A kind of near-infrared fluorescent probe sensitive to environmental polarity and its synthesis method and application

A synthesis method and fluorescent probe technology, applied in the field of synthesis and medicine, to achieve the effects of improved accuracy, simple imaging operation process, and simple synthesis steps

Active Publication Date: 2017-03-01
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, the synthesis and development of new near-infrared fluorescent probes is very necessary, especially the design and synthesis of near-infrared fluorescent probes with ultra-high sensitivity to polarity are still very challenging.

Method used

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  • A kind of near-infrared fluorescent probe sensitive to environmental polarity and its synthesis method and application
  • A kind of near-infrared fluorescent probe sensitive to environmental polarity and its synthesis method and application
  • A kind of near-infrared fluorescent probe sensitive to environmental polarity and its synthesis method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Synthesis of compound I:

[0037] Indole iodide salt (0.63g, 2mmol) and condensing agent (0.34g, 2mmol) were dissolved in toluene 30mL, acetic acid 10mL mixed solution, reacted at 110°C for 2h; after the reaction, concentrated under reduced pressure at 60°C for 30min to remove the solvent, separated by column , and the eluent was dichloromethane:methanol volume ratio 50:1 to obtain 0.42 g of a black-red solid, namely compound I (yield 60%).

[0038] Synthesis of compound II:

[0039] Benzoylacetone (0.48g, 3mmol) was dissolved in 15mL of diethyl ether, 1mL of boron trifluoride diethyl ether solution was dropped into the above mixed solution, refluxed and stirred at 40°C for 2h, after the reaction was completed, cooled to room temperature, a large amount of powder was precipitated, and suction filtered 0.54 g of light yellow solid powder was compound II (yield 85%).

[0040] Under the protection of argon, compound I (0.341g, 1mmol) and compound II (0.315g, 1.5mmol) wer...

Embodiment 2

[0042] Under the protection of argon, compound I (0.171g, 0.4mmol) and compound II (0.158g, 0.5mmol) were dissolved in acetic anhydride 5mL, and anhydrous sodium acetate (0.041g, 0.4mmol) was added to obtain a mixed solution, 55 ℃ reaction 1h. After completion of the reaction, cool to room temperature, add 15mL of 20% sodium bicarbonate solution into the above mixture, and precipitate black-green insoluble matter, re-dissolve the black-green insoluble matter with dichloromethane (8mL), and use column chromatography Separation (the eluent is a mixed solution of dichloromethane and methanol, the volume ratio of dichloromethane and methanol is 90:1), and 0.12 g (45% yield) of a golden-green solid is obtained, which is the near-infrared fluorescent probe MCY -BF.

Embodiment 3

[0044] Under the protection of argon, compound I (0.100g, 0.29mmol) and compound II (0.091g, 0.43mmol) were dissolved in acetic anhydride 10mL, and anhydrous sodium acetate (0.021g, 0.26mmol) was added to obtain a mixed solution, 80 ℃ reaction 3h. After the reaction was completed, cool to room temperature, add 10 mL of 30% sodium bicarbonate solution into the above mixture, and a black-green insoluble matter was precipitated, and the black-green insoluble matter was redissolved with dichloromethane (5 mL), and analyzed by column chromatography Separation (the eluent is a mixed solution of dichloromethane and methanol, the volume ratio of dichloromethane and methanol is 110:1), and 0.063g (40% yield) of a golden-green solid is obtained, which is the near-infrared fluorescent probe MCY -BF.

[0045] Characterization by melting point, infrared, NMR and mass spectrometry

[0046] Probe melting point (m.p.):250-253℃

[0047] Infrared absorption characteristic peak (IR): V C-H =...

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Abstract

The invention relates to a near-infrared fluorescent probe with polarity sensitivity to the environment, and a synthetic method and application thereof. The probe has a structural formula as shown in the specification. The preparation method comprises the following steps: taking a compound I and a compound II to dissolve in acetic anhydride, then adding sodium acetate so as to obtain a mixed liquid, and carrying out reaction; then pouring the mixed solution into a sodium bicarbonate solution so as to obtain a black green insoluble substance; and redissolving the obtained black green insoluble substance with dichloromethane, and carrying out column chromatographic separation so as to obtain a golden green solid which is the target near-infrared fluorescent probe, wherein the compound I is a hemicyanine condensing agent monoaldehyde; the compound II is benzoyldifluoroboron; the maximum ultraviolet absorption and fluorescence emission wavelengths of a probe molecule are located in a near-infrared region (larger than 650nm); and moderate stokes shift (larger than 30nm) is obtained, so self absorption is effectively reduced, and imaging accuracy is improved. The probe molecule can directly realize confocal imaging without the need of a washing process that other probe molecules must undergo after completing staining of living cells and nematodes, so imaging operation process can be greatly simplified.

Description

technical field [0001] The invention belongs to the field of synthesis and technology, and specifically relates to a near-infrared fluorescent probe sensitive to environmental polarity and its synthesis method and application. Background technique [0002] Environmentally sensitive fluorescent probes are widely used in the field of biochemical research, and their fluorescent properties depend on the hydrophobicity of the environment. This type of probe generally has weak fluorescence intensity in aqueous solution, and has higher fluorescence intensity in nonpolar solvents, such as 8-anilino-1-naphthalenesulfonic acid (ANS) and Thioflavin T, or in nonpolar solvents. There are shorter emission wavelengths in solvents, such as Nile Red dye. However, the excitation and emission wavelengths of the above-mentioned polarity-sensitive probes are both in the visible region, which causes relatively great damage to organisms and is not conducive to long-term and in vivo detection. Ce...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C07F5/04G01N21/64
Inventor 唐波李平肖海滨
Owner SHANDONG NORMAL UNIV
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