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Application of sulforaphane and derivatives thereof as bacterial effector protein transcription inhibitor

A technology of sulforaphane and effector protein, applied in the biological field, can solve problems such as drug resistance and destruction of beneficial microorganisms

Active Publication Date: 2021-03-30
INST OF GENETICS & DEVELOPMENTAL BIOLOGY CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of traditional phytoalexins is that they have no selectivity for the target of action. While killing pathogenic microorganisms, they also destroy beneficial microorganisms in the environment and easily lead to drug resistance.

Method used

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  • Application of sulforaphane and derivatives thereof as bacterial effector protein transcription inhibitor
  • Application of sulforaphane and derivatives thereof as bacterial effector protein transcription inhibitor
  • Application of sulforaphane and derivatives thereof as bacterial effector protein transcription inhibitor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0073] Embodiment 1, sulforaphane derivative AS7 and its synthesis method

[0074] Follow the steps below to synthesize AS7:

[0075] (1) Synthesis of Compound 8:

[0076]

[0077] Mercaptoethylamine (compound 7) (300mg, 3.88mmol, 1eq) (purchased from Tissier, catalog number: 60-23-1) and sodium hydroxide (233mg, 5.82mmol, 1.5eq) were dissolved in ethanol ( 7.5 mL), iodomethane (290 μL, 4.66 mmol, 1.2 eq) was added at 0°C. The mixture was stirred at room temperature for 3 hours, then spin-dried and redissolved in chloroform and filtered to obtain the crude product of compound 8 ( figure 2 A).

[0078] (2) Synthesis of Compound 9:

[0079]

[0080] The crude compound 8 was dissolved in ethyl acetate (30 mL) and saturated sodium bicarbonate (20 mL), and o-nitrobenzenesulfonyl chloride (1.29 g, 5.82 mmol, 1.5 eq) was added at 0°C. The mixture was stirred at room temperature for 3 hours, the organic phase was washed with water, concentrated by rotary evaporation to obt...

Embodiment 2

[0097] Embodiment 2, sulforaphane derivative AS8 and its synthesis

[0098] Follow the steps below to synthesize AS8:

[0099] (1) Synthesis of Compound 15:

[0100]

[0101] Compound 13 (40 mg, 0.22 mmol) was dissolved in 2 mL of ether, 3-bromopropyne and cesium carbonate were added at 0°C, and then stirred at room temperature for 15 hours. Quenched with 5 mL of water, extracted with dichloromethane (10 mL×3), dried over anhydrous sodium sulfate, filtered to remove the desiccant, and evaporated the solvent under reduced pressure. Purification by column chromatography (dichloromethane / methanol=50:1) gave compound 15 (20 mg, 43%) as a colorless liquid ( figure 2 h).

[0102] (2) Synthesis of compound AS8:

[0103]

[0104] Compound 15 (10.7 mg, 0.05 mmol) was dissolved in 2 mL of diethyl ether, triphenylphosphine was added, and stirred at 40° C. for 4 hours. Cool to room temperature, add 2 mL of carbon disulfide, and reflux for 5 hours. The solvent was evaporated u...

Embodiment 3

[0106] Example 3, the application of sulforaphane in inhibiting the expression of Pseudomonas syringae effector protein-related genes

[0107] 1. Sulforaphane inhibits the expression of effector proteins in Pseudomonas syringae

[0108] 1. Pick a single colony of Pst DC3000ΔsaxAB / F / D / G and place it in KB medium, culture overnight at 28°C and 220rpm, centrifuge at 4000rpm for 10 minutes, and collect the bacteria.

[0109] 2. After step 1 is completed, the obtained bacterial cells are washed twice with water, and then the bacterial cells are resuspended in the basic medium to OD=0.4 to obtain the resuspended bacterial cells.

[0110] 3. After completing step 2, add sulforaphane to the resuspended cells so that the final concentration in the resuspended cells is 20 μM. After 6 hours, use real-time fluorescent quantitative PCR to detect Pst DC3000ΔsaxAB / Expression of effector proteins (effector proteins secreted by type III secretion system) related genes avrPto, hopAM1, hopH1, ...

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Abstract

The invention discloses application of sulforaphane and derivatives thereof as a bacterial effector protein transcription inhibitor. The invention provides an application of sulforaphane and derivatives thereof in any one of application of the following 1) and 7): 1) prevention and treatment of pathogenic bacteria; 2) improvement of the resistance of plants to pathogenic bacteria; 3) inhibiting ofpathogenicity of pathogenic bacteria; 4) inhibiting of the function of a pathogenic bacterium III type secretion system; 5) inhibiting of the expression of effector protein related genes of a pathogenic bacterium type III secretion system; 6) inhibiting of the expression of a pathogenic bacteria transcription factor hrpL; and 7) using as a pathogenic bacteria effector protein transcription inhibitor. Experiments prove that the sulforaphane and the derivatives thereof can inhibit the function of a pathogenic bacteria type III secretion system by specifically inhibiting transcription of the pathogenic bacteria type III secretion system, can resist invasion of pathogenic bacteria without destroying interaction between plants and beneficial microorganisms, and have a wide application prospectin prevention and treatment of plant pathogenic bacteria.

Description

technical field [0001] The invention belongs to the field of biotechnology, and specifically relates to the application of sulforaphane and its derivatives as bacterial effector protein transcription inhibitors. Background technique [0002] During the long-term co-evolution process of plants and pathogenic microorganisms, a series of complex and efficient protection mechanisms have gradually formed to resist the infection of pathogenic microorganisms, in which secondary metabolites of plants play an important role. After the plant immune system is activated, it will induce the synthesis and release of secondary metabolites with antibacterial activity in the body, helping plants resist the invasion of pathogenic microorganisms. The number of secondary metabolites involved in plant innate immunity is huge and varied in structure. According to the synthesis mechanism and mode of action, they can be divided into two categories: the antibacterial secondary metabolites stored con...

Claims

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Application Information

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IPC IPC(8): A01N47/46A01P1/00A01P21/00
CPCA01N47/46
Inventor 周俭民雷晓光王伟杨靖张健
Owner INST OF GENETICS & DEVELOPMENTAL BIOLOGY CHINESE ACAD OF SCI
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