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A semicyanine compound based on benzothiazole-linked heterocycle and its preparation method and application

A compound, alkylation reaction technology, applied in chemical instruments and methods, organic chemistry, fluorescence/phosphorescence, etc., can solve the problems of inability to meet the research needs of scientific researchers, complex synthesis process, insufficient number of probes, etc. The effect of generalization, low cytotoxicity, and high quantum yield

Active Publication Date: 2021-06-01
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, new organic fluorescent probes targeting different secondary structures of nucleic acids have been reported, but the number of probes is far from enough to meet the research needs of scientific researchers. Common double-stranded nucleic acid fluorescent probes include EB, YOYO, Sybr, DAPI, and Hoechst dyes, etc., but some of them have strong carcinogenicity, and some have complex synthesis process and high price. Therefore, it is of great significance to develop nucleic acid fluorescent dyes with low toxicity, low cost and simple synthesis.

Method used

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  • A semicyanine compound based on benzothiazole-linked heterocycle and its preparation method and application
  • A semicyanine compound based on benzothiazole-linked heterocycle and its preparation method and application
  • A semicyanine compound based on benzothiazole-linked heterocycle and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078]Example 1, Preparation of the compound of formula A and fluorescent probe specific identification nucleic acid double-stranded structure

[0079]First, the synthesis of the probe of formula A

[0080]Such asfigure 1 As shown, synthesized as follows:

[0081]1, 227 mg (1.0 mmol) of 5-bromo-2-methylpain thiazole was added to 25 ml of a single neck round bottom flask equipped with 10 ml of ethanol. After preheating at 78-85 ° C, 124.5 μL (2.0 mmol) of iodide methane was added, and the heat was refluxed for 12 h, and the solution was stopped from light yellow transparent to orange yellow. Cold until the room temperature was distilled and distilled, that is, the formula H molecule was obtained.

[0082]

[0083]2. 36.3 mg (0.15 mmol) HE molecules were added to 10 ml of a 10 ml of a single neck round bottom flask equipped with 2 ml of ethanol. After preheating at 78-85 ° C for 5 min, 24.5 mg (0.1 mmol) coumarin derivative (shown in the following IV), continued to heat and reflux 12h, and the solut...

Embodiment 2

[0108]Example 2, fluorescent probe specifically recognized nucleic acid double-stranded structure

[0109]First, the synthesis of the probe described in Formula B

[0110]36.3 mg (0.15 mmol) of H molecules were added to 10 ml of a single neck round bottom flask equipped with 2 ml of ethanol. After preheating at 78-85 ° C for 5 min, 27.3 mg (0.1 mmol) 5-bromo-2,2'-joint thiophene -5'-formaldehyde was continued to heat and reflux 12h, and the solution turned from light yellow to dark red, cold Decapmetal was distilled off after room temperature to give the crude product.

[0111]

[0112]The crude product B is dissolved in dichloromethane and passed through silica gel chromatography (CH2CL2 / MeOH, V / V, 30: 1 was purified, resulting in a compound of orange red solid B molecule (32 mg, 64.4% yield). The compound is then purified by high performance liquid chromatography. The high-performance liquid chromatography separation purification step is the chromatographic column as the PROMISIL-C18 colum...

Embodiment 3

[0121]Example 3, Fluorescent Probe specifically recognized Nucleic acid G-tetracene structure

[0122]First, the synthesis of the probe described in formula C

[0123]36.3 mg (0.15 mmol) of H molecules were added to 10 ml of a single neck round bottom flask equipped with 2 ml of ethanol. After preheating at 78-85 ° C, 22.3 mg (0.1 mmol) N-ethylcarbazole-3-formaldehyde was added, continued to heat generation 12h, and the solution was stopped from light yellow to orange red, cold to room temperature, decompression distillation To obtain a crude product.

[0124]The crude product C is dissolved in dichloromethane and passed silica gel chromatography (CH2CL2 / MeOH, V / V, 30: 1) Purified to obtain a compound of orange red solid C molecule (39 mg, 87.1% yield). The compound is then purified by high performance liquid chromatography. The high-performance liquid chromatography separation purification step is the chromatographic column as the PROMISIL-C18 column (250 mm × 4.6 mm, 20 μm), and the flo...

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Abstract

The invention discloses a semicyanine compound based on a benzothiazole biheterocycle, a preparation method and an application thereof. The structural formula of this type of compound is shown in formula I: the preparation method of this compound comprises the following steps: using the benzothiazole compound shown in formula II and haloalkane R b X is subjected to an alkylation reaction to obtain a substituted benzothiazole compound, which is then subjected to a Knoevenagel condensation reaction with N-ethylcarbazole-3-formaldehyde to obtain the product. The synthesis and preparation steps of the invention are simple and easy, the raw materials are cheap and easy to obtain, the probe has a stable structure and high specificity, and can be used to specifically detect the secondary structure of G-quadruplex and double helix of nucleic acid. The method for detecting the secondary structure of nucleic acid by the probe has the advantages of low price, simple operation, good selectivity and quickness, and overcomes the disadvantages of high price, high equipment requirements and relatively complicated technical operation of other detection methods.

Description

Technical field[0001]The present invention relates to a half-cycraceine compound based on a benzothiazole combined ring and a preparation method thereof and an application thereof, belonging to the field of small molecule fluorescent materials.Background technique[0002]The nucleic acid contains the genetic information necessary for life, which is one of the most important biological mons in the body. Nucleic acids can form a number of spatial secondary structures under physiological conditions to help increase molecular stability and play corresponding biological functions, including single-stranded clamp structures, hormible double strands, triplets, and tetracene structures. DNA typically exists in a B-type double helix structure through the hydrogen bond between Watson-Crick base pairs; in the gene promoter region, there is often a oligonucleotide fragment enriched in the gene promoter, such an oligonucleotide fragment Foldable formation of tetracene structures, also known as G-t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06C07D417/14C07D471/04C09K11/06G01N21/64
CPCC07D417/06C07D417/14C07D471/04C09K11/06C09K2211/1029C09K2211/1037C09K2211/1044C09K2211/1088C09K2211/1092G01N21/6428G01N21/6456
Inventor 上官棣华卢珊珊张楠魏涌标刘祥军
Owner INST OF CHEM CHINESE ACAD OF SCI
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