A fluorescent probe compound and its preparation method and use

A technology of derivatives and hydrazine hydrate, which is applied in the field of fluorescent probes, can solve the problems of complex instruments and equipment, tediousness, cell damage, etc., and achieve the effects of consistent reaction conditions, simple synthesis routes, and simple and convenient post-processing

Active Publication Date: 2018-09-21
NANJING TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these techniques require cumbersome sample pre-preparation processes, complex instruments and equipment, and actively cause damage to cells, etc.

Method used

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  • A fluorescent probe compound and its preparation method and use
  • A fluorescent probe compound and its preparation method and use
  • A fluorescent probe compound and its preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Embodiment 1: detect the preparation of the fluorescent probe of iron ion, basic synthesis process is as follows:

[0032] (1) Synthesis of Rhodamine Hydrazine Hydrate: Add 2 mL of ethanol dropwise to a 25 mL one-mouth bottle, add 1 mmol of Rhodamine B to it and stir to dissolve it; React for 1 hour to obtain an orange-yellow solution, and rotary evaporate to obtain a viscous solid, then add hydrochloric acid solution dropwise therein until the solid is completely dissolved, then add sodium hydroxide solution dropwise therein until the pH reaches 8, pink flocs appear, pump Filter to obtain a pink solid: 90% yield.

[0033] (2) Synthesis of probe molecules: the 0.9mmol rhodamine hydrazine hydrate obtained in step (1) was dissolved in 10mL glacial acetic acid, then 0.9mmol maleic anhydride was added thereto, reflux reaction was performed for 4 hours, and rotary evaporation, Then the yellow solid rhodamine hydrazide derivative was separated by column chromatography, and t...

Embodiment 2

[0034] Embodiment 2: detect the preparation of the fluorescent probe of iron ion and mercaptan, basic synthesis process is as follows:

[0035] 1) Synthesis of Rhodamine Hydrazine Hydrate: Add 35 mL of ethanol dropwise to a 150 mL one-mouth bottle, add 10 mmol Rhodamine B to it and stir to dissolve it; then add 30 mmol L Hydrazine Hydrate dissolved in 20 mL ethanol dropwise into Rhodamine for reflux reaction 4 hour, an orange solution was obtained, rotary evaporation obtained a viscous solid, sulfuric acid was added dropwise therein until the solid was completely dissolved, and then potassium hydroxide solution was slowly added dropwise until the pH reached 10, pink flocs appeared, suction filtered to obtain a pink solid : 90% yield.

[0036]2) Synthesis of probe molecules: 5mmol rhodamine hydrazine hydrate obtained in step (1) was dissolved in 35mL glacial acetic acid, then 15mmol maleic anhydride was added thereto, refluxed for 7 hours, rotary evaporation, column chromatogra...

Embodiment 3

[0037] Embodiment 3: the fluorescence spectrometry of probe molecule

[0038] Get 3mL concentration among the example 1 and be the probe ethanol water mixed solution of 10 μ mol / L in the quartz cuvette, then add 3 μ L concentration respectively and be the various metal ions of 10 mmol / L (Na + , K + , Ag + ,Mg 2+ ,Cu 2+ ,Cd 2+ ,Pb 2+ ,Zn 2+ ,Mn 2+ ,Co 2+ , Ni 2+ , Fe 3+ ,Al 3+ ) solution, shake well, and measure its fluorescence emission spectrum at an excitation wavelength of 455nm (such as Figure 4 ), the results show that when no metal ions are added, there is no emission peak; when ferric ions are added, an emission peak appears at 581nm; when other metal ions are added, no emission peaks appear; change as Figure 5 As shown, the color changes from colorless to purple; under fluorescent light, the color changes as Figure 6 As shown, the color changed from colorless to pink fluorescent.

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Abstract

The invention relates to a fluorescent probe compound and a preparing method and application thereof. A rhodamine hydrazide derivative serves as the fluorescent probe compound and has the structure formula shown in the description. Rhodamine hydrazine hydrate is synthesized first, and then probe molecules are synthesized. Raw materials of the probe molecules are easy to obtain, the synthesizing route is simple, and aftertreatment is easy and convenient. The solubility of probes in an ethanol and water mixed solution is good, the maximum emission wavelength is at the position of 581 nm, fluorescent signals are weak, and a high emission peak appears at the position of 581 nm of the wavelength of the probe molecules along with addition of ferric ions. Thus, the fluorescent probe compound can be used for detecting ferric ions in aqueous solutions; besides, the probes can effectively detect ferric ions in living cells and can be applied to the field of biological medicine.

Description

technical field [0001] The invention relates to a fluorescent probe compound and its preparation method and application, in particular to a fluorescent probe compound for detecting ferric ions and its preparation and application, belonging to the technical field of fluorescent probes. Background technique [0002] In recent years, with the rapid development of chemical sensors, fluorescent probes have the advantages of high sensitivity, good selectivity, and real-time response, especially through the use of fluorescent confocal microscopy imaging technology to detect the concentration of molecules or ions in living cells in real time. As well as the change process of the structure of biological macromolecules, it has received more and more attention in many fields such as chemistry, biology, medicine, and environment, and has become a major research hotspot. [0003] Iron plays an important role in many physiological processes. Iron is not only the carrier of oxygen in hemo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/643
Inventor 杨文革樊世敏郝建峰李红杰张健赵王丹
Owner NANJING TECH UNIV
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