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Tetraphenylethylene derivative fluorescent probe and preparation method thereof

A fluorescent probe, tetraphenylethylene technology, which is applied in the field of aggregation-induced luminescence fluorescent materials, can solve the problems of difficult preparation conditions of tetraphenylethylene derivatives, insoluble in water, etc., and achieves good water solubility, simple synthesis and wide application. Effect

Active Publication Date: 2019-09-03
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] However, the preparation conditions of the above tetraphenylethylene derivatives are usually difficult, and some of them are insoluble in water, which has a certain impact on the practical application of tetraphenylethylene derivatives.

Method used

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  • Tetraphenylethylene derivative fluorescent probe and preparation method thereof
  • Tetraphenylethylene derivative fluorescent probe and preparation method thereof
  • Tetraphenylethylene derivative fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of tetraphenylethylene derivative fluorescent probe

[0039] 1. Compound M 1 Synthesis

[0040] Take a clean 500mL three-necked flask, evacuate it several times, and add 4-methylbenzophenone (19.6g, 0.1mol) and zinc powder (20g, 0.308mol) to the three-necked flask under the protection of argon. Add 300mL tetrahydrofuran into the flask, turn on the magnetic stirrer to stir, seal a flask mouth with plastic wrap, and tie it tightly with a rubber band. Slowly pour liquid nitrogen into the ethanol bath to cool, when cooled to -78°C, measure 20mL of titanium tetrachloride 4, inhaled into the syringe, pierced the plastic wrap and slowly and evenly added to the flask, while continuously pouring liquid nitrogen to maintain the reaction temperature. After the feeding is completed, put a balloon on the spherical condenser, stir and react for 1.5 hours, and deflate the balloon in time. Stir the reaction for 1.5h, then change the oil bath and heat to ...

Embodiment 2

[0054] Example 2: M 3 Encapsulating doxorubicin as a drug carrier

[0055] Doxorubicin (DOX) was first dissolved in M 3 (246mg, 0.5mmol) in ethanol solution (25mL) (3.3×10 -3 M), add an aqueous solution (5mL) of zinc nitrate hexahydrate (150mg, 0.5mmol) at room temperature, and stir vigorously at room temperature to obtain DOX / Zn (M 3 )ball. The resulting coated metal-organic system was purified by centrifugation and washed multiple times with ethanol to give a red solid. The coated particles were redispersed in ethanol or phosphate buffer to obtain the corresponding colloids.

Embodiment 3

[0056] Embodiment 3: UV absorption spectrometry

[0057] (1) Target product M 3 Molecular UV Absorption Spectrometry

[0058] Pipet 2 mL of M 3 The molecule to be tested (0.01 mmol / L) was transferred to a 4 mL cuvette. The preset ultraviolet absorption wavelength range is determined between 200nm and 600nm, and a blank test is performed first to deduct the blank interference of the solvent used, and finally the ultraviolet absorption spectrum is measured. get figure 1 , which is M 3 The UV absorption spectrum of the molecule.

[0059] (2) Target product M 4 Molecular UV Absorption Spectrometry

[0060] Pipet 2 mL of M 3 The molecule to be tested (0.05 mg / mL) was transferred to a 4 mL cuvette. The preset ultraviolet absorption wavelength range is determined between 200nm and 600nm, and a blank test is performed first to deduct the blank interference of the solvent used, and finally the ultraviolet absorption spectrum is measured. get figure 2 , which is M 4 The UV ...

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Abstract

The invention discloses a tetraphenylethylene derivative fluorescent probe and a preparation method thereof. The method includes: taking dibromo-substituted dimethyl TPE as the main component to synthesize a compound M2, and using imidazole to replace dibromo to prepare a compound M3; and complexing the compound M3 with Zn ion through the coordination bond of lone pair electrons to obtain the target product M4. The compound M3 has the ability of coating adriamycin for drug delivery, and as a fluorescent probe, the target product M4 can undergo fluorescence quenching with some organic explosives, and the response to p-nitrophenol is the most obvious, therefore the target product M4 can be used as a fluorescent detection probe for explosives.

Description

technical field [0001] The invention belongs to the field of aggregation-induced luminescent fluorescent materials, in particular to an imidazole-modified tetraphenylethylene derivative fluorescent material and a preparation method thereof. Background technique [0002] Although the level of modern medical technology and diagnostic methods has been significantly improved, the morbidity and mortality of cancer are still high and tend to increase year by year, which seriously threatens human health and life. Therefore, the development of new probes for cancer diagnosis and treatment as well as the development of new principles and new methods for cancer diagnosis and treatment are of great significance for improving the cure rate of cancer and tumors and the survival treatment of patients. Today, the use of nanomaterial materials is one of the most promising cancer treatment technologies. Furthermore, in situ real-time monitoring of the absorption, distribution, metabolism, a...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D233/56A61P35/00A61K49/00A61K47/24A61K31/704G01N21/64
CPCC09K11/06C07D233/56A61K47/24A61K31/704A61P35/00A61K49/0021G01N21/643C09K2211/1044C09K2211/1007G01N2021/6432
Inventor 吴婷婷李泽忠冯艺叶家海
Owner NANJING UNIV OF SCI & TECH
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