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Compound with aggregation induced luminescence property and preparation method and application thereof

The technology of a compound, azafluorenone, is applied in the application field of lipid droplet-targeted photoactivated fluorescence imaging, which can solve the problems of difficulty in introducing functional groups, limited types of photochemical reactions, aggregation-induced quenching, etc., and achieve low cytotoxicity, Overcome the effects of aggregation-induced quenching and large Stokes shift

Active Publication Date: 2017-04-19
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In order to realize the fluorescence imaging of lipid droplets with temporal and spatial controllability, the following two key problems need to be solved: (1) In order to achieve high-brightness fluorescence imaging of lipid droplets, fluorescent materials need to be concentrated in lipid droplets at high concentrations. The defect of aggregation-induced quenching severely limits their application in high-brightness lipid droplet fluorescence imaging; (2) In order to achieve spatiotemporal controllable lipid droplet fluorescence imaging, it is necessary to establish photoactivatable lipid droplet-targeted fluorescent probes
However, the types of photochemical reactions based on traditional photoactivatable fluorescent probes are limited, and it is difficult to introduce corresponding functional groups with photoactivatable reactive functional groups and lipid droplet targeting.

Method used

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  • Compound with aggregation induced luminescence property and preparation method and application thereof
  • Compound with aggregation induced luminescence property and preparation method and application thereof
  • Compound with aggregation induced luminescence property and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0077] Synthesis of three compounds of formula I:

[0078] (1) Compound I-1: 1-(4-(Diphenylamino)phenyl)-3-morpholino-9-oxo-2,9-dihydro-1H-indeno[2,1-c ] Synthesis of pyridine-4-nitrile (R 1 = 4-(Diphenylamino)phenyl, R 2 =morpholinyl)

[0079]

[0080] 2-((Z)-2-(4-Diphenylamino)-benzylidene)-1,2-dihydro-1-oxindan-3-ylidene)-malononitrile (225mg, 0.5mmol ) And morpholine (43.5 mg, 0.5 mmol) were dissolved in 10 mL of acetonitrile, and then reacted for 12 hours at 50°C under nitrogen protection. After the reaction is completed and the temperature is restored to room temperature, the reaction solution is rotated under reduced pressure to remove the solvent, and the residue is separated by silica gel column chromatography to obtain the red solid product 1-(4-(diphenylamino)phenyl)-3-morpholine Benzyl-9-oxo-2,9-dihydro-1H-indeno[2,1-c]pyridine-4-carbonitrile (126 mg, yield 47%). The relevant structural characterization data are as follows:

[0081] 1 H NMR(CD 2 Cl 2 ,500MHz):δ7.79(d,...

Embodiment 2

[0091] Synthesis of 4 compounds of formula II:

[0092] (1) Compound II-1: 1-(4-(Diphenylamino)phenyl)-3-morpholino-9-oxo-9H-indeno[2,1-c]pyridine-4-carbonitrile Synthetic (R 1 = 4-(Diphenylamino)phenyl, R 2 =morpholinyl)

[0093]

[0094] 2-((Z)-2-(4-Diphenylamino)-benzylidene)-1,2-dihydro-1-oxindan-3-ylidene)-malononitrile (225mg, 0.5mmol ) And morpholine (43.5 mg, 0.5 mmol) were dissolved in 10 mL of acetonitrile, and then irradiated with a 7W white energy-saving lamp under dry air, and reacted under reflux for 12 hours. After the reaction is complete and the temperature is restored to room temperature, the reaction solution is evaporated under reduced pressure to remove the solvent, and the residue is separated by silica gel column chromatography to obtain the orange-red solid product 1-(4-(diphenylamino)phenyl)-3-? Linyl-9-oxo-9H-indeno[2,1-c]pyridine-4-carbonitrile (162 mg, yield 61%). The relevant structural characterization data are as follows:

[0095] 1 H NMR(CD 2 Cl 2 ...

Embodiment 3

[0109] Single crystal structure analysis of compound II-2:

[0110] In the single crystal structure of compound II-2 (see figure 1 In ), the dihedral angle between 2-azafluorenone and 1-aromatic ring is 41.9(6)°, while the triphenylamine fragment is in the propeller conformation, and the dihedral angles between the corresponding aromatic rings are 61.3(2)°, respectively , 67.9(1)° and 73.3(6)°. The twisted molecular conformation helps the solution state to dissipate the absorbed light energy through intramolecular rotation, so that it does not emit fluorescence. In addition, in the crystal structure, there are a variety of CH···π, CH···O and van der Waals forces, which help limit the movement of molecules in the crystalline or aggregate state, prevent non-radiative transitions, and facilitate the passage of radiation The transition emits fluorescence.

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Abstract

The invention discloses a compound with an aggregation induced luminescence property and a preparation method and application thereof in lipid droplet targeting light activating fluorescence imaging. The structure of the compound and the structure of an intermediate product of the compound are represented as the formula I and the formula II, and the formula I can be converted to generate the formula II under the light condition. The compound in the formula I is prepared through the following steps that a compound in the formula III and a compound in the formula IV are dissolved in acetonitrile under the protection of nitrogen, light avoiding reaction is conducted, and the 1,2-dihydro-2-diphenyleneimine ketone compound in the formula I is generated. The novel compound with the aggregation induced luminescence property has the aggregation induced luminescence advantage and can effectively overcome the aggregation induced quenching defect of traditional fluorescent dye, and thus lipid droplet targeting specificity light activating fluorescence imaging in a living cell can be achieved; in addition, the compound has the advantages that the light activating efficiency and the signal-to-noise ratio are high, the cytotoxicity is small, the Stokes shift is large, and the capability of the compound to enter cells is high; and cancer cells and normal cells can be effectively distinguished.

Description

Technical field [0001] The invention belongs to the field of medical materials, and specifically relates to a compound with aggregation-induced luminescence properties, a preparation method thereof, and application in lipid droplet targeted light-activated fluorescence imaging. Background technique [0002] As a new generation of fluorescent materials, aggregation-induced luminescent materials have the advantages of strong resistance to photobleaching, high luminous efficiency in the aggregated state, large Stokes shift and low toxicity. They can effectively overcome the defects of aggregation-induced quenching and are used in biological imaging and detection. The field is increasingly widely used, especially for the imaging of organelles and the exploration of physiological functions. [0003] Lipid droplets are not only an important storage place for lipid molecules and proteins, but also a dynamically changing multifunctional organelle. The size and number of lipid droplets var...

Claims

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Application Information

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IPC IPC(8): C07D221/16C07D401/04C09K11/06G01N21/64
Inventor 唐本忠高蒙秦安军
Owner SOUTH CHINA UNIV OF TECH
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