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Fluorescent probe for detecting ultra-oxygen anion free radical, synthesis method and use

A technology of superoxide anion and fluorescent probe, which is applied in the field of biological detection technology and clinical medical detection, can solve the problems of short free radical life, difficult detection, and many types, and achieve stable performance, no toxic and side effects, and small toxic and side effects Effect

Inactive Publication Date: 2010-09-15
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the short life, low content and many types of free radicals, their detection is still one of the most difficult problems in the field of life science and chemical analysis.
In particular, the detection method with high selectivity, high sensitivity and strong practicability has not yet been reported.

Method used

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  • Fluorescent probe for detecting ultra-oxygen anion free radical, synthesis method and use
  • Fluorescent probe for detecting ultra-oxygen anion free radical, synthesis method and use
  • Fluorescent probe for detecting ultra-oxygen anion free radical, synthesis method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Probe Synthesis

[0044]

[0045] Probe DBZTC

[0046] Get 17 grams of chlorinated dialdehyde cyclohexene and 35 grams of o-aminothiophenol and dissolve in the mixed solution of 500 milliliters of n-butanol and 300 milliliters of benzene to obtain a mixed solution; the mixed solution was refluxed for 3 hours, and the Remove the solvent under pressure (0.02 atmospheres, 55°C) to obtain a crude purple-red fluorescent probe; then recrystallize the crude product with 40 ml of ethanol with a weight concentration of 99%, and vacuum-dry (0.01 atmospheres) to obtain a brown-purple fluorescent probe Pure product (54% yield). 1 H NMR (300MHz, DMSO-d 6 , 25°C, TMS): CR8.10-7.90 (m, 2H), 7.75 (d, 2H), 7.47-7.39 (m, 2H), 7, 24 (d, 2H), 4.10 (m, 2H), 3.12 (m, 2H), 2.3 (m, 3H), 1.15 (m, 4H).IR (KBr tablet): v (cm -1 ) 3245 (N-H), 3110 (C-H), 1592 (C=C). Elemental analysis results (theoretical value): C 20 h 19 N 2 S 2 Cl: C 62.10 (62.02), H 4.92 (4.84), N 7.24 (7.36).

Embodiment 2

[0048] Probe Synthesis

[0049]

[0050] Get 17 grams of chlorinated dialdehyde cyclohexene and 59 grams of methyl o-aminothiophenol and dissolve them in a mixed solution of 500 milliliters of n-butanol and 150 milliliters of benzene to obtain a mixed solution; the mixed solution was heated to reflux for 3 hours , the solvent was evaporated under reduced pressure (0.01 atmosphere, 45° C.) to obtain the crude product of the purple-red fluorescent probe; Pure probe (yield 54.8%).

Embodiment 3

[0052] Probe Synthesis

[0053]

[0054] Get 17 grams of chlorinated dialdehyde cyclohexene and 48 grams of ethyl o-aminothiophenol and dissolve them in a mixed solution of 500 milliliters of n-butanol and 220 milliliters of benzene to obtain a mixed solution; the mixed solution was heated to reflux for 4 hours , the solvent was evaporated under reduced pressure (0.01 atmosphere, 50° C.) to obtain the crude product of the purple-red fluorescent probe; Pure probe (yield 54.2%).

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PUM

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Abstract

The invention discloses a new typed fluorescent probe and synthesizing method and application to detect hyperoxygen anion free radical in the cell selectively, which comprises the following steps: dissolving aromatic o-aminophenyl-sulfhydrate or aromatic o-aminophenyl-sulfhydrate derivant with weight rate at 1:2 -3.5 into composite solution with butanol and benzene with bulk rate at 1:0.3-0.6; heating the composite liquid to reflux 3-5h; decompressing to remove solvent; obtaining rough product; recrystallizing through alcohol; drying in the vacuum; obtaining pure product.

Description

Technical field: [0001] The invention relates to the fields of biological detection technology and clinical medical detection, in particular to a series of fluorescent probes for highly selective detection of intracellular superoxide anion free radicals; at the same time, it relates to a synthesis method of the fluorescent probe; in addition, it also relates to the fluorescent The purpose of the probe. Background technique: [0002] Numerous active oxygen free radicals are produced in the process of biological metabolism, including superoxide anion free radicals (O 2 - ), hydrogen peroxide (H 2 o 2 ), hydroxyl radicals (HO·), nitric oxide (NO), peroxynitroso (ONOO - ), etc., these free radicals are related to the pathogenesis of cancer and inflammation, tissue peroxidation, protein cross-linking denaturation, nucleic acid damage and signal transduction (Wiseman, H.; Halliwell, B.Biochem.J.1996, 313, 17-29; McCord , J.M.; Science.1974, 185, 529-531; Dobashi, K.; Ghosh, B...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/64G01N33/84G01N33/52
Inventor 唐波高静静毛震徐克花
Owner SHANDONG NORMAL UNIV
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