pH fluorescence probe with double-protonation loci of pyridine and morpholine groups and preparation method and application thereof

A fluorescent probe, pyridine group technology, applied in the field of detection, can solve problems such as low sensitivity, and achieve the effects of high sensitivity, rapid response, and good acid-base reversibility

Inactive Publication Date: 2017-09-01
TONGJI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently available pH fluorescent probes have the following disadvantages: low sensitivity, and some excitation in the ultraviolet region
In addition, there are few ideal pH probes for detecting acidic organs, which is considered to be a bottleneck in the development of cell biology and medicine

Method used

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  • pH fluorescence probe with double-protonation loci of pyridine and morpholine groups and preparation method and application thereof
  • pH fluorescence probe with double-protonation loci of pyridine and morpholine groups and preparation method and application thereof
  • pH fluorescence probe with double-protonation loci of pyridine and morpholine groups and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1: Synthesis of Target Fluorescent Probe Molecules

[0033] (a) In a 250mL single-necked flask, add 4-bromo-1,8-dinaphthyl anhydride (15g, 54mmol), 4-(2-aminoethyl) morpholine (7g, 54mmol) and 150mL methanol successively, at reflux React under the conditions for 8h, after cooling to room temperature, filter and dry to obtain compound 1, light yellow solid, 17g, yield 81.0%.

[0034] (b) In a 250mL single-necked flask, sequentially add product 1 (15g, 38.5mmol), sodium methoxide (0.21g, 3.9mmol) and 150mL of anhydrous methanol, react under reflux for 36h, filter with suction, filter the cake with dilute hydrochloric acid (10%), then washed with water, and dried to obtain compound 2, a yellow solid, 10.9 g, with a yield of 83.2%.

[0035] (c) In a 250mL single-necked flask, add product 2 (10g, 29.4mmol) molecules and 100mL concentrated HI (57%), react under reflux for 6h, cool to room temperature, and neutralize to pH 7 with dilute sodium bicarbonate solution -8, ...

Embodiment 2

[0042] Embodiment 2: Fluorescence titration experiment

[0043] The detection of the target fluorescent probe molecule to the pH value can be studied by the fluorescence titration experiment and its fluorescence properties (the fluorescence emission intensity ratio at the two wavelengths of 388nm and 452nm) with the change curve of the pH value, the results are shown in figure 1 The results showed that probe 1 was suitable for detecting the pH value in an environment with a pH range of 3.1-5.0. According to the Henderson-Hasselbatch Type equation (log[(Imax-I) / (I-Imin)]=pKa-pH), the pKa value of probe 1 was calculated to be 4.05. Thus, the compounds of the present invention can be used to detect pH under acidic conditions.

Embodiment 3

[0044] Embodiment three: ion selectivity experiment

[0045] Using the target fluorescent probe molecule obtained in the above-mentioned Example 1, evaluate its selectivity to hydrogen ions, add 5 μ M probe 1 to the solution containing various metal ions (25 mM Na + , 5mM K + , Ca 2+ ; 0.1 mM Mg 2+ , Mn 2+ , Fe 2+ , Ni 2+ , Pb 2+ , Cu 2+ , Cr 2+ ) in aqueous solutions of different pH values ​​(pH 6.6 or 3.0), measure the fluorescence emission spectrum. The results are shown in figure 2 .

[0046] In the figure, the vertical axis is the ratio of the fluorescence emission intensity at 405nm and 450nm in the emission spectrum of the probe in aqueous solutions with different pH values ​​and containing different metal ions. The probe of the present invention has extremely high selectivity to hydrogen ions, that is, the probe has extremely strong selectivity to hydrogen ions, even if a large amount of sodium ions, potassium ions, calcium ions, and magnesium ions that exi...

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PUM

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Abstract

The invention provides a pH fluorescence probe with double-protonation loci of pyridine and morpholine groups and a preparation method and application thereof. The structure of the probe is as shown in formula (I) in the specification. The probe has relatively wide pH response within a pH range of 3.1-5.0, the pKa of the probe is 4.05, in addition, the probe has relatively good water solubleness, optical and chemical stability and relatively good ion selectivity and biological compatibility. Fluorescence microimaging tests show that the probe has relatively good cell permeability and pH response, and has very small cytotoxicity.

Description

[0001] 【Technical field】 [0002] The invention relates to the technical field of detection, in particular to a fluorescent probe for specifically detecting the pH value in an aqueous phase, a preparation method thereof and the application of the fluorescent probe in the detection of living biological cells. [0003] 【Background technique】 [0004] As an important metabolic and intracellular parameter, hydrogen ion concentration plays a key regulatory role in many cellular processes, such as cell growth, calcium ion regulation, enzyme activity, signal transduction, endocytosis, chemotropism and others cellular processes. The optimal pH value of the human body is around 7.35-7.45, which is weakly alkaline, because at this time the cell activity is the strongest and the organs are running most normally. If the pH value is lower than 7.35, the activity of human cells, various enzymes and hormones will be greatly inhibited, the function of tissues and organs will be reduced, and t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D413/14G01N21/64
CPCC07D413/14C09K11/06C09K2211/1007C09K2211/1029C09K2211/1033G01N21/6486
Inventor 金明付鲸铭潘海燕万德成
Owner TONGJI UNIV
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