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Near-infrared fluorescent probe, preparation and application of near-infrared fluorescent probe in detection of transthyroxine tetramer protein

A fluorescent probe, thyroxine technology, applied in the field of biomedicine, can solve the problems of complex inspection methods, high cost, and great physical damage, and achieve the effects of avoiding the interference of self-luminescence, long emission wavelength, and low toxicity

Active Publication Date: 2021-06-01
SOUTH CHINA UNIV OF TECH
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Problems solved by technology

[0003] At present, the detection methods for transthyretin amyloidosis are mainly based on family history investigation and pathological or genetic screening. The inspection methods are complicated, expensive, and harmful to the body.
Fluorescent probes have the advantages of rapid detection, good specificity, sensitive detection, and low toxicity. Among them, near-infrared fluorescent probes have the characteristics of strong tissue penetration, high signal-to-noise ratio, and less light scattering, so there are many researchers. Many small molecular probes have been synthesized in the research of fluorescent probes for transthyretin amyloidosis, but the fluorescent probes reported for transthyretin amyloidosis all have relatively short emission wavelengths (J.Am.Chem. Soc.2015, 137, 7404-7414; ACS Chem.Neurosci.2016, 7, 924-940; Chem.Commun., 2019, 55, 10424—10427; Chem.Commun., 2013, 49, 9188—9190; J.Am .Chem.Soc.2013,135,17869-17880; J.Am.Chem.Soc.2010,132,16043–16051.), so far no fluorescent probes for detecting transthyretin amyloidosis can be found to the near infrared

Method used

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  • Near-infrared fluorescent probe, preparation and application of near-infrared fluorescent probe in detection of transthyroxine tetramer protein
  • Near-infrared fluorescent probe, preparation and application of near-infrared fluorescent probe in detection of transthyroxine tetramer protein
  • Near-infrared fluorescent probe, preparation and application of near-infrared fluorescent probe in detection of transthyroxine tetramer protein

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Experimental program
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Effect test

Embodiment 1

[0062] The synthesis of fluorescent probe QCN-2, its synthetic route is as follows figure 1 Shown:

[0063] (1) Synthetic steps of intermediate compound 1

[0064] First prepare the hydrochloric acid solution (HCl:H 2 O=1:1, v / v) 250ml, stir evenly, add 5.8g (42.6mmol) of N,N-dimethyl-1,4-p-phenylenediamine, after stirring evenly, add 7ml of crotonaldehyde, mix well Then, 30 ml of toluene was added to the reaction liquid, and the reaction was refluxed for 7 h under the protection of argon at 115° C. (oil bath). Thin-layer chromatography confirmed that the reaction was complete, the reaction was stopped, and the reaction was allowed to stand at room temperature. First remove the upper toluene solution, then adjust the pH to neutral with a NaOH saturated solution under ice-water bath conditions, then add an equal volume of dichloromethane (DCM) to extract at least three times, and finally separate and purify by column chromatography (silica gel 100-200 mesh; Petroleum ether:...

Embodiment 2

[0080] Fluorescent Spectrum of Fluorescent Probe QCN-2 Responding to Transthyretin Tetrameric Protein

[0081] The fluorescent probe QCN-2 (14.4 μM), the fluorescent probe QCN-2 (14.4 μM) and the wild-type transthyretin tetramer were respectively measured in 1 × PBS buffer solution (pH 7.4) by a fluorescence spectrophotometer Protein WT-TTR (14.4 μM) was co-incubated for 1 hour, and fluorescent probe QCN-2 (14.4 μM), wild-type transthyretin tetramer protein WT-TTR (14.4 μM) and guanidine hydrochloride (Guanidine Hydrochloride; 6M) Co-incubate the fluorescence emission spectrum for 1 hour, and record its fluorescence intensity value. The excitation wavelength is 484nm. Among them, the wild-type transthyretin tetramer protein WT-TTR according to the reference (Themost pathogenic transthyretin variant, L55P, forms amyloid fibrils under acidic conditions and protofilaments under physiological conditions [J].Biochemistry,1999,38(41):13560- 13573.) Purified by the method.

[0082...

Embodiment 3

[0084] Excitation and emission wavelengths of fluorescent probe QCN-2:

[0085]Compare the fluorescent probe QCN-2 prepared by the present invention with the existing fluorescent probe compound (structural formula shown in 1-7), detect the excitation and emission wavelength of the fluorescent probe; wherein, the fluorescent probe compound 1-7, As well as the acquisition of excitation and emission wavelengths, please refer to: Chem.Commun., 2019, 55, 10424—10427 (compound 1); Chem.Commun., 2013, 49, 9188—9190 (compound 2); J.Am.Chem. Soc.2015,137,7404-7414 (compound 3); J.Am.Chem.Soc.2010,132,16043–16051 (compound 4); ACS Chem.Neurosci.2016,7,924-940 (compound 5); .Am.Chem.Soc.2013, 135, 17869-17880 (Compounds 6, 7).

[0086] The results are shown in Table 1: the excitation wavelength of the fluorescent probe QCN-2 prepared in the present invention is 484nm, and the emission wavelength reaches 690nm, while the emission wavelength of the fluorescent probe compound 1-7 is shorte...

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Abstract

The invention discloses a near-infrared fluorescent probe, preparation and an application of the near-infrared fluorescent probe in detection of transthyroxine tetramer protein. The structural formula of the near-infrared fluorescent probe is shown as a formula (I). The preparation method comprises the following steps: adding 2-aldehyde-6-dimethylaminoquinoline, 2-acetonitrile benzothiazole and tetrabutylammonium bromide into ethanol, carrying out a reflux reaction under the conditions of sealing and oil bath at 80 + / -5 DEG C, cooling to room temperature after the reaction is finished, standing to separate out a solid, carrying out suction filtration, and washing to obtain the near-infrared fluorescent probe. The fluorescent probe prepared in the invention has near-infrared emission wavelength, and can be used for detecting the content of transthyretin tetramer protein and diagnosing transthyretin familial amyloidosis.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a near-infrared fluorescent probe, its preparation and its application in detecting transthyretin tetramer protein. Background technique [0002] The transthyretin (TTR) gene can mediate the synthesis of transthyretin in the body, and the stable state of transthyretin mainly exists in the form of soluble tetramer, which plays an important role in the transthyretin operation and the metabolism of vitamin A . The mutation of the transthyretin gene will lead to the change of the molecular structure of the transthyretin tetramer, which will reduce the structural stability of the transthyrexine tetramer protein, thereby degrading it into transthyretin monomers, and the transthyretin monomers will be erroneously aggregated to form Insoluble amyloid precipitates and deposits in peripheral nerves leading to neurological impairment. Transthyretin amyloidosis mostly occurs in famil...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D417/06C09K11/06G01N21/64
CPCC07D417/06C09K11/06G01N21/6428G01N21/6486C09K2211/1029C09K2211/1037
Inventor 颜金武刘金胜张雷李晶
Owner SOUTH CHINA UNIV OF TECH
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