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Near-infrared fluorescent molecular probe for detecting gamma-glutamyl transpeptidase and preparation method and application of near-infrared fluorescent molecular probe

A fluorescent molecular probe, glutamyl transpeptidase technology, applied in fluorescence/phosphorescence, chemical instruments and methods, material analysis by optical means, etc., can solve the problems of auto-fluorescence interference, difficult fluorescence, etc. Effects of toxicity, high sensitivity, excellent selectivity

Inactive Publication Date: 2021-01-01
CHINA PHARM UNIV
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  • Abstract
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  • Application Information

AI Technical Summary

Benefits of technology

The present inventors discovered that certain compounds called gamma -Glutaminocyclage (gamma G) peptides were found effective at specifically targeted areas within specific tissues such as brain tumor foci but they could cause harm if taken up by other organs like kidneys. This led them to develop new structures containing these agents. These novel probes had improved properties over existing ones due to their unique chemical composition and physical shape. They showed superior biocompatibility compared to previous methods while still being safe enough to perform intravital measurements on mammals. Overall, this innovative technology allows researchers to study how different types of substances bind together inside nerves without causing damage during surgery procedures.

Problems solved by technology

This patented technical problem addressed in this patents relates to finding better ways to identify certain substances called γ -Glutaminotransferp (gamma-GLUT) or other small molecules involved in cellular regulation processes such as DNA synthesis during embryogenic development and differentiation stages. These compounds play an essential role in maintaining normal functioning of cells throughout their lifetimes. They help control gene expressions within specific parts of genome, making them ideal targets for developing therapies against these types of disease.

Method used

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  • Near-infrared fluorescent molecular probe for detecting gamma-glutamyl transpeptidase and preparation method and application of near-infrared fluorescent molecular probe
  • Near-infrared fluorescent molecular probe for detecting gamma-glutamyl transpeptidase and preparation method and application of near-infrared fluorescent molecular probe
  • Near-infrared fluorescent molecular probe for detecting gamma-glutamyl transpeptidase and preparation method and application of near-infrared fluorescent molecular probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042]Preparation of near-infrared fluorescent molecular probes for detecting γ-glutamyl transpeptidase:

[0043]Add dichloromethane (12mL) into a round bottom flask, slowly add compound 1 (1mmol) under nitrogen protection, start stirring, and slowly add Boc-L-glutamic acid-1 under nitrogen protection under stirring -Tert-butyl ester (8mmol), after stirring for 15 minutes, slowly add N,N-diisopropylethylamine (1.2mmol) under nitrogen protection, stir and react at room temperature for about 30 minutes, and add dropwise to the reaction solution Trifluoroacetic acid (18μL), stir at room temperature for about 24 hours, wait for the solution to turn dark blue, pour the reaction solution in the bottle into a separatory funnel, add distilled water, mix thoroughly, and let stand. After the solution in the separatory funnel separates , Take the upper aqueous phase solution and freeze-dry to obtain a blue solid, which is the target probe.

[0044]The probe mass spectrum and hydrogen nuclear magneti...

Embodiment 2

[0046]The fluorescence emission measurement experiment of the response of near-infrared fluorescent molecular probe and γ-glutamyl transpeptidase in vitro:

[0047]Weigh 5.6 mg of the probe prepared in Example 1 and dissolve it in 1 mL of DMSO to prepare a 10 mM probe stock solution. Take 0.14 mg of γ-glutamyl transpeptidase (30 U / 4.2 mg) and dissolve it in 10 mL of PBS buffer to prepare 100 U / L of γ-glutamyl transpeptidase mother solution. Prepare 6 5mL centrifuge tubes, add 2mL PBS buffer (pH=7.4) to each centrifuge tube in turn, and then add 2μL of the probe mother liquor. At this time, the probe concentration of each centrifuge tube is 10μM. After fully mixing, add 0, 4, 8, 12, 16, 20 μL of γ-glutamyl transpeptidase mother solution into each centrifuge tube, and after 20 minutes of reaction, add them to the cuvette for fluorescence emission. Detection (wavelength of excitation light is 658nm), the data obtained is processed by origin softwarefigure 2 ,Such asfigure 2 As shown, as t...

Embodiment 3

[0050]Selective experiments of near-infrared fluorescent molecular probes:

[0051]Pass and concentration (100μM) of different substrates: GGT (γ-GT), KCl, NaCl, MgCl2, CaCl2, Cysteine, GSH, Glutamate, MnO2, Vc, KMnO4Incubation was performed to test the selectivity of the probe (10 μM) prepared in Example 1 to GGT. Such asimage 3 As shown, only GGT has the ability to induce a significant increase in the fluorescence signal, while other substances cannot induce a significant change in the fluorescence signal. The results clearly show that the probe of the present invention is a highly specific probe, and its response to GGT far exceeds that of other different substances.

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Abstract

The invention discloses a near-infrared fluorescent molecular probe for detecting gamma-glutamyl transpeptidase and a preparation method and application of the near-infrared fluorescent molecular probe. The structural formula of the fluorescent probe is shown in the specification. The near-infrared fluorescent molecular probe for detecting gamma-glutamyl transpeptidase is high in selectivity, highin sensitivity and good in response effect, biological autofluorescence interference can be avoided due to the near-infrared absorption and fluorescence emission characteristics of the near-infraredfluorescent molecular probe, gamma-glutamyl transpeptidase in a solution, a cell or a living body can be detected, and the sensitivity of the near-infrared fluorescent molecular probe is improved. Theinvention can be well applied to cell and living body imaging and the like. In addition, the preparation process is simple, the cost is low, the yield is high, the application prospect is wide, and large-scale production and application can be achieved.

Description

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Claims

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Application Information

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Owner CHINA PHARM UNIV
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