Rhodamine-sialic acid conjugate and synthesizing method and application thereof to lysosome imaging

A synthetic method and technology of sialic acid, applied in chemical instruments and methods, sugar derivatives, sugar derivatives, etc., can solve the problems of short cell residence time, loss, poor photostability, etc.

Inactive Publication Date: 2019-07-16
XIAMEN UNIV
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Problems solved by technology

[0009] The purpose of the present invention is to provide rhodamine-sialic acid conjugates and their synthesis methods and lysosome imaging applications in order to solve the shortcomings of traditional lysosomal dyes such as poor photostability, short cell residence time, and loss of acidity.

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  • Rhodamine-sialic acid conjugate and synthesizing method and application thereof to lysosome imaging
  • Rhodamine-sialic acid conjugate and synthesizing method and application thereof to lysosome imaging
  • Rhodamine-sialic acid conjugate and synthesizing method and application thereof to lysosome imaging

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[0042] 1) Synthesis of rhodamine-sialic acid conjugates:

[0043] Take 300mg of 9-aminosialic acid and 400mg of N-hydroxysuccinimide rhodamine X-5 carboxylate, add dioxane (3mL) and water (3mL) to the mixed solution, use saturated sodium carbonate solution to adjust the pH to 9, and react overnight . The solvent in the reaction system was removed, and 289 mg of rhodamine-sialic acid conjugate was obtained by HPLC separation.

[0044] 2) Prepare a standard solution with a concentration of 20mM rhodamine-sialic acid conjugate:

[0045] Weigh 8 mg of rhodamine-sialic acid conjugate and dissolve in 0.5 mL of ultrapure water. That is, a standard solution of 20 mmol / L (20 mM) rhodamine-sialic acid conjugate was obtained.

[0046] 3) Collect the absorption spectrum, fluorescence excitation spectrum and fluorescence emission spectrum of the rhodamine-sialic acid conjugate:

[0047] Take 1 μL rhodamine-sialic acid conjugate standard solution and mix it with 2mL ultrapure water to o...

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Abstract

The invention provides a rhodamine-sialic acid conjugate and a synthesizing method and application thereof to lysosome imaging, and relates to the rhodamine-sialic acid conjugate. In the rhodamine-sialic acid conjugate, a connecting arm connected between rhodamine and sialic acid adopts an amido bond or other structures. The rhodamine-sialic acid conjugate is prepared through the steps of adding 9-amino sialic acid and N-hydroxysuccinimide rhodamine X-5 carboxylic acid ester to a mixed solution of dioxane and water, adjusting pH to 9 through a saturated sodium carbonate solution, performing areaction for a night, removing a solvent of a reaction system, and performing HPLC separation to obtain the rhodamine-sialic acid conjugate. Living cell lysosomes are accurately positioned, and the signal-noise ratio is high; red fluorescence is launched in the lysosomes, the acidity of the lysosomes is changed, and a probe maintains hyperfluorescence; retention in the lysosomes is independent ofthe acidity of the lysosomes; real-time fluorescence imaging is performed on the lysosomes; and the rhodamine-sialic acid conjugate disclosed by the invention is used for the lysosomes to perform random restructured fluorescence microscopic imaging of ultrahigh resolution.

Description

technical field [0001] The present invention relates to a rhodamine-sialic acid conjugate, in particular to a rhodamine-sialic acid conjugate, a synthesis method thereof and applications in fluorescence imaging, long-time and real-time fluorescence tracking of lysosomes in cells. Background technique [0002] Lysosomes (lysosomes) are organelles in eukaryotic cells, which play an important role in many biological processes of cells, mainly involved in processes such as cell autophagy, apoptosis, and cancer development. During the above process, lysosomal parameters such as volume, shape, position, etc. will change significantly [1-2] . Commercial lysosomal probes stay in lysosomes through acidification, and when the pH of lysosomes rises, these probes leave lysosomes (such as Lysotracker Green DND26), losing their ability to localize and image in lysosomes [3] . Fluorescent probes with low background, long-term real-time tracking, and the ability to label the shape and lo...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/04C07H1/00C09K11/06G01N21/64
CPCC07H1/00C07H13/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1088G01N21/6486
Inventor 韩守法薛钟慰李剑
Owner XIAMEN UNIV
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