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Internal standard ratio type fluorescent probe based on fluorescein derivative, preparation method and application thereof

A technology of fluorescent probes and derivatives, applied in the field of internal standard ratio fluorescent probes, can solve the problems of wrong fluorescence ratio, fluorescence ratio error, failure to provide, etc., and achieve the effect of simple synthesis and few synthesis steps

Inactive Publication Date: 2019-05-31
EAST CHINA UNIV OF SCI & TECH
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AI Technical Summary

Problems solved by technology

The disadvantages of this type of fluorescent probe are: (1) the intensity of the fluorescence emission peak as a reference changes before and after the reaction, and cannot provide a fixed fluorescence signal, resulting in an error in the fluorescence ratio; (2) the spectra before and after the reaction cannot be completely separated, resulting in the provision of (3) The fluorescence emission peak before the reaction gradually decreases, resulting in false positive signals and wrong fluorescence ratios
The disadvantages of introducing two fluorescent units are: (1) there may be unnecessary energy transfer between the two fluorescent units; (2) the same biological environment has different effects on the fluorescence properties of the two fluorescent units; (3) it cannot be used Excite two fluorescent units with the same excitation wavelength
So these limit the development of internal standard ratiometric fluorescent probes

Method used

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  • Internal standard ratio type fluorescent probe based on fluorescein derivative, preparation method and application thereof
  • Internal standard ratio type fluorescent probe based on fluorescein derivative, preparation method and application thereof
  • Internal standard ratio type fluorescent probe based on fluorescein derivative, preparation method and application thereof

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preparation example Construction

[0053] In the compound shown in formula I below, A is O; B is O; C is O or a group shown in II-3A; D is a group shown in formula III-1A or III-2A; E is H as an example, The method for synthesizing the compound shown in formula I is further elaborated, and the synthetic method comprises the following steps: it uses fluorescein as a starting material, successively undergoes Vilsmeier-Haack reaction, reacts with halogenated unsaturated hydrocarbon and reacts with active subunit containing Different conjugated groups of the methyl group undergo condensation reactions to obtain the target compound.

[0054] The present invention is further elaborated below by example, and its purpose is only to understand content of the present invention better. Therefore, the examples given do not limit the protection scope of the present invention:

Embodiment 1

[0056]

[0057] In a 100mL three-neck flask, add DMF (15mL), POCl 3 (0.5 mL) and fluorescein (4 g, 12 mmol). After 48 hours of reaction, the reaction was terminated, and 0.5 g of a yellow solid was obtained by recrystallization from acetone, with a yield of 11.2%.

[0058] 1 H-NMR (400MHz, DMSO-d 6 , ppm): δ6.61(s, 1H), 6.62(d, J=1.2Hz, 1H), 6.72(d, J=8.9Hz, 1H), 6.85(d, J=1.2Hz, 1H), 6.96 (d, J=8.9Hz, 1H), 7.32(d, J=7.5Hz, 1H), 7.74(t, J=7.5Hz, 1H), 7.82(t, J=7.5Hz, 1H), 8.03(d , J=7.5Hz, 1H), 10.26(s, 1H, -OH), 10.64(s, 1H, -CHO) 11.89(s, 1H, -OH).

[0059] Mass spectrometry (ESI negative ion mode for [M-H] - ): calcd for [C 21 h 11 o 6 ]: 359.0556; found: 359.0555.

[0060]

[0061] In a 100 mL three-neck flask, add fluorescein aldehyde (500 mg, 1.39 mmol) and acetic anhydride (50 mL). Add 2-Bromocyclohex-1-ene-1-carbaldehyde (523mg, 2.78mmol) into a three-necked flask and react at room temperature for 2h. During the course of the reaction, the color gradua...

Embodiment 2

[0069]

[0070] Add fluorescein derivative (50 mg, 0.078 mmol), dichloromethane (15 mL), and acryloyl chloride (0.5 mL) into a 50 mL three-necked flask. After reacting at room temperature for 18 h, the reaction was terminated. The solvent was spin-dried, and recrystallized from dichloromethane to obtain 10 mg of a black-purple solid with a yield of 18%.

[0071] 1 H-NMR (400MHz, CDCl 3 , ppm): δ1.91 (m, 2H, -CH 2 ), 2.52(t, 2H, -CH 2 ), 2.68(t, 2H, -CH 2 ), 6.08(d, J=10.44Hz, 1H, alkene-H), 6.15(d, J=15.52Hz, 1H, alkene-H), 6.34(dd, J 1 =10.48Hz,J 2=17.32Hz, 1H, alkene-H), 6.64(d, J=8.68Hz, 1H, Ph-H), 6.65(d, J=17.32Hz, 1H, alkene-H), 6.77(s, 1H, alkene -H), 6.79(d, J=8.92Hz, 1H, Ph-H), 6.83(s, 1H, Ph-H), 6.84(d, J=1.8Hz, 1H, Ph-H), 7.04(s , 1H, alkene-H), 7.19 (d, J = 7.4Hz, 1H, Ph-H), 7.25 (d, J = 1.8Hz, 1H, Ph-H), 7.40 (t, J = 7.4Hz, 1H , Ph-H), 7.52 (d, J=7.68Hz, 1H, Ph-H), 7.65-7.73 (m, 3H, Ph-H), 8.04 (d, 1H, J=15.52Hz, alkene-H) , 8.07(d, J=6.80Hz, 1H, Ph-H...

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Abstract

The invention relates to an internal standard ratio type fluorescent probe based on a fluorescein derivative, a preparation method and application thereof. The fluorescein derivative is used as a starting material, malononitrile, tricyanobenzene, indole, pyranonitrile and the like are used as auxiliary fluorescence units, and acryloyl, 2, 4-dinitrobenzenesulfonyl and the like are used as biomarkerresponse units. Through introduction of the auxiliary fluorescence units, the absorption wavelength and the double-channel fluorescence emission wavelength of the fluorescence probe are regulated andcontrolled: the absorption wavelength is 400-750 nm; and double-channel fluorescence emission is implemented, the emission wavelength of a first channel is 520 nm, and the emission wavelength of a second channel is 517 nm-720 nm. Aiming at the detection of different biomarkers, through connecting different recognition groups, the fluorescence intensity of the first channel is regulated and controlled: after the probe responds with the biomarkers, the fluorescence intensity of the first channel is obviously enhanced; and the fluorescence intensity of the second channel is kept unchanged, and quantitative detection of the biomarkers by the internal standard ratio type fluorescence probe is realized.

Description

technical field [0001] The invention relates to a class of internal standard ratio fluorescent probes based on fluorescein derivatives and applications thereof. Background technique [0002] Using fluorescent probes to explore life processes and study disease diagnosis and treatment is one of the most effective means. At present, the main demand for fluorescent probes is: (1) more sensitive and effective fluorescent probes related to the synthesis and biological processes; (2) the synthesized fluorescent probes can provide quantitative fluorescent signals, which are related to the excitation intensity or Probe concentration is independent. In this regard, the most preferred strategy is to design ratiometric fluorescent probes. After the ratiometric fluorescent probe reacts with the biomarker, it provides a signal independent of the probe concentration and excitation light intensity through the ratio of the fluorescence intensity of two different fluorescence emission wavel...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/20C07F5/02C09K11/06G01N21/64
Inventor 郭志前朱为宏石丽敏燕宸旭顾开智付伟张贺贺王若飞
Owner EAST CHINA UNIV OF SCI & TECH
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