CN106674304B - A kind of glycosyl amino-acid compound and its preparation method and application of Value linear label - Google Patents
A kind of glycosyl amino-acid compound and its preparation method and application of Value linear label Download PDFInfo
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- CN106674304B CN106674304B CN201611111598.7A CN201611111598A CN106674304B CN 106674304 B CN106674304 B CN 106674304B CN 201611111598 A CN201611111598 A CN 201611111598A CN 106674304 B CN106674304 B CN 106674304B
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Abstract
The invention discloses a kind of glycosyl amino-acid compound and its preparation method and application of Value linear label, the chemical expression of the compound be [18F]FDGlyNHPHe.With radioactivity 2- [18F] F- fluorodeoxyglucose ([18F]-FDG) and p-Aminophenylalanine (NH2PHe) the glycosyl amino-acid compound that the radioactivity Value linear marks is prepared in reaction in acid condition.The chemical stability and biological property of the compound are good, chemical purity is high, it is simple to prepare, have the advantages that tumor uptake is high, inflammation absorbs that the targets such as low, tumour/muscle, tumour/blood, tumour/brain, the tumour/heart, tumour/inflammation/non-target ratio is good, is a kind of novel tumor imaging agent for having application value.
Description
Technical field
The present invention relates to a kind of glycosyl amino-acid compounds and its preparation method and application of Value linear label, belong to radiation
Property pharmaceutical chemistry and clinical nuclear medicine field.
Background technique
Positron emission tomography (PET) technology is the important means of the diagnosing tumor based on molecular level, is obtained
Clinical extensive use and affirmative.2- [18F]-fluorodeoxyglucose (18F labeled 2-fluoro-2-deoxy-D-
Glucose, 18F-FDG) it is the clinically PET imaging agent of most widely used, irreplaceable tumour glucose metabolism at present.So
And 18F-FDG using glucose metabolism as the imaging of the brain tumor of energy substrate, tumour and inflammation in terms of face
There are still some limitations in bed application.In order to improve diagnosing tumor efficiency, specificity and reduce rate of missed diagnosis, many scholars are from swollen
Proliferation, metabolism and apoptosis of tumor etc. are many-sided to constantly search for and researches and develops different molecular imaging probes to disclose the spy of tumour
Property, to provide more valuable information for clinic diagnosis.Tumour cell is compared with normal cell in addition to abnormal glucose metabolism
Except quickening, a large amount of research confirms that various malignant tumor tissues show amino acid transporter expression and increase, amino acid generation
Thanking to PET imaging is clinically important supplement of certain tumours in conventional 18F-FDG localization diagnosis.Currently, 18F-FDG PET points
Son imaging has irreplaceable tumour diagnosis and treatment advantage in clinic, and research and development retain 18F-FDG effective efficiency group, while can also be real
The double targeted drugs of multiple metabolism of existing amino acid metabolism diagnosis, to improve diagnosing tumor efficiency, reduce fail to pinpoint a disease in diagnosis and the generation of mistaken diagnosis,
And the increase that can avoid multiple PET imaging bring dose of radiation has great importance.In view of tumour cell to glucose, ammonia
Corresponding transporter expresses the biological property increased in the abnormal hypermetabolism feature and tumour cell of the energy matters such as base acid,
The present invention prepares the glycosyl amino acid compound of novel Value linear label by effective condensation of 18F-FDG and amino acids
Object remains the effective efficiency group of 18F-FDG and amino acid, and it is more which is used as the more excellent tumour of close tumor performance
It is metabolized class imaging agent again, is one of the important topic that current radio drug field needs to solve.
Summary of the invention
The present invention is intended to provide a kind of chemical purity is high, stability is good, biological property is good, it is simple to prepare, is applied to tumour
The glycosyl amino-acid compound of the Value linear label in positron e mission computed tomography field.The present invention also provides this
The preparation method and application of compound.
The present invention provides a kind of Value linear label glycosyl amino-acid compound, biomolecule expressions be [18F]
FDGlyNHPHe: its structural formula is as follows:
Wherein: [18F] FDGlyNHPHe be by 2- [18F] F- fluorodeoxyglucose ([18F]-FDG) and p-aminophenyl
Alanine (NH2PHe) 4 bit aminos in structure on phenyl ring connect to obtain.Chemical equation are as follows:
Further, the glycosyl amino-acid compound of Value linear label, [18F] deoxyglucose in FDGlyNHPHe
There are two kinds of tautomeric structures of ring type or chain type for the structure of base.
The present invention provides above-mentioned Value linear label glycosyl amino-acid compound preparation method, with radioactivity 2- [18F]
F- fluorodeoxyglucose [18F]-FDG with to phenalgin alanine NH2PHe reacts in acid condition, and radiation is prepared in wet process
Property Value linear label glycosyl amino-acid compound, comprising the following steps:
A, by 0.1-5mL 3.7MBq~740MBq's18F-FDG injection is set in closed container, and the second of 0.1-5mL is added
Nitrile, and the method through depressurizing azeotropic drying removes18Moisture in F-FDG injection；
B, the mixed solution of the first alcohol and water of the p-Aminophenylalanine of 0.1mg~10mg is then added in a reservoir, with
And 1 the μ of μ l~100 l acid solution, container sealing after under the conditions of 40 DEG C~100 DEG C react 10~60min；
C, finally step b acquired solution is directly purified through preparative high-performance liquid chromatographic.
The ratio of first alcohol and water is 100:0-0:100 in the mixed solution of first alcohol and water in above-mentioned steps b；The step b
The total volume of the mixed solution of middle first alcohol and water is 0.1-5m；In the step b acid can be acetic acid, formic acid, propionic acid, butyric acid,
Trifluoroacetic acid, hydrochloric acid, phosphoric acid, sulfuric acid, acetate buffer solution, phosphate buffer solution, appointing in citrate buffer solution
One kind is, it is preferable to use acetic acid.
The present invention provides another preparation method, with radioactivity 2- [18F] F- fluorodeoxyglucose [18F]-FDG with
To phenalgin alanine NH2PHe reacts in acid condition, and dry process obtains the glycosyl amino acidification of radioactivity Value linear label
Close object, comprising the following steps:
A, by 0.1-5mL 3.7MBq~740MBq's18F-FDG injection is set in closed container, at the same be added 0.1mg~
The acid solution of the p-Aminophenylalanine of 10mg and 1 μ of μ l~100 l；
B, 0.1-5mL acetonitrile is then added, and is removed through the method for negative pressure azeotropic drying18Moisture in F-FDG injection,
After moisture is evaporated, 10~60min is reacted under the conditions of 40 DEG C~100 DEG C after container sealing；
C, finally step b acquired solution is directly purified through preparative high-performance liquid chromatographic.
Acid can be acetic acid, formic acid, propionic acid, butyric acid, trifluoroacetic acid, hydrochloric acid, phosphoric acid, sulfuric acid, acetate in above-mentioned steps a
Any one of buffer solution, phosphate buffer solution, citrate buffer solution are, it is preferable to use acetic acid.
The present invention provides the glycosyl amino-acid compounds of above-mentioned Value linear label to prepare in radiopharmaceutical chemistry field
Purposes in tumor developer, the tumour are breast cancer, lung cancer, hepatocellular carcinoma, prostate cancer, brain tumor, lung cancer, gastric cancer, first
Shape gland cancer, colorectal cancer it is any.
Beneficial effects of the present invention:
(1) chemical reagent that the present invention uses is commercial goods, from a wealth of sources, is easy to get；
(2) present invention with radioactivity 2- [18F] F- fluorodeoxyglucose ([18F]-FDG) and p-Aminophenylalanine
(NH2PHe) in acid condition reaction be prepared the radioactivity Value linear label glycosyl amino-acid compound [18F]
FDGlyNHPHe is a kind of novel multiple metabolic imaging agent of tumour, realizes and introduce radioactive Value linear on amino acid,
It can be used for positron e mission computed tomography (PET)；
(3) prepare by the method for the invention [18F] FDGlyNHPHe has the characteristics that chemical purity is high, biological property is good；
(4) with [18F] FDG compares, and has better tumor-targeting, it can be used for becoming the novel multiple metabolism of tumour
Imaging agent.
Specific embodiment
The present invention is further illustrated below by embodiment, but is not limited to following embodiment.
Embodiment 1: wet process prepare [18F] FDGlyNHPHe's the preparation method is as follows:
By 0.5mL 37MBq's18F-FDG injection is set in closed container, and 2mL acetonitrile, azeotropic under negative pressure is added in two portions
It is dry, be then added in this embodiment the first alcohol and water of the p-Aminophenylalanine of 1.0mg mixed liquor (0.5mL methanol and
0.05mL water) and 50 μ l acetic acid, container sealing after react 30min under the conditions of 100 DEG C；Finally reaction solution is directly carried out
Preparative high performance liquid chromatography is purified.The condition of preparative high performance liquid chromatography are as follows: amino prepare column (250mm ×
10mm), mobile phase is methanol: water=9:1,3mL/min, UV=254nm.The fraction between 10-17min is collected, solution is steamed
Be added after dry after PBS or physiological saline be diluted dissolution obtain [18F] FDGlyNHPHe injection, cross sterilised membrane filter after to
With.
Embodiment 2: dry process [18F] FDGlyNHPHe's the preparation method is as follows:
By 0.5mL 37MBq's18F-FDG injection is set in closed container, while the p-Aminophenylalanine of 1.0mg is added
With the acetic acid of 50 μ l, 2mL acetonitrile, azeotropic drying under negative pressure, after solution is evaporated, in 80 DEG C of items after container sealing is added in two portions
30min is reacted under part；Reaction solution is directly finally carried out to preparative high performance liquid chromatography to purify.Preparative efficient liquid phase
The condition of chromatography are as follows: amino prepares column (250mm × 10mm), and mobile phase is methanol: water=9:1,3mL/min, UV=254nm.
Collect 10-17min between fraction, after solution is evaporated be added PBS be diluted dissolution obtain [18F] FDGlyNHPHe note
Liquid is penetrated, is crossed after sterilised membrane filter for use.
Detection shows: [18F] FDGlyNHPHe is by HPLC identification, and radiochemical purity is greater than 99%, and at 37 DEG C
Radiochemicsl purity is unchanged after placing 4 hours, and stability is good.Putting yield is 15~50% after decay correction.
Will [18F] FDGlyNHPHe and [18F] FDG is compared in normal mouse vivo biodistribution distributed data, the results are shown in Table
1:
Table 1. [18F] FDGlyNHPHe normal mouse vivo biodistribution distributed data (%ID/g ± sd, n=3) and with
[18F] FDG bio distribution (%ID/g ± sd, n=3) performance comparison
Will [18F] FDGlyNHPHe and [18F] FDG is in S-180 lotus knurl and aseptic inflammation bimodel mouse vivo biodistribution
Distributed data is compared, and the results are shown in Table 2:
Table 2. [18F] FDGlyNHPHe with [18F] FDG life in S-180 lotus knurl and aseptic inflammation bimodel Mice Body
Object distributed data (%ID/g ± sd, n=3) comparison
*: referring to the intake ratio of the two
Experiment detection show [18F] FDGlyNHPHe performance it is as follows:
1.[18F] FDGlyNHPHe lipid measurement
It takes 1.0mL phosphate buffer solution (pH=7.2,0.025M) in 10mL centrifuge tube, is added in centrifuge tube
1.0mL n-octyl alcohol and 740KBq [18F] FDGlyNHPHe injection, it sufficiently shakes up after covering plug, is centrifuged at 12000r/min
5min.Then 50 μ L are taken out from organic phase and water phase respectively, measure respective radiocounting, the radioactivity of organic phase and water phase
The ratio between counting is distribution coefficient P, and the fat-soluble size of compound is usually measured with log P, measure [18F] FDGlyNHPHe
Log P value is -2.11, it can be seen that [18F] FDGlyNHPHe is water-soluble substances.
2.[18F] FDGlyNHPHe vitro stability measurement
Will [18F] FDGlyNHPHe PBS solution, [18F] PBS solution of FDGlyNHPHe and the mixed liquor of fetal calf serum
It is incubated for jointly in 37 DEG C, it is activation that its is measured by sampling respectively at different time (5min, 30min, 60min, 120min, 240min)
Purity is learned, the experimental results showed that [18F] FDGlyNHPHe PBS injection and its with the co-culture media of fetal calf serum to place 4 small
When after radiochemical purity be still greater than 95%, illustrate [18F] FDGlyNHPHe is in PBS solution and fetal calf serum under the conditions of 37 DEG C
Vitro stability is good, is suitable for clinical application and needs.
Claims (9)
1. a kind of glycosyl amino-acid compound of Value linear label, it is characterised in that: its biomolecule expressions be [18F]
FDGlyNHPHe: its structural formula is as follows:
Wherein: [18F] FDGlyNHPHe be by 2- [18F] F- fluorodeoxyglucose [18F]-FDG and p-Aminophenylalanine
NH24 bit aminos in PHe structure on phenyl ring connect to obtain；The glycosyl amino-acid compound of the Value linear label can radiate
Tumor developer is prepared in property field of medicinal chemistry.
2. the glycosyl amino-acid compound of Value linear label according to claim 1, it is characterised in that: [18F]
There are two kinds of tautomeric structures of ring type or chain type for the structure of deoxyglucose glycosyl in FDGlyNHPHe.
3. a kind of preparation method of the glycosyl amino-acid compound of Value linear label of any of claims 1 or 2, it is characterised in that:
With radioactivity 2- [18F] F- fluorodeoxyglucose [18F]-FDG with to phenalgin alanine NH2PHe reacts in acid condition, wet
The glycosyl amino-acid compound of radioactivity Value linear label is prepared in method, comprising the following steps:
A, by 0.1-5mL 3.7MBq ~ 740MBq's18F-FDG injection is set in closed container, and the acetonitrile of 0.1-5mL is added, and
The method for being depressurized azeotropic drying removes18Moisture in F-FDG injection；
B, then in a reservoir be added 0.1mg ~ 10mg p-Aminophenylalanine first alcohol and water mixed solution and 1 μ l ~
The acid of 100 μ l reacts 10 ~ 60min after container sealing under the conditions of 40 DEG C ~ 100 DEG C；
C, finally step b acquired solution is directly purified through preparative high-performance liquid chromatographic.
4. the preparation method of the glycosyl amino-acid compound of Value linear label according to claim 3, it is characterised in that: institute
The ratio for stating first alcohol and water in the mixed solution of first alcohol and water in step b is 100:0-0:100；First alcohol and water in the step b
Mixed solution total volume be 0.1-5mL.
5. a kind of preparation method of the glycosyl amino-acid compound of Value linear label of any of claims 1 or 2, it is characterised in that:
With radioactivity 2- [18F] F- fluorodeoxyglucose [18F]-FDG with to phenalgin alanine NH2PHe reacts in acid condition, does
The glycosyl amino-acid compound of radioactivity Value linear label is prepared in method, comprising the following steps:
A, by 0.1-5mL 3.7MBq ~ 740MBq's18F-FDG injection is set in closed container, while being added 0.1mg ~ 10mg's
The acid solution of p-Aminophenylalanine and 1 μ of μ l ~ 100 l；
B, 0.1-5mL acetonitrile is then added, and is removed through the method for negative pressure azeotropic drying18Moisture in F-FDG injection, moisture
After being evaporated, 10 ~ 60min is reacted under the conditions of 40 DEG C ~ 100 DEG C after container sealing；
C, finally step b acquired solution is directly purified through preparative high-performance liquid chromatographic.
6. the preparation method of the glycosyl amino-acid compound of the label of the Value linear according to claim 3 or 5, it is characterised in that:
The acid is acetic acid, formic acid, propionic acid, butyric acid, trifluoroacetic acid, hydrochloric acid, phosphoric acid, sulfuric acid, acetate buffer solution, phosphate-buffered
Any one of solution, citrate buffer solution.
7. the preparation method of the glycosyl amino-acid compound of Value linear label according to claim 6, it is characterised in that: institute
Stating acid is acetic acid.
8. a kind of glycosyl amino-acid compound of Value linear label of any of claims 1 or 2 is in radiopharmaceutical chemistry field
Prepare the purposes in tumor developer.
9. application according to claim 8, it is characterised in that: the tumour is breast cancer, lung cancer, hepatocellular carcinoma, forefront
Gland cancer, brain tumor, lung cancer, gastric cancer, thyroid cancer, colorectal cancer it is any.
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| CN109979598B (en) * | 2019-04-02 | 2021-03-02 | 煋晟医疗技术(杭州)有限公司 | By human body18F-FDG PET data analysis tissue DNA hydroxymethyl background and application |
| CN110483278A (en) * | 2019-08-06 | 2019-11-22 | 唐刚华 | The fluoro- 3- of 2,2- bis-18F- fluoropropionic acid and its synthetic method and application |
| CN111362828A (en) * | 2020-03-30 | 2020-07-03 | 山西医科大学 | A kind of18F-labeled fluoropropionylated ornithine as well as preparation method and application thereof |
| CN113264967B (en) * | 2021-05-17 | 2023-04-18 | 江苏省原子医学研究所 | Programmed death ligand-1 targeted compound and preparation method and application thereof |
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| US20150291647A1 (en) * | 2013-10-24 | 2015-10-15 | The Regents Of The University Of California | Compositions and Methods for 18F-Fluorodeoxyglycosylamines |
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| CN102464690A (zh) * | 2010-11-09 | 2012-05-23 | 医影生物医药科技(上海)有限公司 | 2’，3’-二脱氧-2’-[氟-18]氟腺苷化合物及其制备方法 |
| US20150291647A1 (en) * | 2013-10-24 | 2015-10-15 | The Regents Of The University Of California | Compositions and Methods for 18F-Fluorodeoxyglycosylamines |
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