Naphthalene derivative metal ion fluorescent probe and its application

A metal ion and fluorescent probe technology, applied in the field of biochemistry, can solve the problems of changing spectral properties, difficult to ensure the accuracy of detection results, etc., and achieve the effects of good selectivity, high sensitivity and good application prospects

Inactive Publication Date: 2011-12-07
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of fluorescent molecular probes to detect metal ions such as zinc, copper, iron, and mercury has been reported in the literature. There are many types of fluorescent molecular probes, but many organic fluorescent molecular probe compounds are often affected by protons, resulting in a change in the spectral performance of the response. changes, it is difficult to ensure the accuracy of test results

Method used

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  • Naphthalene derivative metal ion fluorescent probe and its application
  • Naphthalene derivative metal ion fluorescent probe and its application
  • Naphthalene derivative metal ion fluorescent probe and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] R in the general formula 2 is pyridyl, R 1 , R 3 Fluorescent probes for phenyl groups A .

[0023] Synthetic procedure: Dissolve 630.8 mg of 1,3-diphenylacetone in 6 mL of ethanol, and then add 636.6 mg of naphthoethylenedione. After all dissolved, 187.7 mg of KOH solid was added, refluxed for 5 min, cooled and placed in the refrigerator for 5 h, filtered with suction, and washed with ethanol to obtain 855.3 mg of black-purple solid with a yield of 73.9%.

[0024] The intermediate product is characterized as follows:

[0025] 1 H-NMR: δ H (400 MHz; CDCl 3 ; ppm) 8.08 (m, 2H), 7.87 (m, 6H), 7.61(m, 2H), 7.55(m, 4H), 7.43 (m, 2H). 13 C-NMR: δ C (100 MHz, CDCl 3 ): 154.21, 132.14, 131.54, 131.44, 129.07, 128.58, 128.42, 128.29, 127.75, 121.66, 120.93.

[0026]Under the protection of argon, 630.6 mg of the above product was dissolved in 6 mL of o-xylene, pumped three times, and 0.20 mL of 2-alkynylpyridine was added, heated to 150 °C, and refluxed for 15 h. Na...

Embodiment 2

[0029] R in the general formula 2 is the anilino group, R 1 , R 3 Fluorescent probes for phenyl groups B

[0030] 2-alkynylpyridine is replaced by 2-alkynylaniline, and the synthesis steps are the same as in Example 1.

[0031] fluorescent probe B Yield 70.2%. 1 H NMR (400 MHz, CDCl 3 , ppm): 3.60(s,2H), 6.50(d,2H), 6.70(s,1H), 7.00(d,2H), 7.27-7.75(m,17H). 13 C NMR (400 MHz, CDCl 3 , ppm): 114.50(2C), 122.70, 123.26, 126.44, 126.52, 127.15, 127.51, 127.59, 127.73, 128.51(2C), 128.60(2C), 129.14(2C), 129.68, 0( ), 131.09, 131.42, 133.11, 135.11, 136.04, 136.13, 136.76, 137.89, 138.23, 139.70, 140.69, 140.93, 144.53. ESI-MS: m / z = 445.1 H]24 [M + .

Embodiment 3

[0032] Embodiment 3 Application of derivative fluorescent probe of the present invention

[0033] fluorescent probe A. B. Shows high sensitivity for iron and copper ions, such as figure 1 , 5 shown; the difference is the fluorescent probe A The fluorescence of the iron ion is quenched, while the fluorescent probe B significantly enhances the fluorescence of the iron ion. The above experiments have investigated the effects of complex anions, interfering ions and other factors. Depend on image 3 , 7 It can be seen that anions and interfering ions have no effect on the recognition of iron ions and copper ions by the fluorescent probes A and B of the present invention, and have good selectivity and sensitivity. It will be applied to the identification and detection of metal ions in biological tissues and environmental sewage, and has a good application prospect.

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Abstract

The invention discloses novel compounds for fluorescent identification of metal ions, relates to naphthalene biphenyl derivatives used as a fluorescent probe of metal ions and application thereof and belongs to the field of biochemistry. The structural general formula of the naphthalene biphenyl derivatives is shown in the specification, and in the general formula, R1, R2 and R3 represent aromatic groups, namely phenyl, pyridyl, quinolyl, naphthyridinyl, pyrrolyl, anilino and other groups and R1, R2 and R3 are not phenyl at the same. The fluorescent probe can sensitively identify various metal ions such as copper ions, iron ions and other metal ions. Certain probe molecules have identification action to two types of metals. The fluorescent probe has good selectivity and high sensitivity, and has better application prospect in identification and detection of the metal ions in biological samples or the environment.

Description

technical field [0001] The invention relates to a class of novel compounds that can be used for fluorescent recognition of metal ions, in particular to a class of metal ion fluorescent probes of naphthalene biphenyl derivatives and applications thereof, belonging to the field of biochemistry. Background technique [0002] Metal ions are closely related to medicine, life science and environmental science. It is of great significance to identify, detect and qualitatively analyze them. Molecular probe detection of metal ions has the characteristics of real-time detection, low detection threshold, high sensitivity and easy operation, and is a very effective method. Transition metals and heavy metals widely exist in various living organisms and play an important role in life activities. Some transition metals in the living body are too low to cause various diseases, and sometimes heavy metals with very low concentrations have strong Toxicity, endangers the presence of living org...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/16C07C211/61C07C209/68C09K11/06G01N21/64
Inventor 李占先于明明魏柳荷张利锋赵万莹王丽娜
Owner ZHENGZHOU UNIV
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