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Near-infrared fluorescent compounds and preparation method, near-infrared fluorescent imaging probes and application thereof

A fluorescent compound and fluorescent imaging technology, applied in the field of biomedical fluorescent imaging applications, can solve problems such as interference with fluorescent imaging effects, and achieve the effects of broad application prospects, good imaging effects and simple synthesis routes.

Active Publication Date: 2019-07-05
SHENZHEN RES INST OF WUHAN UNIVERISTY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Biological tissues have strong autofluorescence and severe light absorption in the range of <700nm, which will seriously interfere with the fluorescence imaging effect

Method used

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  • Near-infrared fluorescent compounds and preparation method, near-infrared fluorescent imaging probes and application thereof
  • Near-infrared fluorescent compounds and preparation method, near-infrared fluorescent imaging probes and application thereof
  • Near-infrared fluorescent compounds and preparation method, near-infrared fluorescent imaging probes and application thereof

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preparation example Construction

[0036] 1. Preparation of Compound 6

[0037] Accurately weigh compound 4 (2.81g, 10mmol) and compound 5 (2.72g, 11mmol) in a 250mL round bottom flask, add tetrakistriphenylphosphopalladium and potassium carbonate, pump anhydrous and oxygen-free argon protection, inject toluene and Water (100mL:25mL), heated to 120 degrees Celsius and refluxed for 24 hours. After the reaction, it was extracted with ethyl acetate, washed three times with water (100 mL), and washed three times with saturated brine (100 mL). The organic phases were combined, dried with anhydrous sodium sulfate, filtered, and the filtrate was spin-dried, and then purified by a silica gel column (PE:EA=8:1) to obtain 2.35 g of compound 6. Yield: 73%.

[0038] The structure determination data of compound 6 are as follows:

[0039] 1 H NMR (400MHz, CDCl 3 )δ7.96(d, J=15.1Hz, 1H), 7.86–7.78(m, 2H), 7.41(d, J=15.1Hz, 2H), 7.00(s, 1H), 6.92(d, J=15.1 Hz,2H),3.02(s,6H),2.01(s,3H),0.66(s,6H).

[0040] 13 C NMR (101...

Embodiment 7

[0075] Embodiment 7: the preparation of compound 1c

[0076] Add compound 3a (691mg, 1mmol) and compound 2a (369mg, 1mmol) into a 100mL round-bottomed flask, add 45mL of toluene under the protection of argon to dissolve, add 0.5mL of piperidine, 0.5mL of acetic acid, and store at 115°C under the protection of argon. Heated to reflux in an oil bath for 12 hours. After the reaction was completed, it was cooled to room temperature, toluene was removed by rotary evaporation, and 678 mg of compound 1c was obtained by direct silica gel column separation and purification (PE:EA=6:1). Yield: 65%.

[0077] The structure determination data of compound 1c are as follows:

[0078] 1 H NMR (400MHz, CDCl3) δ7.59 (d, J = 14.9Hz, 1H), 7.52–7.42 (m, 3H), 7.40 (d, J = 3.1Hz, 2H), 7.37–7.31 (m, 3H) ,7.26(d,J=14.9Hz,2H),7.20(d,J=15.1Hz,4H),6.92(dd,J=15.0,4.0Hz,4H),6.85–6.78(m,6H),6.50( s,1H),4.33(t,J=15.5Hz,2H),4.04(t,J=15.8Hz,2H),3.40(q,J=12.6Hz,8H),3.02(s,6H),2.67( t,J=15.5Hz,2H),1.12(t,J=1...

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Abstract

The invention discloses near-infrared fluorescent compounds and a preparation method, near-infrared fluorescent imaging probes and an application thereof. A series of intelligent fluorescent probes are obtained by introducing a tetraphenylethylene (TPE) unit with modifiable groups into a novel near-infrared dye mother nucleus. After the target dyes are attached with short peptides targeting specific proteins, abnormal proteins related to liver injury and tumors can be specifically responded, namely the fluorescence intensity of the probes can be significantly enhanced after the probes bind with proteins related to tumors or liver injury in vivo, and thus the sensitivity and signal-to-noise ratio of fluorescent probe imaging in vivo can be significantly improved. Biomedical imaging experiments show that the fluorescent probes have very good imaging effects, so that the fluorescent probes have broad application prospects.

Description

technical field [0001] The invention belongs to the technical field of biomedical fluorescence imaging applications, and in particular relates to a near-infrared fluorescent compound and a preparation method, a near-infrared fluorescent imaging probe and applications thereof. Background technique [0002] Bio-optical imaging refers to the method of using optical detection means combined with optical detection molecules to image cells or tissues or even organisms to obtain biological information. [0003] Cancer (also known as malignant tumor) is a serious threat to human health. Although the level of modern medical technology has reached an unprecedentedly developed level, there is still a lack of effective treatment for advanced cancer. Therefore, early detection of cancer is particularly important for patients. If the tumor can be diagnosed early and timely and effective treatment can be taken, it can be Significantly improve the survival rate of cancer patients. In rece...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08C09K11/06G01N21/64
CPCC07F7/0807C09K11/06C09K2211/1007C09K2211/1096G01N21/6428
Inventor 洪学传陈梓杨曾小东
Owner SHENZHEN RES INST OF WUHAN UNIVERISTY
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