CN106674304A - Fluorine-18 marked sugar-based amino acid compound, as well as preparation method and application thereof - Google Patents
Fluorine-18 marked sugar-based amino acid compound, as well as preparation method and application thereof Download PDFInfo
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- CN106674304A CN106674304A CN201611111598.7A CN201611111598A CN106674304A CN 106674304 A CN106674304 A CN 106674304A CN 201611111598 A CN201611111598 A CN 201611111598A CN 106674304 A CN106674304 A CN 106674304A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K51/00—Preparations containing radioactive substances for use in therapy or testing in vivo
- A61K51/02—Preparations containing radioactive substances for use in therapy or testing in vivo characterised by the carrier, i.e. characterised by the agent or material covalently linked or complexing the radioactive nucleus
- A61K51/04—Organic compounds
- A61K51/0491—Sugars, nucleosides, nucleotides, oligonucleotides, nucleic acids, e.g. DNA, RNA, nucleic acid aptamers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Abstract
The invention discloses a fluorine-18 marked sugar-based amino acid compound, as well as a preparation method and application thereof. The chemical expression of the compound is [18F]FDGlyNHPHe. The fluorine-18 marked sugar-based amino acid compound is prepared by carrying out a reaction of radioactive 2-[18F]F-fludeoxyglucose ([18F]-FDG) and p-aminophenylalanine (NH2PHe) under the acidic condition. The compound has high chemical stability, high biological property and high chemical purity, is simple to prepare, has the advantages of high tumor intake, low inflammation intake, and good target/nontarget ratio of tumor/muscle, tumor/blood, tumor/brain, tumor/heart, tumor/inflammation and the like, and is a novel tumor imaging agent with popularization and application value.
Description
Technical field
The present invention relates to a kind of glycosyl amino-acid compound of Value linear labelling and its preparation method and application, belongs to radiation
Property pharmaceutical chemistry and clinical nuclear medicine field.
Background technology
Positron emission tomography (PET) technology is the important means based on the diagnosing tumor of molecular level, is obtained
The extensive application of clinic and affirmative.2- [18F]-fluorodeoxyglucose (18F labeled 2-fluoro-2-deoxy-D-
Glucose, 18F-FDG) be current clinically most widely used, irreplaceable tumor glucose metabolism PET developers.So
And 18F-FDG facing at aspects such as the Differential Diagnosiss of cerebral tumor imaging, tumor and inflammation with glucose metabolism as energy substrate
Some limitation are still suffered from bed application.In order to improve diagnosing tumor efficiency, specificity and reduce rate of missed diagnosis, many scholars are from swollen
The propagation of tumor, metabolism and apoptosis etc. are many-sided constantly searching for and research and develop different molecular imaging probes to disclose the spy of tumor
Property, to providing more valuable information for clinic diagnosis.Tumor cell is compared with normal cell except to abnormal glucose metabolism
Outside quickening, substantial amounts of research confirms that various malignant tumor tissues show amino acid transporter expression and increase, aminoacid generation
It is clinically important supplement of some tumors in conventional 18F-FDG localization diagnosises to thank to PET imagings.At present, 18F-FDG PET point
Son imaging has irreplaceable tumor diagnosis and treatment advantage clinical, and research and development retain 18F-FDG effective efficiency groups, while can also be real
The double targeted drugs of multiple metabolism of existing amino acid metabolism diagnosis, to improve diagnosing tumor efficiency, reduction fail to pinpoint a disease in diagnosis and mistaken diagnosis generation,
And the increase that multiple PET images the radiation dose for bringing can be avoided to have great importance.In view of tumor cell is to glucose, ammonia
The abnormal hypermetabolism feature of the energy matters such as base acid, and the biological property that corresponding transporter expression is increased in tumor cell,
The present invention prepares the glycosyl amino acid compound of new Value linear labelling by 18F-FDG and effective condensation of amino acidses
Thing, remains the effective efficiency group of 18F-FDG and aminoacid, the compound is used as into the more excellent tumor of close tumor performance many
Again metabolism class developer, is one of important topic that current radio drug world needs solution.
The content of the invention
The present invention is intended to provide a kind of chemical purity height, good stability, biological property is good, it is simple to prepare, be applied to tumor
The glycosyl amino-acid compound of the Value linear labelling in positron e mission computed tomography field.Present invention also offers should
The preparation method and application of compound.
The invention provides a kind of glycosyl amino-acid compound of Value linear labelling, its biomolecule expressions for [18F]
FDGlyNHPHe：Its structural formula is as follows：
Wherein：[18F] FDGlyNHPHe be by 2- [18F] F- fluorodeoxyglucose ([18F]-FDG) and p-aminophenyl
Alanine (NH2PHe) the 4 bit aminos connection in structure on phenyl ring is obtained.Chemical equation is：
Further, the glycosyl amino-acid compound of described Value linear labelling, [18F] deoxyglucose in FDGlyNHPHe
There are two kinds of tautomeric structures of ring type or chain type in the structure of base.
The invention provides the preparation method of the glycosyl amino-acid compound of above-mentioned Value linear labelling, with radioactivity 2- [18F]
F- fluorodeoxyglucose [18F]-FDG with to phenalgin alanine NH2PHe reacts in acid condition, and wet method prepares radiation
The glycosyl amino-acid compound of property Value linear labelling, comprises the following steps：
A, by 0.1-5mL 3.7MBq~740MBq's18F-FDG injection is put in hermetic container, adds the second of 0.1-5mL
Nitrile, and the method removing of Jing decompression azeotropic dryings18Moisture in F-FDG injection；
B and then the in a reservoir mixed solution of the first alcohol and water of the p-Aminophenylalanine of addition 0.1mg~10mg, with
And 1 μ l~100 μ l acid solution, container sealing after under the conditions of 40 DEG C~100 DEG C react 10~60min；
C, finally the direct Jing preparative high-performance liquid chromatographics of step b resulting solution are carried out into purification.
The ratio of first alcohol and water is 100 in the mixed solution of first alcohol and water in above-mentioned steps b:0-0:100；Step b
The cumulative 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, propanoic acid, butanoic acid,
Appointing in trifluoroacetic acid, hydrochloric acid, phosphoric acid, sulphuric acid, acetate buffer solution, phosphate buffered solution, citrate buffer solution
One kind, preferably uses acetic acid.
The invention provides another kind of 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 acidifying of radioactivity Value linear labelling
Compound, comprises the following steps：
A, by 0.1-5mL 3.7MBq~740MBq's18F-FDG injection is put in hermetic container, while addition 0.1mg~
The acid solution of the p-Aminophenylalanine of 10mg and 1 μ l~100 μ l；
B, 0.1-5mL acetonitriles are subsequently adding, and the method for Jing negative pressure azeotropic dryings is removed18Moisture in F-FDG injection,
After moisture is evaporated, container reacts 10~60min after sealing under the conditions of 40 DEG C~100 DEG C；
C, finally the direct Jing preparative high-performance liquid chromatographics of step b resulting solution are carried out into purification.
Acid in above-mentioned steps a can be acetic acid, formic acid, propanoic acid, butanoic acid, trifluoroacetic acid, hydrochloric acid, phosphoric acid, sulphuric acid, acetate
Any one in buffer solution, phosphate buffered solution, citrate buffer solution, preferably uses acetic acid.
The invention provides the glycosyl amino-acid compound of above-mentioned Value linear labelling is prepared in radiopharmaceutical chemistry field
Purposes in tumor developer, the tumor is breast carcinoma, pulmonary carcinoma, hepatocarcinoma, carcinoma of prostate, cerebroma, pulmonary carcinoma, gastric cancer, first
Any one of shape adenocarcinoma, colorectal cancer.
Beneficial effects of the present invention：
(1) chemical reagent that the present invention is adopted is commercial goods, and wide material sources are readily available；
(2) present invention with radioactivity 2- [18F] F- fluorodeoxyglucose ([18F]-FDG) and p-Aminophenylalanine
(NH2PHe) in acid condition reaction prepare described radioactivity Value linear labelling glycosyl amino-acid compound [18F]
FDGlyNHPHe, is a kind of multiple metabolic imaging agent of new tumor, realizes and radioactive Value linear is introduced on aminoacid,
Can be used for positron e mission computed tomography (PET)；
(3) be prepared by the method for the present invention [18F] FDGlyNHPHe has the characteristics of chemical purity is high, biological property is good；
(4) with [18F] FDG compares, and it has more preferable tumor-targeting, the multiple metabolism of the tumor that can be used for becoming new
Developer.
Specific embodiment
The present invention is further illustrated below by embodiment, but is not limited to following examples.
Embodiment 1：Wet method prepare [18F] FDGlyNHPHe preparation method it is as follows：
By 0.5mL 37MBq's18F-FDG injection is put in hermetic container, and 2mL acetonitriles, azeotropic under negative pressure are added at twice
Be dried, then in this embodiment add 1.0mg p-Aminophenylalanine first alcohol and water 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 carries out purification.The condition of preparative high performance liquid chromatography is：Amino prepare post (250mm ×
10mm), mobile phase is methanol:Water=9:1,3mL/min, UV=254nm.The fraction between 10-17min is collected, solution is steamed
Add after dry be diluted after PBS or normal saline dissolving obtain [18F] FDGlyNHPHe injection, cross sterilised membrane filter after treat
With.
Embodiment 2：Dry process [18F] FDGlyNHPHe preparation method it is as follows：
By 0.5mL 37MBq's18F-FDG injection is put in hermetic container, while adding the p-Aminophenylalanine of 1.0mg
With the acetic acid of 50 μ l, 2mL acetonitriles, azeotropic drying under negative pressure, after solution is evaporated, in 80 DEG C of bars after container sealing are added at twice
30min is reacted under part；Finally reaction solution is directly prepared type high performance liquid chromatography carries out purification.Preparative efficient liquid phase
The condition of chromatograph is：Amino prepares post (250mm × 10mm), and mobile phase is methanol:Water=9:1,3mL/min, UV=254nm.
Collect 10-17min between fraction, after solution is evaporated add PBS be diluted dissolving obtain [18F] FDGlyNHPHe note
Liquid is penetrated, crosses stand-by after sterilised membrane filter.
Detection shows：[18F] by HPLC identifications, its radiochemical purity is more than 99% to FDGlyNHPHe, and at 37 DEG C
Radiochemicsl purity is unchanged after placing 4 hours, good stability.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 knurls and aseptic inflammation bimodel mice vivo biodistribution
Distributed data is compared, and the results are shown in Table 2：
Table 2. [18F] FDGlyNHPHe with [18F] FDG lifes in S-180 lotus knurls and aseptic inflammation bimodel mice body
Thing distributed data (%ID/g ± sd, n=3) is contrasted
*：Refer to the intake ratio of the two
Test detection to show, [18F] FDGlyNHPHe performance it is as follows：
1.[18F] FDGlyNHPHe lipid determine
1.0mL phosphate buffered solution (pH=7.2,0.025M) is taken in 10mL centrifuge tubes, is added in centrifuge tube
1.0mL n-octyl alcohols and 740KBq [18F] FDGlyNHPHe injection, cover and fully shaken up after stopper, it is centrifuged under 12000r/min
5min.Then 50 μ L are taken out from organic faciess and water phase respectively, determine respective radiocounting, the radioactivity of organic faciess and water phase
The ratio of counting is partition coefficient P, and the fat-soluble size of compound is generally weighed with log P, measure [18F] FDGlyNHPHe
Log P values are -2.11, it can be seen that [18F] FDGlyNHPHe is water-soluble substanceses.
2.[18F] FDGlyNHPHe vitro stability determine
Will [18F] FDGlyNHPHe PBS solution, [18F] FDGlyNHPHe PBS solution and hyclone mixed liquor
It is common to be incubated in 37 DEG C, its is measured by sampling respectively at different time (5min, 30min, 60min, 120min, 240min) activation
Purity is learned, test result indicate that [18F] FDGlyNHPHe PBS injection and its placing 4 little with the co-culture media of hyclone
When after radiochemical purity still greater than 95%, illustrate [18F] FDGlyNHPHe 37 DEG C in PBS solution and hyclone under the conditions of
Vitro stability is good, is suitable to clinical practice needs.
Claims (9)
1. a kind of glycosyl amino-acid compound of Value linear labelling, it is characterised in that：Its biomolecule expressions for [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 connection in PHe structures on phenyl ring is obtained.
2. the glycosyl amino-acid compound of Value linear labelling according to claim 1, it is characterised in that：[18F]
In FDGlyNHPHe there are two kinds of tautomeric structures of ring type or chain type in the structure of deoxyglucose glycosyl.
3. the preparation method of the glycosyl amino-acid compound of the Value linear labelling described in a kind of claim 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
Method prepares the glycosyl amino-acid compound of radioactivity Value linear labelling, comprises the following steps：
A, by 0.1-5mL 3.7MBq~740MBq's18F-FDG injection is put in hermetic container, adds the acetonitrile of 0.1-5mL, and
The method of Jing decompression azeotropic dryings is removed18Moisture in F-FDG injection；
B and then the in a reservoir mixed solution of the first alcohol and water of the p-Aminophenylalanine of addition 0.1mg~10mg, and 1 μ l
The acid of~100 μ l, container reacts 10~60min after sealing under the conditions of 40 DEG C~100 DEG C；
C, finally the direct Jing preparative high-performance liquid chromatographics of step b resulting solution are carried out into purification.
4. the preparation method of the glycosyl amino-acid compound of Value linear labelling 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 step b
Mixed solution cumulative volume be 0.1-5mL.
5. the preparation method of the glycosyl amino-acid compound of the Value linear labelling described in a kind of claim 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
Method prepares the glycosyl amino-acid compound of radioactivity Value linear labelling, comprises the following steps：
A, by 0.1-5mL 3.7MBq~740MBq's18F-FDG injection is put in hermetic container, while adding 0.1mg~10mg
P-Aminophenylalanine and 1 μ l~100 μ l acid solution；
B, 0.1-5mL acetonitriles are subsequently adding, and the method for Jing negative pressure azeotropic dryings is removed18Moisture in F-FDG injection, moisture
After being evaporated, container reacts 10~60min after sealing under the conditions of 40 DEG C~100 DEG C；
C, finally the direct Jing preparative high-performance liquid chromatographics of step b resulting solution are carried out into purification.
6. the preparation method of the glycosyl amino-acid compound of the Value linear labelling according to claim 3 or 5, it is characterised in that：
The acid is acetic acid, formic acid, propanoic acid, butanoic acid, trifluoroacetic acid, hydrochloric acid, phosphoric acid, sulphuric acid, acetate buffer solution, phosphate-buffered
Any one in solution, citrate buffer solution.
7. the preparation method of the glycosyl amino-acid compound of Value linear labelling according to claim 6, it is characterised in that：Institute
Acid is stated for acetic acid.
8. a kind of glycosyl amino-acid compound of the Value linear labelling described in claim 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 tumor is breast carcinoma, pulmonary carcinoma, hepatocarcinoma, prostatitis
Any one of adenocarcinoma, cerebroma, pulmonary carcinoma, gastric cancer, thyroid carcinoma, colorectal cancer.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109979598A (en) * | 2019-04-02 | 2019-07-05 | 无锡亚纳健康管理咨询有限公司 | Use human body18F-FDG PET data analyzes tissue DNA methylol 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 |
| CN113264967A (en) * | 2021-05-17 | 2021-08-17 | 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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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN109979598A (en) * | 2019-04-02 | 2019-07-05 | 无锡亚纳健康管理咨询有限公司 | Use human body18F-FDG PET data analyzes tissue DNA methylol 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 |
| CN113264967A (en) * | 2021-05-17 | 2021-08-17 | 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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Effective date of registration: 20230704 Address after: 200000 floors 1-2, building 2, Lane 500, Furonghua Road, Pudong New Area, Shanghai Patentee after: Shanghai Shiya Pharmaceutical Technology Co.,Ltd. Address before: 030001 No. 85 Jiefang South Road, Yingze District, Shanxi, Taiyuan Patentee before: FIRST HOSPITAL OF SHANXI MEDICAL University |