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Up-conversion fluorescent probe rhodamine derivative and application thereof

A technology of fluorescent probes and derivatives, applied in the field of up-conversion fluorescence enhancement reagents, to achieve the effects of less damage to biological cells, high yield, and less damage to cells

Active Publication Date: 2019-09-13
SUZHOU UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, detection methods using anti-Stokes fluorescence (i.e., upconversion fluorescence) are rarely reported

Method used

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  • Up-conversion fluorescent probe rhodamine derivative and application thereof
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  • Up-conversion fluorescent probe rhodamine derivative and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Add Rhodamine B (2 g, 4.2 mmoL), ethylenediamine (1 mL, 21 mmoL) and 50 mL of absolute ethanol into a 250 mL three-neck flask, and dissolve them by ultrasonication; heat to reflux at 80 ° C, and track the reaction process with a plate , the developer is methanol:dichloromethane=10:1, the reaction is carried out for 24h, stop the reaction, and cool to room temperature; the ethanol is removed by distillation under reduced pressure to obtain a brown solid mixture, and the product is purified by column chromatography. The developer is methanol / dichloromethane Chloromethane (10 / 1, v / v). 1.5 g (yield: 70%) of the brown intermediate rhodamine B-ethylenediamine was obtained. 1 H NMR (400 MHz, CDCl 3 ) δ 7.91 (dd, J = 5.6, 3.1 Hz,1H), 7.46 (dt, J = 7.2, 3.7 Hz, 2H), 7.10 (dd, J = 5.6, 3.0 Hz, 1H), 6.51-6.24 (m, 6H), 3.35 (q, J = 7.2 Hz, 8H), 3.21 (t, J = 6.5 Hz, 2H), 2.47 (t, J = 6.5 Hz, 2H), 1.18 (t, J = 7.0 Hz, 12H) (see attached figure 1 ). MS, Calculated: [M ...

Embodiment 2

[0041] The probe molecule RhB-NA was added to ethanol to prepare a RhB-NA ethanol mother solution with a concentration of 1 mM.

[0042] Add 3 mL of ethanol / buffer solution (buffer solution is Na 2 HPO 4 / NaH 2 PO 4 aqueous solution, pH=7, 1 / 2, v / v), and then take 30 μL of RhB-NA ethanol mother solution (concentration: 1mM) into the above-mentioned quartz cuvette, ultrasonically dissolve it, and then prepare a 10 μM Probe RhB-NA solution.

[0043] Similarly, add 3 mL ethanol / buffer solution (Na 2 HPO 4 / NaH 2 PO 4 aqueous solution, pH=7, 1 / 2, v / v), and then take 300 μL RhB-NA ethanol mother solution (concentration: 1mM) into the above-mentioned quartz cuvette, ultrasonically dissolve it, and then prepare 100 μM Probe RhB-NA solution.

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Abstract

The invention discloses an up-conversion fluorescent probe rhodamine derivative and an application thereof. The preparation method comprises the following steps: performing a reaction on rhodamine B and ethylenediamine in a nitrogen gas atmosphere and an organic solvent to obtain rhodamine-ethylenediamine; and performing a reaction on the rhodamine-ethylenediamine and phenyl isothiocyanate to obtain the up-convertion fluorescent probe rhodamine derivative. The up-conversion fluorescent probe rhodamine derivative provided by the invention has the high-efficiency down-conversion fluorescence-enhanced response recognition characteristics for mercury ions and has the high-efficiency up-conversion fluorescence-enhanced response recognition characteristics for the mercury ions when used as a fluorescent probe.

Description

technical field [0001] The invention belongs to the field of upconversion fluorescence enhancement reagents and the technical field of heavy metal ion upconversion fluorescence probes, and specifically relates to a rhodamine derivative probe with upconversion fluorescence enhancement response and a preparation method thereof, and the use of the probe in detecting water environment Or the application of mercury ions in living organisms. Background technique [0002] Mercury ions are extremely harmful to organisms and the natural environment, and it is of great significance to make rapid and high-sensitivity detection of mercury ions. At present, many methods for the determination of mercury ions have been reported, mainly including: spectrophotometry, fluorescence analysis, electrochemical method and atomic absorption spectrometry. Among them, the fluorescence analysis method has attracted extensive attention due to its advantages of high sensitivity, specific selectivity, s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64A61K49/00
CPCA61K49/0041C07D491/107C09K11/06C09K2211/1011C09K2211/1029C09K2211/1088G01N21/6428G01N21/643
Inventor 王筱梅宋飒飒夏方媛朱琳叶常青于雪王伟飒
Owner SUZHOU UNIV OF SCI & TECH
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