Fluorescent compound with aggregation-induced luminescence properties and application thereof to cell fluorescence imaging field

A technology for aggregation-induced luminescence and fluorescent compounds, which is applied in the preparation of organic compounds, fluorescence/phosphorescence, carbon-based compounds, etc., can solve problems such as constraints and the influence of fluorescent molecules, and achieve easy operation, sensitive and fast cell staining, and light resistance good bleaching effect

Active Publication Date: 2017-09-26
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, due to the self-quenching phenomenon of common fluorophores, there is a nonlinear relationship between their fluorescence intensity and concentration at high concentrations.
This property limits the detection and analysis methods that use fluorescence as the output signal.
At the same time, common fluorescent dyes require the output of fluorescent signals in a solution state, and fluorescent molecules in this state are more susceptible to photobleaching effects

Method used

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  • Fluorescent compound with aggregation-induced luminescence properties and application thereof to cell fluorescence imaging field
  • Fluorescent compound with aggregation-induced luminescence properties and application thereof to cell fluorescence imaging field
  • Fluorescent compound with aggregation-induced luminescence properties and application thereof to cell fluorescence imaging field

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Preparation of C3NDPA molecule: Weigh 0.2g compound 1, 0.142g compound 2, 0.015g palladium acetate, 0.5g cesium carbonate, 0.04g tert-butylphosphine, add 20mL toluene, reflux reaction under nitrogen protection for 24 hours, after cooling, use 200-300 mesh silica gel powder was separated by column chromatography using dichloromethane as a developer to obtain C3NDPA as a red solid powder with a yield of 0.168 g and a yield of 65%.

[0043]

[0044] 1 H-NMR (500MHz, CDCl 3 )δ9.09(d, J=8.0Hz, 1H), 8.96(dd, J=4.6, 1.9Hz, 1H), 8.73(dd, J=7.9, 1.9Hz, 1H), 8.69(d, J=8.4 Hz,1H),8.18(dd,J=8.5,1.1Hz,1H),7.54(t,J=8.0,1H),7.50(dd,J=7.9,4.6Hz,1H),7.45(d,J= 8.1Hz,1H),7.30-7.23(m,4H),7.12-7.01(m,6H).

[0045] 13 C-NMR (125MHz, CDCl 3 )δ182.71, 153.43, 153.32, 152.27, 148.70, 135.64, 131.14, 130.58, 129.53, 129.00, 128.92, 127.57, 126.51, 126.47, 125.48, 124.72, 123.81, 123.5

[0046] HRMS (TOF LD + ): m / z=398.1429 (C 28 h 18 N 2 o + ,calcd=398.1414).

Embodiment 2

[0048] Dissolve the C3NDPA fluorescent dye in DMSO to obtain a probe solution (0.001mol / L), filter and sterilize it with a 0.22μm filter, add it to DMEM / F12 medium containing 15% FBS and 1% double antibody, shake Evenly, the working solution for cell staining was obtained. After co-culturing the working solution with adherent cells for a certain period of time, the staining was observed under a laser confocal microscope. figure 1 It showed that the cytotoxicity of the dye was very small, and the survival rate of Hela cells was above 95% after 48 hours of culture within 15 μmol / L concentration. Proved by dyeing experiments (for experimental results, see figure 2 ), the dye can quickly enter the living Hela cells within 1 h, and is mainly enriched in the cell lysosomes.

Embodiment 3

[0050] Dissolve the C3NDPA fluorescent dye in DMSO to obtain a probe solution (0.001mol / L), filter and sterilize it with a 0.22μm filter, add it to DMEM / F12 medium containing 15% FBS and 1% double antibody, shake Evenly, the working solution for cell staining was obtained. With this working solution and commercial dyes The adherent cells were co-stained under the same concentration of DND 26. After culturing for a certain period of time, laser scanning was performed under a laser confocal microscope to test the fluorescence signal intensity emitted by the two dyes. The results are shown in image 3 . image 3 The results show that the dye has excellent anti-photobleaching properties: comparable to commercial dyes Compared with DND 26, the signal attenuation of this dye is less than 5% after 250 s excitation light irradiation, while The DND26 dye signal decays by more than 50%.

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Abstract

The invention belongs to the technical field of bio-analytical detection and discloses a fluorescent compound with aggregation-induced luminescence properties and application thereof to the cell fluorescence imaging field. The fluorescent compound with the aggregation-induced luminescence properties adopts one of structures shown as a formula 1 to a formula 4. The fluorescent compound with the aggregation-induced luminescence properties almost does not emit light or emit weak fluorescence in a solution state, can obtain the strong fluorescence emission aggregation-induced luminescence properties in solid state and aggregation states, has room temperature phosphorescent emission properties in a crystalline state, is simple to prepare and wide in luminous spectrum range, is applied to cell fluorescence imaging, biological analysis and other fields, has the characteristics of being sensitive and quick in cell dyeing, small in cytotoxicity, excellent in fluorescence signal anti-photobleaching properties and capable of in-situ real-time monitoring, and has practical application values.

Description

technical field [0001] The invention belongs to the technical field of biological analysis and detection, and in particular relates to a class of fluorescent compounds with aggregation-induced luminescent properties and their application in the field of cell fluorescence imaging. Background technique [0002] Fluorescence analysis has the property of rapidly reporting signals in real time. The duration of fluorescent signal emission is usually shorter than 10ns, so the signal can quickly reflect the state of the system in real time. Fluorescence analysis allows signal acquisition without physical damage to the sample, thus maintaining sample integrity. The collection of fluorescence signals is convenient and intuitive, and can be quickly analyzed qualitatively. However, due to the self-quenching phenomenon of common fluorophores, there is a nonlinear relationship between their fluorescence intensity and concentration at high concentrations. This property restricts detecti...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D221/18C07D417/06C07C45/69C07C49/577C07C253/30C07C255/40C09B57/00C09K11/06G01N21/64
CPCC07C45/69C07C49/577C07C253/30C07C255/40C07D221/18C07D417/06C09B57/00C09K11/06G01N21/6486
Inventor 唐本忠胡蓉蓉臧启光赵祖金秦安军
Owner SOUTH CHINA UNIV OF TECH
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