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Cyanine fluorescent dye and synthesis method thereof

A technology for fluorescent dyes and cyanines, applied in the field of organic fluorescent dyes and applications, can solve the problems of difficult to achieve high-sensitivity fluorescence analysis and imaging, short absorption wavelength and emission wavelength, strong fluorescence self-quenching effect, etc., and achieve high yield , high photostability, simple synthesis method

Active Publication Date: 2018-09-07
江苏协合转化医学研究院有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the cyanine and semi-cyanine fluorescent dyes reported in the literature have short absorption and emission wavelengths, small Stokes shifts, and strong fluorescence self-quenching effects, making it difficult to achieve high sensitivity in cells or in vivo Fluorescence analysis and imaging

Method used

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  • Cyanine fluorescent dye and synthesis method thereof
  • Cyanine fluorescent dye and synthesis method thereof
  • Cyanine fluorescent dye and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1: the synthesis of the I formula cyanine fluorescent dye (DQF-692) of n=1

[0047] (1) Synthesis of compound 4 (5,10-diethyl-7-methoxy-1,2,3,4,4a,5,10,10a-swahydrophenazine)

[0048]

[0049] Weigh 4-methoxy o-phenylenediamine (1.3g, 12.0mmol) and 1,2-cyclohexanedione (1.1g, 10.0mmol) and dissolve them in 60mL of ethanol, stir at 60°C for 2h Separation and purification by silica gel column chromatography (the eluent is petroleum ether and dichloromethane, the volume ratio is 1:1), and the light yellow solid compound 3 (7-methoxy-1,2,3,4-tetrahydrophene Dissolve compound 3 (0.9g, 5.0mmol) in 150mL of anhydrous toluene, add sodium borohydride (1.9g, 50.0mmol) in an ice-bath environment, stir for 15min, then slowly add 10mL of glacial acetic acid dropwise for 1h into the reaction solution, after the glacial acetic acid is dripped, maintain the reaction in an ice bath for 30 minutes, then heat the reaction solution to 110 ° C, and reflux for 6 hours. After t...

Embodiment 2

[0056] Embodiment 2: the synthesis of the I formula cyanine fluorescent dye (DQF-780) of n=2

[0057] (1) Intermediate 8 ((1E,2E)-4-((E)-1,3,3-trimethylindoline-2-methylene)-N-phenyl-2-propenyl-1 -imine) synthesis

[0058]

[0059] Dissolve compound 6 (2,3,3-trimethyl-3H-indole) (1.6g, 10mmol) and iodomethane (2.8g, 20mmol) in 20mL of anhydrous acetonitrile, reflux and stir for 6h; After cooling, the separated pink solid obtained compound 7 (1,2,3,3-tetramethyl-3H-indole iodide) after suction filtration, washing and drying; Compound 7 (1,2,3,3 -Tetramethyl-3H-indole iodide) (2.1g, 7mmol) and condensing agent malondialdehyde diphenylamine hydrochloride (2.6g, 10mmol) were dissolved in 30mL n-butanol-toluene mixed solution, at 110°C Reflux reaction for 4h; after the reaction was completed, the solution was concentrated and separated by column chromatography (dichloromethane:ethanol=100:1, v / v) to obtain intermediate 8 ((1E,2E)-4-((E)-1, 3,3-trimethylindoline-2-methylene)-N...

Embodiment 3

[0063] Embodiment 3: the synthesis of II formula cyanine dye (DQF-Cy7)

[0064] (1) Intermediate 9((E)-2-chloro-3-(2-((E)-1,3,3-trimethylindoline-2-methylene)ethylene)cyclohexyl Synthesis of En-1-ene-1-Carboxaldehyde)

[0065]

[0066]Compound 7 (1,2,3,3-tetramethyl-3H-indole iodide) (3.0 g, 10 mmol) prepared in Example 2 and condensing agent 2-chloro-1-formyl-3-hydroxy Methylenecyclohexene (3.4g, 20mmol) was dissolved in 30mL of n-butanol-toluene mixed solution, reflux reaction at 110°C for 2h; after the reaction was completed, the solution was concentrated and separated by column chromatography (dichloromethane:ethanol=100 :1, v / v) to obtain the intermediate 9 ((E)-2-chloro-3-(2-((E)-1,3,3-trimethylindoline-2-methylene) ethyl) cyclohexene-1-ene-1-carbaldehyde).

[0067] (2) Synthesis of fluorescent dye DQF-Cy7

[0068]

[0069] Anhydrous sodium acetate (2.0g, 25mmol) was mixed with intermediate 9 ((E)-2-chloro-3-(2-((E)-1,3,3-trimethylindoline-2-ylidene Methyl) et...

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Abstract

The invention discloses a cyanine fluorescent dye having the structural formula represented by one of the formula I and the formula II defined in the specification. The cyanine fluorescent dye provided by the invention has both the excitation wavelength and the fluorescence emission wavelength reaching a near infrared region, and the Stokes shifts are each greater than 60 nm; the background fluorescence of the biological environment and the self-quenching and self-absorption effects of the dye in the application of living imaging are significantly reduced, the signal-to-noise ratio is improved, and the sensitivity is improved. The synthesis method of the fluorescent dye provided by the invention is simple, the raw materials are easy to obtain, and the yield is high; the fluorescent dye provided by the invention has good effect in cell imaging and living imaging of small animals, and has high light stability.

Description

technical field [0001] The invention belongs to the technical field of organic fluorescent dyes and applications, in particular to a cyanine fluorescent dye and a synthesis method thereof. Background technique [0002] Fluorescence imaging technology is a rapidly developing optical imaging technology, which has broad application prospects in many fields such as chemistry, biology, environmental science and clinical medicine. At present, fluorescence imaging technology is limited by the fact that the emission wavelength of most fluorescent molecules is in the visible region, which is extremely susceptible to interference from endogenous fluorescence in vivo, and it is also difficult to penetrate deep into tissues because of the short excitation and emission wavelengths. Currently, there are near-infrared region emission wavelengths. Therefore, the development of fluorescent dyes with excitation and emission in the near-infrared region is very necessary for the development of ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/06C09B23/08C09B23/10C07D491/052C09K11/06A61K49/00
Inventor 袁林任天兵张晓兵王志尧
Owner 江苏协合转化医学研究院有限公司
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