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Photodynamic sterilization polymer as well as preparation method and application thereof

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

Active Publication Date: 2018-07-27
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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  • Photodynamic sterilization polymer as well as preparation method and application thereof
  • Photodynamic sterilization polymer as well as preparation method and application thereof
  • Photodynamic sterilization polymer as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1 Preparation of polymer (I)

[0027] 1) In a 100mL round bottom flask, add 2.68g 2,5-dibromohydroquinone (10.0mmol), 32.8g1,12-dibromododecane (100mmol), 4.97g potassium carbonate (36.0 mmol) and 100 mL acetone. Under the catalytic amount of 18-crown-6 phase transfer catalyst, the reaction was stirred and heated to reflux for 5h. The reaction was stopped, after a large amount of solvent was spun off under reduced pressure, 200 mL of dichloromethane was added, and the obtained organic phase was washed 3 times with distilled water (3×100 mL), dried over anhydrous sodium sulfate, and the solvent was removed to obtain a crude product. The crude product is separated by column chromatography (eluent is 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 ...

Embodiment 2

[0030] Example 2 Fluorescence emission spectrum and ultraviolet absorption spectrum test of polymer (I)

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

Embodiment 3

[0032] Example 3 Active oxygen generation ability test of polymer (I)

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

[0034] Add 1.0mL of activated DCFH (40μM) solution and 52.4μL of polymer (I) (100μM) aqueous solution into the cuvette, mix well, and place the resulting solution in white light (1.0mW / cm). 2 ) Irradiate for 5 min, and record the fluorescence emission spectrum of DCFH solution with excitation wavelength of 488nm at 500-700nm every minute. The blank group is the DCFH solution (40μM) without any activation to be tested. After the same illumination treatment, use the same method to detect Its fluorescence emission spectrum. See the test results figure 2 .

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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 sterilization polymer and a preparation method and application thereof. Background technique [0002] Since the discovery of penicillin, many antibiotics have been reported one after another, which has 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 urgently need new and effective anti-infection methods. [0003] Compared with antibiotics, photodynamic bactericidal therapy uses photosensitizers to generate reactive oxygen species (including singlet oxygen, superoxide anion free radicals, hydrogen peroxide, and hydroxyl free radicals, etc.) under light to damage bacteria and cause the death of pathogens, and It will not cause bacteria to develop resistance, and the advantages are more prominent. Among them, photosensitizer is an important element. The d...

Claims

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Application Information

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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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