A kind of carbazole derivative mcab and its preparation method and application

A carbazole derivative, carbazole technology, applied in chemical instruments and methods, fluorescence/phosphorescence, instruments, etc., can solve the problems of cytotoxicity, limited fluorescent probes, and no lysosome targeting, and achieve cost The effect of low cost, simple detection method and good cell membrane permeability

Active Publication Date: 2021-07-02
SHANXI UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, many fluorescent probes based on cysteine ​​detection have been reported in the literature. However, due to the similarity in structure and biological activity of biothiols, cysteine ​​can be compared with homocysteine ​​(Hcy) and glutathione. Fluorescent probes for differential detection of peptide (GSH) are limited and most of these probes do not have lysosomal targeting
In addition, the existing lysosome targeting groups are concentrated on the traditional morpholine ring and dimethylamino structure, and such weakly basic groups are easy to gather in weakly acidic lysosomes to cause the "alkalinization effect" of lysosomes , long-term action can lead to cytotoxicity

Method used

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  • A kind of carbazole derivative mcab and its preparation method and application
  • A kind of carbazole derivative mcab and its preparation method and application
  • A kind of carbazole derivative mcab and its preparation method and application

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Effect test

Embodiment 1

[0024] Preparation and Characterization of 1,4-(3-(9-(2-(2-methoxyethoxy)ethyl-9H-carbazol-3-yl)-3-acryloyl)benzaldehyde (MCAB) :

[0025]

[0026] In a three-necked flask, mix 1-(9-(2-(2-methoxyethoxy)ethyl)-9H-carbazol-3-yl)ethanone (70mg, 0.22mmol) and terephthalaldehyde (45mg, 0.33mmol) was dissolved in ethanol, added 3-5 drops of piperidine, and heated to reflux for 12h until the reaction was complete; the system was cooled to room temperature, and the solvent was removed by rotary evaporation under reduced pressure to obtain a crude product; the crude product was purified by silica gel column (eluent According to the volume ratio of chloroform:methanol=20:1), the dark green solid was obtained as the target compound MCAB (probe).

[0027] 1 H NMR (600MHz, CDCl 3 , figure 1 Middle and upper picture) δ(ppm): 3.30(3H), 3.43(2H), 3.56(2H), 3.96(2H), 4.60(2H), 7.40-7.43(1H), 7.59-7.62(2H), 7.85- 8.00(9H), 8.24-8.28(1H), 8.93(1H).

[0028] 13 C NMR (150MHz, CDCl 3 , ...

Embodiment 2

[0031] The probe MCAB was diluted to 25 μM with DMSO / PBS buffer (pH 7.4) system (v / v=1 / 1), and the ultraviolet absorption spectrum of the reaction between MCAB and Cys (500 μM) changed with time was recorded. Such as image 3 As shown, after adding Cys, the UV absorbance at 300 nm and 388 nm changed to 255 nm and 338 nm.

Embodiment 3

[0033] Dilute the probe MCAB to 25 μM with DMSO / PBS buffer (pH 7.4) system (v / v=1 / 1), record the fluorescence spectrum of the reaction between MCAB and Cys (500 μM) over time, fix the excitation wavelength at 370 nm, and and emission slit broadband are both 2.0nm. After adding Cys, a new emission peak appeared at 440nm and increased sequentially with time. The fluorescence intensity reached the maximum value ( Figure 4 ). Under the irradiation of ultraviolet light, the color of the solution changed from colorless to blue ( Figure 5 ).

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Abstract

The invention discloses a carbazole derivative MCAB as well as its preparation method and application. The Chinese name of the carbazole derivative is 4‑(3‑(9‑(2‑(2‑methoxyethoxy) ethyl‑9H‑carbazole‑3‑yl)‑3‑acryloyl) benzene Formaldehyde, English name is, 4‑(3‑(9‑(2‑(2‑methoxyethoxy) ethyl)‑9H‑carbazol‑3‑yl)‑3‑acryloyl) benzaldehyde, abbreviated as MCAB. Its preparation method is: 1‑(9‑(2‑(2‑methoxyethoxy) ethyl)‑9H‑carbazole‑3‑yl) ethyl ketone and terephthalaldehyde are dissolved in ethanol, piperidine is added, and heated to reflux Obtain crude product; The crude product is removed solvent, obtains pure product through silica gel column separation.Use MCAB as probe with α, β unsaturated acetyl carbazole derivative as fluorophore parent and cysteine ​​(Cys) reactive site, Utilizing thiol to induce nucleophilic addition reaction of α,β-unsaturated ketones, resulting in enhanced fluorescence, specific detection of Cys, and good selectivity, and the reaction with Cys is more active than with other biological thiols. Using laser co- Focused fluorescence imaging technology can detect the changes of Cys in lysosomes with high sensitivity, and has broad application prospects in the field of biomolecular detection.

Description

technical field [0001] The invention relates to the technical field of thiol analysis, in particular to a carbazole derivative MCAB and a preparation method thereof, and the application of the derivative MCAB in the detection of intracellular lysosome cysteine. Background technique [0002] Cysteine ​​(Cys), as an essential amino acid and an important biothiol, plays an important role in regulating human physiological functions, such as biocatalysis, protein post-transcriptional modification and detoxification process. Insufficient Cys in the body can lead to symptoms such as slow growth, muscle weakness, liver injury, and intestinal mucosal atrophy in children; at the same time, excessive Cys concentration is closely related to cardiovascular diseases and atherosclerosis. Therefore, research on highly sensitive and real-time detection of cysteine ​​in biological samples has become a research hotspot in related fields. Lysosome is a very important digestive organ in cells. ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/86C09K11/06G01N21/64
CPCC07D209/86C09K11/06C09K2211/1007C09K2211/1029G01N21/6486
Inventor 王晓东樊丽葛金印董川双少敏
Owner SHANXI UNIV
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