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Targeted estrogen receptor fluorescent probes and preparation and usage methods thereof

An estrogen receptor and fluorescent probe technology, applied in the fields of medicine and biology, can solve the problems of side effects, the inability to dynamically detect the expression of estrogen receptors in real time, and the failure to use surgical navigation, and achieve a good fluorescence quantum yield. Effect

Active Publication Date: 2017-12-15
苏州楚凯药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although 18 F-FES can be used to detect the expression of estrogen receptor at present, but as a radioactive technique, it often has side effects, and it cannot detect the expression of estrogen receptor in real time and dynamically during the treatment process. In addition, its resolution needs to be determined. Improvement, but has not yet been applied to surgical navigation to guide clinical tumor resection

Method used

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  • Targeted estrogen receptor fluorescent probes and preparation and usage methods thereof
  • Targeted estrogen receptor fluorescent probes and preparation and usage methods thereof
  • Targeted estrogen receptor fluorescent probes and preparation and usage methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Example 1: Preparation of 3-bromo-2,5-bis(2-fluoro-4-methoxyphenyl)thiophene (1)

[0050] Weigh 2,3,5-tribromothiophene (0.32g, 1mmol) and p-methoxyphenylboronic acid (0.33g, 2.2mmol) in a 50mL round bottom flask, add tripotassium phosphate (0.64g, 3mmol), Tetrakis(triphenylphosphine)palladium (0.0058g, 0.005mmol), tetrabutylammonium bromide (0.032g, 0.1mmol), 5mL of dioxane, toluene and 5mL of water were reacted at 110°C for 24h, and the reaction was monitored by TLC After the reaction was complete, it was extracted three times with 50 mL of ethyl acetate, the organic layer was dried over anhydrous sodium sulfate, filtered and spin-dried to obtain a crude product, which was purified by column chromatography to obtain a yellow solid product with a yield of 78%. 1 H NMR (400MHz, CDCl 3 )δ7.46(dt,J=12.9,8.9Hz,2H),7.32(s,1H),6.82-6.67(m,4H),3.85(s,3H),3.82(s,3H). 13 C NMR (101MHz, CDCl 3 )δ163.89(d, J=248.0Hz), 163.05(d, J=247.9Hz), 158.39(d, J=10.1Hz), 156.83(d, J=9.7H...

Embodiment 2

[0051] Example 2: Preparation of 3-bromo-2,5-bis(2-fluoro-4-methoxyphenyl)selenophene (2)

[0052] Referring to the preparation method of Compound 1, a yellow solid product was obtained with a yield of 81%. 1 H NMR (400MHz, CDCl 3 )δ7.51-7.28(m,3H),6.73-6.54(m,4H),3.73(s,3H),3.71(s,3H).

Embodiment 3

[0053] Example 3: Preparation of 3-bromo-2,5-bis(2-fluoro-4-hydroxyphenyl)thiophene (3)

[0054] Weigh compound 1 (0.41g, 1mmol) in a 50mL round bottom flask, add 5mL of dichloromethane, slowly add boron tribromide (0.75g, 3mmol) at 0°C, keep the reaction temperature for 8h, and monitor the reaction by TLC Completely, after the reaction was completed, ice water was added to quench the reaction, extracted three times with 50mL ethyl acetate, the organic layer was dried with anhydrous sodium sulfate, filtered and spin-dried to obtain the crude product, which was purified by column chromatography to obtain a white solid product with a yield of 88 %. 1 H NMR (400MHz, acetone-d 6 )δ9.24(s,2H),7.52(t,J=8.8Hz,1H),7.41-7.29(m,2H),6.88-6.67(m,4H). 13 C NMR (101MHz, Acetone) δ160.79(d, J=247.7Hz, 1H), 160.15(d, J=248.4Hz, 1H), 160.32(d, J=11.6Hz, 1H), 159.54(d, J =12.0Hz,1H),138.21(d,J=3.4Hz,1H),133.24(d,J=4.2Hz,1H),131.31(d,J=4.8Hz,1H),129.47(d,J=5.0 Hz,1H),127.86(d,J=5.4Hz,1H),112...

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PUM

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Abstract

The invention belongs to the technical fields of chemistry and medicines, and discloses targeted estrogen receptor fluorescent probes and preparation and usage methods thereof. According to the invention, the fluorescent probes have high affinity to estrogen receptors, relatively high excitement or antagonistic activity to the estrogen receptors, and potential cancer therapeutic efficacy. A confocal fluorescence imaging test result shows that the fluorescent probes have selectivity for imaging of related cancer cells expressed by the estrogen receptors, and locate expression of the estrogen receptors in cells, and provide more detailed and accurate information for related-cancer early diagnosis, treatment and evaluation after healing. The fluorescent probes have diagnosis and treatment efficacy at the same time, thus the fluorescent probes can be used for living cell detection, the costs are low, the related operation is simple, convenient and rapid, and the fluorescent probes have development and application values.

Description

technical field [0001] The invention belongs to the technical fields of biology and medicine, and relates to a kind of fluorescent probe targeting estrogen receptor with functions of cancer diagnosis and treatment and its preparation and application method. Background technique [0002] Estrogen receptors belong to nuclear receptors, and exert hormone effects by binding to estrogen ligands, such as estradiol. When the estrogen signaling pathway is abnormal, it often causes a variety of diseases, such as endometrial cancer, ovarian cancer, osteoporosis, arteriosclerosis, Alzheimer's disease, etc., especially at present more than 70% of breast cancer and estrogen hormone receptor overexpression. [0003] At present, the clinical treatment of breast cancer mainly adopts hormone replacement therapy, such as first-line drugs tamoxifen, raloxifene and lasofoxifene, etc., which mainly regulate the signaling pathway mediated by estrogen receptors to achieve breast cancer. Treatmen...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D333/24C07D345/00C07D409/06C07C255/36C07C253/30C09K11/06G01N21/64
CPCC07C255/36C07D333/24C07D345/00C07D409/06C09K11/06C09K2211/1007C09K2211/1011C09K2211/1092C09K2211/1096G01N21/6486
Inventor 董春娥杨录胡志烨刘现军
Owner 苏州楚凯药业有限公司
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