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Thiazole orange cyanine dye molecule and application thereof

A technology of orange-like cyanine and molecule, which is applied in thiazole orange-like cyanine dye molecule and its application field, can solve problems such as membrane damage, and achieve the effects of low preparation cost, reduced synthesis cost, and high esterase degradation rate

Active Publication Date: 2014-12-10
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a small number of dead cells still retain trace amounts of metabolic activity, in the vast majority of cases this activity is lost faster than, or roughly equal to, the rate of membrane damage

Method used

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  • Thiazole orange cyanine dye molecule and application thereof
  • Thiazole orange cyanine dye molecule and application thereof
  • Thiazole orange cyanine dye molecule and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] A kind of thiazole orange cyanine dye molecule (BOMA-2), its preparation method is as follows:

[0036] The overall chemical reaction formula is

[0037]

[0038] Concrete preparation steps are as follows:

[0039] Preparation of compound 2:

[0040]

[0041] 1.50 g of compound 1 was mixed with 2.00 g of bromoacetic acid, and heated at 120° C. for 5 hours. After the reaction temperature was lowered to room temperature, the obtained brown solid was dissolved in methanol and concentrated in vacuo. The concentrated material was dissolved in 20 mL of dichloromethane and cooled to 0°C. 40 mL of acetone was slowly added dropwise, and the solid was collected by filtration. After washing three times with 15 mL of acetone, the obtained crude material was resuspended in 20 mL of dichloromethane and stirred for 30 minutes. The solid was collected by filtration and washed three times with 15 mL of dichloromethane to obtain 1.32 g of a light gray solid with a yield of 39%...

Embodiment 2

[0073] A kind of thiazole orange cyanine dye molecule (BOMA-5), its preparation method is as follows:

[0074] Preparation of compound 2:

[0075]

[0076] 1.50 g of compound 1 was mixed with 2.26 g of 6-bromohexanoic acid, and heated at 120° C. for 5 hours. After the reaction temperature was lowered to room temperature, the obtained brown solid was dissolved in methanol and concentrated in vacuo. The concentrated material was dissolved in 20 mL of dichloromethane and cooled to 0°C. 40 mL of acetone was slowly added dropwise, and the solid was collected by filtration. After washing three times with 15 mL of acetone, the obtained crude material was resuspended in 20 mL of dichloromethane and stirred for 30 minutes. The solid was collected by filtration and washed three times with 15 mL of dichloromethane to obtain 1.44 g of a light gray solid with a yield of 41%.

[0077] Preparation of compound 3:

[0078]

[0079] After 1.4 g of compound 2 was stirred evenly with d...

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Abstract

The invention discloses thiazole orange cyanine dye molecules and application thereof. The dye molecules structurally comprise binding groups, ELISA groups, crosslinking groups and connecting parts. The molecules are applied to cell fluorescence staining and are used for judging the living states of bacteria based on the bacterium esterase activity and used for selectively inhibiting the amplification of bacterium DNA in PCR reaction, so that that the purpose of rapidly and quantitatively detecting living bacteria is achieved. The dye molecules disclosed by the invention are simple in structure, low in preparation cost and high in esterase degradation rate.

Description

technical field [0001] The invention relates to a molecular structure design for live bacteria detection and its application in bacteria detection technology. The thiazole orange cyanine dye molecule (abbreviated as BOMA) involved in the present invention can be applied to the technical fields of cell staining and bacterial detection, and utilizes the presence or absence of intracellular esterase activity as the basis for judging the living state of bacteria, and inhibits the death of bacteria in the fluorescent quantitative PCR reaction. The DNA amplification of bacteria can achieve the purpose of quantitatively detecting the content of live bacteria in the sample. Background technique [0002] Foodborne pathogenic bacteria are one of the main factors causing foodborne diseases, and have attracted much attention in the field of food safety in the world. In the natural environment, microorganisms exist in a variety of physiological states: viable bacteria that can be cultiv...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/04C12Q1/68C12Q1/06
Inventor 肖性龙黄韵余以刚吴晖李晓凤唐语谦刘冬梅
Owner SOUTH CHINA UNIV OF TECH
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