Near-infrared fluorescent dye based on coumarin skeleton and synthesis method thereof

A technology of coumarin skeleton and fluorescent dye, applied in the field of fluorescent dyes for biomedicine, can solve the problems of short life, high reactivity, low concentration, etc., and achieve the effect of avoiding the interference of self-fluorescence

Inactive Publication Date: 2020-01-14
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the characteristics of low concentration, short lifespan and high reactivity of ROS, accurate detection of ROS is a major challenge in the fields of chemistry, biology and medicine.

Method used

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  • Near-infrared fluorescent dye based on coumarin skeleton and synthesis method thereof
  • Near-infrared fluorescent dye based on coumarin skeleton and synthesis method thereof
  • Near-infrared fluorescent dye based on coumarin skeleton and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] 1. Add 1.2mL (15.6mmol) N,N-dimethylformamide to 1.23mL (13.25mmol) phosphorus oxychloride, stir at room temperature for 30min, then add 5mL containing 339mg (1.56mmol) of formula I-1 4-(Diethylamino)coumarin in N,N-dimethylformamide solution, stirred and reacted at 60°C for 24 hours, after the reaction was completed, pour the reaction solution into ice water, wash with ethyl acetate and saturated saline The reaction solution was extracted, the organic phases were combined, and dry column chromatography (using a mixture of petroleum ether and ethyl acetate at a volume ratio of 30:1 as the eluent) gave the compound of formula II.

[0041]

[0042] 2. Dissolve 98mg (0.4mmol) of the compound of formula II and 155mg (1mmol) of 4-acetonitrile pyridine hydrochloride in 2mL of ethanol, add 221μL (1.6mmol) of triethylamine, stir and react at 40°C for 12 hours, and filter to obtain Compound of formula III.

[0043]

[0044] 3. Dissolve 104 mg (0.3 mmol) of the compound of...

Embodiment 2

[0048] Step 1 and Step 2 of this embodiment are the same as those of Embodiment 1. In step 3 of this example, 104 mg (0.3 mmol) of the compound of formula III was dissolved in 4 mL of N,N-dimethylformamide, 272 μL (3 mmol) of bromopropane was added, and the reaction was stirred at 80°C for 12 hours. Extract the reaction solution with dichloromethane and saturated brine, combine the organic phases, and dry column chromatography after spin-drying (using a mixture of dichloromethane and methanol with a volume ratio of 40:1 as the eluent) to obtain formula IV-2 The indicated fluorochromes were obtained in 75% yield.

[0049]

Embodiment 3

[0051] In this example, bromopropane in Example 2 was replaced with bromohexane in an equimolar amount, and the other steps were the same as in Example 2 to obtain the fluorescent dye shown in Formula IV-3 with a yield of 78%.

[0052]

[0053] The structural characterization data of the resulting product are: 1 H NMR (400MHz, DMSO) δ9.02(d, J=6.9Hz, 2H), 8.83(s, 1H), 8.37(d, J=16.6Hz, 1H), 8.31(d, J=6.9Hz, 2H ), 7.66(d, J=9.1Hz, 1H), 6.88(dd, J=9.1, 2.2Hz, 1H), 6.68(d, J=2.0Hz, 1H), 4.55(t, J=7.4Hz, 2H ), 3.55(q, J=6.9Hz, 4H), 1.89(d, J=2.5Hz, 2H), 1.28(s, 5H), 1.16(t, J=7.0Hz, 5H), 0.85(t, J =6.6Hz,3H).

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Abstract

The invention discloses a near-infrared fluorescent dye based on coumarin structure and a synthesis method thereof. The general structural formula of the fluorescent dye is shown in the description: wherein R represents C1 alkyl group, X- represents PF6- or R represents any one of C2-C12 alkyl groups, X- represents Br-. 4-(diethylamino) coumarin is subjected to Vilsmeier-Haack reaction to synthesize 4-(diethylamino) coumarin aldehyde, 4-(diethylamino) coumarin aldehyde reacts with cyanopyridine and halogenated alkanes with different carbon chain lengths in turn to obtain a series of fluorescent dyes. The fluorescent dye of the invention can specifically label suborganelles in living cells through regulation and control of ammonium salt side chains, and the fluorescent dye with R representing C3 alkyl group can realize rapid dyeing and washing-free in the labeling process; the maximum emission wavelength of fluorescent dye is in the red luminescence region, which can significantly eliminate the interference of self-fluorescence phenomenon in cell imaging. In addition, fluorescent dyes with R representing C9 and C12 alkyl groups have the property of producing singlet oxygen and havecertain application potential in photodynamic therapy of cells and bacteria.

Description

technical field [0001] The invention belongs to the technical field of biomedical fluorescent dyes, and specifically relates to a class of near-infrared luminescent properties and a preparation method of the fluorescent dyes. Background technique [0002] The plasma membrane is the two-dimensional boundary between a living cell and its environment. Life activities associated with the plasma membrane include dynamic membrane remodeling, signal transduction, and nutrient transport, all of which are research hotspots for cell biologists. To study these cellular processes, it is important to develop subcellular fluorescent imaging probes that can recognize the plasma membrane and record dynamic changes. So far, only a few commercial fluorescent dyes are available to track cell membranes, such as DiO 3 and DiI. However, the emission wavelength of most commercial fluorescent dyes is in the visible region, which will generate background fluorescence and lead to low signal-to-noi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B57/02C09K11/06G01N21/64A61K41/00A61P31/04
CPCA61K41/0057A61P31/04C09B57/02C09K11/06C09K2211/1029C09K2211/1088G01N21/6428
Inventor 李楠赵娜尹伟李悦
Owner SHAANXI NORMAL UNIV
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