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Specific double-photon imaging fluorescent probe as well as preparation method and application

A fluorescent probe and detection method technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of inability to real-time, in situ imaging detection, poor selectivity, etc., and achieve good two-photon properties, cell damage, etc. Small, deep penetration effect

Active Publication Date: 2019-07-23
SHANDONG NORMAL UNIV
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Problems solved by technology

However, after research by the inventors, it was found that these probes can also react with Hcy and GSH, resulting in poor selectivity of existing methods, and cannot accurately perform real-time and in situ imaging detection of changes in the concentration of Cys in the living brain

Method used

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  • Specific double-photon imaging fluorescent probe as well as preparation method and application
  • Specific double-photon imaging fluorescent probe as well as preparation method and application
  • Specific double-photon imaging fluorescent probe as well as preparation method and application

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Experimental program
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Effect test

Embodiment

[0052] Synthesis of Fluorescent Probes (TCS)

[0053] Coumarin 120 (0.176 g, 1.0 mmol) was first dissolved in THF (10 mL) under nitrogen protection, and then phenylthiochloroformate (135 μL, 1.0 mmol) was added. Next the mixture was stirred at 28°C under nitrogen for 12 hours. After the reaction was complete, the mixture was concentrated in vacuo. Purify by thin-plate chromatography, the eluent is ethyl acetate:cyclohexane=2:1, to obtain a light yellow solid, namely the fluorescent probe, which is denoted as TCS. Finally, TCS was dissolved in Tris buffer (1% DMSO, pH=7.4) for further characterization and performance evaluation.

[0054] Mass Spectrometry and NMR Characterization of TCS

[0055] HRMS(ESI)m / z calcd.for C 17 h 13 NO 3 S[M+H] + calculated 312.0688, found 312.0670.NMRdata: 1 HNMR (400MHz, d 6 -DMSO), figure 1 Shown: δ8.12(s,1H),7.79(d,2H),7.49(t,2H),7.31(t,1H),7.23(d,2H),6.35(s,1H),5.77(s ,1H),2.42(s,3H). 13 C NMR (101MHz, d 6 -DMSO), figure 2 Shown:...

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Abstract

The invention provides a specific double-photon imaging fluorescent probe as well as a preparation method and application. A compound structure adopted by the fluorescent probe is that the fluorescentprobe provided by the invention not only can be used for carrying out high-specificity and high-sensitivity detection on Cys, but also has the advantages of stable performance, low cytotoxicity, easiness of passing through a blood brain barrier and the like.

Description

technical field [0001] The disclosure belongs to the technical field of biological analysis and detection, and relates to the detection of cysteine, in particular to a specific two-photon imaging fluorescent probe and its preparation method and application. Background technique [0002] The statements herein merely provide background information related to the present disclosure and may not necessarily constitute prior art. [0003] Depression is a global mental disease with high prevalence, relapse rate, mortality rate and disability rate, which seriously endangers human health. Unfortunately, the current understanding of the pathophysiology of depression is still very imperfect. Existing studies have found that depression is closely related to oxidative stress-redox imbalance in the brain. Cysteine ​​(Cys) is an amino acid produced by demethylation of methionine and reduction of cystine. Normal levels of Cys (30-200μM) can maintain various protein conformations and part...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64A61K49/00
CPCA61K49/0039C07D311/16C09K11/06C09K2211/1007C09K2211/1088G01N21/6428
Inventor 唐波李平张彦笛王昕张雯
Owner SHANDONG NORMAL UNIV
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