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Cyanovinylidene derivative fluorescent dye and its preparation method and application

A technology of fluorescence imaging and acetonitrile, applied in the field of chemical sensors, can solve the problems of photophysical properties restricting development and application, and achieve remarkable results

Active Publication Date: 2022-03-25
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the photophysical and chemical properties of some fluorescent probe molecules restrict further development and application.

Method used

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  • Cyanovinylidene derivative fluorescent dye and its preparation method and application
  • Cyanovinylidene derivative fluorescent dye and its preparation method and application
  • Cyanovinylidene derivative fluorescent dye and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035]

[0036] (1) Weigh 2-benzimidazole acetonitrile (266.0 mg, 1.70 mmol) and 4-(N,N-diethyl)aminobenzaldehyde to dissolve in ethanol (20 mL), then add piperidine (1.0 mL, 17.0 mmol), stirred at room temperature for 4h under the protection of an inert gas. After the reaction, a large amount of homogeneous orange-yellow fine sand-like precipitates were formed in the solution. The reaction solution was filtered, washed with ice ethanol, and the filter residue was dried to obtain an orange-yellow powder solid, which was the relatively pure product 3 (396.0 mg, 72%); 1 H NMR (400 MHz, DMSO-d 6 ): δ = 12.79 (s, 1H), 8.11 (s, 1H), 7.90 (d, 2H, J = 8.4 Hz),7.63 (d, 1H, J = 7.2 Hz), 7.50 (d, 1H, J = 7.2 Hz), 7.20 (m, 2H, J = 7.2 Hz),6.84 (d, 2H, J = 8.4 Hz), 3.46 (q, 4H, J = 7.2 Hz), 1.14 (t, 6H, J = 6.4 Hz); 13 C NMR (100 MHz, DMSO-d 6 ): δ = 150.6, 149.5, 145.8, 144.0, 135.3, 132.8, 123.2, 122.3, 119.6, 119.0, 118.4, 111.8, 111.6, 93.4, 44.4, 12.9; HRMS ...

Embodiment 2

[0038] Example 2 Preparation of Compound 12

[0039] The preparation method of compound 3 is the same as that in Example 1.

[0040]

[0041] (1) Weigh p-hydroxybenzaldehyde 6 (257.0 mg, 2.10 mmol) and dissolve it in 1 mol / L sodium hydroxide solution,

[0042] 2, 3, 4, 6-tetraacetyl- β -D-Glucopyranose 7 (867.0 mg, 2.10 mmol), the reaction was stirred at reflux (60 ± 3 °C) for 4 h. When the solution turned yellow completely, the solvent was removed by distillation under reduced pressure after the reaction. The obtained solid was subjected to silica gel column chromatography (eluent: ethyl acetate / petroleum ether = 1 / 3) to obtain compound 8 (598.0 mg, 63%); 1 H NMR (400 MHz, CDCl 3 ) : δ = 9.92 (s, 1H), 7.86 (d, 2H, J =8.8 Hz), 7.12 (d, 2H, J = 8.0 Hz), 5.51 (d, 2H, J = 17.6 Hz), 5.20 (d, 1H, J = 8.0 Hz), 5.15 (d, 1H, J = 9.6 Hz), 4.16 (m, 3H), 2.195 (s, 3H), 2.07 (s,6H), 2.026 (s, 3H). HRMS (ESI): calcd for C 21 h 25 o 11 [M+H] + m / z 452.1319, found 4...

Embodiment 3

[0053] Using a method similar to Example 2, those skilled in the art can easily prepare R 1 independently selected from NH 2 , OH, CN, CH 3 , COOH, SO 3 H, F, Cl, Br or NO 2 , R 2 for compound of.

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Abstract

Fluorescent dyes based on cyanovinylidene derivatives and their preparation methods and applications, the invention discloses a compound represented by the general structural formula (I), the compound R 1 independently selected from H, NH 2 , OH, CN, CH 3 , COOH, SO 3 H, F, Cl, Br or NO 2 ; 2 for. The compound probe molecule of the present invention can realize the quantitative detection of β-Gal in the buffer solution test system without interference from other proteases, biothiols, reactive oxygen species and common cations, and has been successfully applied to SKOV3 cells for the detection of β-Gal in biological cells In situ detection of Gal.

Description

technical field [0001] The invention relates to a fluorescent sensor of cyanovinylidene derivatives and a preparation method thereof, and the sensor is used to detect aging-related β -galactosidase ( β -Gal), belongs to the technical field of chemical sensors. Background technique [0002] Cancer is a general term for a large class of malignant tumors. For most cancer patients, early and accurate diagnosis of cancer is crucial to improve the survival rate of patients and reduce the pain of patients. Therefore, the clinical analysis and detection of cancer biomarkers is of great significance for the diagnosis, treatment and management of early-onset cancer. β -Gal as a hydrolase in enzyme-linked immunosorbent assay (ELISA) ( Armenta, R.; Tarnowski, T.; Gibbons, I.; et al. Anal. Biochem. 1985, 146 , 211-219), gene expression studies (Nolan, G. P.; Fiering, S.; Nicolas, J.-F.; et al. Proc. Natl. Acad. Sci. U.S.A. 1988, 85 , 2603-2607), classification of mycobacteria (...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/16C07H1/00C07H15/203C09B23/14C09K11/06G01N21/64
CPCC07D235/16C09K11/06C07H15/203C07H1/00C09B23/145G01N21/6428C09K2211/1044C09K2211/1007C09K2211/1088
Inventor 张健健李扬宁璐璐杨小峰
Owner NORTHWEST UNIV
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