Rhodamine fluorescent molecular probe using quinoline derivative as identification group and synthesis method thereof

A technology of fluorescent molecular probe and synthesis method, which is applied in the field of rhodamine-based fluorescent molecular probe and its synthesis, can solve the problem of few probe molecules, and achieve the effects of high selectivity and sensitivity, easy availability of raw materials and simple synthesis

Inactive Publication Date: 2013-11-27
QIQIHAR UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The present invention aims to solve the problem that there are fewer probe molecules using quinoline derivatives as recognition groups and rhodamine as fluorophores, thereby providing a rhodamine-like fluorescent molecule with quinoline derivatives as recognition groups Probes and their synthesis methods

Method used

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  • Rhodamine fluorescent molecular probe using quinoline derivative as identification group and synthesis method thereof
  • Rhodamine fluorescent molecular probe using quinoline derivative as identification group and synthesis method thereof
  • Rhodamine fluorescent molecular probe using quinoline derivative as identification group and synthesis method thereof

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specific Embodiment approach 1

[0026] Specific embodiment 1: In this embodiment, a rhodamine-based fluorescent molecular probe using quinoline derivatives as recognition groups has a structural formula:

[0027]

[0028] where the R 1 Is hydrogen, methyl, halogen or 2'-pyridyl; R 2 is hydrogen or halogen.

[0029] This embodiment includes the following beneficial effects:

[0030] 1. The fluorescent molecular probe of this embodiment can be directly used for the fluorescence ratio detection of metal ions in water, methanol, DMSO, DMF solvent or their mixed solvents, and has high selectivity and sensitivity;

[0031] 2. The fluorescent molecular probe of this embodiment is easy to synthesize, and the raw materials are easy to get. Among various common metal ions, Cu 2+ Exhibits good selective fluorescence recognition performance;

[0032] 3. The fluorescent molecular probe synthesized in this embodiment can also be used for fluorescence imaging detection of metal ions in biological tissues and cell mi...

specific Embodiment approach 2

[0033] Specific embodiment two: a kind of synthetic method of the rhodamine class fluorescent molecular probe with quinoline derivative as recognition base described in specific embodiment one is to carry out according to the following steps:

[0034] 1. Dissolve 1-5mmol of rhodamine B and 1-5mmol of 8-aminoquinoline derivatives in 10-30mL of chloroform, then add 2-5mL of phosphorus oxychloride, and reflux for 2 ~4h, the reaction solution was obtained;

[0035] 2. Use ammonia water to adjust the pH of the reaction solution obtained in step 1 to 8-10, then spin dry, and then separate through silica gel column chromatography to obtain a rhodamine-based fluorescent molecular probe with quinoline derivatives as recognition groups.

specific Embodiment approach 3

[0036] Specific embodiment three: In this embodiment, a rhodamine-based fluorescent molecular probe with a quinoline derivative as a recognition base has a structural formula:

[0037]

[0038] where the R 3 is hydrogen, acetylamino, α-C 1 ~C 4 Linear alkylaminoacetamido or C 1 ~C 4 Straight-chain alkylsulfonylamino.

[0039] Specific embodiment four: a kind of synthetic method of the rhodamine class fluorescent molecular probe with quinoline derivative as recognition base described in specific embodiment three is to carry out according to the following steps:

[0040] 1. Dissolve 0.2-0.5 mmol of rhodamine B in 2-8 mL of hydrazine hydrate, reflux for 20-40 minutes under the protection of nitrogen, spin the reaction solution to dryness, and then separate through silica gel column chromatography to obtain the intermediate rhodamine B acyl Hydrazine;

[0041] 2. Dissolve 0.1 to 0.8 mmol of the intermediate rhodamine B hydrazide obtained in step 1, and 0.2 to 1.0 mmol of ...

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Abstract

The invention provides a rhodamine fluorescent molecular probe using a quinoline derivative as an identification group and a synthesis method thereof, and relates to a rhodamine fluorescent molecular probe and a synthesis method thereof, solving the problem that the existing rhodamine fluorescent probe molecules based on the quinoline derivative identification group are few. A structural formula of a fluorescent molecular probe is as shown in specifications. A preparation method comprises the following steps: 1, preparing reaction liquid; and 2, adjusting the pH value of the reaction liquid, carrying out spin-drying and performing silica gel column chromatographic separation to obtain the rhodamine fluorescent molecular probe using the quinoline derivative as the identification group. A structural formula of another fluorescent molecular probe is as shown in specifications. A preparation method comprises the following steps: 1, preparing an intermediate rhodamine B hydrazide; and 2, dissolving the intermediate rhodamine B hydrazide and a quinoline-2-aldehyde derivative into absolute ethanol, refluxing under the protection of nitrogen, carrying out spin-drying and performing silica gel column chromatographic separation to obtain the rhodamine fluorescent molecular probe using the quinoline derivative as the identification group. The rhodamine fluorescent molecular probe disclosed by the invention is applied to the field of fluorescent imaging detection of metal ions in biological tissues and cell microenvironments.

Description

technical field [0001] The invention relates to a rhodamine-based fluorescent molecular probe and a synthesis method thereof. Background technique [0002] Fluorescence detection has been widely used in the detection of metal ions in the fields of life, environment, and medicine because of its simplicity and outstanding advantages in sensitivity, selectivity, response time, and in-situ measurement. People have been working hard to construct probe molecules with new structures and improve their selectivity, sensitivity, water solubility, and biocompatibility to meet various research needs. [0003] In order to ensure that the probe molecules have high selectivity for specific metal ions, a lot of research has been done on their recognition groups. At present, the research on metal ion fluorescent molecular probes using pyridine derivatives as recognition bases has made great progress. For example, 2,6-diaminomethylpyridine (Anal.Chem.2009,81,9993-10001; Dalton Trans.2012,41...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06C07D491/107G01N21/64
Inventor 张宇郭祥峰郑丽波贾丽华杨瑞
Owner QIQIHAR UNIVERSITY
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