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Tspo fluorescent imaging probe and its synthesis method and application

A probe and fluorescence technology, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of low expression level and achieve the effect of novel molecular structure and good TSPO affinity

Active Publication Date: 2020-06-05
SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

In addition, previous studies have shown that TSPO has very high expression in glioma and tumor cell lines, but the expression level in normal brain is very low, indicating that TSPO also has great potential as a glioma marker

Method used

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  • Tspo fluorescent imaging probe and its synthesis method and application
  • Tspo fluorescent imaging probe and its synthesis method and application
  • Tspo fluorescent imaging probe and its synthesis method and application

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preparation example Construction

[0030] The synthetic method of TSPO fluorescence imaging probe of the present invention, comprises the following steps:

[0031] Using a synthetic method similar to that reported in the literature (Tang et al, Tetrahedron Letters 51(35), 4595, Tang et al, Journal of medicinal chemistry 56(8), 3429, Tang et al, Molecular Imaging and Biology (2016)), A variety of compounds 6 were synthesized (such as figure 1 shown). In this reaction process, the microwave synthesis method (MAOS) is mainly used, which can greatly improve the reaction speed and yield. Using the synthesized compound 6, a long linear alkyl substituent was added to its phenolic hydroxyl end, and compound 7 was synthesized, and a compound 9 with a free amino group was generated through a two-step reaction. The last step of the reaction was to Compound 9 reacted with fluorescent or small dye molecules (with isothiocyanate group) to generate new fluorescent probes TDW-F-1, TDW-F-2, TDW-F-3.

[0032] Different compou...

Embodiment 1

[0034] The synthetic method of embodiment 1, TDW-F-1 (as figure 2 ):

[0035] (1) Synthesis of compound 7-1

[0036]6-1 (40mg, 0.109mmol) was dissolved in 5mL of anhydrous tetrahydrofuran, then NaH (7.9mg, 0.327mmol) was added under ice-bath conditions, after 30 minutes of reaction, octane-1,8-diyl bis( 4-methylbenzenesulfonate) (148mg, 0.327mmol), and then the reaction system was placed in a microwave reaction system and heated at 120°C for 30min. The progress of the reaction was detected by mass spectrometry. When the reaction was finished, it was neutralized with 0.5M HCl (50 mL), and extracted with dichloromethane (50 mL*3). Then it was separated by column chromatography (separation condition: DCM / MeOH=95 / 5 (V / V)), and finally compound 7-1 was obtained (yellow solid, 50 mg, 70% yield).

[0037] (2) Synthesis of compound 9-1

[0038] Compound 7-1 (50mg, 0.076mmol) and potassium 1,3-dioxoisoindolin-2-ide (28mg, 0.15mmol) were added to 3mL DMF, and after they were dissol...

Embodiment 2

[0041] The synthetic method of embodiment 2 TDW-F-2 (as image 3 ):

[0042] (1) Synthesis of compound 7-2

[0043] 6-2 (40mg, 0.109mmol) was dissolved in 5mL of anhydrous tetrahydrofuran, then NaH (7.9mg, 0.327mmol) was added under ice-bath conditions, after 30 minutes of reaction, octane-1,8-diyl bis( 4-methylbenzenesulfonate) (148mg, 0.327mmol), and then the reaction system was placed in a microwave reaction system and heated at 120°C for 30min. The progress of the reaction was detected by mass spectrometry. When the reaction was finished, it was neutralized with 0.5M HCl (50 mL), and extracted with dichloromethane (50 mL*3). Then it was separated by column chromatography (separation condition: DCM / MeOH=95 / 5 (V / V)), and finally compound 7-1 was obtained (yellow solid, 52 mg, 74% yield).

[0044] (2) Synthesis of compound 9-2

[0045] Compound 7-2 (50mg, 0.076mmol) and potassium 1,3-dioxoisoindolin-2-ide (28mg, 0.15mmol) were added to 3mL DMF, and after they were dissolv...

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Abstract

The invention relates to a TSPO (Translocator Protein) fluorescent imaging probe as well as a synthetic method and application thereof. A molecular structure of the TSPO fluorescent imaging probe is as shown in the description. In the formula, R1 and R2 are independent straight-chain alkane substituent groups; R1 is C1-C10 straight-chain alkane substituent group; R2 is C1 or C2 straight-chain alkane substituent group; R3 and R4 are straight-chain alkane substituent groups of the same structure and have the length of C1-C10; n is equal to 2-10; Signaling Agent in the molecular structural formula is a signal group. The TSPO fluorescent imaging probe can serve as an in-vitro TSPO detection agent or an in-vivo image detection agent.

Description

technical field [0001] The invention relates to the structure, synthesis method and application of small molecule fluorescent probes, in particular to various TSPO fluorescent imaging probes and their synthesis methods and applications. Background technique [0002] Translocator Protein (TSPO: Translocator Protein) is a 10kDa mitochondrial membrane protein, which forms the mitochondrial transport channel (MPTP) with VDAC and ANT, and plays a role in steroid transport, steroid hormone synthesis, cell proliferation and apoptosis, etc. important role in the process. In humans, TSPO is expressed in many healthy tissues, and its expression level varies with different tissues. For example, in the adrenal gland, pineal gland, salivary gland, gonad and other glandular tissues, the expression level of TSPO is relatively high, the expression level in the kidney and heart is intermediate, and the expression level in the brain and liver is relatively low. The expression level of TSPO ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D519/00C09K11/06G01N21/64A61K49/00
CPCA61K49/0043C07D519/00C09K11/06C09K2211/1044C09K2211/1088G01N21/6486
Inventor 黄钢唐德伟黄辰
Owner SHANGHAI UNIV OF MEDICINE & HEALTH SCI
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