Dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer and preparation method thereof

A technology of resonance energy transfer and dual fluorophores, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of low selectivity and sensitivity of metal ions, weak probe fluorescence, etc.

Inactive Publication Date: 2013-10-09
QIQIHAR UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The present invention is to solve the problem that the existing dual fluorophore ratio fluorescent molecular probes cause energy loss due to energy transfer between the dual fluorophores during excitation, resulting in weak fluorescence of such probes and low selectivity and sensitivity to metal ions To provide a non-fluorescence resonance energy transfer dual-fluorophore ratio fluorescent molecular probe and its preparation method

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  • Dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer and preparation method thereof
  • Dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer and preparation method thereof
  • Dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer and preparation method thereof

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specific Embodiment approach 1

[0038] Embodiment 1: In this embodiment, a non-fluorescence resonance energy transfer dual-fluorophore ratio fluorescent molecular probe has the following structural formula:

[0039]

[0040] The FL 1 for or where the R 1 Is -H, methyl, 2'-pyridyl or -X, wherein X is a halogen element; said FL 2 for or where the R 2 for C 1 ~C 4 Straight-chain alkyl, 2-hydroxyethyl or 2-(2-hydroxyethoxy)ethyl.

[0041] A non-fluorescence resonance energy transfer dual-fluorophore ratio fluorescent molecular probe of this embodiment has the following advantages:

[0042] (1) The fluorescent molecular probe of the present invention 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;

[0043] (2) The fluorescent molecular probe of the present invention is easy to synthesize, the raw materials are easy to obtain, and it has high derivatization, and various ...

specific Embodiment approach 2

[0045] Specific embodiment 2: The preparation method of a non-fluorescence resonance energy transfer dual-fluorophore ratio fluorescent molecular probe described in specific embodiment 1 is carried out according to the following steps:

[0046] 1. Add organic compound A, anhydrous piperazine, potassium iodide and N,N-diisopropylethylamine in sequence to acetonitrile and mix evenly, reflux for 5h~7h under the protection of nitrogen, spin the reaction solution dry, and pass through Column chromatographic separation to obtain the intermediate; the molar ratio of the organic compound A described in step one to anhydrous piperazine is 1:2; the anhydrous piperazine described in step one and N,N-diisopropyl ethyl The molar ratio of base amine is 1:2; the mass ratio of the molar amount of anhydrous piperazine described in step one to potassium iodide is 1mol: (7g~13g); the molar amount of anhydrous piperazine described in step one The volume ratio of the amount to acetonitrile is 1mol...

specific Embodiment approach 3

[0049] Specific embodiment three: The preparation method of a non-fluorescence resonance energy transfer dual-fluorophore ratio fluorescent molecular probe described in specific embodiment one is carried out according to the following steps:

[0050] 1. Add organic compound A and anhydrous piperazine to dichloromethane in sequence and mix evenly, stir at room temperature and under the protection of nitrogen for 3h to 5h, spin the reaction solution to dryness, and then obtain the intermediate through column chromatography; step 1 The molar ratio of organic compound A to anhydrous piperazine is 1:2; the molar ratio of organic compound A to dichloromethane in step 1 is 1mol:(15L-25L);

[0051] 2. Add the organic compound B, the intermediate obtained in step 1, potassium iodide and N,N-diisopropylethylamine to acetonitrile and mix them uniformly, reflux for 5h-7h under the protection of nitrogen, and spin the reaction solution to dryness. Then through column chromatographic separa...

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Abstract

The invention discloses application of dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer, and relates to application of the dual-fluorophore ratio fluorescence molecular probe. The dual-fluorophore ratio fluorescence molecular probe disclosed by the invention is designed for solving the technical problems that due to energy loss caused by energy transfer between double fluorophores when the existing dual-fluorophore ratio fluorescence molecular probes are excited, the probes are poor in fluorescence, and not high in metal ion selectivity and sensitivity. The dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer is used for identifying fluorescence peak quenching of Cu2+, Cu2+ to the dual-fluorophore ratio fluorescence molecular probe for non-fluorescence resonance energy transfer at the position of 474nm, while the fluorescence peak strength at the wavelength of 351nm basically remains unchanged. The dual-fluorophore ratio fluorescence molecular probe disclosed by the invention can be applied to the fluorescence imaging detection of metal ions in biological tissue and cell microenvironments.

Description

technical field [0001] The invention relates to a dual fluorophore ratio fluorescent molecular probe and a preparation method thereof. Background technique [0002] In recent years, the design and synthesis of ratiometric fluorescent molecular probes have aroused widespread interest. Compared with traditional probe molecules that detect changes in fluorescence intensity, ratiometric fluorescent molecular probes can detect target molecules by measuring the ratio of fluorescence peak intensities at two different wavelengths emitted by themselves when bound to target molecules. Since the self-reference function of the relative change of the double fluorescence peak intensity can avoid the influence of many non-target factors such as probe concentration, excitation light intensity, detection environment, etc. in the change of single fluorescence peak intensity, this kind of probe molecule can realize quantitative detection. [0003] Many probe molecules have been reported for r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/14C07D413/14C07D401/12C09K11/06G01N21/64
Inventor 张宇郭祥峰郑丽波贾丽华马翔宇杨瑞
Owner QIQIHAR UNIVERSITY
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