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CYP1B1 enzyme targeting probe precursor for radioactivity <18> F labeling

A radioactive and labeling technology, applied in the field of PET imaging and tumor diagnosis, can solve the problems of low diagnostic specificity and difficult diagnosis

Active Publication Date: 2021-02-09
SHANGHAI JIAO TONG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Finish 18 After F labeling, through PET imaging of intracellular CYP1B1 enzyme, its expression site and level are displayed in vivo, providing a new method for early diagnosis of tumors, and solving the problems of difficult diagnosis and low diagnostic specificity in current tumor treatment

Method used

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  • CYP1B1 enzyme targeting probe precursor for radioactivity &lt;18&gt; F labeling
  • CYP1B1 enzyme targeting probe precursor for radioactivity &lt;18&gt; F labeling
  • CYP1B1 enzyme targeting probe precursor for radioactivity &lt;18&gt; F labeling

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Embodiment 1

[0028] The present embodiment relates to a kind of radioactive compound derived from 6,7,10-trimethoxy-3'-fluoro-α-naphthalene flavonol with structural formula I 18 Preparation method of F-labeled probe precursor I-3, such as figure 1 shown, including the following steps:

[0029] Step 1: Dissolve 2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethanol (2mmol) in 6mL of dichloromethane, add dropwise in 4mL dichloromethane under ice-cooling Di-tert-butyl dicarbonyl ester of methyl chloride (2.3 mmol). After the dropwise addition, the ice bath was removed, and the reaction solution was stirred overnight at room temperature. After the reaction, the reaction solution was diluted with 10 mL of dichloromethane, and the organic phase was washed successively with an equal volume of water, saturated sodium bicarbonate solution and saturated sodium chloride solution. After drying the organic phase with anhydrous sodium sulfate, it was concentrated under reduced pressure to obtain a colorless oi...

Embodiment 2

[0035] The present embodiment relates to a kind of radioactive compound derived from 6,7,10-trimethoxy-3'-fluoro-α-naphthalene flavonol with structural formula I 18 The preparation method of F-labeled probe precursor I-1, such as figure 1 shown, including the following steps:

[0036] Step 1: Same as Step 5 of Example 1, replace V-3 with V-1 (see published paper J.Med.Chem., 2018, 61, 10901-10909 for the synthesis method), Rf=27.525min, and obtain an orange-yellow solid I-1 (n=1). Yield, 52.4%. 1 H NMR (600MHz, DMSO-d 6 ):δ9.80(s,1H),8.27-8.35(m,2H),7.67-7.70(m,1H),7.58(d,J=6.0Hz,2H),7.41-7.44(m,3H), 7.30-7.32(m,3H),4.41(s,2H),4.28(s,2H),4.06(s,3H),3.94(s,3H),3.84(s,3H),3.75(s,2H) ,3.64(s,2H),3.55-3.57(m,2H),3.42-3.47(m,4H),3.30(m,2H),3.11(m,4H),3.00-3.03(m,2H),2.79 (m,2H),2.61-2.68(m,4H). 13 C NMR (150MHz, DMSO-d 6 ): δ181.09, 173.26, 173.12, 162.52(d, J=207.0Hz), 154.57, 152.61, 151.26, 151.05, 147.83, 140.92, 133.60(d, J=7.5Hz), 131.09(d, J=6.0Hz), 130.87, 125.00, ...

Embodiment 3

[0038] The present embodiment relates to a kind of radioactive compound derived from 6,7,10-trimethoxy-3'-fluoro-α-naphthalene flavonol with structural formula I 18 Preparation method of F-labeled probe precursor I-2, such as figure 1 shown, including the following steps:

[0039] step one:

[0040] Same as Step 5 of Example 1, replace V-3 with V-2 (see the published paper J.Med.Chem., 2018, 61, 10901-10909 for the synthesis method, Rf=27.865min, and obtain orange-yellow solid I-2 (n=2), yield: 72%. 1 H NMR (600MHz, DMSO-d 6 ):δ9.77(s,1H),8.28-8.37(m,2H),7.67-7.71(m,1H),7.57(d,J=6.6Hz,2H),7.43-7.49(m,3H), 7.31-7.33(m,3H),4.40(m,2H),4.29(s,2H),4.07(s,3H),3.95(s,3H),3.85(s,3H),3.72(m,2H) ,3.62(m,2H),3.53-3.54(m,6H),3.42-3.48(m,4H),3.30(m,2H),3.12(m,4H),3.01-3.03(m,2H),2.79 (m,2H),2.61-2.68(m,4H). 13 C NMR (150MHz, DMSO-d 6 ): δ181.03, 173.25, 173.14, 162.52(d, J=207.0Hz), 154.57, 152.57, 151.28, 151.08, 147.82, 140.90, 133.62(d, J=7.5Hz), 131.09(d, J=6.8Hz), 130.87, 125...

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Abstract

The invention discloses a CYP1B1 enzyme targeting probe precursor for radioactivity <18> F labeling. The probe precursor comprises an affinity ligand capable of being combined with CYP1B1 enzyme, a chelating group capable of being used for 18F rapid labeling and a connecting chain used for connecting the ligand and the chelating group; wherein the connecting chain comprises a plurality of ethyleneglycol fragments; the affinity ligand is an alpha-naphthalene flavone derivative, and the chelating group capable of being used for 18F rapid labeling is a 1, 4, 7-triazacyclononane-1, 4-diacetic acid molecule. The CYP1B1 enzyme targeting probe precursor is a molecular probe precursor which can be combined with tumor-specific expressed CYP1B1 enzyme and can be used for 18F labeling, and after radiolabeling, the level of the CYP1B1 enzyme in tumors can be displayed in PET imaging, so that the tumors are visualized. The invention can effectively promote the application of a molecular imaging technology in tumor diagnosis.

Description

technical field [0001] The invention relates to the fields of PET imaging and tumor diagnosis, and relates to a radionuclide targeting CYP1B1 enzyme 18 F-labeled probe precursors; specifically one composed of ethylene glycol chains will be available for 18 The diagnostic reagent complex composed of F-labeled chelating groups and ligands that can specifically bind to cytochrome P450 1B1 enzymes is radioactive 18 F labeling allows visualization of tumors in PET imaging by showing levels of cytochrome P450 1B1 enzyme for tumor diagnosis. Background technique [0002] Compared with traditional medical imaging, molecular imaging shows a better application prospect in the early diagnosis of tumors. Through the high-affinity enrichment effect of molecular probes on specific targets of tumor tissue, tumor imaging can be performed in the early stage of tumor occurrence or even before symptoms appear, and the effect of early diagnosis can be achieved. With the development of tumor ...

Claims

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Application Information

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IPC IPC(8): C07D405/12A61K51/04A61K101/02
CPCC07D405/12A61K51/044C07B2200/05
Inventor 孟青青陈冬梅范琪琪李绍顺董金云崔家华王增涛
Owner SHANGHAI JIAO TONG UNIV
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