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Ferrous ion fluorescent probe molecule based on dansyl acid structure, preparation method and application

A fluorescent probe, ferrous ion technology, applied in the field of metal ion fluorescent probe detection, achieves the effects of high synthesis yield, wide practicability and broad application prospects

Active Publication Date: 2019-12-13
HENAN AGRICULTURAL UNIVERSITY
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  • Abstract
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  • Claims
  • Application Information

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Problems solved by technology

Most of the current reports are about the detection of Fe 3+ Quenched and enhanced fluorescent probes, while for Fe 2+ There are few fluorescent probes reported for detection. As far as the current development of iron ion probes is concerned, the use of Fe 2+ The development of fluorescent probes for efficient recognition is full of challenges and opportunities

Method used

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  • Ferrous ion fluorescent probe molecule based on dansyl acid structure, preparation method and application
  • Ferrous ion fluorescent probe molecule based on dansyl acid structure, preparation method and application
  • Ferrous ion fluorescent probe molecule based on dansyl acid structure, preparation method and application

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Experimental program
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Effect test

Embodiment 1

[0038] The method of the ferrous ion fluorescent probe molecule based on the dansulphonic acid structure, the steps are as follows:

[0039] Under ice-cooling conditions, m-chloroperoxybenzoic acid (172 mg, 1 mmol) in 10 mL of anhydrous dichloromethane was slowly added dropwise to a solution of dansyl chloride (269.5 mg, 1 mmol) in 10 mL of anhydrous dichloromethane , then raised to room temperature and reacted for 2 hours, added basic alumina (204 mg, 2 mmol) and stirred for 1 hour. The solvent was spin-dried, separated by column chromatography, the developer DCM / MeOH=4:1, and 107 mg of a yellow product was obtained, with a yield of 40%.

[0040] H NMR 1 H NMR (DMSO-d 6, 400 MHz) δ : 4.15 (s, 6 H), 7.72 (m, 2 H),8.14 (d, J = 7.2 Hz, 2 H), 8.78 (d, J = 9.2 Hz, 1 H), 9.24 ( d, J = 8.4 Hz, 1H), 13.47 (s, 1 H); C NMR 13 C NMR (DMSO-d 6 , 100 MHz) δ: 60.3, 119.9, 124.3, 125.1, 125.7, 125.8, 127.2, 131.8, 132.8, 142.6, 146.1; HR-ESI-MScalcd for: C 12 h 14 NO 4 S: 267.0565, ...

Embodiment 2

[0042] The method of the ferrous ion fluorescent probe molecule based on the dansulphonic acid structure, the steps are as follows:

[0043] Under ice-cooling conditions, m-chloroperoxybenzoic acid (374 mg, 2 mmol) in 15 mL of anhydrous dichloromethane was slowly added dropwise to a solution of dansyl chloride (269.5 mg, 1 mmol) in 10 mL of anhydrous dichloromethane , then raised to room temperature and reacted for 4 hours, added basic alumina (204 mg, 2 mmol) and stirred for 2 hours. The solvent was spin-dried, separated by column chromatography, and the developing solvent DCM / MeOH=5:1 to obtain 133.5 mg of a yellow product with a yield of 50%.

[0044] H NMR 1 H NMR (DMSO-d 6 , 400 MHz) δ : 4.15 (s, 6 H), 7.72 (m, 2 H),8.14 (d, J = 7.2 Hz, 2 H), 8.78 (d, J = 9.2 Hz, 1 H), 9.24 ( d, J = 8.4 Hz, 1H), 13.47 (s, 1 H); C NMR 13 C NMR (DMSO-d 6 , 100 MHz) δ: 60.3, 119.9, 124.3, 125.1, 125.7, 125.8, 127.2, 131.8, 132.8, 142.6, 146.1; HR-ESI-MScalcd for: C 12 h 14 NO 4 S: 26...

Embodiment 3

[0046] The method of the ferrous ion fluorescent probe molecule based on the dansulphonic acid structure, the steps are as follows:

[0047] Under ice-cooling conditions, m-chloroperoxybenzoic acid (430 mg, 2.5 mmol) in 15 mL of anhydrous dichloromethane was slowly added dropwise to a solution of dansyl chloride (269.5 mg, 1 mmol) in 10 mL of anhydrous dichloromethane , then raised to room temperature and reacted for 7 hours, added basic alumina (306 mg, 3 mmol) and stirred for 2 hours. The solvent was spin-dried, separated by column chromatography, the developer DCM / MeOH=6:1, and 174 mg of a yellow product was obtained with a yield of 65%.

[0048] H NMR 1 H NMR (DMSO-d 6 , 400 MHz) δ : 4.15 (s, 6 H), 7.72 (m, 2 H),8.14 (d, J = 7.2 Hz, 2 H), 8.78 (d, J = 9.2 Hz, 1 H), 9.24 ( d, J = 8.4 Hz, 1H), 13.47 (s, 1 H); C NMR 13 C NMR (DMSO-d 6 , 100 MHz) δ: 60.3, 119.9, 124.3, 125.1, 125.7, 125.8, 127.2, 131.8, 132.8, 142.6, 146.1; HR-ESI-MScalcd for: C 12 h 14 NO 4 S: 267.056...

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Abstract

The invention provides a ferrous ion fluorescent probe molecule based on dansyl acid structure, a preparation method and application. The molecular formula of the ferrous ion fluorescent probe molecule is C12H14NO4S, and is called FeP1 for short. The probe is prepared by one-step reaction of a commercial reagent dansyl chloride, the synthesis yield is high, and the preparation cost is low. Recognition characteristics of the probe FeP1 in a Tris-DMSO (4:1, pH=7.4, v / v) solution with metal ions, common anions, active sulfur, active oxygen and other small molecular substances are studied througha fluorescence spectrometer. The result shows that: the probe FeP1 has efficient and specific selectivity on ferrous ions (Fe<2+>), has strong anti-interference capability, fast recognition speed andwide pH value application range, has a lowest detection limit of 18 nM, and can be widely applied to detection of ferrous ions in biological systems and environmental samples.

Description

technical field [0001] The invention relates to the field of metal ion fluorescent probe detection, in particular to a ferrous ion fluorescent probe molecule based on a dansulphonic acid structure, a preparation method and an application. Background technique [0002] Iron is an indispensable metal element in living organisms and participates in many physiological activities of living organisms, such as the transmission of oxygen in cells, the maintenance of hematopoietic function, the synthesis of many coenzymes and the synthesis of DNA, etc. Iron is an important component of hemoglobin, myoglobin and cytochrome, participates in the metabolic process of maintaining life, and directly participates in the transportation and storage of oxygen in the living body. Iron must be maintained at a certain concentration in the organism, otherwise it will have a very adverse effect on the health of the organism. [0003] Active iron plays a regulatory role in organisms, and active iro...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/47C09K11/06G01N21/64C07C303/22
CPCC07C309/47C09K11/06C09K2211/1011G01N21/6428G01N21/643G01N2021/6443
Inventor 高光芹谢普会王志敏周晶晶申丽婕党玉丽苏惠
Owner HENAN AGRICULTURAL UNIVERSITY
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