material Dex-NH
2
Nano imaging medicine carrier material Dex-NH
2synthesis.Be dissolved in the NaOH solution of 6M by polymer carrier Dextran, ice bath is cooled to 0 DEG C, adds chloracetic acid sodium.After 60 DEG C of stirring reaction 50min, reactant liquor is cooled to room temperature, dropwise adds in methanol and obtain white flock precipitate Dex-COOH.Dex-COOH is soluble in water, dropwise add the DMF solution of 2-ethyoxyl-1-ethoxy carbonic acyl radical-1,2-dihydroquinoline (EEDQ).This mixed liquor is added drop-wise in ethylenediamine, stirring at normal temperature 4 hours.Concentrated by rotary evaporation reactant liquor, to 3mL, obtains white fluffy solid Dex-NH in instillation methanol
2.By Dex-NH
2aqueous solution filter sizes is the super filter tube ultrafiltration purification 3 times of 10k, and removing reaction raw materials and by-product, concentrated solution lyophilization obtains White Flocculus and carrier material Dex-NH
2;
(2) labelling of PEG and fluorescence imaging radicals R ho
The labelling of PEG and fluorophor rhodamine (Rho).Carrier material Dex-NH
2be dissolved in 0.1M HEPES buffer solution, fully dissolve and regulate pH to 8.3.The PEG(PEG-NHS that slow instillation N-hydroxy-succinamide (NHS) activates), stirring at room temperature reacts 6 hours, and reactant liquor filter sizes is the super filter tube ultrafiltration purification 3 times of 10kDa.Concentrated solution lyophilization obtains white fluffy solid product D ex-PEG.Dex-PEG is dissolved in 0.1M HEPES buffer solution, the DMF solution of the Rho-NHS of instillation NHS activation.Room temperature reaction is after 6 hours, and be the super filter tube ultrafiltration purification 3 times of 10kDa with filter sizes, concentrated solution lyophilization obtains red fluffy solid product Rho-Dex-PEG;
(3) SPECT imaging group DTPA-
99mthe labelling of Tc
SPECT imaging group DTPA-
99mthe labelling of Tc.Rho-Dex-PEG is dissolved in 0.1M NaHCO
3(pH9.5) in solution, under stirring condition, DTPA gradation added, controlling pH value of solution is 9.5.After stirring at room temperature reacts 12 hours, be the super filter tube ultrafiltration purification 3 times of 10kDa with filter sizes.Concentrated solution lyophilization obtains red fluffy solid product Rho-Dex-PEG-DTPA.Rho-Dex-PEG-DTPA and stannous chloride 0.1M HCl dissolves, and adds sodium pertechnetate (Na
99mtcO
4) aqueous solution.60 DEG C of reaction 30min(mixing in every 5 minutes once).Reactant liquor filter sizes is the super filter tube ultrafiltration purification 3 times of 10kDa.Concentrated solution is target image medicine Dex-Rho-
99mthe solution of Tc.
Bimodal diagnostic nano imaging medicine prepared by the present invention, particle diameter is 10-20nm, can labelling 1-6 molecule PEG, the DTPA of 1-2 molecule Rho and 20-60 molecule on per molecule Dextran carrier.
Compared with existing diagnostic agent, the outstanding advantages of bimodal diagnostic nano imaging medicine provided by the invention is:
(1) Dex-Rho-for preparing of the present invention
99mtc, has the bimodal molecular image probe characteristic of SPECT/ optical imagery.By merging between different images pattern, comparing, more single imaging pattern more horn of plenty and lesion information accurately can be obtained.
(2) nano imaging medicine that prepared by the present invention overcomes the short shortcoming of micromolecule imaging medicine circulation time.And there is good biocompatibility.Synthetic method is simple, and mild condition, required raw material are easy to get, cheap.
(3) nano imaging medicine that prepared by the present invention utilizes permeability difference between tumor and Normal tissue vascular to realize tumor passive target, is lessly subject to tumor type, and the individual factors such as growth stage and receptor expression level limits, and has spike universality.
(4) method provided by the invention, by selecting different molecular content of starting materials, can prepare the nano imaging medicine of different-grain diameter, can be used for the evaluation of brain diseases blood brain barrier integrity.
(5) amino residue of the finishing of nano imaging medicine prepared of the present invention can further with bio-ligand coupling, make it to have and certain organize active targeting.
Bimodal diagnostic nano imaging medicine prepared by the inventive method, as the one of passive target imaging medicine, by intravenous injection, after alternative enters tumor tissues, also high concentration is gathered in this.By comparing between two kinds of image modes, obtain abundant and lesion information accurately.Promptly and accurately diagnose realizing tumor, the therapeutic effect and the prognosis that improve cancer patient have important clinical significance.
Accompanying drawing explanation
Fig. 1, bimodal nano imaging medicine Dex-Rho-
99mt
csynthetic route chart.
Detailed description of the invention
Below in conjunction with specific embodiment, the invention will be further described:
Embodiment 1:
(1) nano imaging medicine carrier material Dex-NH
2synthesis
Molecular weight is the Dextran(200mg of 20kDa) be dissolved in the NaOH solution of 7mL6M, ice bath is cooled to 0 DEG C, adds chloracetic acid sodium (503mg), after 60 DEG C of reaction 50min, dropwise adds in methanol and obtains white flock precipitate Dex-COOH.By Dex-COOH(200mg) be dissolved in (pH3.0) in 20ml water, dropwise add the DMF solution of 1ml2-ethyoxyl-1-ethoxy carbonic acyl radical-1,2-dihydroquinoline (EEDQ, 320mg).By in this solution instillation 0.414mL ethylenediamine, under room temperature, stir 4h.Reactant liquor concentrated by rotary evaporation, to 3mL, obtains white fluffy solid Dex-NH in instillation methanol
2. by Dex-NH
2. aqueous solution take molecular cut off as the super filter tube ultrafiltration purification 3 times of 3kDa, and concentrated solution lyophilization obtains white fluffy solid product and is imaging medicine carrier material Dex-NH
2;
(2) labelling of PEG and fluorescence imaging radicals R ho.Dex-NH
2(100mg) be dissolved in 2.0mL0.1M HEPES buffer solution, fully dissolve and regulate pH to be 8.3.Slow instillation 200 μ l PEG
2k-NHS(47.5mg) DMF solution, after stirring at room temperature reaction 6h, be the super filter tube ultrafiltration purification 3 times of 3kDa by reactant liquor molecular cut off.Concentrated solution lyophilization obtains white fluffy solid product D ex-PEG.By Dex-PEG(100mg) be dissolved in 2.0mL0.1M HEPES(pH8.3) in buffer solution, slowly instillation 200 μ l Rho-NHS(3.395mg) DMF solution.Room temperature reaction is after 6 hours, and be the super filter tube ultrafiltration purification 3 times of 10kDa with molecular cut off, concentrated solution lyophilization obtains red fluffy solid product Rho-Dex-PEG;
(3) SPECT imaging group DTPA-
99mthe labelling of Tc.Rho-Dex-PEG(100mg) 2ml0.1M NaHCO is dissolved in
3(pH9.5) in solution, by DTPA(40mg) gradation adds above-mentioned solution, and it is 9.5 that 1M NaOH controls pH value of solution.Stirring at room temperature reacts 12 hours, and reactant liquor molecular cut off is the super filter tube ultrafiltration purification 3 times of 10kDa.Concentrated solution lyophilization obtains red fluffy solid product Rho-Dex-PEG-DTPA.Rho-Dex-PEG-DTPA(10mg) and stannous chloride (1.5mg) dissolve 0.2ml0.1M HCl, add 0.5ml sodium pertechnetate (Na
99mt
co
4, 5mCi) aqueous solution.60 DEG C of every 5min mixings of reaction 30min(once).Reactant liquor molecular cut off is the super filter tube ultrafiltration purification 3 times of 10kDa, obtains target image medicine Dex-Rho-
99mtc(8.5mg, 3.15mCi).
Embodiment 2
(1) synthesis of nano imaging medicine carrier material Dex-NH
2
Molecular weight is the Dextran(200mg of 20kDa) be dissolved in the NaOH solution of 7mL6M, ice bath is cooled to 0 DEG C, adds chloracetic acid sodium (503mg), after 60 DEG C of reaction 50min, dropwise adds in methanol and obtains white flock precipitate Dex-COOH.By Dex-COOH(200mg) be dissolved in (pH3.0) in 20ml water, dropwise add the DMF solution of 1ml2-ethyoxyl-1-ethoxy carbonic acyl radical-1,2-dihydroquinoline (EEDQ, 320mg).By in this solution instillation 0.414mL ethylenediamine, under room temperature, stir 4h.Reactant liquor concentrated by rotary evaporation, to 3mL, obtains white fluffy solid Dex-NH in instillation methanol
2. by Dex-NH
2. aqueous solution take molecular cut off as the super filter tube ultrafiltration purification 3 times of 3kDa, and concentrated solution lyophilization obtains white fluffy solid product and is imaging medicine carrier material Dex-NH
2;
(2) labelling PEG and fluorescence imaging radicals R ho
Dex-NH
2(100mg) be dissolved in 2.0mL0.1M HEPES buffer solution, fully dissolve and regulate pH to be 8.3.Slow instillation 200 μ l PEG
2k-reactant liquor molecular cut off, after stirring at room temperature reaction 6h, is the super filter tube ultrafiltration purification 3 times of 3000 by DMF solution NHS(20.5mg).Concentrated solution lyophilization obtains white fluffy solid product D ex-PEG.By Dex-PEG(100mg) be dissolved in 2.0mL0.1M HEPES(pH8.3) in buffer solution, slowly instillation 200 μ l Rho-NHS(6.535mg) DMF solution.Room temperature reaction is after 6 hours, and be the super filter tube ultrafiltration purification 3 times of 10kDa with molecular cut off, concentrated solution lyophilization obtains red fluffy solid product Rho-Dex-PEG;
(3) labelling SPECT imaging group DTPA-99mTc
Rho-Dex-PEG(100mg) 2ml0.1M NaHCO is dissolved in
3(pH9.5) in solution, by DTPA(60mg) gradation adds above-mentioned solution, and it is 9.5 that 1M NaOH controls pH value of solution.Stirring at room temperature reacts 12 hours, and reactant liquor molecular cut off is the super filter tube ultrafiltration purification 3 times of 3000.Concentrated solution lyophilization obtains red fluffy solid product Rho-Dex-PEG-DTPA.Rho-Dex-PEG-DTPA(10mg) and stannous chloride (1.5mg) dissolve 0.2ml0.1M HCl, add 0.5ml sodium pertechnetate (Na-
99mtcO
4, 15mCi) aqueous solution.60 DEG C of every 5min mixings of reaction 30min(once).Reactant liquor molecular cut off is the super filter tube ultrafiltration purification 3 times of 10kDa, obtains target image medicine Dex-Rho-
99mtc(8.0mg, 9.4mCi).
Embodiment 3
With the test method of embodiment 1, the molecular weight of immobilization carrier material Dextran is decided to be 50kDa, changes PEG molecular weight, the obtained imaging medicine Rho-Dex connecting 1kDa, 2kDa, 3.5kDa, 5kDa, 10kDa molecular weight PEG
50k-PEG-DTPA-
99mtc.
Embodiment 4
With the test method of example 1, the molecular weight of fixing PEG is 2kDa, changes the molecular weight of carrier material Dextran, and employing molecular weight is the Dextran resultant image medicine Rho-Dex-PEG of 10kDa, 20kDa, 50kDa, 70kDa, 100kDa respectively
2k-DTPA-
99mtc, nano imaging medicine particle diameter obviously can increase with the increase of carrier molecule amount.
Above-described embodiment is only preference of the present invention, is not used for limiting the present invention, and all within principle of the present invention, any amendment made, change, accommodation or alternative, all within protection scope of the present invention.
Claims (8)
1. the bimodal nano imaging medicine-Dex-Rho-based on glucosan
99mtc, its general formula is as follows:
Rho-Dex-PEG-DTPA-
99mTc
In general formula, Dex represents carrier material glucosan (Dextran); PEG represents Polyethylene Glycol; Rho represents fluoroscopic image group rhodamine B, and DTPA represents radioactivity image radionuclide chelator diethyl pentetic acid,
99mtc represents the radiosiotope for SPECT imaging
99mtechnetium.
2. by the bimodal nano imaging medicine-Dex-Rho-based on glucosan according to claim 1
99mtc, is characterized in that, the structural formula of described imaging medicine is:
3. as claimed in claim 1 based on the bimodal nano imaging medicine-Dex-Rho-of glucosan
99mtc, is characterized in that, described carrier material Dextran molecular weight is 10k-100k, and PEG molecular weight used is 1k-10k.
4. as claimed in claim 1 based on the bimodal nano imaging medicine-Dex-Rho-of glucosan
99mtc, is characterized in that, described carrier material Dextran molecular weight is 20k, and PEG molecular weight used is 2k.
5. the bimodal nano imaging medicine-Dex-Rho-based on glucosan of claim 1
99mthe preparation method of Tc, is characterized in that, it comprises step:
Step 1: synthesis of nano imaging medicine carrier material Dex-NH
2
Be dissolved in the NaOH solution of 6M by polymer carrier Dextran, ice bath is cooled to 0 DEG C, adds chloracetic acid sodium; After 60 DEG C of stirring reaction 50min, reactant liquor is cooled to room temperature, is added dropwise in methanol and obtains white flock precipitate Dex-COOH; Dex-COOH is soluble in water, be added dropwise to the DMF solution of 2-ethyoxyl-1-ethoxy carbonic acyl radical-1,2-dihydroquinoline (EEDQ); The mixed liquor of acquisition is added drop-wise in ethylenediamine, stirring at normal temperature 4 hours; Concentrated by rotary evaporation reactant liquor, to 3mL, obtains white fluffy solid Dex-NH in instillation methanol
2; By Dex-NH
2aqueous solution molecular cut off is the super filter tube ultrafiltration purification 3 times of 3kDa, and removing reaction raw materials and by-product, concentrated solution lyophilization obtains White Flocculus and carrier material Dex-NH
2;
Step 2: labelling PEG and fluorophor rhodamine
Carrier material Dex-NH
2be dissolved in 0.1M HEPES buffer solution, dissolve and regulate pH to 8.3; The PEG of instillation N-hydroxy-succinamide activation, stirring at room temperature reacts 6 hours, and reactant liquor molecular cut off is the super filter tube ultrafiltration purification 3 times of 3kDa; Concentrated solution lyophilization obtains white fluffy solid product D ex-PEG; Dex-PEG is dissolved in 0.1M HEPES buffer solution, the DMF solution of the Rho-NHS of instillation NHS activation; Room temperature reaction is after 6 hours, and be the super filter tube ultrafiltration purification 3 times of 10kDa with molecular cut off, concentrated solution lyophilization obtains red fluffy solid product Rho-Dex-PEG;
Step 3: labelling SPECT imaging group DTPA-
99mtc
Rho-Dex-PEG is dissolved in 0.1M NaHCO
3(pH9.5) in solution, under stirring, DTPA gradation added, controlling pH value of solution is 9.5; After stirring at room temperature reacts 12 hours, with super filter tube ultrafiltration purification 3 times; Concentrated solution lyophilization obtains red fluffy solid product Rho-Dex-PEG-DTPA; Rho-Dex-PEG-DTPA and stannous chloride 0.1M HCl dissolves, and adds sodium pertechnetate (Na
99mtcO
4) aqueous solution; 60 DEG C of reaction 30min; Reactant liquor molecular cut off is the super filter tube ultrafiltration purification 3 times of 10kDa; Concentrated solution is target image medicine Dex-Rho-
99mthe solution of Tc.
6. the bimodal nano imaging medicine of claim 1 is preparing the purposes in tumor imaging diagnostic preparation.
7. the bimodal nano imaging medicine of claim 1 is following the tracks of the purposes in curative effect evaluation preparation for the preparation of tumor imaging.
8. the bimodal nano imaging medicine of claim 1 is evaluating the purposes in preparation for the preparation of tumor brain blood brain barrier integrity.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106188226A (en) * | 2016-07-04 | 2016-12-07 | 江苏省原子医学研究所 | A kind of macromole developer for checking lymph node and preparation method thereof |
| CN111317829A (en) * | 2018-12-14 | 2020-06-23 | 复旦大学附属肿瘤医院 | SPECT/FI bimodal molecular imaging probe and preparation method thereof |
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Cited By (4)
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| CN111317829A (en) * | 2018-12-14 | 2020-06-23 | 复旦大学附属肿瘤医院 | SPECT/FI bimodal molecular imaging probe and preparation method thereof |
| CN111317829B (en) * | 2018-12-14 | 2022-07-19 | 复旦大学附属肿瘤医院 | SPECT/FI bimodal molecular imaging probe and preparation method thereof |
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