CN104725473B - A kind of [18F] AlF marks PET polypeptide probes and preparation method thereof - Google Patents
A kind of [18F] AlF marks PET polypeptide probes and preparation method thereof Download PDFInfo
- Publication number
- CN104725473B CN104725473B CN201410460832.1A CN201410460832A CN104725473B CN 104725473 B CN104725473 B CN 104725473B CN 201410460832 A CN201410460832 A CN 201410460832A CN 104725473 B CN104725473 B CN 104725473B
- Authority
- CN
- China
- Prior art keywords
- alf
- tmtp1
- nota
- pet
- mark
- 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.)
- Expired - Fee Related
Links
Landscapes
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Peptides Or Proteins (AREA)
Abstract
The invention discloses it is a kind of [18F] AlF marks PET polypeptide probes and preparation method thereof, including the TMTP1 polypeptides and NOTA to link together, its structural formula be as follows：.The present invention designs G TMTP1 polypeptides, it is not influenceed its bioactivity, and use after radioactive label by increasing a glycine to TMTP118F is radionuclide, utilize [18F] AlF NOTA method mark G TMTP1 polypeptides, obtained [18F] AlF mark PET polypeptide probes there are excellent pharmacokinetics, its background clearance rate is fast, liver intake it is low, internal stability is good, tumor locus intake is high, can be used for the diagnosis or therapeutic evaluation of the malignant tumour of high transfer with the tumour of the high transfer of specific diagnosis.
Description
Technical field
The invention belongs to radio-labelled compound field, and in particular to a kind of [18F] AlF mark PET polypeptide probes
And preparation method thereof.
Background technology
According to the development trend of current cancer, the year two thousand twenty whole world cancer morbidity will be more every than increase by 50% now, the whole world
Year newly-increased cancer patient's number is up to 15,000,000 people, and (World Health Organization delivers in the recent period《World's cancer report》).To tumour
Early detection, early treatment are to reduce cancer death to lead maximally efficient method, at present in developing country, 80% cancer
Disease patient is just found in cancer of late stage.Metastases are the important biomolecule features of malignant tumour, and it is oncotherapy
The main reason for failure, and the main cause that tumor patient is dead.In the tumor patient made a definite diagnosis for the first time, 70% or so patient can be with
By operation, adjuvant radiotherapy or chemotherapy means symptom management, but some patient tumorigenic can recur or turn
Move, 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 can be carried out in early stage to cancer
Diagnosis, and the grade malignancy and transfer ability of tumour are determined, then formulate corresponding operation, radiotherapy or chemotherapy regimen, so that it may
To improve the survival rate of patient, and improve the life quality of patient.Imaging method currently used for cancer diagnosis mainly has X- to penetrate
Line (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 can not detect tumor group on a molecular scale
The physiological change knitted, it is impossible to determine the grade malignancy of tumour, and for frequently-occurring tumour (such as breast cancer, liver cancer, prostate
Cancer etc.) specificity and sensitivity it is poor, therefore we need badly exploitation it is a kind of it is new can specificity differentiate malignancy
Radioactive tracer, he can realize the early diagnosis to malignant tumour, and can detect growth and the tumour of tumour
Reaction to therapeutic scheme.
Positron emission computed tomography (Positron emission tomography, PET) has due to it
The features such as sensitive, accurate and registration, shown in diagnosis and guiding treatment tumour, coronary heart disease and brain diseases etc.
Go out unique superiority.PET technologies have three key elements：PET probes, signal amplification, highly sensitive detector, wherein PET are visited
Pin is mostly important, and it is the primary premise for realizing signal amplification and highly sensitive detection, at present clinically to diagnosing tumor using most
Wide be [18F] FDG, but because of the specific low of it, the limitation such as false positive is easily caused, it can not fully meet clinic
It is required that in addition [18F] whether FDG there is transfer ability can not also make accurate judgement tumour, it is therefore new18F mark molecules
Image probe is still urgently developed.
The exploitation of polypeptide PET probes is an important direction, has had numerous studies to be directed to vasoactive at present
Peptide (Vasoactive intestinal peptide, VIP), Octreotide, bombesin, RGD, VEGF, TNF, gastrin, life
The polypeptides such as long plain inhibin carry out radioactive label research (M.Fani, H.R. Maecke, S.M.Okarvi, Radiolabeled
peptides:valuable tools for the detection and treatment of cancer,
Theranostics,2012,2(5):481-501), but there has been no can really be widely applied to clinic so far18F is marked
Remember polypeptide molecular image probe, it is quicker to flag condition main reason is that polypeptide possesses substantial amounts of active function groups
Feel, the polypeptide active change after progress radioactive label is bigger, and the pharmacokinetics in probe body after mark are undesirable, example
As liver absorbs, higher, internal stability is poor, tumor uptake value is low.
The content of the invention
It is an object of the invention to overcome prior art defect, there is provided a kind of [18F] AlF mark PET polypeptide probes.
Another object of the present invention is to provide it is above-mentioned [18F] AlF mark PET polypeptide probes preparation method
The concrete technical scheme of the present invention is as follows：
A kind of [18F] AlF marks PET polypeptide probes, including the TMTP1 polypeptides and NOTA to link together, its structure
Formula is as follows：
It is a kind of it is above-mentioned [18F] AlF mark PET polypeptide probes preparation method, comprise the following steps：
(1) G-TMTP1 is dissolved in DMF, adds NOTA-NHS ester, then added DIEA and 8.0- is arrived into pH regulations
8.5, it is stirred overnight at room temperature, is isolated and purified through HPLC, collect the cut of target product, is freezed after merging, obtain NOTA-G-TMTP1,
The reaction equation of the step is as follows：
(2) nuclear reaction is used on cyclotron18O(p,n)18F be made [18F]F-, it is then enriched with Sep-Park
On light QMA posts, eluted with deionized water to remove metal impurities ion of the absorption on QMA posts, eluted with physiological saline,
Obtain 925~1850MBq's (25~150mCi)18F normal saline solutions；
(3) AlCl is added into reaction vessel3With pH=4.0 sodium-acetate buffer, then add step (2) and be made
's18F-Normal saline solution, uniformly mixing adds NOTA-G-TMTP1 deionized water solution, mixture shake up after
80~110 DEG C of 10~30min of reaction, are cooled to normal temperature, its mark rate are determined with HPLC, obtain [18F]AlF-NOTA-G-TMTP1
Reaction solution；
(4) by step (3) prepare [18F] AlF-NOTA-G-TMTP1 reaction solutions are slowly injected into the Sep- that activated in advance
Pak C18 posts, then water-solubility impurity is removed with distillation water wash, ethanol rinse, gained leacheate physiological saline are used after drying
Ethanol content is diluted to less than 10%, its retention time and top coal drawing is determined with HPLC, observes whether its appearance character is colourless
Clear liquid, produce it is described [18F] AlF mark PET polypeptide probes.
In a preferred embodiment of the invention, the step (1) is：10mg G-TMTP1 are dissolved in 1mL DMF
In, 15mg NOTA-NHS ester are added, DIEA is then added and 8.0-8.5 is arrived into pH regulations, be stirred overnight at room temperature, through HPLC
Isolate and purify, collect the cut of target product, freezed after merging, obtain NOTA-G-TMTP1.
It is further preferred that the first mobile phase is that 0.1% trifluoroacetic acid is water-soluble during step (1) HPLC is isolated and purified
Liquid, the second mobile phase are 0.1% trifluoroacetic acid acetonitrile, condition of gradient elution, 0~10min, 95% the first mobile phase；10~
25min, 95%~15% the first mobile phase；25~40min, 15% the first mobile phase；The flow velocity of mobile phase is 5mL/
Min, Detection wavelength 220nm.
In a preferred embodiment of the invention, the step (2) is：Nuclear reaction is used on cyclotron18O
(p,n)18F be made [18F]F-, it is then enriched with Sep-Park light QMA posts, is eluted with 5mL deionized waters and inhaled with removing
The metal impurities ion being attached on QMA posts, eluted with 0.2~1mL physiological saline, obtain 925~1850MBq (25~150mCi)
's18F normal saline solutions.
In a preferred embodiment of the invention, the step (3) is：10 μ L are added into reaction vessel
2nmol/L AlCl3With 300 μ L 0.1mol/L pH=4.0 sodium-acetate buffer, 100 μ L steps (2) system is then added
18F-Normal saline solution, uniformly mix 3min, add 1000 μ L 1mg/mL NOTA-G-TMTP1 deionization
The aqueous solution, mixture shake up after 80~110 DEG C react 10~30min, be cooled to normal temperature, determine its mark rate with HPLC, obtain
[18F] AlF-NOTA-G-TMTP1 reaction solutions.
In a preferred embodiment of the invention, the step (4) is：By step (3) prepare [18F]AlF-
NOTA-G-TMTP1 reaction solutions are slowly injected into the Sep-Pak C18 posts activated in advance, then remove water with 20mL distillation water wash
Solubility impurity, it is less than 10% with 800 μ L ethanol rinses, gained leacheate normal saline dilution to ethanol content after drying, uses
HPLC determines its retention time and top coal drawing, observes whether its appearance character is achromaticity and clarification transparency liquid, produce it is described [18F]
The PET polypeptide probes of AlF marks.
The beneficial effects of the invention are as follows：
1st, the present invention designs G-TMTP1 polypeptides, it is being passed through radioactivity mark by increasing a glycine to TMTP1
After note, its bioactivity is not influenceed, and use18F is radionuclide, utilize [18F] AlF-NOTA method mark G-
TMTP1 polypeptides, obtained [18F] AlF mark PET polypeptide probes there are excellent pharmacokinetics, its background clearance rate
It hurry up, liver intake is low, and internal stability is good, and tumor locus intake is high, can be with the tumour of the high transfer of specific diagnosis, Ke Yiyong
In the diagnosis or therapeutic evaluation of the malignant tumour of height transfer；
2nd, of the invention [18F] AlF mark PET polypeptide probes, utilize the biology of its selectively targeted high metastatic tumour
Characteristic, high metastatic tumour can be early diagnosed；
3rd, of the invention [18F] AlF mark PET polypeptide probes use Al-18F labeling method is marked, mark
Note method is simple, it is easy to accomplish Fully automated synthesis, mark yield are high, it is not necessary to which HPLC is purified, this radiation shorter to half-life period
It is extremely important for property nucleic, advantageously in radio-labelled compound business application in clinical expansion.
Brief description of the drawings
Fig. 1 be the specific embodiment of the invention in [18F] AlF mark PET polypeptide probes determine its putting using HPLC
The result of purity；
Fig. 2 be the specific embodiment of the invention in [18F] AlF mark PET polypeptide probes in tumor-bearing mice (B16)
MicroPET images coronal-plane tomograph；
Fig. 3 be the specific embodiment of the invention in [18F] AlF mark PET polypeptide probes in tumor-bearing mice (4T1)
MicroPET images coronal-plane tomograph.
Embodiment
It is further detailed and describes below by way of embodiment combination accompanying drawing technical scheme.
(1) 10mg G-TMTP1 (customizing in polypeptide Science and Technology Ltd. of the U.S.) are dissolved in 1mL DMF (dimethyl formyls
Amine) in, add 15mg NOTA-NHS ester (Isosorbide-5-Nitrae-oxalic acid-Isosorbide-5-Nitrae, 7- 7-triazacyclononane -7- acetic acid-N- hydroxyl amber cypresses
Imide ester, buy in CheMatech companies), then add DIEA (DIPEA) and 8.0- is arrived into pH regulations
8.5, it is stirred overnight at room temperature, is isolated and purified through HPLC, collect the cut of target product, is freezed after merging, by mass spectral analysis
(MS,m/z:957.2 ([M+H]+) after confirmation, NOTA-G-TMTP1 is obtained, the first mobile phase is during above-mentioned HPLC is isolated and purified
0.1% trifluoroacetic acid aqueous solution, the second mobile phase are 0.1% trifluoroacetic acid acetonitrile, condition of gradient elution, 0~10min, 95%
The first mobile phase；10~25min, 95%~15% the first mobile phase；25~40min, 15% the first mobile phase；Stream
The flow velocity of dynamic phase is 5mL/min, Detection wavelength 220nm；
(2) nuclear reaction is used on cyclotron18O(p,n)18F be made [18F]F-, it is then enriched with Sep-Park
On light QMA posts, eluted with 5mL deionized waters to remove metal impurities ion of the absorption on QMA posts, given birth to 0.2~1mL
Salt water is managed, obtains 925~1850MBq's (25~150mCi)18F normal saline solutions；
(3) 10 μ L 2nmol/L AlCl is added into 1.5mL EP pipes3With 300 μ L 0.1mol/L pH=4.0 vinegar
Sour sodium buffer solution, it is obtained then to add 100 μ L steps (2)18F-Normal saline solution, uniformly mix 3min, add
1000 μ L 1mg/mL NOTA-G-TMTP1 deionized water solution, mixture shake up after 80~110 DEG C react 10~
30min, normal temperature is cooled to, its mark rate is determined with HPLC, obtain [18F] AlF-NOTA-G-TMTP1 reaction solutions；
(4) by step (3) prepare [18F] AlF-NOTA-G-TMTP1 reaction solutions are slowly injected into the Sep- that activated in advance
Pak C18 posts, then water-solubility impurity is removed with 20mL distillation water wash, used after drying with 800 μ L ethanol rinses, gained leacheate
Normal saline dilution to ethanol content is less than 10%, determines its retention time and top coal drawing with HPLC, observing its appearance character is
No is achromaticity and clarification transparency liquid, produce it is described [18F] AlF marks PET polypeptide probes, its structural formula is as follows：
As shown in figure 1, the putting yield about 10~40% through decay correction, radiochemicsl purity ＞ 95%；
(5) lotus B16 tumours nude mice MicroPET is imaged：Injected respectively through tail vein under B16 tumor bearing nude mice narcosises
0.1mL[18F] AlF marks PET polypeptide probes (7.4MBq) and 30min carries out static microPET/CT tomographies and swept after injection
Retouch (Siemens Inveon), pass through three-dimensional order subset maximum expected value method (ordered subset after IMAQ
Expectation maximization with three-dimensional resolution recovery, OSEM3D) enter
Row Space Reconstruction.In the coronal-plane imaging figure of decay correction, tumour, normal structure are irised out with ASI Pro 5.2.4.0 softwares
With the area-of-interest (region of interest, ROI) of organ, tumour/non-tumour (T/NT) in tumor model is calculated
Radioactivity ratio, tumour/muscle=4.31 ± 0.63, in addition, its background clearance rate is fast, liver intake is low, has excellent
Internal pharmacokinetics property (as shown in Figure 2).
(6) lotus 4T1 tumours nude mice MicroPET is imaged：Injected respectively through tail vein under 4T1 tumor bearing nude mice narcosises
0.1mL[18F] AlF marks PET polypeptide probes (7.4MBq) and 30min carries out static microPET/CT tomographies after injection
Scan (Siemens Inveon), pass through three-dimensional order subset maximum expected value method (ordered subset after IMAQ
Expectation maximization with three-dimensional resolution recovery, OSEM3D) enter
Row Space Reconstruction.In the coronal-plane imaging figure of decay correction, tumour, normal structure are irised out with ASI Pro 5.2.4.0 softwares
With the area-of-interest (region of interest, ROI) of organ, tumour/non-tumour (T/NT) in tumor model is calculated
Radioactivity ratio, tumour/muscle=4.87 ± 0.43, in addition, its background clearance rate is fast, liver intake is low, has excellent
Internal pharmacokinetics property (as shown in Figure 3).
The foregoing is only a preferred embodiment of the present invention, therefore can not limit the scope that the present invention is implemented according to this, i.e.,
The equivalent changes and modifications made according to the scope of the claims of the present invention and description, all should still it belong in the range of the present invention covers.
Claims (7)
1. a kind of [18F] AlF mark PET polypeptide probes, it is characterised in that：Including the TMTP1 polypeptides that link together and
NOTA, its structural formula are as follows：
2. described in a kind of claim 1 [18F] AlF mark PET polypeptide probes preparation method, it is characterised in that：Including such as
Lower step：
(1) G-TMTP1 is dissolved in DMF, adds NOTA-NHS ester, then added DIEA and 8.0-8.5, room are arrived into pH regulations
Temperature is stirred overnight, and is isolated and purified through HPLC, collects the cut of target product, is freezed after merging, is obtained NOTA-G-TMTP1；
(2) nuclear reaction is used on cyclotron18O(p,n)18F be made [18F]F-, it is then enriched with Sep-Park light QMA
On post, eluted with deionized water to remove metal impurities ion of the absorption on QMA posts, eluted with physiological saline, obtain 925~
1850MBq's18F normal saline solutions；
(3) AlCl is added into reaction vessel3With pH=4.0 sodium-acetate buffer, it is obtained then to add step (2)18F gives birth to
Manage saline solution, uniformly mixing, add NOTA-G-TMTP1 deionized water solution, mixture shake up after at 80~110 DEG C
10~30min is reacted, normal temperature is cooled to, its mark rate is determined with HPLC, obtain [18F] AlF-NOTA-G-TMTP1 reaction solutions；
(4) by step (3) prepare [18F] AlF-NOTA-G-TMTP1 reaction solutions are slowly injected into the Sep-Pak that activated in advance
C18 posts, then water-solubility impurity is removed with distillation water wash, ethanol rinse, gained leacheate normal saline dilution are used after drying
It is less than 10% to ethanol content, determines its retention time and top coal drawing with HPLC, observe whether its appearance character is achromaticity and clarification
Transparency liquid, produce it is described [18F] AlF mark PET polypeptide probes.
3. described in a kind of claim 1 as claimed in claim 2 [18F] AlF mark PET polypeptide probes preparation method,
It is characterized in that：The step (1) is：10mg G-TMTP1 are dissolved in 1mL DMF, add 15mg NOTA-NHS ester,
Then add DIEA and 8.0-8.5 arrived into pH regulations, be stirred overnight at room temperature, isolated and purified through HPLC, collect the cut of target product,
Freezed after merging, obtain NOTA-G-TMTP1.
4. described in a kind of claim 1 as claimed in claim 3 [18F] AlF mark PET polypeptide probes preparation method,
It is characterized in that：The first mobile phase is 0.1% trifluoroacetic acid aqueous solution during step (1) HPLC is isolated and purified, and second flows
It is mutually 0.1% trifluoroacetic acid acetonitrile, condition of gradient elution, 0~10min, 95% the first mobile phase；10~25min, 95%~
15% the first mobile phase；25~40min, 15% the first mobile phase；The flow velocity of mobile phase is 5mL/min, and Detection wavelength is
220nm。
5. described in a kind of claim 1 as claimed in claim 2 [18F] AlF mark PET polypeptide probes preparation method,
It is characterized in that：The step (2) is：Nuclear reaction is used on cyclotron18O(p,n)18F be made [18F]F-, it is then enriched with
On Sep-Park light QMA posts, eluted with 5mL deionized waters to remove metal impurities ion of the absorption on QMA posts,
Eluted with 0.2~1mL physiological saline, obtain 925~1850MBq's18F normal saline solutions.
6. described in a kind of claim 1 as claimed in claim 2 [18F] AlF mark PET polypeptide probes preparation method,
It is characterized in that：The step (3) is：10 μ L 2nmol/L AlCl is added into reaction vessel3With 300 μ L 0.1mol/L
PH=4.0 sodium-acetate buffer, it is obtained then to add 100 μ L steps (2)18F normal saline solutions, uniformly mix 3min,
Add 1000 μ L 1mg/mL NOTA-G-TMTP1 deionized water solution, mixture at 80~110 DEG C reacts 10 after shaking up
~30min, is cooled to normal temperature, and its mark rate is determined with HPLC, obtain [18F] AlF-NOTA-G-TMTP1 reaction solutions.
7. described in a kind of claim 1 as claimed in claim 2 [18F] AlF mark PET polypeptide probes preparation method,
It is characterized in that：The step (4) is：By step (3) prepare [18F] AlF-NOTA-G-TMTP1 reaction solutions are slowly injected into thing
The Sep-Pak C18 posts first activated, then water-solubility impurity is removed with 20mL distillation water wash, drenched after drying with 800 μ L ethanol
Wash, gained leacheate normal saline dilution to ethanol content is less than 10%, and its retention time and top coal drawing are determined with HPLC, sees
Examine whether its appearance character is achromaticity and clarification transparency liquid, produce it is described [18F] AlF mark PET polypeptide probes.
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 CN104725473A (en) | 2015-06-24 |
| CN104725473B true 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) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 |
Citations (5)
| 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 |
| 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 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 (5)
| 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 |
| 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 |
| 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 |
|---|
| First 18F-labeled ligand for PET imaging of uPAR: In vivo studies in human prostate cancer xenografts;Morten Perssona等;《Nucl Med Biol》;20130731;第40卷(第5期);全文 * |
| PET imaging of tumor metastasis using 68Ga-labeled a novel tumor-homing peptide TMTP1;Jiyun Shi等;《J Nucl Med 》;20140531;第55卷(第supplement 1期);摘要 * |
| Targeting the prostate for destruction through a vascular address;Wadih Arap等;《PNAS》;20020228;第99卷(第3期);全文 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104725473A (en) | 2015-06-24 |
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 | |
| CN108434468B (en) | Radioiodinated protein binding ligand and application thereof | |
| CN112851637B (en) | PSMA inhibitor, compound, preparation method and application thereof | |
| Garai et al. | Limitations and pitfalls of 99mTc-EDDA/HYNIC-TOC (Tektrotyd) scintigraphy | |
| CN111905112A (en) | Polypeptide compound targeting PD-L1 and application thereof | |
| CN112898270B (en) | Diagnosis and treatment integrated PSMA inhibitor and compound, and preparation method and application thereof | |
| CN106581700B (en) | A kind of novel polypeptide radiopharmaceutical for targeting HER2 and its preparation method and application | |
| CN107353323A (en) | Al18PSMA targeted inhibition agent of F marks and preparation method and application | |
| CN111467510A (en) | Specific targeting radionuclide marker 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 | |
| WO2020238795A1 (en) | Rk polypeptide radiopharmaceutical targeting her2, and preparation method therefor | |
| TWI765195B (en) | Dual-targeted carbonic anhydrase ix complex and a contrast agent thereof | |
| CN117624278B (en) | Specific tumor diagnosis probe and imaging agent for targeting heat shock protein 90 | |
| CN107308466A (en) | With tumor vascular targeted polypeptide, molecular probe and its preparation method and application | |
| CN109045313B (en) | D-type polypeptide radiopharmaceutical targeting HER2 and preparation method thereof | |
| CN109705193B (en) | Radiolabelled tEB-TMTP1 compound and preparation method and application thereof | |
| CN114075268A (en) | Affinity body targeting HER2 and application thereof | |
| CN115286693A (en) | Tumor targeting peptide aiming at carcinoembryonic antigen related cell adhesion molecule CEACAM6 and application thereof | |
| CN104447955B (en) | A kind of polypeptide combined with PSMA film outskirt targetings and its application | |
| CN107496943A (en) | The preparation method for the Dimer San A Cyclopeptide derivatives cancer of pancreas molecular probes that F 18 is marked | |
| Pacak et al. | Diagnostic imaging of pheochromocytoma | |
| CN107312070A (en) | It is a kind of18PET polypeptide probes of F marks and preparation method thereof | |
| CN107674117B (en) | Preparation method of Cu-64 labeled Dimer-San A cyclic peptide derivative pancreatic cancer molecular probe |
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 | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180320 Termination date: 20180911 |