Novel high-selectivity fluorescence probe for bivalent copper ions as well as preparation method and biological application of novel high-selectivity fluorescence probe

A divalent copper ion, high-selectivity technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problem of lack of near-infrared luminescent fluorescent probes, low biological application value, and insufficient sensitivity of detection signals, etc. problems, to achieve the effect of simple preparation method, easy identification and obvious phenomenon

Inactive Publication Date: 2015-09-09
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The current fluorescent probes for copper ions still have shortcomings such as fewer types of probes and insufficient sensitivity of the detection signal. The currently developed fluorescent probes are mainly visible light fluorescent probes, lacking near-infrared fluorescent probes, and have low biological application value.

Method used

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  • Novel high-selectivity fluorescence probe for bivalent copper ions as well as preparation method and biological application of novel high-selectivity fluorescence probe
  • Novel high-selectivity fluorescence probe for bivalent copper ions as well as preparation method and biological application of novel high-selectivity fluorescence probe
  • Novel high-selectivity fluorescence probe for bivalent copper ions as well as preparation method and biological application of novel high-selectivity fluorescence probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] A novel highly selective divalent copper ion fluorescent probe has a structure shown in formula (I):

[0043]

[0044] The reaction scheme is as follows:

[0045]

[0046] The preparation process comprises steps as follows:

[0047] (1) Compound 1 (0.377g, 1.0mmol) and p-cyanobenzaldehyde (0.157g, 1.2mmol) were reacted in 20ml of acetic acid at 50°C for 12h to obtain a dark solution, and the solvent was removed by rotary distillation. Dissolved in methyl chloride, separated by column chromatography with a mixed solvent of dichloromethane and methanol to obtain compound 2; yield: 50%. 1 H NMR (400MHz, CDCl3) δ7.96(d, J=7.2,1H),7.65(m,3H),7.56(t,J=7.2,1H),7.48(d,J=8.4,1H),7.37 (s,1H),7.23(d,J=7.6,1H),6.50(d,J=8.8,1H),6.38(m,2H),3.36(q,J=6.4,4H),2.65(m, 2H), 2.07(m, 1H), 1.63(m, 4H), 1.17(t, J=6.8, 2H). 13 C NMR(101MHz,CDCl3)δ169.94,152.38,152.09,149.39,146.29,142.08,134.56,133.47,131.95,129.98,129.38,128.59,127.52,125.04,123.45,119.00,110.20,109.77,108.93,104.61...

Embodiment 2

[0050] The preparation method of novel highly selective divalent copper ion fluorescent probe as described in Example 1, the difference is:

[0051] The amount of cyanobenzaldehyde described in step (1) was 3 mmol, acetic acid was replaced by acetic anhydride, the amount of acid was 20 mL, the reaction temperature was 60° C., and the reaction time was 12 h.

[0052] The consumption of hydrazine hydrate in step (2) is 3mL.

Embodiment 3

[0054] The preparation method of novel highly selective divalent copper ion fluorescent probe as described in Example 1, the difference is:

[0055] The amount of cyanobenzaldehyde described in step (1) was 1 mmol, acetic acid was replaced by methanesulfonic acid, the amount of acid was 10 mL, the reaction temperature was 50° C., and the reaction time was 10 h.

[0056] The consumption of hydrazine hydrate in step (2) is 2mL.

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Abstract

The invention discloses a novel high-selectivity fluorescence probe for bivalent copper ions as well as a preparation method and biological application of the novel high-selectivity fluorescence probe. The fluorescence probe has a structure as shown in the formula (I) in the specification. The invention also discloses a preparation method and application of the fluorescence probe. The fluorescence probe can be used for selectively detecting bivalent copper ions in a water system and is changed from colorlessness to a dark color when the bivalent copper ions exist, and the fluorescence is remarkably enhanced. Due to the characteristics, the fluorescence probe disclosed by the invention has a remarkable advantage when being used for detecting the content of heavy metal ions in an environment and an organism and has a potential application value in the fields of fluorescence labeling and bioimaging.

Description

technical field [0001] The invention relates to a fluorescent probe for highly selective recognition of metal copper ions and its preparation method and biological application. The fluorescent probe can specifically recognize divalent copper ions in a water system, and belongs to the field of organic small molecule fluorescent probes. Background technique [0002] Copper element is an important metal chemical element that exists in nature. Its chemical symbol is Cu, and its electron arrangement is: 1s 2 2s 2 2p 6 3s 2 threesome 6 3d 10 4s 1 . Copper is widely distributed in the earth's crust and oceans. The content of copper in the earth's crust is about 0.01%, and the content in some copper mines can reach 3%-5%. [0003] Copper is also one of the essential trace elements for the human body, and the copper content in the blood is about 1.0-1.5mg. The bactericidal effect of copper has long been studied, and some copper compounds also have anticancer functions. The l...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
Inventor 林伟英刘克印尚慧明刘勇
Owner UNIV OF JINAN
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