Fluorescent probe for detecting mercury ion in cell, and synthesizing method and usage

A fluorescent probe, mercury ion technology, used in chemical instruments and methods, luminescent materials, biological testing, etc., can solve the problems of poor solubility of the host compound, sensitive to pH changes, long response time, etc., to achieve no toxic side effects, response time Short, easy-to-synthesize effects

Inactive Publication Date: 2009-02-18
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Most of the chemical sensors currently used to measure mercury ions have some problems in practical applications, such as the interference of various competing metal ions on the determination, the poor solubility of the main compound in water, and the long response time, etc. , especially for the detection of biological systems, the autofluorescence interference of the biological body is serious, and it is sensitive to pH changes, which makes it subject to certain restrictions

Method used

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  • Fluorescent probe for detecting mercury ion in cell, and synthesizing method and usage
  • Fluorescent probe for detecting mercury ion in cell, and synthesizing method and usage
  • Fluorescent probe for detecting mercury ion in cell, and synthesizing method and usage

Examples

Experimental program
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Effect test

Embodiment 1

[0034] (1) Synthesis of rhodamine B acid chloride

[0035] Dissolve 1 g of rhodamine B in 15 mL of dry 1,2-dichloroethane, slowly add 0.5 g of POCl dropwise under stirring 3 , heated to reflux for 4 hours, cooled to room temperature, and removed the solvent under reduced pressure, and the obtained rhodamine B acid chloride crude product was directly used for the next reaction;

[0036] (2) Synthesis of compound (I)-1

[0037] Dissolve 0.5g of 2-mercaptoethylamine hydrochloride in 15mL of dry acetonitrile, add 1.2g of triethylamine, and slowly add 30mL of rhodamine B acid chloride acetonitrile solution dropwise under ice-bath conditions, slowly rise to room temperature and react for 12 hours , the solvent was removed under reduced pressure, and the precipitate was precipitated by adding water. After filtration, the product was vacuum-dried to obtain 0.58 g of the product, with a yield of 50.4%.

[0038] 1 HNMR (CDCl 3 , 400MHz) δ (ppm): 1.12 (12H, t, J = 7.0Hz), 1.59 (1H, s...

Embodiment 2

[0042] (1) Synthesis of rhodamine B acid chloride

[0043] Dissolve 1 g of Rhodamine B in 15 mL of dry 1,2-dichloroethane, slowly add 0.5 mL of POCl dropwise under stirring 3 , heated to reflux for 4 hours, cooled to room temperature, and removed the solvent under reduced pressure, and the obtained rhodamine B acid chloride crude product was directly used for the next reaction;

[0044] (2) Synthesis of compound (II)-1

[0045] Dissolve 0.5g of cystamine dihydrochloride in 15mL of dry acetonitrile, add 1.2mL of triethylamine, and slowly add 30mL of rhodamine B acid chloride in acetonitrile solution dropwise under ice-bath conditions, slowly rise to room temperature and react for 12 hours, The solvent was removed under reduced pressure, and the precipitate was precipitated by adding water. After filtration, the product was vacuum-dried to obtain 0.64 g of the product, with a yield of 55.6%.

[0046] 1 HNMR (CDCl 3 , 400Hz) δ (ppm): 1.17 (24H, t, J = 7.0Hz), 2.27 (4H, q), 3....

Embodiment 3

[0050] (1) Synthesis of rhodamine B acid chloride

[0051] Dissolve 1 g of Rhodamine B in 15 mL of dry 1,2-dichloroethane, slowly add 0.5 mL of POCl dropwise under stirring 3 , heated to reflux for 4 hours, cooled to room temperature, and removed the solvent under reduced pressure, and the obtained rhodamine B acid chloride crude product was directly used for the next reaction;

[0052] (2) Synthesis of compound (II)-1

[0053] Dissolve 0.5g of cystamine dihydrochloride in 15mL of dry acetonitrile, add 1.2mL of triethylamine, and slowly add 30mL of rhodamine B acid chloride in acetonitrile solution dropwise under ice-bath conditions, slowly rise to room temperature and react for 12 hours, The solvent was removed under reduced pressure, and the precipitate was precipitated by adding water. After filtration, the product was vacuum-dried to obtain 0.64 g of the product, with a yield of 55.6%;

[0054] (3) Synthesis of compound (II)-2

[0055] 1.3g of compound (II)-1 and 0.52g ...

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Abstract

The invention relates to a fluorescent probe for detecting the intracellular mercury ions, a synthesizing method thereof and the purposes. The fluorescent probe has a good selectivity on the mercury ions and also has good cell permeability; and the probe has no toxic side effects and is applied to the intracellular mercury ion detection. The method comprises the following steps: dissolving 1 mol of 3-carboxyl rhodamine into a dry organic solvent, slowly dripping 1-2 mol of POCl3 under stirring, heating, refluxing, removing the organic solvent and obtaining the crude rhodamine chloride; dissolving 1 mol of 2-aminoethanethiol hydrochloride or cystamine dihydrochloride in a dry organic solvent, adding 4-8 mol of acid binding agent, slowing dripping the obtained rhodamine chloride in ice bath, removing the organic solvent and obtaining the target product of the formula (I) or the formula (II), wherein, X is O; and dissolving the equivalent mol of the target product and the Lawson reagent in a dry organic solvent, heating and refluxing under the protection of inert gas, and finally obtaining the target product of the formula (I) or the formula (II) through column chromatography separation , wherein, X is S.

Description

technical field [0001] The invention relates to highly selective detection of mercury ions, in particular to a fluorescent probe for detecting intracellular mercury ions, a synthesis method and application thereof. Background technique [0002] As we all know, mercury is a heavy metal that is harmful to human health. Due to its persistence, easy migration and high bioaccumulation, it has become one of the most concerned environmental pollutants in the world. Mercury pollution can be produced through many natural ways and human social activities, thus causing many human health and environmental problems. Mercury ions will be deposited in the brain, liver and other organs, resulting in chronic poisoning, damage to the kidneys, brain, stomach and intestinal tract, and even death. In addition, mercury and its compounds can be absorbed through the skin, causing diseases such as stomatitis, gingivitis and nervous disorders. Mercury ions show a strong affinity for ligands contain...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): G01N33/52G01N33/84C09K11/06
Inventor 汪鹏飞刘卫敏张小玲徐丽卫
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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