Coumarin-based relay-responsive fluorescent molecular probe and its preparation method and use

A fluorescent molecular probe, coumarin-based technology, applied in the field of chemical fluorescence sensing materials, can solve the problems of difficult rapid and effective detection, poor anti-interference, complicated operation, etc., and achieves easy control of synthesis conditions and fast response time. , post-processing simple effects

Inactive Publication Date: 2019-12-03
JIANGSU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Traditional detection techniques usually include inductively coupled plasma, atomic absorption, ion chromatography, ultraviolet-visible spectrophotometry, and electrochemical methods, but these techniques usually require large instruments and have high requirements for samples. Strict pretreatment is required, and it has the disadvantages of complex operation, time-consuming, high cost, poor anti-interference, etc., and it is difficult to achieve the purpose of fast and effective detection

Method used

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  • Coumarin-based relay-responsive fluorescent molecular probe and its preparation method and use
  • Coumarin-based relay-responsive fluorescent molecular probe and its preparation method and use
  • Coumarin-based relay-responsive fluorescent molecular probe and its preparation method and use

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Experimental program
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Effect test

Embodiment 1

[0040] Step 1, preparation of compound R: Dissolve 0.5g (3mmol) 4-methylumbelliferone and 0.1mL triethylamine in 25mL anhydrous dichloromethane in a round-bottomed flask, and cool the mixture down in an ice bath to 0°C, add 0.24mL (3mmol) chloroacetyl chloride dropwise to the above solution, and then 2 The reaction was stirred under protection for 6h. After the reaction, add 100mL of distilled water, and then use CH 2 Cl 2 Extract three times. Combine the organic layers with anhydrous Na 2 SO 4 Dry, filter and distill off the solvent under reduced pressure to give the product as a white solid. The crude product was purified by recrystallization in ethanol to obtain 0.47 g of compound R with a yield of 63%.

[0041] Step 2. Preparation of fluorescent molecular probe XDS: 0.45g (4mmol) 2-aminomethylpyridine, 0.34g (4mmol) NaHCO 3 , 0.55 g (4 mmol) K 2 CO 3 and 0.64g (4mmol) KI were placed in a round-bottomed flask, and 1.006g (4mmol) of compound R was weighed and dissol...

Embodiment 2

[0043] Step 1, preparation of compound R: Dissolve 1 g (6 mmol) 4-methylumbelliferone and 0.3 mL triethylamine in 35 mL anhydrous dichloromethane in a round-bottomed flask, and cool the mixture in an ice bath to to 0°C, add 0.48g (6mmol) chloroacetyl chloride dropwise to the above solution, and then 2 The reaction was stirred for 9h under protection. After the reaction, add 100mL of distilled water, and then use CH 2 Cl 2 Extract three times. Combine the organic layers with anhydrous Na 2 SO 4 Dry, filter and distill off the solvent under reduced pressure to give the product as a white solid. The crude product was purified by recrystallization in ethanol to obtain 0.87 g of compound R with a yield of 70%.

[0044] Step 2. Preparation of fluorescent molecular probe XDS: 1.35g (12mmol) 2-aminomethylpyridine, 1.02g (12mmol) NaHCO 3 , 1.65 g (12 mmol) K 2 CO 3 and 1.86g (12mmol) KI were placed in a round-bottomed flask, and 3.018g (12mmol) of compound R was weighed and di...

Embodiment 3

[0046] Step 1, preparation of compound R: 1.6g (9mmol) 4-methylumbelliferone and 0.5mL triethylamine were dissolved in 50mL anhydrous dichloromethane and placed in a round bottom flask, and the mixture was cooled down in an ice bath to 0°C, add 0.72mL (9mmol) chloroacetyl chloride dropwise to the above solution, and then 2 The reaction was stirred for 12h under protection. After the reaction, add 100mL of distilled water, and then use CH 2 Cl 2 Extract three times. Combine the organic layers with anhydrous Na 2 SO 4 Dry, filter and distill off the solvent under reduced pressure to give the product as a white solid. The crude product was purified by recrystallization in ethanol to obtain 1.27 g of compound R with a yield of 68%.

[0047] Step 2. Preparation of fluorescent molecular probe XDS: 2.2g (20mmol) 2-aminomethylpyridine, 3.5g (20mmol) NaHCO 3 , 2.8g (20mmol) 2.5g K 2 CO 3 (20mmol) and 3.4g (20mmol) KI were placed in a round-bottomed flask, and 1.006g (20mmol) o...

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Abstract

The invention relates to a coumarin-based relay responsive fluorescent molecular probe and a preparation method and an application thereof and belongs to the technical field of fluorescent chemical sensing materials. The preparation method comprises the following steps of: by taking 4-methylum-belliferyl as a fluorescent group, substituting hydroxyl hydrogen on a site C-7 on 4-methylum-belliferyl by chloroacetyl chloride to form an intermediate compound R; and then performing a substituting reaction on the compound R and 2-methyl pyridinamine as well to combine to prepare the fluorescent molecular probe material. The fluorescent molecular probe prepared by the method has strong blue fluorescent emission. Charge distribution of the probe molecular structure is changed in the presence of Fe<3+>. The blue fluorescence is quenched. After further adding phosphate anions, the fluorescence of the probe is recovered by means of the supplementary effect of metal ions and negative charges, so that the relay identifying detection on Fe3<+> and phosphate anions in a same system is realized, detection and recognition under 100% water soluble condition are realized, and change of the fluorescent signal is macroscopic.

Description

technical field [0001] The invention relates to a relay-responsive fluorescent molecular probe based on coumarins and its preparation method and [0002] The invention belongs to the technical field of chemical fluorescence sensing materials. Background technique [0003] As one of the important trace elements in living organisms, iron plays a pivotal role in the growth and development of living organisms. It participates in the synthesis of hemoglobin, myoglobin, cytochrome, cytochrome oxidase, etc. and can activate the activity of succinic dehydrogenate, xanthine oxidase, etc. [0004] Iron also participates in hematopoietic function, affecting the synthesis of protein and deoxyribonucleic acid and the metabolism of hematopoietic vitamins. When iron is deficient, the synthesis of deoxyribonucleic acid in the liver will be inhibited, the development of the liver will slow down, and the mitochondria and particles in liver cells and other cells will be damaged. Abnormal bod...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/12C09K11/06G01N21/64
CPCC07D405/12C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/6486
Inventor 唐旭韩娟王赟鲍煦王蕾倪良刘仁杰
Owner JIANGSU UNIV
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