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Fluorescent probe based on 8-aminoquinoline derivative and synthetic method and application thereof

A fluorescent probe, aminoquinoline technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of fluorescent probes that are rarely reported, application limitations, complex synthesis process, etc., and achieve product separation The purification process is easy, the synthesis method is simple, and the raw materials are easy to obtain

Inactive Publication Date: 2015-11-11
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the reported literature, there are many fluorescent probes based on 8-aminoquinoline derivatives, but most of them are designed for the highly selective recognition of a specific ion. Single relay recognition of sulfide ions or pyrophosphate ions, such fluorescent probes that achieve continuous recognition of three ions under the same conditions are rarely reported, and the only literature (RSCAdv., 2015, 5, 10505–10511 ) is also limited in its application due to the complexity of the synthesis process

Method used

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  • Fluorescent probe based on 8-aminoquinoline derivative and synthetic method and application thereof
  • Fluorescent probe based on 8-aminoquinoline derivative and synthetic method and application thereof
  • Fluorescent probe based on 8-aminoquinoline derivative and synthetic method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0037] (1) Synthesize a reaction formula based on 8-aminoquinoline derivative fluorescent probe:

[0038]

[0039] (2) Synthesize a specific step based on 8-aminoquinoline derivative fluorescent probe:

[0040] Weigh 330mg of 2-chloro-N-(quinolin-8-yl)acetamide and 55mg of 2-propynylamine, dissolve in 20ml of acetonitrile, add 30mg of potassium iodide (KI) and 150mg of N,N-diisopropyl Diethylamine (DIPEA), refluxed for 10 hours, spin out acetonitrile, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, evaporated the solvent under reduced pressure, and the obtained oil was purified by silica gel column chromatography, and purified with ethyl acetate Separation with petroleum ether = 1:1 (v / v) as eluent to obtain 179 mg of light yellow solid compound, fluorescent probe L, with a yield of 75%.

[0041] Basic data of fluorescent probe L:

[0042] 1 HNMR (400MHz, CDCl 3 )δ11.106(s,1H),8.855(dd,J=4.2,1.6Hz,1H),8.816(dd,J=6.9,2.1Hz,1H),8.156(dd,J=8.3,...

Embodiment 2

[0044] Weigh 396mg of 2-chloro-N-(quinolin-8-yl)acetamide and 82mg of 2-propynylamine, dissolve in 25ml of acetonitrile, add 35mg of potassium iodide (KI) and 165mg of N,N-diisopropyl diethylamine (DIPEA), refluxed for 15 hours, spin out acetonitrile, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, evaporated the solvent under reduced pressure, and the obtained oily matter was purified by silica gel column chromatography and purified with ethyl acetate Separation with petroleum ether = 1:3 (v / v) as eluent to obtain 280 mg light yellow solid compound, fluorescent probe L, with a yield of 78%.

[0045] 13 CNMR (101MHz, CDCl 3 ( s), 81.196(s), 72.141(s), 52.133(s), 38.228(s), such as figure 2 .

Embodiment 3

[0047] Weigh 528mg of 2-chloro-N-(quinolin-8-yl)acetamide and 110mg of 2-propynylamine, dissolve in 35ml of acetonitrile, add 50mg of potassium iodide (KI) and 258mg of N,N-diisopropyl Diethylamine (DIPEA), refluxed for 18 hours, spin out acetonitrile, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered, evaporated the solvent under reduced pressure, and the obtained oil was purified by silica gel column chromatography, and purified with ethyl acetate Separation with petroleum ether = 1:5 (v / v) as eluent to obtain 406 mg light yellow solid compound, namely fluorescent probe L, with a yield of 85%.

[0048] High resolution mass spectrum (electrospray, positive mode) of embodiment 3: calculated value of fluorescent probe L [L+H] + :240.1059, the measured value is 240.1157, such as image 3 .

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Abstract

The invention discloses a fluorescent probe based on an 8-aminoquinoline derivative and a synthetic method and application thereof. The structural formula of the fluorescent probe is shown in the specification. The specific preparation method comprises the steps that acetonitrile is used as a solvent, raw materials comprising 2-chlorine-N-(quinoline-8-base) acetamide and 2-propargylamine are fed at the mole ratio being 1:1-1.5:1, a certain amount of KI and N, N-DIPEA are added, backflowing is carried out overnight, pressure is reduced, acetonitrile is obtained in a back-out mode, ethyl acetate is extracted, anhydrous sodium sulfate drying is carried out overnight, filtering is carried out, ethyl acetate is obtained in a back-out mode, the obtained oily matter is purified through silica gel column chromatography, the ethyl acetate and petroleum ether with the ratio being 1:1-1.5(v / v) is used as eluent for separation, and a light yellow solid compound L is obtained. The fluorescent probe based on the 8-aminoquinoline derivative has the advantages of being easy to synthesize, good in water solubility, capable of recognizing Zn<2+> in a water environment system and a biological cell system, capable of monitoring, analyzing and tracking sulfur ions and pyrophosphate ions and good in sensitivity.

Description

technical field [0001] The invention relates to a fluorescent probe based on 8-aminoquinoline derivatives and its synthesis method and application, which are used for relay recognition of zinc ions (Zn 2+ ), sulfide ion (S 2- ) and pyrophosphate ion (PPi). Background technique [0002] Zinc is the second largest trace heavy metal element and nutrient necessary in the body. It plays a very important role in many biological processes. It is widely distributed in the cells and body fluids of the human body. It is the key to more than 200 enzymes in the human body. Components directly participate in various life metabolic processes such as cell growth and development, reproduction and tissue repair in the body. Zn 2+ It plays a very important role in the life activities of cells, and Zn is present in gene transcription, metalloenzyme catalysis, neurotransmission and other processes. 2+ Participation. Zn 2+ It is closely related to many physical diseases, such as Alzheimer'...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D215/40G01N21/64
Inventor 钟克利郭宝峰曲秀莉汤立军励建荣蔡克迪许家胜侯淑华
Owner BOHAI UNIV
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