Near infrared fluorescence probe for monitoring lysosomal pH as well as preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of analytical chemistry, can solve problems such as poor photostability and difficult fluorescent signals, and achieve the effects of easy synthesis, reduced background interference, and excellent photostability

Active Publication Date: 2019-08-30
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the pH near-infrared probes designed based on near-infrared cyanine dyes have poor photostability, and it is difficult to obtain accurate and stable fluorescent signals in long-term and multiple imaging.

Method used

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  • Near infrared fluorescence probe for monitoring lysosomal pH as well as preparation method and application thereof
  • Near infrared fluorescence probe for monitoring lysosomal pH as well as preparation method and application thereof
  • Near infrared fluorescence probe for monitoring lysosomal pH as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Synthesis of Fluorescent Probe Compound Lyso-NIR-pH

[0031] (1) Synthesis of Compound 1

[0032]At -78°C, under the protection of argon, 6g of 3-bromo-N,N-dimethylaniline and 60ml of anhydrous tetrahydrofuran were added to a dry 250ml round-bottomed flask, stirred magnetically for 5 minutes to dissolve, Subsequently, 13 milliliters of n-butyllithium n-hexane solution with a molar concentration of 2.4mol / L was added dropwise to the reaction solution, and after the dropwise addition was completed, it was reacted at 0°C for 2 hours, and then 2.2 milliliters of dichlorodimethylsilane was dissolved in 10 ml of anhydrous tetrahydrofuran, then added dropwise to the above reaction solution, after the dropwise addition, reacted to room temperature and stirred overnight, added 50 ml of water to quench the reaction, and extracted the reaction solution with ether (50 ml × 2). The extracted ether solution was washed with saturated NaCl aqueous solution (50 mL×3), anhydrous NaCl 2...

Embodiment 2

[0044] Determination of Fluorescent Spectrum of Fluorescent Probe Compound Lyso-NIR-pH under Different pH Conditions

[0045] Fluorescence spectra were measured in 40 mM Britton-Robinson buffer solution (containing 1% DMSO). The Lyso-NIR-pH fluorescent probe was dissolved in dimethyl sulfoxide (DMSO) to make a 500 μM stock solution. The test solution Lyso-NIR-pH (5.0 μM) was prepared by diluting the above 500 μM stock solution. The different pHs are obtained by adding small amounts of equal concentrations of HCl or NaOH. The test solution was stored at room temperature for 30 min, and the fluorescence spectrum was measured at an excitation wavelength of 620 nm. The fluorescence emission spectrum ranges from 640 to 800nm, the excitation slit is 3nm, and the emission slit is 3nm. Fluorescence spectra such as figure 1 As shown, when the pH value of the BR buffer is greater than 7.4, the probe Lyso-NIR-pH is almost non-fluorescent because it is a stable non-fluorescent helical...

Embodiment 3

[0047] Determination of UV-Vis Absorption Spectra of Fluorescent Probe Compound Lyso-NIR-pH at Different pH Conditions

[0048] figure 2 It is the ultraviolet-visible absorption spectrum of the probe Lyso-NIR-pH (5 μM) under the condition of pH 7.4-pH 3. from figure 2 It can be seen that as the pH decreases, a gradually increasing absorption peak can be observed at 655 nm. This indicates that the probe Lyso-NIR-pH responds to pH, and its helical ring structure is located at the proton H + The action is opened and the absorption increases. The instrument used for the determination of the UV-Vis absorption spectrum is a TU-1900 UV-Vis spectrophotometer (Beijing Purkinje General Instrument Co., Ltd.).

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Abstract

The invention discloses a near infrared fluorescence probe for monitoring lysosomal pH as well as preparation method and application thereof, belonging to the technical field of analytical chemistry.The near infrared fluorescence probe is characterized by having the following structural formula: (shown in the specification). The invention further discloses the preparation method of the near infrared fluorescence probe for monitoring lysosomal pH and the application thereof in selective detection of pH in water environments and biological cell systems. The near infrared fluorescence probe provided by the invention had the advantages of near infrared region emission, good selectivity, good light stability, good reversibility, and excellent lysosome targeting capacity.

Description

technical field [0001] The invention relates to a near-infrared fluorescent probe for monitoring lysosome pH, a preparation method and application thereof, and belongs to the technical field of analytical chemistry. Background technique [0002] As an important acidic (pH about 3.8-5.5) organelle in eukaryotic cells, lysosomes are the decomposition sites of biological macromolecules such as proteins, nucleic acids, and polysaccharides, and are called "digestive organs" in cells. Lysosomes play important roles in many life processes, such as endocytosis, cell growth and apoptosis, autophagy, ion metabolism, oxidative stress, etc. Abnormal fluctuations in lysosomal pH can cause lysosomal dysfunction, which is closely related to lysosomal storage diseases, cancer and other diseases. Therefore, it is of great significance to develop analytical techniques that can monitor lysosomal pH in real time. [0003] Fluorescent molecular probes have become an indispensable tool in the f...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/12C09K11/06G01N21/64
CPCC07F7/122C09K11/06G01N21/64C09K2211/1096C09K2211/1029C09K2211/1033
Inventor 冯素玲王盈盈毛国江高广琦
Owner HENAN NORMAL UNIV
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