Fluorescent probes based on pyrene, and preparation method and application thereof

A fluorescent probe and azido-based technology, applied in the field of chemistry, can solve the problems of few reports and unreported fluorescent probes

Inactive Publication Date: 2015-05-06
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, the fluorescent probes based on pyrene in the reported literature are mainly based on the derivatives of monosubstituted pyrene, while the fluorescent probes of derivatives of disubstituted pyrene are rarely reported; and two kinds of pyrene-based The method of fluorescent probes based on pyrene is also rarely reported; the fluorescent probes connecting quinoline derivatives and pyrene derivatives through triazoles have not been reported; the fluorescent probes based on pyrene-based fluorescent probes recognize copper ions and pyrophosphate ions. Needle also not reported

Method used

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  • Fluorescent probes based on pyrene, and preparation method and application thereof
  • Fluorescent probes based on pyrene, and preparation method and application thereof
  • Fluorescent probes based on pyrene, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] (1) One-step reaction synthesizes two kinds of reaction formulas based on pyrene-based fluorescent probes:

[0043]

[0044] (2) The specific steps of one-step reaction synthesis two kinds of fluorescent probes based on pyrene:

[0045] Weigh 100mg of 1,8-diethynylpyrene and 273mg of 2-azido-N-(quinolin-8-yl)acetamide, dissolve in 10ml THF:H 2 O=4:1, stirred overnight at 60°C. Ammonia was added for extraction, the solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel chromatography, using pure dichloromethane as the eluent to obtain 73 mg of light yellow solid compound 1 with a yield of 38%. Methane=1:15 (volume ratio) was used as the eluent to obtain 43 mg of compound 2 as a yellow solid with a yield of 15%.

Embodiment 2

[0047] Weigh 200mg of 1,8-diethynylpyrene and 545mg of 2-azido-N-(quinolin-8-yl)acetamide, dissolve in 10ml THF:H 2O=4:1, stirred overnight at 65°C. Ammonia was added for extraction, the solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel chromatography, using pure dichloromethane as the eluent to obtain 156 mg of light yellow solid compound 1 with a yield of 41%. Methane=1:16 (volume ratio) was used as the eluent to obtain 101 mg of compound 2 as a yellow solid, with a yield of 18%.

Embodiment 3

[0049] Weigh 250mg of 1,8-diethynylpyrene and 680mg of 2-azido-N-(quinolin-8-yl)acetamide, dissolve in 10ml THF:H 2 O=4:1, stirred overnight at 66°C. Ammonia was added for extraction, the solvent was distilled off under reduced pressure, and the obtained solid was purified by silica gel chromatography, using pure dichloromethane as the eluent to obtain 215 mg of light yellow solid compound 1 with a yield of 45%. Methane=1:13 (volume ratio) was used as the eluent to obtain 155 mg of compound 2 as a yellow solid, with a yield of 22%.

[0050] Basic data of the fluorescent probes 1 and 2 of Embodiment 1 to Embodiment 3:

[0051] Fluorescent probe 1:

[0052] 1 H NMR (400MHz, DMSO-d 6 )δ10.822(s, 1H), 9.001-8.956(dd, J=14.1, 6.5Hz, 2H), 8.875(s, 1H), 8.615(d, J=7.6Hz, 1H), 8.533(d, J =9.5Hz, 1H), 8.451-8.38(m, 3H), 8.314-8.197(m, 4H), 7.715(d, J=8.4Hz, 1H), 7.669-7.637(m, 1H), 7.588(t, J=8.0Hz, 1H), 5.830(s, 2H), 4.794(s, 1H). (such as figure 1 )

[0053] 13 C NMR (101MHz...

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Abstract

The invention discloses fluorescent probes based on pyrene, and a preparation method and application thereof. The concrete preparation method comprises taking a mixture of THF and H2O with the ratio of 4:1 as a solvent, controlling the molar ratio of raw materials 1,8-diethynylpyrene to 2-azido-N-(quinolin-8-yl)acetamide to be 1:2-1:3, and stirring at 50-80 DEG C for a night; adding ammonia water for extraction, performing reduced-pressure distillation to remove the solvent, purifying the obtained solid by using silica gel chromatography, and using dichloromethane as an eluant for processing, so as to obtain a light yellow solid 1, and employing a mixture of ethyl acetate and dichloromethane according to the volume ratio of 1:15 as an eluant for processing, so as to obtain a yellow solid compound 2. Two fluorescent probes are obtained through the one-step reaction, tailed detection on copper ion and pyrophosphate ion in water environment can be realized, and the fluorescent probes have relatively high sensitivity and interference resistance.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and relates to a pyrene-based fluorescent probe and its preparation method and application, in particular, to a method and application of one-step reaction synthesis of two pyrene-based fluorescent probes. Background technique [0002] Copper is a trace heavy metal element and nutrient necessary for living organisms. Its content in cells is second only to zinc and iron, and it plays an important role in the basic physiological processes of various organisms. As a metalloenzyme, it participates in the catalysis of more than 20 enzymes (such as cytochrome oxidase, superoxide dismutase, tyrosinase, dopamine β-hydroxylase, lysyl oxidase, etc.). The content of copper ions in the organism is very small, but the lack of it can lead to growth and metabolic disorders, and the excessive content will have a huge toxic effect on the organism. Disruption of the metabolic balance of copper ions in the body ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D401/12C07D401/14G01N21/64
Inventor 钟克利曲秀莉汤立军励建荣侯淑华徐永霞边延江周雪张悦
Owner BOHAI UNIV
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