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A kind of 1,8-naphthalimide derivative and its application

A technology of naphthalimide and derivatives, which is applied in the field of fluorescent probes, can solve problems affecting sensitivity, etc., and achieve high sensitivity and selectivity, good water solubility, and reduced interference

Active Publication Date: 2020-11-10
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For the near-neutral range, for example, there are not many probes for the pH change of the cytoplasmic matrix, and the reported related probes usually need to be co-dissolved with a certain volume of organic solvent for detection, which affects the sensitivity of the detection to a certain extent

Method used

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  • A kind of 1,8-naphthalimide derivative and its application
  • A kind of 1,8-naphthalimide derivative and its application
  • A kind of 1,8-naphthalimide derivative and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Probe 3-[6-(4-benzylpiperazin-1-yl)-1,3-dioxo-1H-benzo[iso]quinolin-2(3H)-yl] in Example 1 Propionic acid was stored in a stock solution prepared with a concentration of 1 mM in dimethyl sulfoxide. In the experiment, the probe was diluted to a final concentration of 10 μM with phosphate buffer with different pH values, and the UV absorption spectrum of the probe was recorded as the pH changed ( figure 2 ). As the pH value decreased from 11.00 to 3.00, the absorption peak at 402nm gradually increased and blue-shifted to 383nm. At the same time, the color of the solution changed from colorless to yellow ( image 3 ).

Embodiment 2

[0030] Similarly, the probe 3-[6-(4-benzylpiperazin-1-yl)-1,3-dioxo-1H-benzo[iso] in Example 1 was used in phosphate buffer with different pH values Quinoline-2(3H)-yl]propionic acid was diluted to a final concentration of 10 μM, the excitation wavelength was fixed at 402 nm, and the fluorescence emission spectrum changes of the probe with pH changes ( Figure 4 ). As the pH value decreased from 11.00 to 3.00, the fluorescence intensity at 526nm gradually increased. The Stokes shift is as high as 124nm, which is beneficial to reduce the interference of excitation light during imaging. Under the irradiation of ultraviolet light, the color of the solution changed from colorless to bright green ( Figure 5 ). pK was calculated from the Singmoidal fitting curve of the fluorescence intensity value at 526 nm as a function of pH a The value is 6.69 ( Image 6 ), the pH response linear range is 6.40-8.00 (the linear regression equation is I=-229144.02×pH+1.87×10 6 , the linear c...

Embodiment 3

[0032] Keep the probe 3-[6-(4-benzylpiperazin-1-yl)-1,3-dioxo-1H-benzo[iso]quinolin-2(3H)-yl]propanoic acid concentration at At 10 μM, respectively examine the probe in the presence of common metal ions, the H + selectivity. like Figure 8 As shown, when the pH is 4.0, 6.8, 7.4, the probe has almost no response to the above substances, which proves that the probe is sensitive to H + Has high selectivity. Figure 8 The sequence and concentration of the substances in it are: 1, Blank; 2, Mg 2+ (1mM); 3, Pd 2+ (1mM); 4, Ca 2+ (1mM); 5, K +(1mM); 6, Zn 2+ (1mM); 7, Fe 3+ (1mM); 8, Sr 2+ (1mM); 9, Ni 2+ (1mM); 10, Al 3+ (1mM); 11, Ba 2+ (1mM); 12, Mn 2+ (1mM); 13, Na + (1mM); 14. Histidine(1mM); 15. Glutamate(1mM); 16. Aspartic acid(1mM); 17. Leucine(1mM); 18. Phenylalanine(1mM); 19. Lysine(1mM); 20. Alanine 21, Serine (1mM); 22, Leucine (1mM); 23, Arginine (1mM); 24, Proline (1mM); 25, Threonine (1mM); 26, Tryptophan (1mM); 27, Isoleucine ( 1 mM); 28. Cysteine ​​(1...

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Abstract

The invention belongs to the technical field of fluorescent probes, and particularly relates to a 1, 8-naphthalimide derivative and application. The invention discloses application of 3-[6-(4-benzyl piperazine-1-yl)-1, 3-dioxo-1H-benzo [iso] quinoline-2 (3H)-yl] propionic acid in preparation of a fluorescent probe for detecting intracellular pH, and application in cell imaging. The derivative is excited at 402nm in an aqueous solution, and has maximum emission at 526nm. In a phosphate buffer system, the fluorescence intensity at 526nm is gradually enhanced along with the reduction of the pH value from 9.00 to 4.00. The pKa value is 6.69, and the pH linear range is 6.40 to 8.00. Besides, the probe has good selectivity, water solubility and low toxicity, is suitable for detecting the pH change of a water environment, and can be used for detecting the pH change in cells by utilizing a laser confocal microscopy imaging technology.

Description

technical field [0001] The invention belongs to the technical field of fluorescent probes, and specifically relates to a 1,8-naphthalimide derivative and its application. Background technique [0002] Intracellular pH, as an important metabolic and intracellular parameter, plays a key role in regulating the physiological and pathological processes of many cells. Under normal physiological conditions, the pH range of different organelles in the cell ranges from alkaline to weakly acidic, for example: the pH value in the mitochondrial matrix is ​​alkaline, about pH 8.0; the pH range in the Golgi is between pH 6.0-6.7; The pH of lysosomes, endosomes and autophagosomes is slightly acidic, between 4.0 and 6.0. In addition, the pH of the cytoplasmic matrix and extracellular fluid is in the near-neutral range, about pH 6.8-7.4. Abnormal pH is often accompanied by cellular dysfunction, which eventually leads to inflammation, cancer and neurodegenerative diseases. In addition, man...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64C07D221/14
CPCC07D221/14G01N21/6428G01N21/643
Inventor 樊丽王宇斌董川双少敏
Owner SHANXI UNIV
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