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Qijiachuan functional cyanine dye based on click-activated large-space impedance aggregation quenching and its preparation method and application

A technology of alkyl and methyl, applied in biomedical imaging, anti-aggregation and quenching heptamethine functional cyanine dye and its preparation field, can solve the problem of low background signal-to-noise ratio and achieve an increase in signal-to-noise ratio , to achieve the effect of targeted positioning and easy operation

Active Publication Date: 2022-03-01
XIDIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, it solves the problem of low background signal-to-noise ratio of Qijiachuan cyanine dyes in biomedical optical imaging

Method used

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  • Qijiachuan functional cyanine dye based on click-activated large-space impedance aggregation quenching and its preparation method and application
  • Qijiachuan functional cyanine dye based on click-activated large-space impedance aggregation quenching and its preparation method and application
  • Qijiachuan functional cyanine dye based on click-activated large-space impedance aggregation quenching and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0068] The synthetic route of diethylene glycol bromoethyl methyl ether parent dye CyBI7P:

[0069]

[0070] 1.1 Synthesis of diethylene glycol bromoethyl methyl ether benzindole quaternary ammonium salt:

[0071] Dissolve 0.611g of 1,1,2-trimethyl 1[H]benzindole, 0.917g of diethylene glycol-2-bromoethyl methyl ether in 10ml of acetonitrile, and react the mixture in a reaction kettle at 80°C for 36 hours , standing to cool, then poured into diethyl ether for washing, filtered, and recrystallized from methanol to obtain 0.96 g of diethylene glycol bromoethyl methyl ether benzindole bromide quaternary ammonium salt, with a yield of 80%.

[0072] 1.2 Synthesis of condensing agent 2-chloro-1-formyl-3-hydroxymethinecyclohexene:

[0073] 18ml POCl 3 Add 17ml of dry dichloromethane solution and mix for later use. Add 40ml of dry dichloromethane and 40ml of dry DMF in turn to a 250mL round bottom flask and mix well. Under ice bath conditions, the mixed POCl 3 The dichlorometha...

Embodiment 2

[0077] Synthesis of CyP-Tz, a functionalized Anti-ACQ heptamethine cyanine dye with click activation:

[0078]

[0079] The parent dye CyBI7P prepared in Example 1 was pre-dried in a vacuum oven at 40° C. overnight. Add dry 0.5g CyBI7P and 0.51g Tz in turn to a 100ml round bottom flask, add 15ml anhydrous DMF to dissolve. After stirring for 1.5 h at 80°C under the protection of nitrogen, the reaction solution was quenched by pouring into ice water, and a blue solid was precipitated by filtration, separated by column chromatography (methanol:dichloromethane=1:50v / v), and concentrated with petroleum ether to precipitate a solid , vacuum dried overnight to obtain the blue dye CyP-Tz 0.3g, yield 50.92%. The product structure is identified by high resolution. Calculated value: 1012.5701, Tested value: 1012.5843. Mass spectrometry results such as figure 1 Shown in (b).

Embodiment 3

[0081] The spectral characteristics of the click-activated mid-position-substituted functionalized Anti-ACQ heptamethine cyanine dye CyP-Tz, the parent dye CyBI7P, and the commercial heptamethine cyanine dye ICG (CAS: 3599-32-4):

[0082] Accurately weigh 5 mg of CyP-Tz solid with a balance, dissolve it in 1 ml of dimethyl sulfoxide (DMSO) to prepare a mother solution with a concentration of 4.58 mM; then take the mother solution and dilute it in methanol to obtain a test solution. The absorption intensity and fluorescence emission intensity of CyP-Tz were measured by UV spectrophotometer and Edinburgh 1000 fluorescence spectrometer. The molar absorptivity of the compounds was calculated using the Lambert-Beer law. The calculation formula is A=εcb, where A represents the absorption intensity, ε represents the molar extinction coefficient, c is the concentration of the compound (in mol / L), and b is the thickness of the quartz cell (in cm). The test result shows that the UV abs...

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Abstract

The invention belongs to the technical field of organic dyes, and in particular relates to an anti-aggregation quenching (Anti-ACQ) heptamethine functional cyanine dye represented by formula I, a preparation method thereof, and an application in biomedical imaging. The new Qijiachuan fluorescent dye provided by the present invention can be activated to produce a large steric hindrance structure through molecular design, thereby realizing the responsive Anti-ACQ effect, effectively avoiding the problem of fluorescence quenching caused by the ACQ effect, and to a large extent The aggregation-induced quenching problem of traditional organic cyanine dyes is solved.

Description

technical field [0001] The invention belongs to the technical field of organic dyes, and in particular relates to an anti-aggregation quenching (Anti-ACQ) heptamethine functional cyanine dye, a preparation method thereof and an application in biomedical imaging. Background technique [0002] With the development of biological analysis technology, fluorescence analysis technology has become a powerful tool for non-destructive real-time monitoring. It is widely used in various aspects of biology and medicine, including physiology and biochemistry, biopharmaceuticals, cells, immunity, genetics, etc. Through the detection of fluorescent signals, the existence, distribution and quantity of samples containing natural fluorescent substances such as aromatic amino acids, porphyrin, and chlorophyll can be determined. At the same time, some artificially synthesized exogenous fluorescent probes can be used to achieve fluorescent labeling of proteins, nucleic acids, and biofilms; fluor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D403/14C09B23/08C09K11/06G01N21/64
CPCC07D403/14C09B23/086C09K11/06G01N21/6428C09K2211/1007C09K2211/1029C09K2211/1074G01N2021/6432
Inventor 张象涵高靖凯王忠良夏玉琼宁蓬勃张瑞丽
Owner XIDIAN UNIV
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