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Cyanine near-infrared fluorescent probe as well as preparation method and application thereof

A fluorescent probe, near-infrared technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of crosstalk, small shift of fluorescence emission peak, unfavorable accurate imaging of tumor cells/tissues, etc., and achieve high sensitivity , the effect of simple operation and good industrial application potential

Active Publication Date: 2021-08-27
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that a single channel or emitted probe is easily affected by factors such as the test environment (such as temperature, pH, solvent polarity, etc.) and probe concentration
[0004] Most of the currently reported ratiometric esterase fluorescent probes are designed based on the photophysical mechanism of intramolecular charge transfer (ICT) and fluorescence resonance energy transfer (FRET). Signal crosstalk is not conducive to precise imaging of tumor cells / tissues

Method used

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  • Cyanine near-infrared fluorescent probe as well as preparation method and application thereof
  • Cyanine near-infrared fluorescent probe as well as preparation method and application thereof
  • Cyanine near-infrared fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Synthesis of cyanine near-infrared fluorescent probe compound (Cy-NE):

[0055] Mix CY-N (0.43mmol) and 2.6-lutidine (2.1mmol) in dichloromethane (20mL), heat and stir at 22°C for 10h; after the reaction is over, distill off the solvent under reduced pressure to obtain blue solid; then the crude reaction product was extracted with dichloromethane and water, the solvent was distilled off under reduced pressure, and purified by column chromatography with dichloromethane and methanol to obtain pure fluorescent probe Cy-NE.

Embodiment 2

[0057] Synthesis of cyanine near-infrared fluorescent probe compound (Cy-NE):

[0058] CY-N (0.43mmol) and 2.6-lutidine (3.9mmol) were mixed in dichloromethane (20mL), and acetyl chloride (43.0mmol) diluted with anhydrous dichloromethane was added dropwise under airtight conditions, at room temperature Stir the reaction for 10 hours; after the reaction is completed, the solvent is distilled off under reduced pressure to obtain a blue solid; after the reaction crude product is extracted with dichloromethane and water, the organic phase is distilled off under reduced pressure, and then the solvent is distilled off with dichloromethane and methanol After purification by column chromatography, pure fluorescent probe Cy-NE was obtained.

Embodiment 3

[0060] Synthesis of cyanine near-infrared fluorescent probe compound (Cy-NE):

[0061] CY-N (0.43mmol) and 2.6-lutidine (2.58mmol) were mixed in dichloromethane (20mL), and acetyl chloride (34.0mmol) diluted with anhydrous dichloromethane was added dropwise under airtight conditions, at room temperature Stir the reaction for 10 hours; after the reaction is completed, the solvent is distilled off under reduced pressure to obtain a blue solid; after the reaction crude product is extracted with dichloromethane and water, the organic phase is distilled off under reduced pressure, and then the solvent is distilled off with dichloromethane and methanol After purification by column chromatography, pure fluorescent probe Cy-NE was obtained.

[0062] Each embodiment in this specification is described in a progressive manner, each embodiment focuses on the difference from other embodiments, and the same and similar parts of each embodiment can be referred to each other.

[0063] The co...

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Abstract

The invention discloses a cyanine near-infrared fluorescent probe as well as a preparation method and application thereof, the cyanine near-infrared fluorescent probe disclosed by the invention takes hydrolysis of ester bonds bonded in cyanine dye by esterase as a basic action mechanism, and takes H-type aggregate luminescence of cyanine-amino alcohol as a fluorescence signal reporter group. When esterase is added into a system, ester bonds in a Cy-NE structure can be cut off by the esterase, and Smiles rearrangement reaction is caused by O-ions, so that the color and fluorescence of the solution are changed. The recognition effect of the cyanine near-infrared fluorescent probe on esterase is researched through a colorimetric method, an ultraviolet-visible absorption spectrometry and a fluorescence spectrometry, and the result shows that the near-infrared fluorescent probe can efficiently and selectively recognize esterase in a PBS solution system and has very high response sensitivity on esterase.

Description

technical field [0001] The invention belongs to the technical field of esterase detection, and relates to a method strategy for detecting carboxylesterase, in particular to a detection method of a fluorescent probe Cy-NE based on a Smiles rearrangement process. The invention also relates to the synthesis method of the probe and its application in detecting esterase. Background technique [0002] So far, several cases of fluorescent probes for detecting esterase activity have been reported. Most of the detected signals are the substances released after the enzyme cleavage of the probe. enzyme activity. The disadvantage is that a single channel or emitted probe is easily affected by factors such as the test environment (such as temperature, pH, solvent polarity, etc.) and probe concentration. [0003] Compared with ultraviolet-visible light, near-infrared (NIR) light has less photodamage to biological samples, better tissue penetration, and less interference from autofluores...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/14C09K11/06G01N21/64
CPCC07D209/14C09K11/06G01N21/6402G01N21/6428G01N21/6456C09K2211/1029C09K2211/1007
Inventor 张倩李家家万晨阳张鹏丁彩凤
Owner QINGDAO UNIV OF SCI & TECH
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