CN104725473A - [<18>F] AlF marked positron emission tomography (PET) polypeptide probe and preparation method thereof - Google Patents
[<18>F] AlF marked positron emission tomography (PET) polypeptide probe and preparation method thereof Download PDFInfo
- Publication number
- CN104725473A CN104725473A CN201410460832.1A CN201410460832A CN104725473A CN 104725473 A CN104725473 A CN 104725473A CN 201410460832 A CN201410460832 A CN 201410460832A CN 104725473 A CN104725473 A CN 104725473A
- Authority
- CN
- China
- Prior art keywords
- alf
- tmtp1
- pet
- nota
- polypeptide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
Abstract
The invention discloses a [<18>F] AlF marked positron emission tomography (PET) polypeptide probe and a preparation method thereof. The probe comprises TMTP1 polypeptide and NOTA, which are connected together, and the structural formulae of the TMTP1 polypeptide and the NOTA are shown in the description. According to the [<18>F] AlF marked positron emission tomography (PET) polypeptide probe and the preparation method thereof, a glycine is added to the TMTP1, and a G-TMTP1 polypeptide is designed, so that the polypeptide does not influence the biological activity after being radioactively marked; furthermore, 18F is taken as a radionuclide, and the G-TMTP1 polypeptide is marked by utilizing a [<18>F] AlF-NOTA method, so that the obtained [<18>F] AlF-marked PET polypeptide probe has excellent pharmacokinetics properties, the background cleaning rate is high, the liver uptake rate is low, in-vivo stability is good, the uptake rate of tumor site is high, highly metastatic tumor can be diagnosed specifically, and the polypeptide probe can be applied to diagnosis or therapeutic evaluation of highly metastatic malignant tumor.
Description
Technical field
The invention belongs to radio-labeled compound field, be specifically related to one [
18f] the PET polypeptide probe and preparation method thereof of AlF mark.
Background technology
According to the development trend of current cancer, the year two thousand twenty whole world cancer morbidity will than increasing by 50% now, and the annual newly-increased cancer patients's number in the whole world will reach 1,500 ten thousand people (World Health Organization delivers in the recent period " report of world's cancer ").Be reduce cancer death to lead the most effective way to the early discovery of tumour, early treatment, at present in developing country, the cancer patients of 80% is just found at cancer of late stage.Metastases is the important biomolecule feature of malignant tumour, and it is the major cause of oncotherapy failure, is also the main cause of tumour patient death.In the tumour patient made a definite diagnosis for the first time, the patient of about 70% can by operation, adjuvant radiotherapy or chemotherapy means symptom management, but some patient can tumorigenic recurrence or transfer, its 5 annual survival rate is less than 50%, therefore just most important to the diagnosis of the small transfer of malignant tumour.
Although the clear and definite mechanism that tumour betides transfer is still unclear at present, if but can diagnose cancer in early days, and determine grade malignancy and the transfer ability of tumour, then corresponding operation, radiotherapy or chemotherapy regimen is formulated, just can improve the survival rate of patient, and improve the life quality of patient.Formation method at present for cancer diagnosis mainly contains X-ray (CT), ultrasonic (US), Magnetic resonance imaging (MRI) and nuclear medicine SPECT/PET.
CT, US and MRI are the anatomical structure analyses based on solid tumor, therefore they cannot detect the physiological change of tumor tissues on a molecular scale, can not determine the grade malignancy of tumour, and for the specificity of frequently-occurring tumour (such as mammary cancer, liver cancer, prostate cancer etc.) and susceptibility poor, therefore we need that exploitation is a kind of novelly specificity can differentiate the radioactive tracer of malignancy badly, he can realize the early diagnosis to malignant tumour, and can detect the growth of tumour and tumour to the reaction for the treatment of plan.
Positron emission computed tomography (Positron emission tomography, PET) due to it, there is the features such as sensitive, accurate and registration, in diagnosis and guiding treatment tumour, coronary heart disease and encephalopathy etc., all demonstrated unique superiority.PET technology has three key elements: PET probe, and signal amplifies, highly sensitive detector, and wherein PET probe is the most important, and it realizes signal to amplify and the primary prerequisite of highly sensitive detection, at present clinically to diagnosing tumor most widely used be [
18f] FDG, but because its specificity is low, easily cause the limitations such as false positive, it can not meet clinical requirement completely, in addition [
18f] whether FDG has transfer ability to tumour also cannot make and judging accurately, thus novel
18f tagged molecule image probe is still urgently developed.
The exploitation of polypeptide class PET probe is an important direction, there is large quantity research for vasoactive intestinal peptide (Vasoactive intestinal peptide at present, VIP), Sostatin, bombesin, RGD, VEGF, TNF, gastrin, the polypeptide such as growth hormone statin carry out radio-labeling research (M.Fani, H.R.Maecke, S.M.Okarvi, Radiolabeled peptides:valuable tools for the detection andtreatment of cancer, Theranostics, 2012, 2 (5): 481-501), but not yet have so far really can be widely applied to clinical
18f labeling polypeptide quasi-molecule image probe, its major cause is that polypeptide has a large amount of active function groups, more responsive to flag condition, carrying out the polypeptide active after radio-labeling changes larger, pharmacokinetics in probe body after mark is undesirable, and such as liver picked-up is higher, body internal stability is poor, tumor uptake value is low.
Summary of the invention
The object of the invention is to overcome prior art defect, provide a kind of [
18f] AlF mark PET polypeptide probe.
Another object of the present invention is to provide above-mentioned [
18f] preparation method of PET polypeptide probe of AlF mark
Concrete technical scheme of the present invention is as follows:
A kind of [
18f] AlF mark PET polypeptide probe, comprise the TMTP1 polypeptide and NOTA that link together, its structural formula is as follows:
A kind of above-mentioned [
18f] preparation method of PET polypeptide probe of AlF mark, comprise the steps:
(1) G-TMTP1 is dissolved in DMF, adds NOTA-NHS ester, then add DIEA by pH regulator to 8.0-8.5, stirred overnight at room temperature, through HPLC separation and purification, collects the cut of target product, freeze-drying after merging, obtain NOTA-G-TMTP1, the reaction formula of this step is as follows:
(2) on magnetic resonance acceleator, nuclear reaction is used
18o (p, n)
18f obtains [
18f] F
-, be then enriched on Sep-Park light QMA post, with deionized water drip washing to remove the metallic impurity ion be adsorbed on QMA post, use physiological saline wash-out, obtain 925 ~ 1850MBq's (25 ~ 150mCi)
18f normal saline solution;
(3) in reaction vessel, AlCl is added
3with the sodium-acetate buffer of pH=4.0, it is obtained then to add step (2)
18f
-normal saline solution, Homogeneous phase mixing, then the deionized water solution adding NOTA-G-TMTP1, after mixture shakes up 80 ~ 110 DEG C reaction 10 ~ 30min, be cooled to normal temperature, measure its mark rate with HPLC, [
18f] AlF-NOTA-G-TMTP1 reaction solution;
(4) prepared by step (3) [
18f] AlF-NOTA-G-TMTP1 reaction solution slowly injects the Sep-Pak C18 post activated in advance, again with distilled water drip washing removing water-soluble impurity, dry up rear ethanol rinse, gained leacheate normal saline dilution is less than 10% to ethanol content, its retention time and top coal drawing is measured with HPLC, whether observe its appearance character is achromaticity and clarification transparent liquid, described in obtaining [
18f] AlF mark PET polypeptide probe.
In a preferred embodiment of the invention, described step (1) is: be dissolved in by 10mg G-TMTP1 in 1mL DMF, add 15mg NOTA-NHS ester, then DIEA is added by pH regulator to 8.0-8.5, stirred overnight at room temperature, through HPLC separation and purification, collects the cut of target product, freeze-drying after merging, obtains NOTA-G-TMTP1.
Preferred further, in described step (1) HPLC separation and purification, the first moving phase is 0.1% trifluoroacetic acid aqueous solution, and the second moving phase is 0.1% trifluoroacetic acid acetonitrile, condition of gradient elution, 0 ~ 10min, first moving phase of 95%; 10 ~ 25min, first moving phase of 95% ~ 15%; 25 ~ 40min, first moving phase of 15%; The flow velocity of moving phase is 5mL/min, and determined wavelength is 220nm.
In a preferred embodiment of the invention, described step (2) is: on magnetic resonance acceleator, use nuclear reaction
18o (p, n)
18f obtains [
18f] F
-, be then enriched on Sep-Park light QMA post, with the drip washing of 5mL deionized water to remove the metallic impurity ion be adsorbed on QMA post, with 0.2 ~ 1mL physiological saline wash-out, obtain 925 ~ 1850MBq's (25 ~ 150mCi)
18f normal saline solution.
In a preferred embodiment of the invention, described step (3) is: the AlCl adding 10 μ L 2nmol/L in reaction vessel
3with the sodium-acetate buffer of 300 μ L 0.1mol/L pH=4.0, it is obtained then to add 100 μ L steps (2)
18f
-normal saline solution, Homogeneous phase mixing 3min, then the deionized water solution of NOTA-G-TMTP1 adding 1000 μ L1mg/mL, at 80 ~ 110 DEG C of reaction 10 ~ 30min after mixture shakes up, be cooled to normal temperature, measure its mark rate with HPLC, [
18f] AlF-NOTA-G-TMTP1 reaction solution.
In a preferred embodiment of the invention, described step (4) is: prepared by step (3) [
18f] AlF-NOTA-G-TMTP1 reaction solution slowly injects the Sep-Pak C18 post activated in advance, again with 20mL distilled water drip washing removing water-soluble impurity, dry up rear use 800 μ L ethanol rinse, gained leacheate normal saline dilution is less than 10% to ethanol content, its retention time and top coal drawing is measured with HPLC, whether observe its appearance character is achromaticity and clarification transparent liquid, described in obtaining [
18f] AlF mark PET polypeptide probe.
The invention has the beneficial effects as follows:
1, the present invention is by increasing a glycine to TMTP1, and design G-TMTP1 polypeptide, makes it after radio-labeling, do not affect its biological activity, and adopt
18f is radionuclide, utilize [
18f] the method mark G-TMTP1 polypeptide of AlF-NOTA, obtain [
18f] the PET polypeptide probe of AlF mark has excellent pharmacokinetics, and its background clearance rate is fast, and liver picked-up is low, body internal stability is good, tumor locus picked-up is high, specificly can diagnose the tumour of high transfer, may be used for diagnosis or the therapeutic evaluation of the malignant tumour of high transfer;
2, of the present invention [
18f] AlF mark PET polypeptide probe, utilize the biological characteristics of its selectively targeted high metastatic tumour, early diagnosis can be carried out to high metastatic tumour;
3, of the present invention [
18f] AlF mark PET polypeptide probe adopt Al-
18the marking method of F marks it, and marking method is simple, easily is automated synthesis, mark productive rate is high, do not need HPLC purifying, this is concerning extremely important transformation period shorter radionuclide, advantageously in the commercial applications of radio-labeled compound in clinical expansion.
Accompanying drawing explanation
Fig. 1 be in the specific embodiment of the invention [
18f] AlF mark PET polypeptide probe utilize HPLC to measure the result of its radiochemicsl purity;
Fig. 2 be in the specific embodiment of the invention [
18f] PET polypeptide probe microPET video picture coronal-plane tomograph in the tumor-bearing mice (B16) of AlF mark;
Fig. 3 be in the specific embodiment of the invention [
18f] PET polypeptide probe microPET video picture coronal-plane tomograph in the tumor-bearing mice (4T1) of AlF mark.
Embodiment
Below by way of embodiment by reference to the accompanying drawings technical scheme of the present invention be further detailed and describe.
(1) 10mg G-TMTP1 (customizing in polypeptide Science and Technology Ltd. of the U.S.) is dissolved in 1mL DMF (dimethyl formamide), add 15mg NOTA-NHS ester (1,4-oxalic acid-1,4,7-7-triazacyclononane-7-acetic acid-N-hydroxyl amber cypress imide ester, buy in CheMatech company), then DIEA (N is added, N-diisopropylethylamine) by pH regulator to 8.0-8.5, stirred overnight at room temperature, through HPLC separation and purification, collect the cut of target product, freeze-drying after merging, through mass spectroscopy (MS, m/z:957.2 ([M+H]
+) after confirmation, obtain NOTA-G-TMTP1, in above-mentioned HPLC separation and purification, the first moving phase is 0.1% trifluoroacetic acid aqueous solution, and the second moving phase is 0.1% trifluoroacetic acid acetonitrile, condition of gradient elution, 0 ~ 10min, first moving phase of 95%; 10 ~ 25min, first moving phase of 95% ~ 15%; 25 ~ 40min, first moving phase of 15%; The flow velocity of moving phase is 5mL/min, and determined wavelength is 220nm;
(2) on magnetic resonance acceleator, nuclear reaction is used
18o (p, n)
18f obtains [
18f] F
-, be then enriched on Sep-Park light QMA post, with the drip washing of 5mL deionized water to remove the metallic impurity ion be adsorbed on QMA post, with 0.2 ~ 1mL physiological saline wash-out, obtain 925 ~ 1850MBq's (25 ~ 150mCi)
18f normal saline solution;
(3) in the EP pipe of 1.5mL, add the AlCl of 10 μ L 2nmol/L
3with the sodium-acetate buffer of 300 μ L 0.1mol/LpH=4.0, it is obtained then to add 100 μ L steps (2)
18f
-normal saline solution, Homogeneous phase mixing 3min, then the deionized water solution of NOTA-G-TMTP1 adding 1000 μ L 1mg/mL, at 80 ~ 110 DEG C of reaction 10 ~ 30min after mixture shakes up, be cooled to normal temperature, measure its mark rate with HPLC, [
18f] AlF-NOTA-G-TMTP1 reaction solution;
(4) prepared by step (3) [
18f] AlF-NOTA-G-TMTP1 reaction solution slowly injects the Sep-Pak C18 post activated in advance, again with 20mL distilled water drip washing removing water-soluble impurity, dry up rear use 800 μ L ethanol rinse, gained leacheate normal saline dilution is less than 10% to ethanol content, its retention time and top coal drawing is measured with HPLC, whether observe its appearance character is achromaticity and clarification transparent liquid, described in obtaining [
18f] AlF mark PET polypeptide probe, its structural formula is as follows:
As shown in Figure 1, through the putting productive rate about 10 ~ 40%, radiochemicsl purity > 95% of decay correction;
(5) lotus B16 tumour nude mice MicroPET video picture: under B16 tumor bearing nude mice narcosis through tail vein inject respectively 0.1mL [
18f] AlF mark PET polypeptide probe (7.4MBq) and in injection after 30min carry out static microPET/CT tomoscan (Siemens Inveon), Space Reconstruction is carried out by three-dimensional order subset maximum expected value method (ordered subset expectation maximization withthree-dimensional resolution recovery, OSEM3D) after IMAQ.In the coronal-plane video picture figure of decay correction, area-of-interest (the region of interest of tumour, healthy tissues and organ is irised out with ASI Pro 5.2.4.0 software, ROI), calculate the radioactivity ratio of tumour/non-tumour (T/NT) in tumor model, tumour/muscle=4.31 ± 0.63, in addition, its background clearance rate is fast, liver picked-up is low, has excellent Internal pharmacokinetics character (as shown in Figure 2).
(6) lotus 4T1 tumour nude mice MicroPET video picture: under 4T1 tumor bearing nude mice narcosis through tail vein inject respectively 0.1mL [
18f] AlF mark PET polypeptide probe (7.4MBq) and in injection after 30min carry out static microPET/CT tomoscan (Siemens Inveon), Space Reconstruction is carried out by three-dimensional order subset maximum expected value method (ordered subset expectation maximization withthree-dimensional resolution recovery, OSEM3D) after IMAQ.In the coronal-plane video picture figure of decay correction, area-of-interest (the region of interest of tumour, healthy tissues and organ is irised out with ASI Pro 5.2.4.0 software, ROI), calculate the radioactivity ratio of tumour/non-tumour (T/NT) in tumor model, tumour/muscle=4.87 ± 0.43, in addition, its background clearance rate is fast, liver picked-up is low, has excellent Internal pharmacokinetics character (as shown in Figure 3).
The above, be only preferred embodiment of the present invention, therefore can not limit scope of the invention process according to this, the equivalence change namely done according to the scope of the claims of the present invention and description with modify, all should still belong in scope that the present invention contains.
Claims (7)
1. one kind [
18f] AlF mark PET polypeptide probe, it is characterized in that: comprise the TMTP1 polypeptide and NOTA that link together, its structural formula is as follows:
2. one kind according to claim 1 [
18f] preparation method of PET polypeptide probe of AlF mark, it is characterized in that: comprise the steps:
(1) be dissolved in DMF by G-TMTP1, add NOTA-NHS ester, then add DIEA by pH regulator to 8.0-8.5, stirred overnight at room temperature, through HPLC separation and purification, collect the cut of target product, freeze-drying after merging, obtains NOTA-G-TMTP1;
(2) on magnetic resonance acceleator, nuclear reaction is used
18o (p, n)
18f obtains [
18f] F
-, be then enriched on Sep-Park light QMA post, with deionized water drip washing to remove the metallic impurity ion be adsorbed on QMA post, use physiological saline wash-out, obtain 925 ~ 1850MBq's (25 ~ 150mCi)
18f normal saline solution;
(3) in reaction vessel, AlCl is added
3with the sodium-acetate buffer of pH=4.0, it is obtained then to add step (2)
18f
-normal saline solution, Homogeneous phase mixing, then the deionized water solution adding NOTA-G-TMTP1, after mixture shakes up 80 ~ 110 DEG C reaction 10 ~ 30min, be cooled to normal temperature, measure its mark rate with HPLC, [
18f] AlF-NOTA-G-TMTP1 reaction solution;
(4) prepared by step (3) [
18f] AlF-NOTA-G-TMTP1 reaction solution slowly injects the Sep-Pak C18 post activated in advance, again with distilled water drip washing removing water-soluble impurity, dry up rear ethanol rinse, gained leacheate normal saline dilution is less than 10% to ethanol content, its retention time and top coal drawing is measured with HPLC, whether observe its appearance character is achromaticity and clarification transparent liquid, described in obtaining [
18f] AlF mark PET polypeptide probe.
3. as claimed in claim 2 a kind of according to claim 1 [
18f] preparation method of PET polypeptide probe of AlF mark, it is characterized in that: described step (1) is: 10mg G-TMTP1 is dissolved in 1mL DMF, add 15mg NOTA-NHS ester, then DIEA is added by pH regulator to 8.0-8.5, stirred overnight at room temperature, through HPLC separation and purification, collects the cut of target product, freeze-drying after merging, obtains NOTA-G-TMTP1.
4. as claimed in claim 3 a kind of according to claim 1 [
18f] preparation method of PET polypeptide probe of AlF mark, it is characterized in that: in described step (1) HPLC separation and purification, the first moving phase is 0.1% trifluoroacetic acid aqueous solution, second moving phase is 0.1% trifluoroacetic acid acetonitrile, condition of gradient elution, 0 ~ 10min, first moving phase of 95%; 10 ~ 25min, first moving phase of 95% ~ 15%; 25 ~ 40min, first moving phase of 15%; The flow velocity of moving phase is 5mL/min, and determined wavelength is 220nm.
5. as claimed in claim 2 a kind of according to claim 1 [
18f] preparation method of PET polypeptide probe of AlF mark, it is characterized in that: described step (2) is: on magnetic resonance acceleator, use nuclear reaction
18o (p, n)
18f obtains [
18f] F
-, be then enriched on Sep-Park light QMA post, with the drip washing of 5mL deionized water to remove the metallic impurity ion be adsorbed on QMA post, with 0.2 ~ 1mL physiological saline wash-out, obtain 925 ~ 1850MBq's (25 ~ 150mCi)
18f normal saline solution.
6. as claimed in claim 2 a kind of according to claim 1 [
18f] preparation method of PET polypeptide probe of AlF mark, it is characterized in that: described step (3) is: the AlCl adding 10 μ L2nmol/L in reaction vessel
3with the sodium-acetate buffer of 300 μ L 0.1mol/L pH=4.0, it is obtained then to add 100 μ L steps (2)
18f
-normal saline solution, Homogeneous phase mixing 3min, then the deionized water solution of NOTA-G-TMTP1 adding 1000 μ L 1mg/mL, at 80 ~ 110 DEG C of reaction 10 ~ 30min after mixture shakes up, be cooled to normal temperature, measure its mark rate with HPLC, [
18f] AlF-NOTA-G-TMTP1 reaction solution.
7. as claimed in claim 2 a kind of according to claim 1 [
18f] preparation method of PET polypeptide probe of AlF mark, it is characterized in that: described step (4) is: prepared by step (3) [
18f] AlF-NOTA-G-TMTP1 reaction solution slowly injects the Sep-Pak C18 post activated in advance, again with 20mL distilled water drip washing removing water-soluble impurity, dry up rear use 800 μ L ethanol rinse, gained leacheate normal saline dilution is less than 10% to ethanol content, its retention time and top coal drawing is measured with HPLC, whether observe its appearance character is achromaticity and clarification transparent liquid, described in obtaining [
18f] AlF mark PET polypeptide probe.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410460832.1A CN104725473B (en) | 2014-09-11 | 2014-09-11 | A kind of [18F] AlF marks PET polypeptide probes and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410460832.1A CN104725473B (en) | 2014-09-11 | 2014-09-11 | A kind of [18F] AlF marks PET polypeptide probes and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN104725473A true CN104725473A (en) | 2015-06-24 |
| CN104725473B CN104725473B (en) | 2018-03-20 |
Family
ID=53449948
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201410460832.1A Expired - Fee Related CN104725473B (en) | 2014-09-11 | 2014-09-11 | A kind of [18F] AlF marks PET polypeptide probes and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN104725473B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN106478820A (en) * | 2016-10-10 | 2017-03-08 | 米度（南京）生物技术有限公司 | A kind of liver cancer PET diagnosis tracer and preparation method thereof and purposes |
| CN107286243A (en) * | 2017-07-27 | 2017-10-24 | 北京大学第医院 | Radiate iodine labeling PD L1 monoclonal antibodies and preparation method and application |
| CN107312070A (en) * | 2017-05-03 | 2017-11-03 | 厦门大学附属第医院 | It is a kind of18PET polypeptide probes of F marks and preparation method thereof |
| CN109705193A (en) * | 2018-12-18 | 2019-05-03 | 厦门大学附属第一医院 | A kind of radioactive label tEB-TMTP1 compound and its preparation method and application |
| CN112194651A (en) * | 2020-10-12 | 2021-01-08 | 南方医科大学南方医院 | Precursor compound of PET tracer and application thereof |
| CN114044804A (en) * | 2021-10-29 | 2022-02-15 | 厦门大学附属第一医院 | TMTP1 polypeptide ligand radioactive probe and preparation method and application thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101440126A (en) * | 2007-11-20 | 2009-05-27 | 深圳市奥尼克斯基因技术有限公司 | Acquisition and use of homing polypeptide with targeting specificity related to tumor and metastases thereof |
| CN103041412A (en) * | 2013-01-29 | 2013-04-17 | 江苏省原子医学研究所 | PET (Positron Emission Tomography) tracer with FSHR (Follicle-stimulating Hormone Receptor) targeting as well as preparation method and application thereof |
| US20130323171A1 (en) * | 2012-06-05 | 2013-12-05 | The Board Of Trustees Of The Leland Stanford Junior University | Radiolabeled bbn analogs for pet imaging of gastrin-releasing peptide receptors |
| CN103613671A (en) * | 2013-12-04 | 2014-03-05 | 厦门大学附属第一医院 | Al-18F mark fusion peptide and application thereof |
| CN103656666A (en) * | 2012-09-14 | 2014-03-26 | 深圳市奥尼克斯基因技术有限公司 | Preparation and application of novel targeting peptide for specifically inhibiting tumor cell metastasis |
| CN103833829A (en) * | 2014-01-07 | 2014-06-04 | 江苏省原子医学研究所 | Radioactive <18>F-labeled imaging drug <18>F-AL-NOTA-IF7 targeting Anxa1 in tumor blood vessels and preparation method thereof |
| WO2014086364A1 (en) * | 2012-12-03 | 2014-06-12 | Rigshospitalet | Positron emitting radionuclide labeled peptides for human upar pet imaging |
-
2014
- 2014-09-11 CN CN201410460832.1A patent/CN104725473B/en not_active Expired - Fee Related
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101440126A (en) * | 2007-11-20 | 2009-05-27 | 深圳市奥尼克斯基因技术有限公司 | Acquisition and use of homing polypeptide with targeting specificity related to tumor and metastases thereof |
| US20130323171A1 (en) * | 2012-06-05 | 2013-12-05 | The Board Of Trustees Of The Leland Stanford Junior University | Radiolabeled bbn analogs for pet imaging of gastrin-releasing peptide receptors |
| CN103656666A (en) * | 2012-09-14 | 2014-03-26 | 深圳市奥尼克斯基因技术有限公司 | Preparation and application of novel targeting peptide for specifically inhibiting tumor cell metastasis |
| WO2014086364A1 (en) * | 2012-12-03 | 2014-06-12 | Rigshospitalet | Positron emitting radionuclide labeled peptides for human upar pet imaging |
| CN103041412A (en) * | 2013-01-29 | 2013-04-17 | 江苏省原子医学研究所 | PET (Positron Emission Tomography) tracer with FSHR (Follicle-stimulating Hormone Receptor) targeting as well as preparation method and application thereof |
| CN103613671A (en) * | 2013-12-04 | 2014-03-05 | 厦门大学附属第一医院 | Al-18F mark fusion peptide and application thereof |
| CN103833829A (en) * | 2014-01-07 | 2014-06-04 | 江苏省原子医学研究所 | Radioactive <18>F-labeled imaging drug <18>F-AL-NOTA-IF7 targeting Anxa1 in tumor blood vessels and preparation method thereof |
Non-Patent Citations (3)
| Title |
|---|
| JIYUN SHI等: "PET imaging of tumor metastasis using 68Ga-labeled a novel tumor-homing peptide TMTP1", 《J NUCL MED 》 * |
| MORTEN PERSSONA等: "First 18F-labeled ligand for PET imaging of uPAR: In vivo studies in human prostate cancer xenografts", 《NUCL MED BIOL》 * |
| WADIH ARAP等: "Targeting the prostate for destruction through a vascular address", 《PNAS》 * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| CN105669855B (en) * | 2016-02-04 | 2020-02-11 | 江苏省原子医学研究所 | A kind of 18Method for rapidly marking Cys-Annexin V by using F and application thereof |
| CN106478820A (en) * | 2016-10-10 | 2017-03-08 | 米度（南京）生物技术有限公司 | A kind of liver cancer PET diagnosis tracer and preparation method thereof and purposes |
| CN107312070A (en) * | 2017-05-03 | 2017-11-03 | 厦门大学附属第医院 | It is a kind of18PET polypeptide probes of F marks and preparation method thereof |
| CN107286243A (en) * | 2017-07-27 | 2017-10-24 | 北京大学第医院 | Radiate iodine labeling PD L1 monoclonal antibodies and preparation method and application |
| CN109705193A (en) * | 2018-12-18 | 2019-05-03 | 厦门大学附属第一医院 | A kind of radioactive label tEB-TMTP1 compound and its preparation method and application |
| CN109705193B (en) * | 2018-12-18 | 2021-05-25 | 厦门大学附属第一医院 | Radiolabelled tEB-TMTP1 compound and preparation method and application thereof |
| CN112194651A (en) * | 2020-10-12 | 2021-01-08 | 南方医科大学南方医院 | Precursor compound of PET tracer and application thereof |
| CN112194651B (en) * | 2020-10-12 | 2021-11-09 | 南方医科大学南方医院 | Precursor compound of PET tracer and application thereof |
| CN114044804A (en) * | 2021-10-29 | 2022-02-15 | 厦门大学附属第一医院 | TMTP1 polypeptide ligand radioactive probe and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104725473B (en) | 2018-03-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN104725473B (en) | A kind of [18F] AlF marks PET polypeptide probes and preparation method thereof | |
| CN111592584B (en) | HER2 affinity body and diagnosis and treatment nuclide marker as well as preparation method and application thereof | |
| Denoyer et al. | High-contrast PET of melanoma using 18F-MEL050, a selective probe for melanin with predominantly renal clearance | |
| US10159759B2 (en) | Pet tracer for imaging of neuroendocrine tumors | |
| CN112851637B (en) | PSMA inhibitor, compound, preparation method and application thereof | |
| CN108434468B (en) | Radioiodinated protein binding ligand and application thereof | |
| Garai et al. | Limitations and pitfalls of 99mTc-EDDA/HYNIC-TOC (Tektrotyd) scintigraphy | |
| CN106084005A (en) | The Al of targeting somatostatin receptor18f NOTA PEG6tATE and its preparation method and application | |
| CN112898270B (en) | Diagnosis and treatment integrated PSMA inhibitor and compound, and preparation method and application thereof | |
| CN106075484A (en) | Isotopically labeled prostate specific membrane antigen targeted inhibition agent and preparation method thereof | |
| TW202005669A (en) | The structural molecule of peptide derivative for PSMA-targeted radiotherapy diagnosis and treatment | |
| CN106581700A (en) | Novel HER2-targeting polypeptide radioactive medicine and preparation method and application thereof | |
| CN112043839A (en) | Radioisotope-labeled polypeptide imaging agent targeting transferrin receptor and application thereof | |
| CN113648434A (en) | PET molecular probe targeting PD-L1 and preparation method and application thereof | |
| CN113583089A (en) | PET imaging agent targeting tumor PD-L1, labeled precursor thereof, preparation method and application | |
| CN107308466A (en) | With tumor vascular targeted polypeptide, molecular probe and its preparation method and application | |
| CN109705193B (en) | Radiolabelled tEB-TMTP1 compound and preparation method and application thereof | |
| CN108434469A (en) | A kind of HER2 affinities body68Ga markers and preparation method thereof, application | |
| US20200078478A1 (en) | Structural molecule of peptide derivative for PSMA-targeting radiotherapy diagnosis and treatment | |
| CN107496943A (en) | The preparation method for the Dimer San A Cyclopeptide derivatives cancer of pancreas molecular probes that F 18 is marked | |
| CN115286693A (en) | Tumor targeting peptide aiming at carcinoembryonic antigen related cell adhesion molecule CEACAM6 and application thereof | |
| CN114075268A (en) | Affinity body targeting HER2 and application thereof | |
| CN104447955B (en) | A kind of polypeptide combined with PSMA film outskirt targetings and its application | |
| Pacak et al. | Diagnostic imaging of pheochromocytoma | |
| CN107021998B (en) | Positron nuclide labeled polypeptide for tumor imaging |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180320 Termination date: 20180911 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |