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Fluorescence probe for detecting pH of lysosome in cancer cells

A fluorescent probe and endolysosome technology, applied in the field of analytical chemistry, can solve the problems of lack of lysosome targeting, achieve good fluorescence emission spectrum characteristics, easy promotion, and broad application prospects

Inactive Publication Date: 2016-11-16
UNIV OF JINAN
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of the currently reported and commercialized lysosomal pH fluorescent probes do not have lysosome targeting, and generally have a corresponding response to all cells.

Method used

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  • Fluorescence probe for detecting pH of lysosome in cancer cells
  • Fluorescence probe for detecting pH of lysosome in cancer cells
  • Fluorescence probe for detecting pH of lysosome in cancer cells

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of fluorescent probe for detecting lysosome pH in cancer cells according to the present invention

[0030] Compound a1 (1 mmol), a2 (1 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (2 mmol), 1-hydroxybenzene Add triazole (1.5 mmol), triethylamine (2.2 mmol) and N,N-dimethylformamide (5 mL) into a 50 mL one-necked flask, stir at room temperature for 24 hours, filter, and dry. The obtained solid is purified by column chromatography to obtain a light yellow product, which is the ratiometric fluorescent probe for detecting intracellular lysosome pH according to the present invention. The resulting solid was purified by column chromatography (dichloromethane:methanol=20:1) to obtain a yellow product, which is the fluorescent probe 1a for detecting the pH of lysosomes in cancer cells according to the present invention, with a yield of 56%.

[0031] The above-mentioned fluorescent probes for detecting intracellular lysosome pH 1 H NMR spectrum see figure ...

Embodiment 2

[0033] The fluorescence spectrum of the fluorescent probe for detecting lysosome pH in cancer cells according to the present invention under different pH conditions

[0034] Prepare in advance 10 parts of 5 mL of 5 μM probe B-F buffer solution, containing 5% methanol, pH 3.0, 3.5, 4.0, 4.5, 5.0, 5.5, 6.0, 6.5, 7.0, 7.5, 8.0, 8.5, 9.0. Fluorescence detection is then performed (λ Ex = 445 nm); calculate the fluorescence intensity in each system; evaluate the response performance of the probe to pH (see figure 2 ). When the pH of the analysis solution rises from 3.0 to 9.0, the fluorescence intensity at 531nm is gradually weakened, see image 3 . Among them, when the pH of the analysis solution is in the range of 4.5~6.5, the linear relationship between the fluorescence intensity at 531nm and the pH can be expressed by the formula Y = 12022 - 1723 * X (R = 0.9886), where Y is the fluorescence intensity and X is the pH value.

Embodiment 3

[0036] Fluorescence spectra of fluorescent probes reacted with different substances

[0037] Prepare 10 parts of 5 mL of 5 μM probe B-F buffer solution (containing 5% methanol, pH = 7.4), and then add 50 μL of 10 mM Hcys, Na 2 S, Na 2 SO 3 , NO, H 2 o 2 , HClO 4 , Cys, GSH, NaNO 2 , VC, etc. in PBS solution. Fluorescence detection is then performed (λEx = 445 nm); calculate the fluorescence intensity in each system; evaluate the interference of the different substances on the fluorescent probe solution (see Figure 4 ). pass Figure 4 It can be seen that when the pH of the solution is 4.5 or 7.4, adding Hcys, Na 2 S, Na 2 SO 3 When small molecules are used, the fluorescence intensity of the solution remains basically unchanged, which means that the detection results are basically not affected by other interfering substances.

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Abstract

The invention discloses a fluorescence probe for detecting pH of lysosome in cancer cells. The fluorescence probe is a naphthalimide derivative containing biotin groups. The fluorescence probe is easy to prepare, low in cost and high in specificity, can rapidly detect the pH value of a solution environment, is not disturbed by other ingredients in the corresponding pH detection process, can be used for measuring the pH of the lysosome in the cancer cells, and has wide application prospects.

Description

technical field [0001] The invention relates to a novel ratio fluorescent probe for lysosome pH imaging in cancer cells and its application, belonging to the technical field of analytical chemistry. Background technique [0002] As an important parameter of metabolism, intracellular pH value plays a very important role in cell cycle regulation, cell z proliferation and apoptosis, ion transport, enzyme activity, calcium regulation, muscle contraction and other cell physiological regulation and pathological processes . At the same time, the endocytosis of cells and the internalization of receptor ligands are also affected by intracellular pH. Abnormal intracellular pH will lead to physiological dysfunction of cells and tissues and organs in organisms, inhibition of enzyme and protein activity, decreased immunity of the human body, and eventually lead to diseases such as inflammation, cancer, and Alzheimer's disease. Studies have shown that in the early stage of apoptosis, ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D495/04C09K11/06G01N21/64
CPCC07D495/04C09K11/06C09K2211/1044G01N21/6428G01N2021/6432
Inventor 林伟英董宝利宋学真孔秀琪王超
Owner UNIV OF JINAN
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