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Fe<3+> molecular fluorescence sensor based on Rhodamine B and preparation method and application of Fe<3+> molecular fluorescence sensor

A fluorescent sensor and reaction technology, applied in the field of biochemistry, can solve the problems of poor probe sensitivity, high fluorescence intensity, and low production cost, and achieve the effects of high quantum yield, simple synthesis steps, and low cost

Inactive Publication Date: 2016-08-24
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] (1) As in Document 1, the sensitivity of the synthesized probe is poor, and Cu 2+ ,Cr 3+ interference
[0009] (2) As in document 2, there are more steps for synthesis, and the yield is lower, and Al 3+ and Cr 3+ Obvious interference
[0010] The above defects have caused it to be difficult to obtain Fe with low production cost, high fluorescence intensity and good selectivity by using existing processes. 3+ Sensor preparation method

Method used

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  • Fe&lt;3+&gt; molecular fluorescence sensor based on Rhodamine B and preparation method and application of Fe&lt;3+&gt; molecular fluorescence sensor
  • Fe&lt;3+&gt; molecular fluorescence sensor based on Rhodamine B and preparation method and application of Fe&lt;3+&gt; molecular fluorescence sensor
  • Fe&lt;3+&gt; molecular fluorescence sensor based on Rhodamine B and preparation method and application of Fe&lt;3+&gt; molecular fluorescence sensor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Synthesis of fluorescent chemical sensors

[0045] 1. Synthesis of compound 1

[0046] Rhodamine B (960mg, 2mmol) and ethylenediamine (0.65ml, 10mmol) were dissolved in absolute ethanol (40ml), the reaction temperature was controlled at 80°C, and the reaction time was 12h. After the reaction was completed, the solvent was removed under reduced pressure, and extracted , separated by silica gel column to obtain light yellow solid (880 mg, 92%). Compound 1 1 H NMR, 13 C NMR respectively as figure 1 , figure 2 shown.

[0047] 2. Synthesis of compound 2

[0048] Compound 1 (97mg, 0.2mmol) was dissolved in chloroform (2ml), maleic anhydride (78mg, 0.4mmol), and heated to reflux for 10h. After the reaction was completed, the solvent was removed under reduced pressure, extracted, and finally a light red solid (130 mg, 91%) was obtained after column separation. Compound 2 1 H NMR, 13 C NMR respectively as image 3 , Figure 4 shown.

[0049] 3. Synthesis of Target ...

Embodiment 2

[0052] UV selective performance test

[0053] The target compound has good solubility in methanol. After verification, the target compound can be dissolved in 30% acetonitrile in Tris-HCl (1.0mM, pH=7.4) solvent, prepare 500ml of this solution as a stock solution (pH=7.4) .

[0054] Precisely configure the target compound as 1 x 10 -3 mol / L in 30% MeCN aqueous solution, CdCl 2 2.5H 2 O, CuCl 2 2H 2 O,AlCl 3 ,KCl,FeCl 3 ·6H 2 O,PbCl 2 ,AgNO 3 ,HgCl 2 ,NiCl 2 ·6H 2 O,MgCl 2 ·6H 2 O, NaCl, ZnCl 2 ,CrCl 3 ·6H 2 O,Ba(NO 3 ) 2 , CuCl, LiCl·H 2 O,MnCl 2 4H 2 O,CoCl 2 ·6H 2 O,CaCl 2 Isoconcentration is 5×10 -3 mol / L aqueous solution, and dissolved with 30% acetonitrile in Tris-HCl (1.0mM, pH=7.4) solution.

[0055] UV selectivity experiments such as Figure 7 As shown, take 3ml of the stock solution and place it in the liquid pool, add 30uL of the target compound, measure its initial absorbance, then add 30uL of various prepared cations respectively, and me...

Embodiment 3

[0057] Fluorescent selective performance test

[0058] The target compound has good solubility in methanol. After verification, the target compound can be dissolved in 30% acetonitrile in Tris-HCl (1.0mM, pH=7.4) solvent, prepare 500ml of this solution as a stock solution (pH=7.4) .

[0059] Precisely configure the target compound as 1 x 10 -3 mol / L in 30% MeCN aqueous solution, CdCl 2 2.5H 2 O, CuCl 2 2H 2 O,AlCl 3 ,KCl,FeCl 3 ·6H 2 O,PbCl 2 ,AgNO 3 ,HgCl 2 ,NiCl 2 ·6H 2 O,MgCl 2 ·6H 2 O, NaCl, ZnCl 2 ,CrCl 3 ·6H 2 O,Ba(NO 3 ) 2 , CuCl, LiCl·H 2 O,MnCl 2 4H 2 O,CoCl 2 ·6H 2 O,CaCl 2 Isoconcentration is 5×10 -3 mol / L aqueous solution, and dissolved with 30% acetonitrile in Tris-HCl (1.0mM, pH=7.4) solution.

[0060] Fluorescent selectivity experiments such as Figure 8 As shown, take 3ml of the stock solution and place it in the liquid pool, add 30uL of the target compound, measure its initial fluorescence intensity value, then add 30uL of various p...

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Abstract

The invention discloses a Fe<3+> molecular fluorescence sensor based on Rhodamine B and a preparation method and application of the Fe<3+> molecular fluorescence sensor. Rhodamine B is taken as a precursor, and a target product N1-(benzene[d] thiazole-2-yl)-N4-(2-(3',6'-bi(diethylin)-3-carbonyl screw[iso-indoline-1,9'-xanthene]-2-yl)ethyl) maleimide is synthesized at two steps. Detection on Fe<3+> by using the target product shows that the target product has a very good detection effect on Fe<3+>; and meanwhile the raw materials of the Fe<3+> molecular fluorescence sensor are easy to obtain, synthesis steps are simple, after-treatment is convenient to implement, and large-scale production can be relatively easily achieved.

Description

technical field [0001] The invention belongs to the field of biochemistry, in particular to a rhodamine B-based Fe 3+ Fabrication and application of fluorescent sensors. Background technique [0002] Among many transition metal ions, Fe 3+ It is one of the necessary ions in the human body. As one of the most important trace elements in biological systems, it plays an important role in many biochemical processes at the cellular level, including oxygen uptake, oxygen metabolism, electron transfer, and more. However, when Fe in the body 3+ When the content is not normal, it can cause many diseases. Too little iron can lead to permanent loss of motor skills. Too much Fe in the body 3+ A Fenton reaction will occur to generate active oxygen, which will cause damage to lipids, nucleic acids, and proteins. More seriously, when Fe in the central nervous system 3+ When the content accumulates to a certain concentration, it may cause a series of diseases, such as Parkinson's, H...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC09B11/24C09B69/103C09K11/06C07D491/107C09K2211/1029C09K2211/1037C09K2211/1088G01N21/643
Inventor 包晓峰陈海浪舒海吴小磊李峰
Owner NANJING UNIV OF SCI & TECH
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