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Photosensitizer with fluorescence imaging and photodynamic gram-positive bacterium killing activity as well as preparation method and application of photosensitizer

A Gram-positive bacteria, fluorescence imaging technology, applied in photodynamic therapy, fluorescence/phosphorescence, chemical instruments and methods, etc., can solve the problem of few photosensitizers, achieve good luminescence ability, strong reactive oxygen species Generating ability, efficient photodynamic killing effect

Pending Publication Date: 2022-06-28
INNER MONGOLIA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, some photosensitizers that can be used for photodynamic antibacterial have been reported in the literature, but there are very few photosensitizers that have both fluorescence imaging and bactericidal capabilities

Method used

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  • Photosensitizer with fluorescence imaging and photodynamic gram-positive bacterium killing activity as well as preparation method and application of photosensitizer
  • Photosensitizer with fluorescence imaging and photodynamic gram-positive bacterium killing activity as well as preparation method and application of photosensitizer
  • Photosensitizer with fluorescence imaging and photodynamic gram-positive bacterium killing activity as well as preparation method and application of photosensitizer

Examples

Experimental program
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Effect test

preparation example Construction

[0052] In the present invention, when the photosensitizer has the structure shown in formula I, the preparation method comprises the following steps:

[0053] (1-1) The compound having the structure shown in formula III is mixed with 3,6-dichloropyridazine, a palladium catalyst and an inorganic base to carry out Suzuki reaction to obtain the compound having the structure shown in formula IV;

[0054]

[0055] (1-2) The compound having the structure represented by the formula IV and N,N-dimethylethylenediamine are mixed to carry out a substitution reaction to obtain the compound having the structure represented by the formula V.

[0056]

[0057] (1-3) Mixing the compound with the structure of formula V and methyl iodide to carry out a salt-forming reaction to obtain a photosensitizer with the structure of formula I.

[0058] In the present invention, the compound with the structure shown in formula III is mixed with 3,6-dichloropyridazine, a palladium catalyst, an inorga...

Embodiment 1

[0085] To prepare the photosensitizer with the structure of formula II where R is hydrogen, the synthetic route is as follows, the raw materials are denoted as compound 1 to compound 4 according to the labels in the synthesis route, and the product is denoted as DAPO-O:

[0086]

[0087] (1) Compound 1 (1 g, 6 mmol), compound 2 (2.67 g, 7.2 mmol), [1,1'-bis(diphenylphosphonium)ferrocene]dichloropalladium dichloromethane complex ( 245mg, 0.3mmol), potassium phosphate (3.82g, 18mmol) and tetrahydrofuran were mixed, refluxed at 65°C under the protection of nitrogen, and the reaction progress was monitored with TLC plate until compound 1 disappeared completely, and the obtained reaction solution was mixed with saturated aqueous ammonium chloride solution. Methylene chloride was mixed for extraction, the organic phase was separated, and the aqueous phase was extracted twice with dichloromethane. The organic phases were combined and purified by silica gel column chromatography. Th...

Embodiment 2

[0129] To prepare a photosensitizer with the structure shown in formula II where R is a methoxy group, other conditions are the same as those in Example 1, except that compound 2 is replaced with the following compound:

[0130]

[0131] The NMR analysis of the final product shows that the structure of the final product is as follows:

[0132]

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Abstract

The invention relates to the technical field of biochemical materials, and provides a photosensitizer with fluorescence imaging and photodynamic gram-positive bacterium killing activity as well as a preparation method and application of the photosensitizer. The photosensitizer provided by the invention has good luminous capacity, quaternary ammonium salt groups in the molecular structure of the photosensitizer enable molecules to have positive electricity, the surface of bacteria is electronegative, and due to electrostatic interaction, the photosensitizer can be effectively combined with gram-positive bacteria to realize fluorescence imaging of the gram-positive bacteria; in addition, the photosensitizer provided by the invention also has strong reactive oxygen species generation ability, and can perform efficient photodynamic killing on gram-positive bacteria; meanwhile, the photosensitizer provided by the invention is non-toxic to normal cells and can be used for constructing a bacterial infection diagnosis and treatment reagent integrating diagnosis and treatment functions. The preparation method of the photosensitizer provided by the invention is simple in steps and easy to operate.

Description

technical field [0001] The invention relates to the technical field of biochemical materials, in particular to a photosensitizer with both fluorescence imaging and photodynamic killing activities of Gram-positive bacteria, and a preparation method and application thereof. Background technique [0002] Bacterial infections are one of the most serious health problems worldwide, sickening millions of people each year and posing a serious threat to global public health. Antibiotics have been widely used to treat bacterial infections since the discovery of penicillin in 1928. However, due to the misuse of antibiotics in clinical practice in recent decades, drug-resistant bacteria and even multidrug-resistant strains have emerged and spread widely. These strains have weakened the therapeutic effect of antibiotics, resulting in high mortality and serious waste of medical resources. The World Health Organization has warned that in the near future, we will enter a post-antibiotic er...

Claims

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Application Information

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IPC IPC(8): C07D237/20C09K11/06A61K41/00A61P31/04G01N21/64
CPCC07D237/20C09K11/06A61K41/0057A61P31/04G01N21/6428G01N21/6456C09K2211/1044C09K2211/1007C09K2211/1014Y02A50/30
Inventor 王建国姜国玉龚建业
Owner INNER MONGOLIA UNIVERSITY
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