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Hemicyanine compound based on benzothiazole biheterocycle, and preparation method and application thereof

A compound and alkylation reaction technology, applied in chemical instruments and methods, organic chemistry, instruments, etc., can solve the problems of unable to meet the research needs of scientific researchers, complex synthesis process, insufficient number of probes, etc., to achieve easy promotion, Effect of low cytotoxicity and high quantum yield

Active Publication Date: 2020-06-02
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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  • Hemicyanine compound based on benzothiazole biheterocycle, and preparation method and application thereof
  • Hemicyanine compound based on benzothiazole biheterocycle, and preparation method and application thereof
  • Hemicyanine compound based on benzothiazole biheterocycle, and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0078] Embodiment 1, the preparation of the compound represented by formula A and the specific recognition of nucleic acid double-stranded structure by fluorescent probe

[0079] One, the synthesis of the described probe of formula A

[0080] like figure 1 As shown, it is synthesized according to the following steps:

[0081] 1. Add 227mg (1.0mmol) of 5-bromo-2-methylbenzothiazole into a 25mL single-necked round bottom flask filled with 10mL of ethanol. After preheating at 78-85°C for 5 minutes, add 124.5 μL (2.0 mmol) methyl iodide, continue to heat and reflux for 12 hours, and stop when the solution turns from light yellow transparent to orange yellow. After cooling to room temperature, distill under reduced pressure to obtain the molecule of formula H.

[0082]

[0083] 2. Add 36.3 mg (0.15 mmol) of the molecule of formula H into a 10 mL single-necked round bottom flask filled with 2 mL of ethanol. After preheating at 78-85°C for 5 minutes, add 24.5 mg (0.1 mmol) of ...

Embodiment 2

[0108] Embodiment 2, the fluorescent probe described in formula B specifically recognizes the nucleic acid double-stranded structure

[0109] One, the synthesis of the described probe of formula B

[0110] 36.3 mg (0.15 mmol) of the molecule of formula H was added to a 10 mL single necked round bottom flask containing 2 mL of ethanol. After preheating at 78-85°C for 5 minutes, add 27.3mg (0.1mmol) of 5-bromo-2,2'-bithiophene-5'-carboxaldehyde, continue heating and reflux for 12 hours, the solution turns from light yellow to deep red, then stop, cool After reaching room temperature, it was distilled under reduced pressure to obtain the crude product of formula B.

[0111]

[0112] Crude product B was dissolved in dichloromethane and chromatographed on silica gel (CH 2 Cl 2 / MeOH, v / v, 30:1) to obtain the compound as an orange-red solid formula B molecule (32 mg, 64.4% yield). Then, the compound was further purified by high performance liquid chromatography. The separati...

Embodiment 3

[0121] Embodiment 3, the fluorescent probe described in formula C specifically recognizes the nucleic acid G-quadruplex structure

[0122] One, the synthesis of the described probe of formula C

[0123] 36.3 mg (0.15 mmol) of the molecule of formula H was added to a 10 mL single necked round bottom flask containing 2 mL of ethanol. After preheating at 78-85°C for 5 minutes, add 22.3mg (0.1mmol) N-ethylcarbazole-3-carboxaldehyde, continue to heat and reflux for 12 hours, the solution turns from light yellow to orange red and then stops, cool to room temperature and distill under reduced pressure , to obtain the crude product of formula C.

[0124] The crude product C was dissolved in dichloromethane and chromatographed on silica gel (CH 2 Cl 2 / MeOH, v / v, 30:1) to obtain the compound as an orange-red solid formula C molecule (39 mg, 87.1% yield). Then, the compound was further purified by high performance liquid chromatography. The separation and purification steps of high...

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Abstract

The invention discloses a hemicyanine compound based on benzothiazole biheterocycle, and a preparation method and an application thereof. The structural formula of the compound is represented by formula I. The preparation method of the compound comprises the following steps: carrying out an alkylation reaction on a benzothiazole compound represented by formula II and alkyl halide RbX to obtain a substituted benzothiazole compound, and then carrying out a Knoevenagel condensation reaction on the substituted benzothiazole compound and N-ethylcarbazole-3-formaldehyde to obtain the target compound. The synthesis and preparation steps are simple and easy to implement, raw materials are cheap and easy to obtain, and the product serving as a probe is stable in structure and high in specificity and can be used for specifically detecting G-quadruplex and double-helix secondary structures of nucleic acid. A detection method of the probe for the nucleic acid secondary structure has the advantagesof low price, simplicity and convenience in operation, good selectivity and quickness, and overcomes the defects of high price, high equipment requirement and relatively complex technical operation of other detection methods.

Description

technical field [0001] The invention relates to a semicyanine compound based on a benzothiazole-linked heterocycle and a preparation method and application thereof, belonging to the field of small molecule fluorescent materials. Background technique [0002] Nucleic acid contains the genetic information necessary for life and is one of the most important biological macromolecules in the body. Nucleic acid can form many spatial secondary structures under physiological conditions to help increase molecular stability and exert corresponding biological functions. These secondary structures include single-stranded hairpin structure, homoduplex, triplex and quadruplex structure. DNA usually exists in a B-type double helix structure through the hydrogen bond interaction between Watson-Crick base pairs; the gene promoter region often contains oligonucleotide fragments rich in guanine G, such oligonucleotide fragments It can be folded to form a quadruplex structure, also known as G-...

Claims

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Application Information

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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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