Fluorescence probe, preparation method and application thereof

A technology of fluorescent probes and fluorescent dyes, applied in the direction of fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of limited fluorescence enhancement of probes

Active Publication Date: 2018-12-11
FLUORESCENT DIAGNOSIS (SHANGHAI) BIOTECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, on the one hand, there is a highly polar hydration layer on the surface of the protein itself, which limits the fluorescence enhancement of the probe; on the other hand, the cell or tissue itself is a very complex system, and the polarity of each organelle changes rapidly Large, these can cause polarity-sensitive probes to have high background in cell or tissue imaging

Method used

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  • Fluorescence probe, preparation method and application thereof
  • Fluorescence probe, preparation method and application thereof
  • Fluorescence probe, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0144]

[0145] Compound 2:

[0146] Compound 1 (0.39g, 2mmol) was dissolved in a 100ml round bottom flask by adding 60ml of anhydrous methanol, adding malonic acid (0.25g, 2.4mmol), a catalytic amount of zinc chloride, and heating to reflux overnight in an oil bath under the protection of Ar. The next day, filter, remove part of the solvent by rotary evaporation, put the system in a refrigerator to cool and crystallize, filter, and rinse with cold ethanol three times to obtain 0.28 g of yellow crystals, with a yield of 61%. 1 H-NMR (400MHz, DMSO-d 6): δ=11.96(s, 1H), 7.82(d, 1H, J=16.0Hz), 7.49(d, 1H, J=7.2Hz), 6.69(d, 1H, J=7.2Hz), 6.52(s, 1H), 6.48 (d, 1H, J = 16.0 Hz), 6.44 (s, 1H).

[0147] Probe 1:

[0148] Compound 2 (0.23g, 1mmol) was added to a 25ml pear-shaped bottle, and compound 3 (refer to the published literature C.R.Jing, V.C.Cornish.ACS Chem.Biol., 2013, 8, 1704-1712.) (0.40g, 1.2mmol) , benzotriazol-1-yl-oxytripyrrolidinylphosphonium hexafluorophosphate...

Embodiment 2

[0150]

[0151] Compound 5:

[0152] Compound 4 (Refer to the method disclosed in the literature: X.P. Zhang. et al. ACS Macro Lett. 2016, 5, 229-233.) (0.49 g, 2 mmol) According to the method of compound 2, the yield was 89%. 1 H-NMR (400MHz, DMSO-d 6 ): δ=11.96(s, 1H), 7.78(d, 1H, J=16.0Hz), 7.51(d, 1H, J=7.2Hz), 6.71(d, 1H, J=7.2Hz), 6.49(d , 1H, J=16.0Hz), 6.52(s, 1H), 6.44(s, 1H), 3.41(t, 4H, J=8.2Hz), 1.21(d, 6H, J=8.2Hz).

[0153] Probe 2:

[0154] Referring to the synthesis method of probe 1, the yield was 92%. 1 H-NMR (400MHz, DMSO-d 6 ): δ=11.96(s, 1H), 7.78(d, 1H, J=16.0Hz), 7.51(d, 1H, J=7.2Hz), 7.28(s, 1H), 6.71(d, 1H, J= 7.2Hz), 6.64(s, 2H), 6.49(d, 1H, J=16.0Hz), 6.52(s, 1H), 6.44(s, 1H), 4.12(t, 2H, J=5.4Hz), 3.87 (s, 6H), 3.70(s, 2H), 3.41(t, 4H, J=8.2Hz), 3.30(t, 2H, J=6.0Hz), 2.08(m, 2H), 1.21(d, 6H, J = 8.2 Hz).

Embodiment 3

[0156]

[0157] Compound 7:

[0158] Compound 6 (refer to the method disclosed in the literature: WO 2006023821 (A2)) (0.53 g, 2 mmol) was synthesized according to the synthesis method of compound 2, and the yield was 66%. 1 H-NMR (400MHz, DMSO-d 6 ): δ=12.10(s, 1H), 7.76(d, 1H, J=16.0Hz), 7.46(d, 1H, J=9.2Hz), 6.84(s, 1H), 6.70(d, 1H, J= 16.0Hz), 5.99(d, 1H, J=9.2Hz), 3.26(m, 4H), 2.88(t, 2H, J=6.5Hz), 2.75(t, 2H, J=6.5Hz), 1.96(m , 4H).

[0159] Probe 3:

[0160] According to the synthesis method of probe 1, the yield was 88%. 1 H-NMR (400MHz, DMSO-d 6 ): δ=7.76(d, 1H, J=16.0Hz), 7.46(d, 1H, J=9.2Hz), 7.28(s, 1H), 6.84(s, 1H), 6.70(d, 1H, J= 16.0Hz), 6.64(s, 2H), 5.99(d, 1H, J=9.2Hz), 4.12(t, 2H, J=5.4Hz), 3.87(s, 6H), 3.70(s, 2H), 3.30 (t, 2H, J=6.0Hz), 3.26(m, 4H), 2.88(t, 2H, J=6.5Hz), 2.75(t, 2H, J=6.5Hz), 2.08(m, 2H), 1.96 (m, 4H).

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Abstract

The invention relates to a fluorescence probe, a preparation method and an application thereof. The fluorescence probe is arranged as an addition activating type probe, can be used for specific fluorescent mark of protein and also can be used for ration, detection, dynamic and activity study of protein and cell, tissue and in vivo images.

Description

technical field [0001] The invention relates to a fluorescent probe and its preparation method and application. Background technique [0002] Fluorescent specific labeling is an important means to study protein function and quantify it. Compared with other research methods, fluorescent labeling has irreplaceable advantages such as sensitivity, in situ, instant, and visualization. Although the molecular structures of organic small-molecule fluorescent dyes are abundant, there are still many defects in the specific labeling of small-molecule fluorescent probes. The same fluorescence emission exists for both free and labeled probes, that is, both labeled and unlabeled probes emit fluorescence in the system. This non-characteristic fluorescence emission is obviously a serious defect of current ligand labeling technology. To remove unlabeled probes by washing is the only effective way to solve the above problems. Obviously, in some occasions that need to be fast or cannot be ...

Claims

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Application Information

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IPC IPC(8): C07D209/24C07D239/49C07D311/16C07D311/82C07D403/14C07D405/12C07D405/14C07D409/14C07D487/04C07D487/22C07D491/052C07D491/147C07D491/16C07D491/22C07F5/02C07F7/08C08G65/333C09K11/06G01N21/64A61K49/00
CPCA61K49/0021A61K49/0032A61K49/0036A61K49/0039A61K49/0041A61K49/0056G01N21/6428C09K11/06C07D209/24C07D239/49C07D311/16C07D311/82C07D403/14C07D405/12C07D405/14C07D409/14C07D487/04C07D487/22C07D491/052C07D491/147C07D491/16C07D491/22C07F5/022C07F7/0816C08G65/33317C09K2211/1466C09K2211/1088C09K2211/1096C09K2211/1092C09K2211/1074C09K2211/1044C09K2211/1029G01N2021/6432A61K49/00C07D239/47C07D413/12C07D417/12C07D473/18C07F5/02C07F7/08C08G65/333G01N21/64
Inventor 朱麟勇杨弋张大生刘韧玫鲍丙坤林秋宁陈显军杨立朋包春燕葛一会张晨霞陈政达张思铜李宁峰华鑫
Owner FLUORESCENT DIAGNOSIS (SHANGHAI) BIOTECH CO LTD
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