Sensing array with mitochondrial targeting and aggregation-induced emission effects and application of sensing array in cell discrimination

A technology of aggregation-induced luminescence and sensing array, which is applied in the application field of sensing array with mitochondrial targeting and aggregation-induced luminescence effect and cell discrimination, and can solve the problems of low accuracy, low sensitivity of cancer, complicated operation steps, etc. , to achieve the effect of easy synthesis, good biocompatibility and photostability

Inactive Publication Date: 2020-09-22
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

While solving the problems of low sensitivity, low precision and complicated operation steps in th

Method used

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  • Sensing array with mitochondrial targeting and aggregation-induced emission effects and application of sensing array in cell discrimination
  • Sensing array with mitochondrial targeting and aggregation-induced emission effects and application of sensing array in cell discrimination
  • Sensing array with mitochondrial targeting and aggregation-induced emission effects and application of sensing array in cell discrimination

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Embodiment 1: Synthesis of PT1

[0042] Structural formula: Synthesis process see figure 1 The synthetic route shown.

[0043] (1) Synthesis of TPE-2OH: get 4,4'-dihydroxybenzophenone (3.00g, 14mmol), 4,4'-dimethoxybenzophenone (3.39g, 14mmol) and zinc powder ( 7.28g, 112mmol) into a 250mL two-necked flask, add a magnet, add anhydrous THF 150mL, deoxygenate and keep N 2 environment. In an acetone bath, slowly to N 2 Titanium tetrachloride (6.15 mL, 56 mmol) was added dropwise into a protected two-necked flask, stirred in an acetone bath for 0.5 h, returned to room temperature naturally, and then refluxed for 9 h. After the reaction was completed, room temperature was restored, and saturated potassium carbonate solution was added to the mixture to quench the reaction. The zinc powder was removed by suction filtration, and the filtrate was extracted with water and dichloromethane (100 mL*3). The organic phase was collected, washed with water, and dried over anhydr...

Embodiment 2

[0046] Embodiment 2: Synthesis of PT2

[0047] Structural formula: Synthesis process see figure 2 The synthetic route shown.

[0048] Synthesis of PT2: Take TPE-CN-2OC 3 Br (100.00mg, 0.13mmol) and Me 3 N (76.83mg, 1.3mmol) was added to a 50mL one-necked flask, and 30mL of anhydrous THF was added to remove oxygen, and stirred at 25°C for 2 days. After the reaction was completed, the mixture was filtered and the residue was washed with excess THF to obtain a red solid (52.61 mg, 0.06 mmol, yield: 45%). 1 H NMR (400MHz, CD 3 OD,δ):7.71(d,J=7.2Hz,1H),7.64–7.55(m,1H),7.54–7.49(m,2H),7.48–7.41(m,1H),7.40–7.28(m, 1H),7.26–7.09(m,4H),7.08–6.98(m,3H),6.98–6.82(m,5H),6.79–6.65(m,4H),4.04(t,J=4.8Hz,4H) ,3.56(t,J=8.0Hz,4H),3.17(s,18H),2.31–2.17(m,4H); HR-MS(ESI,positive)m / z:[M-2Br] 2+ / 2calcd.for[C 48 h 52 N 4 o 2 ] 2+ / 2,358.20396; found, 358.20413.

Embodiment 3

[0049] Embodiment 3: synthetic PT3

[0050] Structural formula:

[0051] Synthesis process see image 3 The synthetic route shown.

[0052] (1) Synthesis of TPE-2Br: Take 4,4'-dibromobenzophenone (3.00g, 8.82mmol), 4,4'-dimethoxybenzophenone (2.13g, 8.82mmol) and zinc Powder (7.28g, 70.56mmol) was added to a 250mL two-necked flask, a magnet was added, anhydrous THF 150mL was added, and oxygen was removed to keep N 2 environment. In an acetone bath, slowly to N 2 Titanium tetrachloride (6.15 mL, 35.82 mmol) was added dropwise into a protected two-neck flask, stirred in an acetone bath for 0.5 h, returned to room temperature naturally, and then refluxed for 9 h. After the reaction was completed, room temperature was restored, and saturated potassium carbonate solution was added to the mixture to quench the reaction. The zinc powder was removed by suction filtration, and the filtrate was extracted with water and dichloromethane (100 mL*3). The organic phase was collected...

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PUM

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Abstract

The invention relates to a sensing array capable of distinguishing cells. The sensing array provided by the invention comprises five tetraphenyl ethylene derivatives with mitochondrial targeting and aggregation-induced emission effects. According to the tetraphenyl ethylene derivatives disclosed by the invention, a molecular probe D-A structure is adjusted by adjusting donor-acceptor groups and different cationic groups, so that different fluorescence spectrum properties are realized, and different electrostatic and hydrophobic interactions with cells are realized; the synthesis is easy; goodbiocompatibility and light stability are realized; cell mitochondria can be effectively targeted for cell imaging; different probes and different cells generate differential fluorescence response; byanalyzing different fluorescence responses, different cancer cells can be discriminated and cell types can be predicted. A new method for early cancer detection is designed and has potential application in the aspect of cancer cell clinical examination.

Description

technical field [0001] The invention relates to the structural design, preparation method and application of a sensing array with mitochondrial targeting and aggregation-induced luminescence effects and its application in cell discrimination. Contains a series of tetraphenylethylene derivatives with aggregation-induced luminescent properties that can target mitochondria, and compose them into a sensing array, and realize the application of different cell discrimination through the difference in charge properties, fluorescence signals, and spectral properties of compounds. Background technique [0002] In recent years, aggregation-induced emission fluorescent probes (AIEgens) have been vigorously developed in the fields of chemistry, physics and biology, showing unique advantages in living cells. The intracellular environment affects the aggregation state of AIEgens, such as microenvironment, proteins and plasmids. Tetraphenylethylene-based AIEgens are easy to adjust molecul...

Claims

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Application Information

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IPC IPC(8): C07F9/54C07D213/38C07D209/12C07C255/37C07C253/30C09K11/06G01N21/64
CPCC07C253/30C07C255/37C07D209/12C07D213/38C07F9/5442C09K11/06C09K2211/1007C09K2211/1029G01N21/6428
Inventor 王卓马宇帆
Owner BEIJING UNIV OF CHEM TECH
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