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Thiophene derivative for DNA detection and preparation method thereof

A technology of thiophene derivatives and thiophene acetic acid, which is applied in the fields of biochemical equipment and methods, determination/inspection of microorganisms, organic chemistry, etc., can solve the problems of less reports of complex formation and interference, etc.

Inactive Publication Date: 2014-06-18
BEIJING FLUORESCENCE BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of electrostatic interaction force to detect DNA has a disadvantage that it is easily interfered by other charged substances in the solution.
So far, there are few reports on the use of DNA intercalators as the main force to form complexes between polymers and DNA

Method used

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  • Thiophene derivative for DNA detection and preparation method thereof
  • Thiophene derivative for DNA detection and preparation method thereof
  • Thiophene derivative for DNA detection and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Weigh 3.34ml (50mmol) of ethylenediamine and 1ml of triethylamine and dissolve it in 30ml of chloroform, lower the temperature to 0°C, weigh di-tert-butyl dicarbonate (1.09g, 5mmol) and dissolve it in 20ml of chloroform and slowly add it dropwise into the above solution, stirred and reacted for 3 hours, then the reaction solution gradually rose to room temperature (about 25° C.), and continued to react for 10 hours. After the reaction, insoluble matter was removed by filtration, unreacted ethylenediamine was removed by a rotary evaporator, and concentrated to obtain a light yellow oily liquid which was compound 1 (0.71 g, 89%). 1 H-NMR: (400MHZ, CDCL 3 , ppm): δ1.45(s, 9H), 1.74(s, 2H), 2.78(t, 2H), 3.17(q, 2H), 5.12(broad s, 1H).

Embodiment 2

[0025] Weigh 10ml (99.5mmol) of 1,4-butanediamine and dissolve it in 70ml of dichloromethane, lower the temperature to 0°C, weigh di-tert-butyl dicarbonate (7.24g 33.2mmol) and dissolve it in 20ml of chloroform and slowly Add it dropwise to the above solution, stir and react for 3 hours, then the reaction solution gradually rises to room temperature (about 25° C.), and continue to react for 10 hours. After the reaction was completed, 70 ml of chloroform was added to the mixed solution for dilution, washed with 5% sodium carbonate solution, dried over anhydrous magnesium sulfate, and excess solvent was removed with a rotary evaporator. The residue was dissolved in 10 ml of 1M aqueous hydrochloric acid and washed twice with ether. The resulting aqueous layer was made basic (pH = 10) with 2M aqueous sodium hydride solution, and then extracted with ethyl acetate. The extract was dried with anhydrous magnesium sulfate, and the excess solvent was removed to obtain compound 2 withou...

Embodiment 3

[0027] Compound 3 can be prepared by using 1,6-hexanediamine instead of 1,4-butanediamine in Example 2, and the synthesis method is the same as that of Example 2. 1 H-NMR: (400MHZ, CDCL 3 , ppm): δ1.55-1.27 (m, 17H), 2.67 (t, 2H), 3.11 (q, 2H), 4.90 (broad s, 1H).

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Abstract

The invention belongs to the field of chemical synthesis and discloses a thiophene derivative for DNA detection and a preparation method thereof. The thiophene derivative for DNA detection has the following structure of formula (1) shown in the description, wherein n is integer of 2 to 10, preferably n is 2, 4, 6, 8, 10. The thiophene derivative can be synthesized by the following synthesis route shown in the description, wherein n is 2, 4, 6, 8; the thiophene derivative not only retains the property that the polythiophene derivative forms a complex along with a polymer by utilizing interaction of static electricity between a substrate and the polymer in detecting DNA, enzyme, protein, metal ions and the like, but overcomes the defect that the detection of the polythiophene derivative on the DNA by employing interaction of static electricity is easily interfered by other substances with electric charges in the solution, and capability of the polythiophene derivative in distinguishing single and double chain DNAs is remarkably improved.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and relates to a thiophene derivative used for DNA detection and a preparation method thereof. Background technique [0002] In recent years, scientists have designed many biosensing systems for DNA and enzyme detection. In 2002, Leclerc's research group synthesized water-soluble polythiophene derivatives and applied it to detect DNA; Bazan's research group designed and synthesized a new benzothiazole-doped cationic polyfluorene, and used it to detect single-stranded DNA and double-stranded DNA. The concentration of strand DNA; our laboratory has also synthesized a series of cationic polyfluorene derivatives and polythiophene derivatives in recent years, and used them to detect DNA, enzymes, proteins, metal ions, etc. The common feature of these biochemical sensing systems is that they almost mainly use the electrostatic interaction force between the substrate and the polymer to form a complex ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/12C12Q1/68
Inventor 杜池敏
Owner BEIJING FLUORESCENCE BIOTECHNOLOGY CO LTD