Near infrared waveband reaction type biological thiol two-photon fluorescent probe as well as preparation method and application thereof

A fluorescent probe and near-infrared technology, applied in the field of fluorescent probes, can solve problems such as limiting the scope of application, and achieve the effects of high sensitivity, good biocompatibility and strong selectivity

Active Publication Date: 2018-06-22
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the biothiol fluorescent probes in the prior art only emit linear fluorescence without two-photon fluorescence, and most of the linear fluorescence emission wavelengths are less than 630nm, which greatly limits its application range

Method used

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  • Near infrared waveband reaction type biological thiol two-photon fluorescent probe as well as preparation method and application thereof
  • Near infrared waveband reaction type biological thiol two-photon fluorescent probe as well as preparation method and application thereof
  • Near infrared waveband reaction type biological thiol two-photon fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0019] (1) The preparation method of fluorescent probe molecule BODIPY-DS is:

[0020] Under the protection of an inert gas and at 0°C, fluoroboron dipyrrole conjugated arylphenol BODIPY-OH (0.59g, 1.00mmol) was dissolved in 10mL of dry dichloromethane, and 2,4-dinitrobenzenesulfonyl chloride ( 0.58g, 2.18mmol), then add 10mL of dry dichloromethane and triethylamine (2.18mmol), stir and react for 10h, after the reaction, extract, dry, concentrate, and purify by column chromatography to obtain the fluorescent probe molecule BODIPY -DS, yield 45%.

[0021] The synthetic route of compound BODIPY-DS is as follows:

[0022]

[0023] Among them, fluoroboron dipyrrole conjugated arylphenol BODIPY-OH was prepared according to the literature method (Bao-xingShen, YingQian. A novel triphenylamine-BODIPY dendron: click synthesis, near-infraredemission and a multi-channelchemosimeter for Hg 2+ and Fe 3+ . Journal of Materials Chemistry B, 2016, 4, 7549-7559).

[0024] (2) Structura...

Embodiment 2

[0030] The preparation method of fluorescent probe molecule BODIPY-DS is basically the same as in Example 1, the difference is:

[0031] Under the protection of an inert gas and at 0°C, fluoroboron dipyrrole conjugated arylphenol BODIPY-OH (0.59g, 1.00mmol) was dissolved in 10mL of dry dichloromethane, and 2,4-dinitrobenzenesulfonyl chloride ( 0.64g, 2.40mmol), then add 10mL of dry dichloromethane and triethylamine (2.40mmol), and stir the reaction for 12h. After the reaction, the fluorescent probe molecule BODIPY-DS was obtained through extraction, drying, concentration and column chromatography purification, with a yield of 48%.

Embodiment 3

[0033] The preparation method embodiment 1 of fluorescent probe molecule BODIPY-DS is basically the same, the difference is:

[0034] Under the protection of an inert gas and at 0°C, fluoroboron dipyrrole conjugated arylphenol BODIPY-OH (0.59g, 1.00mmol) was dissolved in 10mL of dry dichloromethane, and 2,4-dinitrobenzenesulfonyl chloride ( 0.66g, 2.48mmol), then added 10mL of dry dichloromethane and triethylamine (2.48mmol), and stirred for 12h. After the reaction is completed, the fluorescent probe molecule BODIPY-DS is obtained through extraction, drying, concentration and column chromatography purification, with a yield of 50%.

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Abstract

The invention provides a fluorescent probe molecule BODIPY-DS, which has a diaryl sulfonate structure of conjugate fluoroboron dipyrrole. The invention also provides a preparation method and application of the fluorescent probe molecule BODIPY-DS. According to a near infrared waveband reaction type biological thiol two-photon fluorescent probe, fluorescent molecules are prepared through reaction between fluorboron dipyrrole conjugate arylphenol and 2,4-dinitrobenzene sulfonyl chloride; through biological thiol induced aromatic nucleophilic substitution reaction, the diaryl sulfonate structureis removed; the biphoton fluorescence emission performance of the probe molecule can be sensitively regulated and controlled; the sensitivity is high; the selectivity is high; the biocompatibility ishigh; the fluorescent probe can be used as the near infrared waveband reaction type biological thiol two-photon fluorescent probe with excellent performance, and can be widely applied to the aspects of near infrared wave band fluorescent imaging, fluorescent sensing, biological fluorescence analysis, fluorescent marking and endogenic and ectogenic biological thiol detection.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a near-infrared band reactive biothiol two-photon fluorescent probe and its preparation method and application. Background technique [0002] Biothiols are important components of many proteins and small molecules, and participate in signal transduction, cell apoptosis, and sulfur metabolism in organisms. The imbalance of thiols in organisms can lead to Alzheimer's disease, osteoporosis, growth arrest, and edema , drowsiness, skin damage, decreased resistance. Glutathione is one of the small molecular thiols with the highest content in cells. The concentration in the organism is about 10mmol / L. There is a redox dynamic balance between oxidized glutathione and reduced glutathione. Biothiols play an important role in maintaining cellular redox homeostasis, oxidative stress, and in cell growth and function. Therefore, the detection of thiols in vivo, especially glutathi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1014C09K2211/1029C09K2211/1096G01N21/6402G01N21/6458G01N21/6486
Inventor 钱鹰夏祥
Owner SOUTHEAST UNIV
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