Lysosome-targeted infrared two-window emission fluorescent dye as well as preparation method and application thereof

A fluorescent dye and lysosome technology, applied in the field of bioluminescent detection materials, can solve the problems of long-term toxicity and excretion time, and achieve the effect of rich raw materials, good photostability, and mild synthesis conditions

Active Publication Date: 2020-11-20
SHENZHEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Therefore, the technical problem to be solved by the present invention is to overcome the defects of long-term toxicity and long excretion time of the infrared second-windo

Method used

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  • Lysosome-targeted infrared two-window emission fluorescent dye as well as preparation method and application thereof
  • Lysosome-targeted infrared two-window emission fluorescent dye as well as preparation method and application thereof
  • Lysosome-targeted infrared two-window emission fluorescent dye as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052]This example provides a method for preparing a lysosome-targeted infrared two-window emitting fluorescent dye, and the synthetic route is as follows:

[0053]

[0054] Specific steps include:

[0055] Synthesis of compound 2-1:

[0056] In 1.46g of 1-1 (about 10mmol), 1.91g (about 10mmol) of p-ethylaminoethanone and 30mL of pure ethanol mixed solution, slowly add 10mL of sodium hydride aqueous solution (containing 2.00g of sodium hydroxide). After reacting at room temperature for 12 hours, filter with suction. A yellow solid was obtained, which was washed with cold ethanol and dried in vacuo. 2.59 g of compound 2-1 was obtained (about 81% yield).

[0057] NMR of compound 2-1: 1 H NMR (400MHz, CDCl 3 )δ (ppm) = 8.04 (d, J = 6.4Hz, 2H), 7.77 (dd, J = 15.2, 2.4Hz, 1H), 7.66 (dd, J = 15.6, 3.2Hz, 1H), 7.59 (d, J=7.6Hz, 1H), 7.51(d, J=8.0Hz, 1H), 7.38–7.33(m, 1H), 7.26–7.22(m, 1H), 6.96(d, J=1.2Hz, 1H), 6.68 (d, J=7.2Hz, 2H), 3.44 (q, J=6.4Hz, 4H), 1.22 (t, J=5.2Hz,...

Embodiment 2

[0069] This example provides a method for preparing a lysosome-targeted infrared two-window emitting fluorescent dye, and the synthetic route is as follows:

[0070]

[0071] Specific steps include:

[0072] Synthesis of compound 2-2:

[0073] In the mixed solution of 1.62g 1-2 (about 10mmol), 1.91g (about 10mmol) of p-ethylaminoethanone and 30mL of pure ethanol, slowly add 10mL of sodium hydride aqueous solution (containing 2.00g of sodium hydroxide). After reacting at room temperature for 12 hours, filter with suction. A yellow solid was obtained, which was washed with cold ethanol and dried in vacuo. 3.02 g of compound 2-2 was obtained (about 90% yield).

[0074] Synthesis of Compound 3-2:

[0075] The mixed solution of 3.35g 2-2 (about 10mmol), 15mL nitromethane, 8mL diethylamine and 20mL pure ethanol was reacted overnight under reflux conditions (75°C), separated by silica gel column chromatography (developing agent ethyl acetate : Petroleum ether=4:1, v / v) 3.29g ...

Embodiment 3

[0081] This example provides a method for preparing a lysosome-targeted infrared two-window emitting fluorescent dye, and the synthetic route is as follows:

[0082]

[0083] Specific steps include:

[0084] Synthesis of compound 2-3:

[0085] In the mixed solution of 1.73g 1-3 (about 10mmol), 1.91g (about 10mmol) of p-ethylaminoethanone and 30mL of pure ethanol, slowly add 10mL of sodium hydride aqueous solution (containing 2.00g of sodium hydroxide). After reacting at room temperature for 24 hours, filter with suction. A yellow solid was obtained, which was washed with cold ethanol and dried in vacuo. 3.08 g of compound 2-3 was obtained (about 91% yield).

[0086] Synthesis of compound 3-3:

[0087] The mixed solution of 3.46g 2-3 (about 10mmol), 15mL nitromethane, 8mL diethylamine and 20mL pure ethanol was reacted overnight under reflux condition (70 ℃), separated by silica gel column chromatography (developing agent ethyl acetate : Petroleum ether=4:1, v / v) 3.30 g ...

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Abstract

The invention belongs to the technical field of bioluminescence detection materials, and particularly relates to lysosome-targeted infrared two-window emission fluorescent dye as well as a preparationmethod and application thereof. According to the invention, an aniline derivative and a five-membered heterocyclic conjugated derivative are connected to an aza-fluoroborane parent structure, so thatthe infrared two-window emission of the material is realized. The target fluorescent dye has good light stability, thermal stability and chemical stability; excellent photo-thermal performance, photoacoustic imaging and tumor photo-thermal treatment properties are also shown; meanwhile, the preparation method of the lysosome-targeted infrared two-window emission fluorescent dye provided by the invention has theoretical basis support for design and synthesis, and has the advantages of simple preparation method, mild synthesis conditions, abundant raw materials and high target product yield, thereby having important guiding significance for designing and synthesizing efficient diagnosis and treatment reagents.

Description

technical field [0001] The invention belongs to the technical field of biological fluorescence detection materials, and in particular relates to a lysosome-targeted infrared two-window emitting fluorescent dye and a preparation method and application thereof. Background technique [0002] Lysosome is an important organelle in cells and plays a vital role in the normal life activities of cells: degradation and recycling of intracellular macromolecules, degradation of various intracellular and extracellular materials, and damage to organelles recycling, etc. Lysosomes are highly dynamic, and their shape and spatial distribution are constantly changing, and changes in their number and shape can often represent the state of life activity in cells. Lysosomal abnormalities usually cause a variety of diseases (such as gout, lysosomal storage disease or silicosis, etc.), and the disease process is often accompanied by changes in the number, size, shape, and structure of lysosomes. ...

Claims

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Application Information

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IPC IPC(8): C07F5/02C09B57/00C09K11/06G01N21/64A61K49/00A61K41/00A61P35/00
CPCC07F5/022C09K11/06C09B57/00G01N21/6428A61K49/0021A61K41/0057A61P35/00C09K2211/1029C09K2211/107C09K2211/1088C09K2211/1092
Inventor 屈军乐徐云剑刘丽炜陈振江
Owner SHENZHEN UNIV
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