A kind of photodynamic bactericidal polymer and its preparation method and application

A polymer, photodynamic technology, applied in photodynamic therapy, chemical instruments and methods, antibacterial drugs, etc., can solve the problems of limited sterilization range, general sterilization effect, inability to kill fungi, etc., and achieves simple preparation method and strong killing. Ability, low concentration effect

Active Publication Date: 2020-01-03
SHANXI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Yet the bactericidal effect of the quaternary ammonium salt compound that has been reported is general at present, and the scope of sterilization is limited, as can only kill bacteria, can not kill fungi etc., in view of this, it is the aim of the present invention to obtain excellent and broad-spectrum antibacterial materials of bactericidal performance

Method used

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  • A kind of photodynamic bactericidal polymer and its preparation method and application
  • A kind of photodynamic bactericidal polymer and its preparation method and application
  • A kind of photodynamic bactericidal polymer and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation of embodiment 1 polymer (I)

[0027] 1) In a 100mL round bottom flask, add 2.68g 2,5-dibromohydroquinone (10.0mmol), 32.8g 1,12-dibromododecane (100mmol), 4.97g potassium carbonate (36.0 mmol) and 100mL acetone. Under the catalytic amount of 18-crown-6 phase transfer catalyst, stirring and heating under reflux for 5h. Stop the reaction, spin off a large amount of solvent under reduced pressure, add 200 mL of dichloromethane, wash the obtained organic phase with distilled water 3 times (3×100 mL), dry over anhydrous sodium sulfate, and remove the solvent to obtain a crude product. The crude product was separated by column chromatography (eluent: dichloromethane / petroleum ether=1 / 2, v / v) to obtain 1,4-dibromo-2,5-bis(12-bromododecyloxy)benzene (II) 2.68 g (35.1% yield). 1 H NMR (400MHz, CDCl 3 ,ppm)δ:1.23-1.49(m,32H),1.77-1.89(m,8H),3.36(t,JJ=7.2Hz,4H),3.94(t,JJ=8.0Hz,4H),7.08(s ,2H); 13 C NMR (100MHz, CDCl 3 , ppm) δ: 25.88, 28.15, 28.68, 29.14, 29...

Embodiment 2

[0030] The test of the fluorescence emission spectrum and the ultraviolet absorption spectrum of embodiment 2 polymer (I)

[0031] Polymer (I) was dissolved in DMSO to prepare a solution with a concentration of 0.02 mg / mL. Accurately pipette 2.0mL of the above solution into the UV sample cell, and use DMSO solvent as a reference, measure it on a HITACHI UH5300 UV absorber, and the obtained maximum absorption peak is 540nm. Also accurately pipette the above-mentioned DMSO solution with a concentration of 0.02mg / mL and add it to a 2.0mL fluorescence sample cell, measure it on a HITACHI F-4600 fluorescence instrument, the excitation and emission slit width is 5n, the excitation wavelength is 513nm, and the obtained maximum emission wavelength 665nm. The normalized spectrum of the obtained results can be seen in figure 1 .

Embodiment 3

[0032] The active oxygen generation ability test of embodiment 3 polymer (I)

[0033] Take 50 μL of 10.0 mM ethanol solution of 2,7-dichlorofluorescein diacetate, add 450 μL of ethanol to dilute, then add 2.0 mL of 0.01M NaOH aqueous solution, and activate at room temperature for 30 min in the dark. After activation, 10 mL of 1×PBS buffer solution was added, and the final concentration of the mixed DCFH solution was 40 μM.

[0034] Add 1.0 mL of activated DCFH (40 μM) solution and 52.4 μL of polymer (I) (100 μM) aqueous solution into a cuvette, mix well, and expose the resulting solution under white light (1.0 mW / cm 2 ) under irradiation for 5 minutes, record the fluorescence emission spectrum of the DCFH solution with an excitation wavelength of 488nm at 500-700nm every minute, and the blank group is the DCFH solution (40 μ M) without adding any activated DCFH to be tested. After the same light treatment, use the same method to detect its fluorescence emission spectrum. For...

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Abstract

The invention provides a photodynamic sterilization polymer as well as a preparation method and application thereof. The polymer is composed of a main chain and a side chain; the side chain is composed of a long alkyl chain with a quaternized tail end and can be combined with the surface of bacteria with negative charge to form a tight combined body, so that a bacterial membrane is transparent; the main chain is composed of benzene, fluorene and thiophene and has a relatively strong rigid structure; under a light illumination condition, the main chain is excited by light to sensitize air in the periphery to generate active oxygen, so that an efficient sterilization effect is realized. The polymer can be used as an antibacterial agent and can be used for killing gram positive bacteria and gram negative bacteria; the polymer also can be used for killing fungi and has a broad-spectrum antibacterial function. The polymer is simple to prepare and moderate to react and has relatively high yield. The polymer is used as an efficient photodynamic antibacterial material, concentration needed by sterilization is low and the light dosage is small; common white illumination can reach an efficient sterilization effect. The polymer provided by the invention emits fluorescent light in a long-wave region and also can be used for biological fluorescent imaging.

Description

technical field [0001] The invention relates to a conjugated polymer, in particular to a photodynamic bactericidal polymer and its preparation method and application. Background technique [0002] Since the discovery of penicillin, many antibiotics have been reported one after another, and have played a very good bactericidal effect for a period of time. However, the widespread use and abuse of antibiotics has led to the emergence of drug-resistant bacteria, and people are in urgent need of new and effective anti-infection methods. [0003] Compared with antibiotics, photodynamic sterilization uses photosensitizers to generate reactive oxygen species (including singlet oxygen, superoxide anion radicals, hydrogen peroxide, and hydroxyl radicals) under light to damage bacteria and cause death of bacteria, and It will not cause bacteria to develop drug resistance, and the advantages are more prominent. Among them, photosensitizer is an important element. The development of ph...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G61/12C09K11/06A61P31/04A61P31/10A61K41/00A61K49/00
CPCA61K41/0057A61K49/0019A61P31/04A61P31/10C08G61/123C08G61/126C08G2261/122C08G2261/143C08G2261/3142C08G2261/3223C08G2261/3246C08G2261/354C08G2261/522C09K11/06C09K2211/1483Y02B20/00
Inventor 冯丽恒王皓萍
Owner SHANXI UNIV
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