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Cis tetraphenylethylene macrocyclic bisquaternary ammonium salt and preparation and application methods thereof

A cis-type and general-type technology, which is applied in the field of cis-tetraphenylethylene macrocyclic diquaternary ammonium salt and its preparation, can solve the problem of low detection sensitivity of DNA concentration and achieve high sensitivity

Inactive Publication Date: 2019-07-26
HUAZHONG UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The invention solves the technical problem of low DNA concentration detection sensitivity in the prior art

Method used

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  • Cis tetraphenylethylene macrocyclic bisquaternary ammonium salt and preparation and application methods thereof
  • Cis tetraphenylethylene macrocyclic bisquaternary ammonium salt and preparation and application methods thereof
  • Cis tetraphenylethylene macrocyclic bisquaternary ammonium salt and preparation and application methods thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of DNA detection reagent I (in general formula I, m=1; X=Cl):

[0045]

[0046] 0.05 g of the compound of formula II and 5 mL of acetonitrile were added into a round bottom flask, and then 0.5 mL of triethylamine was added. After heating and stirring at 70° C. for 4 h, the solvent was removed by evaporation, and the remaining solid was recrystallized from dichloromethane / ethyl acetate to obtain the compound described in formula I with a yield greater than 85%.

[0047] Compound of formula I in CH 3 in OD 1 H-NMR spectrum see figure 1 , 13 C-NMR spectrum see figure 2 , HRMS spectrum see image 3 . Depend on figure 1 , figure 2 and image 3 It can be concluded that the compound prepared in this example is the compound with the structure shown in formula I (m=1; X=Cl).

Embodiment 2

[0049] Synthesis of DNA detection reagent I (in general formula I, m=1; X=Cl):

[0050]

[0051] 0.2 g of compound of formula II and 10 mL of acetonitrile were added into a round bottom flask, and then 2 mL of triethylamine was added. After heating and stirring at 80° C. for 10 h, the solvent was removed by evaporation, and the remaining solid was recrystallized from dichloromethane and ethyl acetate to obtain the compound described in formula I with a yield greater than 85%.

Embodiment 3

[0053] Synthesis of DNA detection reagent I (in general formula I, m=1; X=Cl):

[0054]

[0055] 0.5 g of the compound of formula II and 20 mL of acetonitrile were added into a round bottom flask, and then 5 mL of triethylamine was added. After heating and stirring at 100° C. for 20 h, the solvent was removed by evaporation, and the remaining solid was recrystallized from dichloromethane and ethyl acetate to obtain the compound described in formula I with a yield greater than 85%.

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Abstract

The invention discloses a cis tetraphenylethylene macrocyclic bisquaternary ammonium salt and preparation and application methods thereof and belongs to the technical field of biochemical detection. The preparation method comprises heating cis dichloromethylene tetraphenylethylene crown ether or cis dibromomethylene tetraphenylethylene crown ether and triethylamine at 70-100 DEG C for 4-20 h for nucleophilic substitution, removing solvent through evaporation and then performing recrystallization to obtain the cis tetraphenylethylene macrocyclic bisquaternary ammonium salt. The cis tetraphenylethylene macrocyclic bisquaternary ammonium salt is in a cis cyclic structure, so that when two quaternary ammonium salt groups are aggregated onto DNA (deoxyribonucleic acid) chains through electrostatic interaction, not only is rotation of unit benzene rings of tetraphenylethylene restricted, but also rotation of the double bond of the tetraphenylethylene can be hampered, further the cis tetraphenylethylene macrocyclic bisquaternary ammonium salt can be ultrahigh in sensitivity when applied to detecting DNA; when the DNA contains 30 basic groups, the minimum concentration of the cis tetraphenylethylene macrocyclic bisquaternary ammonium salt for DNA detection is 32 pmol / L.

Description

technical field [0001] The invention belongs to the technical field of biochemical detection, and more specifically relates to a cis-tetraphenylethylene macrocyclic diquaternary ammonium salt and a preparation method and application thereof. Background technique [0002] DNA carries biological genetic codes and regulates the reproductive process and results of living organisms. Gene deletions and defects can cause major diseases and abnormal living organisms, so DNA testing is of great significance. The fluorescence detection of DNA is a fast, simple and sensitive method, but the traditional DNA fluorescence detection needs to label the nucleotide chain, which is very time-consuming and laborious. In order to overcome this problem, non-labeled DNA fluorescence detection and analysis methods through the non-covalent interaction of fluorescent reagents and DNA have received attention in recent years. [0003] Among the non-labeled DNA fluorescence detection and analysis metho...

Claims

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Application Information

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IPC IPC(8): C07D323/00C09K11/06G01N21/64
CPCC07D323/00C09K11/06C09K2211/1007C09K2211/1088G01N21/6428
Inventor 郑炎松袁迎雪
Owner HUAZHONG UNIV OF SCI & TECH