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Fluorescent probe as well as preparation method and application thereof

A fluorescent probe and reaction technology, used in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of lack of TP fluorescent probes, and achieve good photophysical stability, easy purification, and simple synthesis steps. Effect

Inactive Publication Date: 2015-12-16
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are currently adequate protocols for visualizing O in living tissue and intact organisms. 2 ˙- TP fluorescent probes are still very lacking

Method used

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  • Fluorescent probe as well as preparation method and application thereof
  • Fluorescent probe as well as preparation method and application thereof
  • Fluorescent probe as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: the synthesis of PY-NH2

[0045] Proceed as follows:

[0046] 2,5-bis(4'-aminostyryl)pyrazine (PY-NH2): p-nitrobenzaldehyde (7.55g, 0.05mol), 2,5-dimethylpyrazine ( 3.24 g, 0.01 mol) and phthalic anhydride (7.40 g, 0.05 mol). Heated to 180°C, refluxed for 15 hours, cooled to room temperature, and dissolved with 50 mL of chloroform. After the solution was extracted with 5% sodium hydroxide solution, the organic layer was separated by silica gel column chromatography (eluent: n-hexane / ethyl acetate=2 / 1) to obtain PY-NO2. Add 10ml of sodium polysulfide to PY-NO2, and reflux in ethanol solution for 3 hours to obtain PY-NH2.

[0047] PY-NH2. 1 HNMR(400MHz,DMSO):δ8.55(s,4H),δ8.43(s,2H),δ7.56(d,J=16.0,2H),δ7.35(d,J=8.0,4H) ,δ6.99(d,J=16.0,2H),δ6.59(d,J=8.0,4H); 13 CHNMR (400MHz, DMSO): δ150.27, 144.11, 142.27, 134.29, 129.08, 129.01, 118.95, 114.31; MSdata, m / zcalcdfor[C 20 h 18 N 4 +H]315.1565,found315.1600.

Embodiment 2

[0048] Embodiment 2: the synthesis of fluorescent probe

[0049] The synthesis steps of PY-CA are as follows: PY-NH2 (0.314g, 1.0mmol), caffeic acid (0.525g, 3.0mmol), triethylamine (1.0mL), HOBT (0.636g, 3.0mmol) were added to a 250mL three-necked flask and EDC (0.576 g, 3.0 mmol) into a mixed solvent of dichloromethane (8.0 mL) and DMF (1.2 mL). Under the protection of argon, the mixture was stirred overnight at room temperature to obtain a crude product. After part of the solvent was removed by rotary evaporation, the product was separated by thin layer chromatography (silica gel GF 254 ), the eluent was toluene / methanol / ethyl acetate=4 / 0.5 / 2, and a yellow product was obtained.

Embodiment 3

[0050] Embodiment 3: the synthesis of fluorescent probe

[0051] The synthesis steps of PY-CA are as follows: PY-NH2 (1.0mmol), caffeic acid (2.0mmol), triethylamine (1.0mL), HOBT (2.0mmol) and EDC (3.5mmol) were added to a 250mL three-necked flask to dichloro In a mixed solvent of methane (8.0 mL) and DMF (3.0 mL). Under the protection of argon, the mixture was stirred overnight at room temperature to obtain a crude product. After part of the solvent was removed by rotary evaporation, the product was separated by thin layer chromatography (silica gel GF 254 ), the eluent was toluene / methanol / ethyl acetate=6 / 1 / 4, and a yellow product was obtained.

[0052] PY-CA. 1 HNMR (400MHz, DMSO): δ8.30(s, 2H), δ8.16(d, J=8.0, 4H), δ7.92(d, J=8.0, 4H), δ7.9278(d, J= 16.0,2H),δ7.63(d,J=8.0,4H),δ7.47(d,J=16.0,2H),δ7.45(d,J=16.0,2H),δ7.43(s, 4H), δ7.37(d, J=16.0, 2H), δ7.35(s, 4H); 13 CHNMR (400MHz, DMSO): δ164.38, 162.96, 143.24, 132.48, 132.03, 129.58, 129.13, 128.26, 127.94, 125.96,...

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Abstract

The invention discloses a fluorescent probe as well as a preparation method and application thereof. A structural formula of the fluorescent probe is shown in a formula I in the specification. The preparation method of the fluorescent probe comprises the following steps: mixing p-nitrobenzaldehyde, 2,5-dimethylpyrazine and a catalyst to obtain mixed liquor and heating the mixed liquor to 150-180 DEG C to react, thus obtaining PY-NO2; adding sodium polysulfide to PY-NO2 to react to obtain PY-NH2; adding PY-NH2, caffeic acid, triethylamine, HOBT and EDC.HCL to a mixed solvent of dichloromethane and DMF to obtain mixed liquor; and stirring the mixed liquor under the protection of an inert gas to obtain a crude product of a two-photon fluorescent probe, and purifying the crude product to obtain a pure product of the two-photon fluorescent probe. The fluorescent probe has good chemical stability and photo-physical stability, can sensitively respond to O2<.-> in acidic, neutral and alkaline ranges, has higher measurement sensitivity and is very short in response time.

Description

technical field [0001] The invention belongs to the technical field of biological detection, and in particular relates to a fluorescent probe and its preparation method and application. Background technique [0002] Organismal lifespan is influenced by multiple complex factors such as cellular mechanisms and environment. A large amount of evidence shows that cellular energy metabolism is closely related to ROS. However, so far, there is no consensus on the role of ROS. Many studies have found that ROS are involved in cell damage and thus accelerate the aging process. However, many have also found that the role of ROS signaling can delay aging-related diseases or aging itself. The existence of these controversies is caused by the difficulty of lacking ideal tools for accurately monitoring ROS changes in biological systems. Considering O 2 ˙- It is the first ROS produced and can be converted into other ROS, sensitive and instantaneous tracer O in vivo 2 ˙ - For sorting...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D239/26G01N21/64
Inventor 唐波李平张雯肖海滨
Owner SHANDONG NORMAL UNIV
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