CN102861346A - PET/CT (Positron Emission Tomography/Computed Tomography) in vivo molecular imaging probe 18F-Annexin B1 for apoptosis and preparation method and purposes thereof - Google Patents
PET/CT (Positron Emission Tomography/Computed Tomography) in vivo molecular imaging probe 18F-Annexin B1 for apoptosis and preparation method and purposes thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of nuclear medicine and molecular imaging, and relates to a PET/CT (Positron Emission Tomography/Computed Tomography) in vivo molecular imaging probe 18F-Annexin B1 for apoptosis and a preparation method and application thereof. The PET/CT in vivo molecular imaging probe 18F-Annexin B1 for apoptosis is 18F-marked annexin B1, an 18F-marked prosthetic group and an annexin B1 are coupled under certain conditions, and the 18F-annexin B1 is separated out and purified. The invention also provides the preparation method for the PET/CT in vivo molecular imaging probe 18F-Annexin B1 for apoptosis. The PET/CT in vivo molecular imaging probe 18F-Annexin B1 for apoptosis can be applied in the experiment on the in vitro association capability of the 18F-annexin B1 with apoptotic cells and PET/CT imaging in the disease diagnosis of tumours, the kidney, the liver, the thymus and other related tissues and organs, the evaluation of curative effect and the screening and evaluation of new curatives and new methods.
Description
Technical field
The invention belongs to nuclear medicine and molecular image technical field, relate to a kind of apoptosis PET/CT living body molecule image probe
18F-Annexin B1 and its production and use.
Background technology
Apoptosis is a kind of cell has typical morphology and biochemical character under the gene guiding programmed death.Apoptosis and human numerous disease are closely related, such as tumor, cardiovascular and cerebrovascular disease, degeneration, inflammation, disease of immune system and graft-rejection etc., the medicine take the apoptosis path as target spot is expected to bring new Therapeutic Method as some disease.For example, apoptosis plays an important role in the tumorigenesis process unusually, and closely related with many biological behaviours of tumor, affects neoplasm metastasis and prognosis.But the apoptosis inhibition tumor cell hypertrophy of human-induced, thereby reach the purpose for the treatment of tumor.Can the effect of radiotherapy, many chemotherapeutics and other cancer therapy drugs be namely by playing a role its responsive target cell apoptosis, and apoptosis-inducedly become one of standard of screening cancer therapy drug.
In the at present medical practice, the external apoptosis detection method of employing comprises morphologic detection, TUNEL method, dna segment detection, the detection of mitochondrial membrane potential energy, the detection of cysteine proteinase Caspase family active and flow cytometry etc.; These external detection methods all must obtain a certain amount of tissue specimen, can not in vivo detect, can not the visual evaluation apoptosis at the effect of disease pathophysiological process and the effectiveness of therapeutic scheme, and exist missampling, sample process and preservation etc. artificial, uncertain factor, therefore in the clinical practice using value significant limitation is arranged.
Current, molecular imaging is the most active research frontier of biomedical sector, is that directly " seeing " in vivo with biology growing is grown, disease development is relevant biochemical variation, performance, feature and quantitatively with 3-D view at molecule, cell and subcellsular level.The nuclear medicine molecular image, comprise positron emission tomography scanning (PET), single photon emission computerized tomography,SPECT SPECT and with fusion mode PET/CT, the SPECT/CT of CT, it is the area of origin of molecular imaging, be used widely clinically with in the basic research, and become the goldstandard of other molecular image pattern.Therefore, utilized in recent years animal scanning technology and the method for nuclear medicine molecular image, the research apoptosis has become hot fields in major disease such as the application in the diagnosis of tumor and the treatment.The basis of active somatic cell apoptosis imaging is that electronegative Phosphatidylserine (PS) is turned to the cell outside during cell apoptosis from the cell inboard, at Ca
2+Annexin can optionally be combined with PS in the situation about existing, and the two has very high affinity, then, utilizes the radioisotope labeling annexin to realize apoptotic molecular image research.
There is report to point out, annexin is a huge protein families, have 160 protein members, their common characteristics are phospholipid surfaces of calcium ion dependency combined belt negative charge, and aminoacid sequence structurally all shows as the N end tail and conservative C end nuclear that same layout namely changes.Annexin V is a member in the annexin family that is separated the earliest, is used at first apoptosis and detects.Annexin B1 is a newcomer of annexin family, is to be waited by professor Sun Shuhan recently to clone successfully first.Studies show that, it is active that Annexin B1 has stronger Ca-dependent phospholipids incorporate equally, and the PS that is turned to the apoptotic cell surface is had very high affinity, the apoptotic ability of its vitro detection even also be better than Annexin V.
Summary of the invention
The purpose of this invention is to provide a kind of apoptosis PET/CT living body molecule image probe
18The preparation method of F-Annexin B1 and application.
Apoptosis PET/CT living body molecule image probe of the present invention
18F-Annexin B1 serves as reasons
18The annexin Annexin B1 (can prepare by prior art) of F labelling, be by
18Coupling occurs under certain condition and generates, makes after separation and purification in the prothetic group of F labelling and Annexin B1.
Apoptosis PET/CT living body molecule image probe of the present invention
18F-Annexin B1 prepares by following method;
Under alkali condition, when temperature is 25 ℃～40 ℃,
18The prothetic group of F labelling is with the gentle hybrid reaction 20～60min of annexin Annexin B1, and again separation and purification makes probe
18F-Annexin B 1 solution; Utilize analytical type gel HPLC to detect its radiochemical purity, and in three half-life of tracking and monitoring (6h)
8The vitro stability of F-Annexin B1 in the systems such as PBS solution, calf serum.
Among the present invention, described alkali condition is: pH is 8.0～9.0 alkaline buffer salt solution system;
Among the present invention, described
18The prothetic group of F labelling is selected from
18F-SFB (N-succinimidyl 4-[
18F] fluorobenzoate),
18F-FBA (4-[
18F] fluorobenzoic acid)
18F-FPA (4-[
18F] fluoropropio acid),
18F-NFP (p-nitrophenyl[
18F] fluoropropionate) or
18F-SFMB (N-succinimidyl 4-([
18F] fluoromethyl) benzoate) etc.;
Among the present invention, described isolation and purification method comprises the multiple separate mode of gel filtration chromatography method, the centrifugal membrane separation process of ultrafiltration or gel HPLC method etc.:
The gel filtration chromatography method is used and is comprised commercialization prepackage type gel column (comprising the models such as PD-10 post, micro-spin G-25 post, micro bio-spin P-6z post) and self-control type gel column (filler comprises the gel of the models such as Sephadex G-25, G-50, G-75, G-100), the leacheate that uses comprises PBS solution (pH 7.4), phosphate buffered solution (pH 7.4) and normal saline, collects corresponding eluate and has both obtained purification
18F-AnnexinB1;
Ultracentrifugation membrane separation process commodity in use ultra-filtration centrifuge tube (comprising the models such as NanoSep, Milipore, Vivaspin), its retaining molecular weight scope is 3K-100K, namely comprises 3K, 10K, 30K and 50K interior, the solution that uses comprises PBS solution (pH 7.4), phosphate buffered solution (pH 7.4) and normal saline, repeated washing, filter 2-3 all over after, hold back composition on the dissolving film and both obtained purification
18F-AnnexinB1;
Gel HPLC method is used and is comprised commercialization half preparation type and preparation type gel column and self-control type gel column (filler comprises the gel of the models such as Sephadex G-25, G-50, G-75, G-100), the mobile phase of using comprises PBS solution (pH7.4), phosphate buffered solution (pH 7.4) and normal saline, collect with
18The radioactive component peak that F-AnnexinB1 is corresponding namely obtains purification
18F-AnnexinB 1.
Apoptosis PET/CT living body molecule image probe of the present invention
18F-Annexin B1 shows through the internal and external test result, and is described
18F-Annexin B1 vitro stability is good; The combination of apoptosis-induced cell is more than the twice of matched group; PET/CT bio distribution video picture experimental image shows initial period
18F-Annexin mainly is distributed in liver, kidney, and then little by little Liver and kidney is removed, and discharges finally by bladder;
18Tumor image is clear after the F-Annexin B1 injection, has high contrast; Experimental result shows, apoptosis PET/CT living body molecule image probe of the present invention
18F-Annexin B1 can be used for the external binding ability experiment of itself and apoptotic cell and PET/CT video picture the medical diagnosis on disease of linked groups's organs such as tumor, kidney, liver, thymus, treatment therapeutic evaluation, with the screening and assessment for the treatment of new drug and new method.
Of the present invention
18F-Annexin B1 can be used for the PET/CT localization diagnosis of inside and outside apoptosis relevant disease and the screening and assessment of therapeutic evaluation and associated treatment new drug and new technique thing; Particularly, described
18F-Annexin B1 can be used for interior evaluation and the rapid screening that are used for the new drugs such as antitumor of disease model animal body such as tumor, also can be used for the evaluation of chemicotherapy induced tumor apoptosis, and carry out the clinical evaluation of tumor chemoradiotherapy curative effect monitoring and assessment and associated treatment new method, also can be used for the various histoorgan relevant diseases such as kidney, liver, thymus, heart diagnosis, treatment therapeutic evaluation, with the screening and assessment for the treatment of new drug and new method.
For the ease of understanding, below by the drawings and specific embodiments the present invention is described in detail.It needs to be noted, specific embodiments and the drawings only are in order to illustrate, obviously those skilled in the art can illustrate according to this paper, and the present invention is carried out various corrections or change, and these corrections and changing also will be included within the scope of the invention.
Description of drawings
Fig. 1 prepares among the present invention
18The Annexin B1 of F-Annexin B1 and [
18F] the gel HPLC collection of illustrative plates of SFB labeled reactant mixture.
Fig. 2 is purification among the present invention
18The gel HPLC collection of illustrative plates of F-Annexin B1.
Fig. 3 is rabbit kidney apoptosis among the present invention
18F-Annexin B1PET/CT figure, wherein, the left side arrow is apoptosis-induced right kidney, right side arrow is the left kidney of normal control.
The specific embodiment
Embodiment 1: preparation
18F-Annexin B1
Under 40 ℃, [
18F] SFB and Annexin B1 be mixed together reaction 20min at the borate buffer solution of pH 8.4, use first analytical type gel HPLC (mobile phase is PBS solution (pH 7.4)) to detect its mark rate, then use gel filtration chromatography method (PD-10, leacheate are PBS solution (pH 7.4)) to carry out separation and purification
18F-Annexin B1, its mark rate be～15% and radiochemical purity be～95%.
Embodiment 2: preparation
18F-Annexin B1
Under the room temperature, [
18F] SFB and Annexin B1 be mixed together reaction 60min at the borate buffer solution of pH 8.6, use first analytical type gel HPLC (mobile phase is PBS solution (pH 7.4)) to detect its mark rate, then use the centrifugal membrance separation of ultrafiltration (NanoSep, solution are PBS (pH 7.4)) to carry out separation and purification
18F-Annexin B1, its mark rate be～10% and radiochemical purity be～95%.
Embodiment 3: preparation
18F-Annexin B1
Under 35 ℃, [
18F] SFB and Annexin B1 be mixed together reaction 40min at the borate buffer solution of pH 8.5, use first analytical type gel HPLC (mobile phase is PBS solution (pH 7.4)) to detect its mark rate, then use half preparation type gel HPLC method (mobile phase is PBS solution (pH 7.4)) to carry out separation and purification
18F-Annexin B1, its mark rate be～20% and radiochemical purity be～97%, corresponding HPLC collection of illustrative plates is seen respectively Fig. 1 and Fig. 2.
Embodiment 4:
18The vitro stability evaluation experimental of F-Annexin B1
Under 37 ℃,
18F-Annexin B1 is three half-life of incubation (6h) in the systems such as PBS solution and calf serum respectively, and each half-life is utilized analytical type gel HPLC to follow the tracks of and detects its radiochemical purity, estimates its vitro stability.Experimental result shows that its vitro stability in two kinds of systems is good.
Embodiment 5:
18The external binding ability experiment of F-Annexin B1 and apoptotic cell
The trophophase people Pancytopenia Jurkat cell of taking the logarithm, adjusting concentration is 1 * 10
6/ ml adds final concentration to each experimental group and is 200ng/ml anti-Fas antibody induction apoptosis, and matched group does not add anti-Fas antibody.Experimental group and matched group are all at 37 ℃, volume fraction 5%CO
2Cultivate 210min in the incubator, with the centrifugal 5min of 800 * g, with adding 100 μ L binding buffer liquid re-suspended cells after the flushing of PBS solution, then two groups of cells are divided into some parts, all add equivalent
18F-Annexin B1 solution, after hatching 30min on the blending instrument under the room temperature, with the centrifugal 5min of 800 * g, separating and combining part and free fraction, measure respectively the radiocounting of precipitation (bound fraction) and supernatant (free fraction) with gamma counter, calculations incorporated rate and competition combination rate.Experimental result shows,
18The combination of F-Annexin B1 and the apoptosis-induced cell of experimental group is more than the twice of matched group.
Embodiment 6: normal rat
18F-Annexin B1 PET/CT bio distribution video picture experiment
Through the tail vein with 100～200 μ Ci
18F-Annexin B1 injection of solution in the normal rat body, respectively at after the injection 10,30,60,120, the capable PET/CT video picture of 180min, observe
18Bio distribution and the metabolic pathway of F-Annexin B1 B1 in the normal rat body.The PET/CT image shows, initial period (in the 60min)
18F-Annexin mainly is distributed in liver, kidney.Then little by little Liver and kidney is removed, and discharges finally by bladder.
18This distribution and metabolism rule of F-Annexin B1 is for its best visualization time at each organs and tissues provides reference frame.
Embodiment 7: the tumor death rat model
18F-Annexin B1 PET/CT video picture experiment
The tumor death of taking the mode of intraperitoneal injection of cyclophosphamide to induce lotus W256 tumor rat.With 10～200 μ Ci
18F-Annexin B1 solution in the tail vein will be expelled to the mice with tumor body, then respectively at after the injection 30,60,120,180, the capable PET/CT video picture of 240min, observe
18F-Annexin B1 concentrates and distribution situation apoptosis tumor tissues and other organs and tissues.The PET/CT image shows, from injecting rear 30min,
18F-Annexin B1 all is woven with very high concentrating in tumor group, along with its quick removing from other internal organs, and 120min after the injection
18F-Annexin B1 reaches about 8.0 at the absorptance of tumor and muscle, has high contrast, and clear picture can be used in the Monitoring and assessing of oncotherapy curative effect.
Embodiment 8: rabbit kidney Apoptosis Model rat
18F-Annexin B1 PET/CT video picture experiment
Take the mode of ischemia-reperfusion to induce the right kidney apoptosis of rabbit.With 50～300 μ Ci
18F-Annexin B1 solution in auricular vein will be expelled to the rabbit body, then respectively at after the injection 30,60,90,120, the capable PET/CT video picture of 240min, observe
18F-Annexin B1 concentrates and distribution situation apoptosis kidney and other organs and tissues.The PET/CT image shows, after the injection during 240min,
18F-Annexin B1 is 2.5 times (the results are shown in Figure 3) of the left kidney of offside concentrating of the right kidney of apoptosis.Because kidney is
18One of main metabolic organ of F-Annexin B1, therefore, the time of developing that kidney etc. are drained internal organs should more than 4h after the injection, can be used for the diagnosis of kidney relevant disease preferably.
Embodiment 9: heart Apoptosis Model rat
18F-Annexin B1 PET/CT video picture experiment
Take the mode of intravenous injection cycloheximide to induce the rat liver apoptosis.With 50～500 μ Ci
18F-Annexin B1 solution through tail vein injection in the rat body, then respectively at after the injection 30,60,120, the capable PET/CT video picture of 180min, observe
18F-Annexin B1 concentrates and distribution situation apoptosis liver and other organs and tissues.The PET/CT image shows,
18F-Annexin B1 has a large amount of concentrating at the apoptosis liver, and very fast because of its hepatic clearance speed, injection can obtain high-contrast, PET/CT image clearly behind the 120min, can be used for the diagnosis of liver related disease.
Embodiment 10: the Thymic Apoptosis rat model
18F-Annexin B1 PET/CT video picture experiment
Take the mode of lumbar injection dexamethasone to induce the rat chest gland apoptosis.With 50～500 μ Ci
18F-Annexin B1 solution through tail vein injection in the rat body, then respectively at after the injection 30,60,120, the capable PET/CT video picture of 180min, observe
18F-Annexin B1 concentrates and distribution situation apoptosis thymic tissue and other organs and tissues.The PET/CT image shows,
18F-Annexin B1 concentrates obviously at the apoptosis thymic tissue, because its clearance rate of adjacent tissue around the thymus is very fast, can obtain high-contrast, PET/CT image clearly behind the injection 120min, can be used for the evaluation of thymus relevant disease.
Experimental result shows, apoptosis PET/CT living body molecule image probe of the present invention
18F-Annexin B1 can be used for the external binding ability experiment of itself and apoptotic cell and PET/CT video picture the medical diagnosis on disease of linked groups's organs such as tumor, kidney, liver, thymus, treatment therapeutic evaluation, with the screening and assessment for the treatment of new drug and new method.
Claims (10)
1. apoptosis PET/CT living body molecule image probe
18F-Annexin B1 is characterized in that, and is described
18F-Annexin B1 serves as reasons
18The annexin Annexin B1 of F labelling.
2. by apoptosis PET/CT living body molecule image probe claimed in claim 1
18F-Annexin B1 is characterized in that, and is described
18F-Annexin B1 be by
18Coupling occurs under certain condition and generates, makes after separation and purification in the prothetic group of F labelling and Annexin B1.
3. the apoptosis PET/CT living body molecule image probe of claim 1
18The preparation method of F-Annexin B1 is characterized in that, comprises the following steps:
Under alkali condition, when temperature is 25 ℃～40 ℃
18The prothetic group of F labelling
18F-SFB or
18F-FPA is with the gentle hybrid reaction 20～60min of annexin Annexin B1, and then separation and purification makes target-probe
18F-Annexin B1 solution.
4. by method claimed in claim 3, it is characterized in that, described
18The prothetic group of F labelling is selected from
18F-SFB,
18F-FBA
18F-FPA,
18F-NFP or
18F-SFMB.
5. by Preparation Method claimed in claim 3, it is characterized in that, described alkali condition is: pH is 8.0～9.0 alkaline buffer salt solution system.
6. by method claimed in claim 3, it is characterized in that, the method for described separation and purification is selected from gel filtration chromatography method, the centrifugal membrane separation process of ultrafiltration or gel HPLC method.
7. the apoptosis PET/CT living body molecule image probe of claim 1
18F-Annexin B1 is the purposes in the screening and assessment of the PET/CT localization diagnosis of apoptosis relevant disease and therapeutic evaluation and associated treatment medicine and Therapeutic Method in vivo and in vitro.
8. by purposes claimed in claim 7, it is characterized in that described apoptosis PET/CT living body molecule image probe
18F-Annexin B1 is in the evaluation of antineoplastic agent and the purposes in the rapid screening.
9. by purposes claimed in claim 7, it is characterized in that described apoptosis PET/CT living body molecule image probe
18F-Annexin B1 is in the evaluation of chemicotherapy induced tumor apoptosis, and the purposes in the evaluation of tumor chemoradiotherapy curative effect monitoring and assessment and related methods for the treatment of.
10. by purposes claimed in claim 7, it is characterized in that described apoptosis PET/CT living body molecule image probe
18The purposes of F-Annexin B1 in the screening and assessment of diagnosis, therapeutic evaluation or the curative of kidney, liver, thymus or cardiac-related diseases and method.
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Cited By (2)
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| CN105669855A (en) * | 2016-02-04 | 2016-06-15 | 江苏省原子医学研究所 | Method for rapidly marking Cys-Annexin V through <18>F and application of method |
| CN113388003A (en) * | 2021-06-11 | 2021-09-14 | 江苏省原子医学研究所 | Aspartic acid proteolytic enzyme recognition reduction type molecular probe and application |
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Cited By (4)
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| CN105669855A (en) * | 2016-02-04 | 2016-06-15 | 江苏省原子医学研究所 | Method for rapidly marking Cys-Annexin V through <18>F and application of method |
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| CN113388003A (en) * | 2021-06-11 | 2021-09-14 | 江苏省原子医学研究所 | Aspartic acid proteolytic enzyme recognition reduction type molecular probe and application |
| CN113388003B (en) * | 2021-06-11 | 2023-04-07 | 江苏省原子医学研究所 | Aspartic acid proteolytic enzyme recognition reduction type molecular probe and application |
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