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Probe for early diagnosis of tumor as well as synthesis and application of probe

A compound and reaction temperature technology, which is applied in the field of near-infrared fluorescent probe compounds, can solve the problems of decreased chemotherapy effect, high cost, and ambiguous lesion location, and achieves the effect of novel structure and good quinone oxidoreductase response ability.

Inactive Publication Date: 2018-08-24
淮北新思拓生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Some malignant tumor cells highly express NQO1, such as U87 cell line, MCF-7 cell line, etc. This highly expressed NQO1 helps malignant tumor cells resist the production of reactive oxygen species chemotherapy drugs, resulting in decreased chemotherapy effect
[0003] Although radiographic examination has been successfully used for tumor imaging, it is expensive and requires high equipment
At the same time, the resolution is limited and the location of the lesion is blurred

Method used

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  • Probe for early diagnosis of tumor as well as synthesis and application of probe
  • Probe for early diagnosis of tumor as well as synthesis and application of probe
  • Probe for early diagnosis of tumor as well as synthesis and application of probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Add 2,3,5-trimethylbenzene-1,4-diol (304.4mg, 2mol, 1equiv.) and methanesulfonic acid (5ml) into the reaction flask, pump nitrogen, inject 3-methylbutanol -2-enoic acid methyl ester solution (0.3ml, 273.94mg, 2.4mol, 1.2equiv.) was then heated to 50°C and stirred for 0.5h. Sodium bicarbonate solution and saturated sodium chloride solution terminated the reaction, and extracted with ethyl acetate. The solvent was removed to obtain compound 3. Add compound 3 (232.32mg, 1mol, 1equiv.) and acetonitrile (9ml), acetone (2ml), water (9ml), NBS (266.97mg, 1.5mol, 1.5equiv.) Rinse with ethyl acetate after reacting for 0.5h. Extract with saturated brine and ethyl acetate, and adjust the pH value of the aqueous layer to 2-3. The organic layer was collected and the solvent was spin-off to obtain yellow oil compound 4.

[0037] In an ice bath, the POCl 3 (10.5 mL, 115 mmol) in dichloromethane (5 mL) was slowly added to a mixed solution of DMF (20 mL, 258 mmol) and dichlorometha...

Embodiment 2

[0041] Add 2,3,5-trimethylbenzene-1,4-diol (304.4mg, 2mol, 1equiv.) and methanesulfonic acid (5ml) into the reaction flask, pump nitrogen, add 3-methylbutane- Methyl 2-enoate solution (0.3ml, 273.94mg, 2.4mol, 1.2equiv.) was then heated to 70°C and stirred for 2h. Sodium bicarbonate solution and saturated sodium chloride solution terminated the reaction, and extracted with ethyl acetate. The solvent was removed to obtain compound 3. Compound 3 (232.32mg, 1mol, 1equiv.) and acetonitrile (9ml), acetone (2ml), water (9ml), NBS (266.97mg, 1.5mol, 1.5equiv.) were added to the reaction flask, pumped into nitrogen, and the Rinse with ethyl acetate after reacting for 1 h. Extract with saturated brine and ethyl acetate, and adjust the pH value of the aqueous layer to 2-3. The organic layer was collected and the solvent was spin-off to obtain yellow oil compound 4.

[0042] POCl 3 (10.5 mL, 115 mmol) in dichloromethane (5 mL) was slowly added to DMF (20 mL, 258 mmol) at room temper...

Embodiment 3

[0046] Add 2,3,5-trimethylbenzene-1,4-diol (304.4mg, 2mol, 1equiv.) and methanesulfonic acid (5ml) into the reaction flask, pump nitrogen, add 3-methylbutane- Methyl 2-enoate solution (0.3ml, 273.94mg, 2.4mol, 1.2equiv.) was then heated to 70°C and stirred for 2h. Sodium bicarbonate solution and saturated sodium chloride solution were quenched and extracted with ethyl acetate. The solvent was removed to obtain compound 3. Add compound 3 (232.32mg, 1mol, 1equiv.) and acetonitrile (9ml), acetone (2ml), water (9ml), NBS (266.97mg, 1.5mol, 1.5equiv.) After reacting for 1 h, rinse with ethyl acetate. Extract with saturated brine and ethyl acetate, and adjust the pH value of the aqueous layer to 2-3. The organic layer was collected and the solvent was spin-off to obtain yellow oil compound 4.

[0047] In an ice bath, the POCl 3 (10.5 mL, 115 mmol) in dichloromethane (5 mL) was slowly added to a mixed solution of DMF (20 mL, 258 mmol) and dichloromethane (15 mL), and stirred for...

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PUM

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Abstract

The invention discloses an NQO (quinone oxidoreductase) response type near infrared fluorescence probe compound related to early diagnosis of tumor. The structure of the compound is represented as theformula (I), wherein R1 and R2 are the same or different, and R1 and R2 are independently selected from C1-6 linear alkyl, C1-6 linear alkyl carboxyl, sulfonyl or C1-6 linear alkyl ester; X is halogen. The primary cell confocal experiment of the compound proves that the compound has good NQO response capacity, can produce strong fluorescence easy to detect, and can be applied to early detection of tumor.

Description

technical field [0001] The invention relates to the fields of advanced organic synthesis and biological imaging related to early diagnosis of tumors, in particular to a class of quinone oxidoreductase-responsive near-infrared fluorescent probe compounds, and the synthesis and application of such compounds. Background technique [0002] Tumor is a serious threat to human health, and its diagnosis and treatment have become an important research direction of precision medicine. Quinone oxidoreductase 1 (NQO1) is an enzyme used to scavenge superoxide and superoxide when the oxygen concentration in human cells increases, and plays an important role in the process of cells removing exogenous toxic substances. It uses NADPH as an acceptor to catalyze the reduction reaction of quinone compounds. Some malignant tumor cells highly express NQO1, such as U87 cell line, MCF-7 cell line, etc. This high expression of NQO1 helps malignant tumor cells resist the production of reactive oxyge...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/14C09K11/06G01N21/64
CPCC07D209/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044G01N21/6402G01N21/6486
Inventor 杨林陈海燕顾明徐铭均袁振伟
Owner 淮北新思拓生物科技有限公司
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