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A ratiometric zinc ion fluorescent probe and its preparation and application

Active Publication Date: 2022-06-21
ZHEJIANG UNIV CITY COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Aiming at the problems of complex preparation, poor water solubility, high biological toxicity and poor biological stability of existing fluorescent probes, the first purpose of the present invention is to provide a ratiometric zinc ion fluorescent probe

Method used

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  • A ratiometric zinc ion fluorescent probe and its preparation and application
  • A ratiometric zinc ion fluorescent probe and its preparation and application
  • A ratiometric zinc ion fluorescent probe and its preparation and application

Examples

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Embodiment 1

[0050] Pyrrole (2.7g, 0.04mol), benzaldehyde (2.1g, 0.02mol), o-nitrobenzaldehyde (3.0g, 0.02mol) were dissolved in 100mL of xylene to form pyrrole 0.4mmol / mL, benzaldehyde and o-nitrobenzaldehyde Nitrobenzaldehyde is a solution of 0.2 mmol / mL, heated to reflux, and the heating is stopped after 2 hours of reaction; an equal volume of petroleum ether is added to the reaction solution to precipitate a black paste, and the solution is taken and spin-dried to obtain 5-ortho-nitro Crude product of phenyl-10,15,20-triphenylporphyrin (o-NTPP);

[0051] The crude o-NTPP product (2.0 g) was dissolved in 80 mL of concentrated hydrochloric acid, 20 g of stannous chloride was added to form a mixture of 0.275 g / mL, heated to 70 degrees, and the heating was stopped after 8 h of reaction. A solid was obtained, which was a crude product of 5-o-aminophenyl-10,15,20-triphenylporphyrin (o-ATPP). Silica gel column separation, dichloromethane as the developing solvent, collect the second color ba...

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Abstract

The invention discloses a ratio type zinc ion fluorescent probe, its preparation method and application. The method comprises: (1) 5-ortho amino p-sulfonate phenyl-10,15,20-trisulfonate phenylporphyrin (o-PNH 2 ) aqueous solution and the dichloromethane solution of triphosgene are mixed in equal volumes and then reacted at room temperature to obtain 5-ortho isothiocyanate group p-sulfonate phenyl-10,15,20-trisulfonate phenyl porphyrin (o‑PNCS). (2) o‑PNCS reacts with aminomethylpyridine derivatives at room temperature to obtain the final product porphyrin-pyridine (o‑SP) probe. The probe has good water solubility, and when the fluorescence detection of zinc ions in aqueous solution is performed, the double emission peaks of the fluorescence signal change proportionally, and are not interfered by metal ions such as sodium, potassium, magnesium, iron, manganese; combined with laser confocal Scanning microscopy technology can also realize the fluorescent detection and imaging of zinc ions by the probe in living cells.

Description

technical field [0001] The invention relates to a ratio-type zinc ion fluorescent probe, in particular to a porphyrin-pyridine (o-SP) water-soluble zinc ion fluorescent probe using pyridine as a signal recognition group and a porphyrin molecule as a fluorescent chromophore A preparation method of a needle is provided, and the probe molecule is applied to the detection of zinc ions in aqueous solution and cells. Background technique [0002] Zinc is the second most abundant trace metal element in the human body, and is widely distributed in various tissues and organs in the form of divalent cations. As an important cofactor, zinc ion is the core component of more than 200 enzymes in the human body, participating in a series of physiological processes including brain function and regulation, gene transcription, immune response and mammalian reproduction. In addition, changes in zinc content are also associated with the occurrence of diseases such as Alzheimer's disease, epile...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/64
CPCC09K11/06C07D487/22G01N21/643G01N21/6428C09K2211/1007C09K2211/1029C09K2211/1074
Inventor 吕媛媛应飞鹏王欣怡易小琴沈王兴
Owner ZHEJIANG UNIV CITY COLLEGE