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A kind of coumarin derivative that specifically recognizes and distinguishes dna and rna and its preparation method and application

A coumarin derivative and a species-specific technology are applied in the field of molecular biology to achieve the effects of simple synthesis, high quantum yield and high yield

Active Publication Date: 2021-02-05
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The currently reported probes for detecting RNA will cause greater interference when DNA exists in the system, so it is necessary to design a fluorescent probe for detecting RNA and distinguishing it from DNA

Method used

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  • A kind of coumarin derivative that specifically recognizes and distinguishes dna and rna and its preparation method and application
  • A kind of coumarin derivative that specifically recognizes and distinguishes dna and rna and its preparation method and application
  • A kind of coumarin derivative that specifically recognizes and distinguishes dna and rna and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The preparation principle of the coumarin derivative probe 1 of this embodiment is as follows:

[0032]

[0033]The specific preparation steps are as follows: 7-diethylaminocoumarin-3 aldehyde (76 mg, 0.31 mmol) and 2,3-dimethylbenzothiazole ammonium iodide (98 mg, 0.34 mmol) were dissolved in 10 mL ethanol solution middle. The reaction mixture was stirred at reflux for 12 hours, then cooled to room temperature, and the precipitate was collected with a filter, and then subjected to silica gel column chromatography (CH 2 Cl 2 / MeOH, 50:1 v / v) to obtain a dark blue solid (135 mg, 84% yield), which is Probe 1, and its structural formula is as follows: (probe 1), the H NMR spectrum of probe 1 is as follows Figure 8 As shown, the carbon NMR spectrum is shown as Figure 10 shown.

[0034] 1 H NMR (600 MHz, DMSO-d6) δ 8.61 (s,1H), 8.38 (d, J =7.4 Hz, 1H),8.22 (d, J =8.5 Hz, 1H) ,8.05 (q, J 1 =15.4 Hz, J 2 = 12.6 Hz ,2H), 7.84 (t, J =7.56 Hz, 1H), 7.75 (t, J =7.74...

Embodiment 2

[0036] The preparation principle of the coumarin derivative probe 1 of this embodiment is as follows:

[0037]

[0038] The specific preparation steps are as follows: 7-diethylaminocoumarin-3 aldehyde (76 mg, 0.31 mmol) and 2,3-dimethylbenzothiazole ammonium iodide (89.4 mg, 0.31 mmol) were dissolved in 10 mL ethanol solution middle. The reaction mixture was stirred at reflux for 12 hours, then cooled to room temperature, and the precipitate was collected with a filter, and then subjected to silica gel column chromatography (CH 2 Cl 2 / MeOH, 50:1 v / v) to obtain a dark blue solid, namely probe 1.

Embodiment 3

[0040] The preparation principle of the coumarin derivative probe 1 of this embodiment is as follows:

[0041]

[0042] The specific preparation steps are as follows: 7-diethylaminocoumarin-3 aldehyde (76 mg, 0.3 mmol) and 2,3-dimethylbenzothiazole ammonium iodide (129.7 mg, 0.45 mmol) were dissolved in 10 mL ethanol solution middle. The reaction mixture was stirred at reflux for 12 hours, then cooled to room temperature, and the precipitate was collected with a filter, and then subjected to silica gel column chromatography (CH 2 Cl 2 / MeOH, 50:1 v / v) to obtain a dark blue solid, namely probe 1.

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Abstract

The invention belongs to the field of molecular biology, in particular to a coumarin derivative that specifically recognizes and distinguishes DNA and RNA, a preparation method and application thereof. The coumarin derivative has the structural formula of probe 1 or the structural formula of probe 2 . The probe in the invention is simple to synthesize, has high yield, can specifically recognize and distinguish DNA and RNA, and has good specificity and high sensitivity. This provides a new idea and method for the development of small molecule fluorescent probes for the specific distinction of DNA and RNA.

Description

technical field [0001] The invention belongs to the field of molecular biology, in particular to a coumarin derivative that specifically recognizes and distinguishes DNA and RNA, a preparation method and application thereof. Background technique [0002] DNA is a double helix structure and is the genetic material. RNA is generally single-stranded and does not serve as genetic material. RNA is a single strand formed by transcription based on a strand of DNA as a template and based on the principle of complementary base pairing. Unlike DNA, RNA is generally a single-stranded long molecule and does not form a double helix structure, but many RNAs also need to form a certain secondary structure or even a tertiary structure through the principle of base pairing to perform biological functions. The base pairing rules of RNA are basically the same as those of DNA, but in addition to A-U and G-C pairing, G-U can also be paired. In terms of viruses, many viruses only use RNA as th...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C07D417/14C09K11/06G01N33/53
CPCC07D417/06C07D417/14C09K11/06C09K2211/1037C09K2211/1088C09K2211/1092G01N33/5308
Inventor 孙远强李朝辉曾华金王霞杨冉屈凌波孟红敏
Owner ZHENGZHOU UNIV
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