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Preparation method and application of non-fluorescent organic small molecule compound and pentamethine cyanine dye

A small molecule compound, non-fluorescence technology, applied in the direction of organic dyes, methine-based/polymethine-based dyes, organic chemistry, etc., which can solve the limitations of sensitivity, stability, background fluorescence, space/time controllable, and fluorescence turn-on controllable and other problems to achieve the effect of simplifying the operation steps

Active Publication Date: 2021-08-17
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the design and development of fluorescence imaging systems are limited by sensitivity, stability, background fluorescence, space / time controllability, and controllable fluorescence on-off.

Method used

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  • Preparation method and application of non-fluorescent organic small molecule compound and pentamethine cyanine dye
  • Preparation method and application of non-fluorescent organic small molecule compound and pentamethine cyanine dye
  • Preparation method and application of non-fluorescent organic small molecule compound and pentamethine cyanine dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Photo-induced preparation of pentamethine dyes: 2-thiophene-Cy5 indole compounds with amino side chain structure

[0037] (1) Add 1-propylamine-2,3,3-trimethylindole (75.6mg), 2-thiophene-succinimide active ester (23.9mg) into a 25mL single-necked flask, and then add 5mLCHCl 3 , 56 μL triethylamine, ultrasonically dissolve the solid completely, heat to 65°C, use white LED light to illuminate, reflux the mixture for 12h, then cool to room temperature, spin the organic solvent to dry, add dichloromethane and neutral alumina dry method The sample was mixed, and the product was further separated and purified by neutral alumina chromatography (the eluent ratio was dichloromethane:methanol=50:1). The reaction yield was 8%, and 3.2 mg of 2-thiopheneB-Cy5 was obtained. figure 1 For the synthetic pentamethine cyanine dye fluorescent molecule (2-thiophene B-Cy5) in embodiment 1 step (1) 1 H-NMR spectrum. 1 HNMR (400MHz, CDCl 3 δ): 8.33(t, J=5.2Hz, 2H), 7.74(t, J=13.0Hz, 2H), ...

Embodiment 2

[0040] Photoinduced Preparation of Pentamethine Dye: Benzene-Cy5

[0041] (1) Add 1-propylamine-2,3,3-trimethylindole (75.6mg), benzyl-succinimide active ester (21.9mg) into a 25mL one-necked flask, then add 5mLCHCl 3 , 56 μL triethylamine, ultrasonically dissolve the solid completely, heat to 65°C, use white LED light to illuminate, reflux the mixture for 12h, then cool to room temperature, spin the organic solvent to dry, add dichloromethane and neutral alumina dry method The sample was mixed, and the product was further separated and purified by neutral alumina chromatography (the eluent ratio was dichloromethane:methanol=50:1). The reaction yield was 6%, and 2.3 mg of benzyl-Cy5 was obtained. image 3For the synthetic pentamethine cyanine dye fluorescent molecule (benzyl-Cy5) in embodiment 2 step (1) 1 H-NMR spectrum. 1 H NMR (400MHz, MeODδ): 8.19(t, J=3.1Hz, 2H), 7.87-7.83(m, 4H), 7.58-7.54(m, 2H), 7.51-7.46(m, 6H), 7.38(dd , J=6.5, 5.5Hz, 2H), 7.29(dd, J=12.2, 7.7Hz,...

Embodiment 3

[0043] Photoinduced Preparation of Pentamethine Dye: 3-Indoleethyl-Cy5

[0044] (1) Add 1-propylamine-2,3,3-trimethylindole (75.6mg), 3-indoleethyl-succinimide active ester (27.2mg) into a 25mL single-necked flask, then add 5mLCHCl 3 , 56 μL triethylamine, ultrasonically dissolve the solid completely, heat to 65°C, use white LED light to illuminate, reflux the mixture for 12h, then cool to room temperature, spin the organic solvent to dry, add dichloromethane and neutral alumina dry method The sample was mixed, and the product was further separated and purified by neutral alumina chromatography (the eluent ratio was dichloromethane:methanol=50:1). The reaction yield was 6%, and 2.6 mg of 3-indoleethyl-Cy5 was obtained. Figure 5 For the synthetic pentamethine cyanine dye fluorescent molecule (3-indole ethyl-Cy5) in embodiment 2 step (1) 1 H-NMR spectrum. 1 H NMR (400MHz, MeODδ): 8.16-8.03(m, 2H), 7.52(t, J=7.9Hz, 2H), 7.38-7.33(m, 2H), 7.27(t, J=9.1Hz, 3H), 7.14(dt, J=10.0...

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Abstract

The invention discloses a non-fluorescent organic small molecule compound, a pentamethine cyanine dye and application thereof. The pentamethine cyanine dye with wide biological application is directly synthesized through LED white light induction of the non-fluorescent organic small molecule compound without using a condensing agent and a photosensitizer, and the near-infrared fluorescent pentamethine cyanine functional dye with various structures can be obtained by changing the non-fluorescent organic small molecule compound. The non-fluorescent small organic molecule compound and human cervical cancer cells or human normal liver cells are co-incubated, and after LED white light illumination, the intracellular fluorescence enhancement can be achieved, and almost no fluorescence exists in the cells without illumination so that the synthesis method can be used for intracellular near-infrared fluorescence imaging, and the visible light regulation and control can be utilized, the near-infrared fluorescence imaging with controllable time and space in cells can be realized, and the method can be used for time and space resolution imaging of lysosome in cells.

Description

technical field [0001] The present invention relates to a small molecular compound and its application, in particular to a non-fluorescent organic small molecular compound and a preparation method and application of a pentamethine dye. Background technique [0002] In recent years, fluorescence imaging technology has developed rapidly and has been widely used in the fields of chemistry, biology, biomedicine and microscopic imaging. Cyanine dye is a kind of near-infrared fluorescent dye, and its synthesis method is relatively complicated. The development of synthetic methods different from traditional pentamethine dyes and their application in the field of low background, spatiotemporal controllable fluorescence imaging has not been studied. In order to carry out real-time tracking and qualitative and quantitative detection of important signaling molecules or chemical processes in cells, researchers have designed a large number of fluorescent imaging bioprobes, so as to bett...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/08C09B23/08C09K11/06G01N21/64
CPCC07D209/08C09B23/083C09K11/06G01N21/6486C09K2211/1029C09K2211/1092Y02B20/00
Inventor 冯福德宋刚衡浩
Owner NANJING UNIV
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