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Application of rhodamine B derivatives

A derivative and compound technology, applied in the field of rhodamine B derivatives and cell lysosomal fluorescent dyes, can solve the problems of short retention period, loss of probes, low stability, etc., and achieve high photostability and retention time. Long, stable effect

Inactive Publication Date: 2011-10-12
XIAMEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Common disadvantages of this type of probe include (1) relatively high background signal, resulting in non-specific labeling; (2) low stability, easy to be quenched by light, and loss of fluorescence properties; (3) short retention period in cells, Prolonged time, intracellular probes are easy to lose

Method used

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  • Application of rhodamine B derivatives
  • Application of rhodamine B derivatives
  • Application of rhodamine B derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] 1) Add rhodamine B (2g) into a flask containing 20mL of ethylenediamine, stir the system electromagnetically, react at 80°C for 12 hours, remove unreacted solvent, separate and purify through a silica gel column to obtain rhodamine B-ethylenediamine Amine, its chemical structure formula is as follows:

[0025]

[0026] R=-NH 2 ,-N(CH 3 ) 2 ,-CH 2 -N(CH 3 ) 2

[0027] 2) Detection of the fluorescence emission intensity of rhodamine B-ethylenediamine (1 μg / mL) containing a 5-membered ring in the molecule in buffer solutions of different pH values ​​(7.0, 6.5, 6.0, 5.5, 5.0, 4.5, 4.0) . It was found that the fluorescence intensity of rhodamine B-ethylenediamine at pH4.0 was 800 times higher than that at pH7.0 (Ex: 530 / Em 560nm) (see figure 1 ), the acid of rhodamine B-ethylenediamine derivatives in embodiment 1 initiates and produces fluorescent chemical reaction scheme as follows:

[0028]

[0029]3) Rhodamine B-ethylenediamine (10 μg / mL) and lysosome probe...

Embodiment 2

[0034] Embodiment 2: Rhodamine B-N, the application of N-dimethylethylenediamine as cell lysosome fluorescent dye

[0035] 1) Add rhodamine B (2g) into a flask containing 20mL N,N-dimethylethylenediamine, stir the system electromagnetically, react at 80°C for 12h, remove unreacted solvent, separate and purify it through a silica gel column Rhodamine B-N,N-dimethylethylenediamine was obtained.

[0036] 2) Utilize rhodamine B-N, the step 2) of N-dimethylethylenediamine repeats embodiment 1), 3), 4), 5), 6), 7) the result obtained and rhodamine B-ethylenediamine derivative The experimental results of the two substances are similar, indicating that the performance of the two as specific probes for lysosomes in cells is basically the same.

Embodiment 3

[0037] Embodiment 3: the application of Rhodamine B-propylenediamine as the fluorescent dye of cell lysosome

[0038] 1) Add rhodamine B (2g) into a flask containing 20mL propylenediamine, stir the system electromagnetically, react at 80°C for 12h, remove unreacted solvent, separate and purify through a silica gel column to obtain rhodamine B-propanediamine diamine.

[0039] 2) utilize rhodamine B-propylenediamine to repeat the step 2) of embodiment 1), 3), 4), 5), 6), 7) the result obtained is similar to the experimental result of rhodamine B-ethylenediamine, illustrates The performances of the two as specific probes for lysosomes of cells are basically the same.

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Abstract

The invention discloses application of rhodamine B derivatives, and relates to application of rhodamine B derivatives provided with intra-molecular spiral rings and used as cell lysosome fluorescent colorants. The rhodamine B derivatives are rhodamine B derivatives with intra-molecular five-member rings; and the rhodamine B derivatives can be used as the cell lysosome fluorescent colorants and used for high-selectivity and long-term stably labeled cell lysosome. The application has the advantages that: (1) the amino-containing rhodamine B derivatives with intra-molecular five-member rings can be used as lysosome fluorescent labeling substances of cells of different types; (2) the rhodamine B derivatives have long retention time in cells and high light stability; and (3) the rhodamine B derivatives can be used for labeling and tracking intra-molecular lysosome for long time.

Description

technical field [0001] The invention relates to the use of a class of rhodamine B derivatives with intramolecular spiral rings as cell lysosome fluorescent staining agents. Background technique [0002] Lysosome (lysosome) is a kind of organelle in eukaryotic cells, its internal environment is slightly acidic (pH 4-6), and contains a variety of hydrolytic enzymes. Lysosomes not only have intracellular digestion function, but also are directly related to the development of cell autophagy, apoptosis, immune defense and cancer (1, Luis Avila J. [Structure and function of lysosomes]. Acta Cient Venez.1974 25: 130-131; 2. Luzio JP, Pryor PR, Bright NA. Lysosomes: fusion and function. Nat Rev Mol Cell Biol. 2007; 8: 622-632; 3. Kroemer G, Jaatela M. Lysosomes and autophagy in cell death control.Nat Rev Cancer.2005; 5:886-897), so the development and application of molecular probes that can label and track lysosomes in living cells are important for the study of biological functio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12Q1/04G01N21/64
Inventor 韩守法韩家淮李柱孟宪军
Owner XIAMEN UNIV
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