CN107011511B - A kind of protoporphyrin fluorescent carbon dots and preparation method and application - Google Patents
A kind of protoporphyrin fluorescent carbon dots and preparation method and application Download PDFInfo
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- CN107011511B CN107011511B CN201710404826.8A CN201710404826A CN107011511B CN 107011511 B CN107011511 B CN 107011511B CN 201710404826 A CN201710404826 A CN 201710404826A CN 107011511 B CN107011511 B CN 107011511B
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Abstract
The present invention relates to a kind of protoporphyrin fluorescent carbon point and preparation method and applications, and protoporphyrin and polyethyleneimine PEI are specially reacted 7-10h at 170-220 DEG C, protoporphyrin fluorescent carbon point is obtained after cooling, dialysis, filtering.The protoporphyrin fluorescent carbon point that the present invention is prepared not only has good water solubility, also completely remains the property of protoporphyrin, the light power that Porphyrin-Based Sensitizer generates can effectively inactive yeast cell, play bactericidal effect.The advantages that this method has reaction step simple, and reaction condition is mild, and risk is small, less toxic.
Description
Technical field
The invention belongs to synthesis of polymer material and preparation technical field, it is related to a kind of protoporphyrin fluorescent carbon point and its preparation
Method.
Background technique
In recent years, since the abuse of antibiotic results in the appearance and propagation of " superbacteria ".So-called " superbacteria " is
Refer to that these bacteriums have current antibiotic the characteristic of multidrug resistant, this adds very the treatment of clinical wound infection
Big difficulty.Therefore it is extremely urgent to develop new anti-infective strategy.Light power antibacterial therapy method, exactly wherein most prospect
One of new treatment shows good curative effect especially for drug-fast bacteria infection for infection caused by bacterium, fungi and virus.
Protoporphyrin is well-known aromatic macrocyclic compounds and is widely present in nature.Protoporphyrin is puce knot
Crystalline substance powder, is soluble in methanol, is insoluble in diluted acid, not soluble in water, chloroform, ether and acetone etc..Studies have shown that porphyrin is photosensitive
The light power that agent generates can effectively inactive yeast cell.Its action principle is living by light due to the protoporphyrin in culture medium
Changing generation active oxygen radical changes the permeability of somatic cells film, and then destroys the metabolism of thallus normal physiological,
So as to cause the death of thallus.Protoporphyrin is not soluble in water, greatly limits protoporphyrin in the application of biological field.And dissolution or
Well dispersed derivatives of porphyrin can more effectively kill bacterium than hydrophobicity or the derivatives of porphyrin of reunion.
In conclusion a kind of method for developing protoporphyrin antibacterial agent with good aqueous solubility is necessary.
Summary of the invention
In view of this, the disadvantage that it is an object of the invention to overcome protoporphyrin not soluble in water, obtains a kind of water-soluble original
Porphyrin fluorescence carbon dots, and propose a kind of preparation method and application of protoporphyrin fluorescent carbon point.
In order to achieve the above objectives, the invention provides the following technical scheme:
1, a kind of protoporphyrin fluorescent carbon point, which is characterized in that have the following structure:
The positive integer of n=13~15
Further, the protoporphyrin fluorescent carbon point has bactericidal effect to staphylococcus aureus and staphylococcus epidermis.
2, a kind of preparation method of protoporphyrin fluorescent carbon point, using hydro-thermal method by protoporphyrin and polyethyleneimine in 170-
7-10h is reacted at 220 DEG C, protoporphyrin fluorescent carbon point is obtained after cooling, dialysis, filtering.
Further, according to parts by weight, protoporphyrin 20-33 parts, 50-80 parts of polyethyleneimine.
Further, molecular weight Mn=550~650 of the polyethyleneimine.
3, application of a kind of protoporphyrin fluorescent carbon point in terms of anti-Staphylococcus aureus and staphylococcus epidermis.
The beneficial effects of the present invention are: the protoporphyrin fluorescent carbon point being prepared not only has good water solubility, also
Completely remain the property of protoporphyrin, the light power that Porphyrin-Based Sensitizer generates can effectively inactive yeast cell, play and kill
Bacterium effect.The advantages that this method has reaction step simple, and reaction condition is mild, and risk is small, less toxic.
Detailed description of the invention
In order to keep the purpose of the present invention, technical scheme and beneficial effects clearer, the present invention provides following attached drawing and carries out
Illustrate:
Fig. 1 is the reaction schematic diagram for preparing protoporphyrin fluorescent carbon point.
Fig. 2 is the ultra-violet absorption spectrum of protoporphyrin fluorescent carbon point aqueous solution (C=0.125mg/mL).
Fig. 3 is the fluorogram of protoporphyrin fluorescent carbon point aqueous solution (C=0.125mg/mL).
Fig. 4 is the photobleaching lab diagram of protoporphyrin fluorescent carbon point.
Fig. 5 is the growth curve chart of staphylococcus aureus and staphylococcus epidermis.
Specific embodiment
Below in conjunction with attached drawing, a preferred embodiment of the present invention will be described in detail.
Protoporphyrin fluorescent carbon point of the invention is made by reaction as shown in Figure 1: with protoporphyrin and PEI (Mn=550~
It 650) is reactant, hydrothermal reaction kettle is reaction vessel, and hydro-thermal reaction 7-10h is carried out at 170-220 DEG C；Then, to product
It is down to room temperature, product is put into 1000D bag filter and is dialysed with deionized water, is filtered after the completion of dialysis with 0.22 μm of pin hole
Device filtering can obtain protoporphyrin fluorescent carbon point.
Light dynamic pasteurization measure of merit is carried out with protoporphyrin fluorescent carbon point obtained.In the method, golden yellow Portugal is chosen
Grape coccus (S.aureus), Escherichia coli (E.coli), Pseudomonas aeruginosa (P.aeruginosa) and staphylococcus epidermis
(S.epidermidis) representative as gram-positive bacteria and negative bacterium, the sterilization for studying protoporphyrin fluorescent carbon point are made
With.
Embodiment 1
The preparation method of protoporphyrin fluorescent carbon point 1, comprising the following steps:
1) PEI (Mn=550~650) the solution 10mL for matching 2mg/mL, weighs 10mg protoporphyrin, it is anti-to be added to hydro-thermal together
It answers in kettle, reacts 10h at 220 DEG C；
2) it after the reaction was completed, is cooled to room temperature, dialysis 3 days is carried out with 1000D bag filter, later again with 0.22 μm of pin hole
Filter is filtered the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 2
The preparation method of protoporphyrin fluorescent carbon point 2, comprising the following steps:
1) PEI (Mn=550~650) the solution 10mL for matching 2mg/mL, weighs 10mg protoporphyrin, it is anti-to be added to hydro-thermal together
It answers in kettle, reacts 8h at 220 DEG C；
2) it after the reaction was completed, is cooled to room temperature, dialysis 3 days is carried out with 1000D bag filter, later again with 0.22 μm of pin hole
Filter is filtered the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 3
The preparation method of protoporphyrin fluorescent carbon point 3, comprising the following steps:
1) PEI (Mn=550~650) the solution 10mL for matching 2mg/mL, weighs 10mg protoporphyrin, it is anti-to be added to hydro-thermal together
It answers in kettle, reacts 8h at 180 DEG C；
2) it after the reaction was completed, is cooled to room temperature, dialysis 3 days is carried out with 1000D bag filter, later again with 0.22 μm of pin hole
Filter is filtered the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 4
The preparation method of protoporphyrin fluorescent carbon point 4, comprising the following steps:
1) PEI (Mn=550~650) the solution 10mL for matching 2mg/mL, weighs 15mg protoporphyrin, it is anti-to be added to hydro-thermal together
It answers in kettle, reacts 10h at 220 DEG C；
2) it after the reaction was completed, is cooled to room temperature, dialysis 3 days is carried out with 1000D bag filter, later again with 0.22 μm of pin hole
Filter is filtered the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 5
The preparation method of protoporphyrin fluorescent carbon point 5, comprising the following steps:
1) PEI (Mn=550~650) the solution 10mL for matching 4mg/mL, weighs 10mg protoporphyrin, it is anti-to be added to hydro-thermal together
It answers in kettle, reacts 10h at 220 DEG C；
2) it after the reaction was completed, is cooled to room temperature, dialysis 3 days is carried out with 1000D bag filter, later again with 0.22 μm of pin hole
Filter is filtered the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 6
The preparation method of protoporphyrin fluorescent carbon point 6, comprising the following steps:
1) PEI (Mn=550~650) the solution 10mL for matching 4mg/mL, weighs 20mg protoporphyrin, it is anti-to be added to hydro-thermal together
It answers in kettle, reacts 10h at 220 DEG C；
2) it after the reaction was completed, is cooled to room temperature, dialysis 3 days is carried out with 1000D bag filter, later again with 0.22 μm of pin hole
Filter is filtered the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
The structural characterization of protoporphyrin fluorescent carbon point is as shown in Figure 2,3, 4:
Fig. 2 is the ultra-violet absorption spectrum of protoporphyrin fluorescent carbon point aqueous solution (C=0.125mg/mL), can from figure
Out, occur the feature ultraviolet absorption peak of protoporphyrin within the scope of 350-700nm, illustrate protoporphyrin and PEI (Mn=550~
650) structure and property of protoporphyrin are still maintain after reacting.
Fig. 3 is the fluorogram of protoporphyrin fluorescent carbon point aqueous solution (C=0.125mg/mL), it can be seen from the figure that
Protoporphyrin fluorescent carbon point launches strong fluorescence when excitation wavelength is 405nm, 488nm and 633nm.
Fig. 4 is the photobleaching lab diagram of protoporphyrin fluorescent carbon point, it can be seen from the figure that the protoporphyrin after illumination can generate
ROS, produced ROS act on colored indicator.After illumination 2min, ultraviolet peak value is almost unchanged, it was demonstrated that protoporphyrin fluorescent carbon point
It is fastish for generating oxygen radical.Protoporphyrin fluorescent carbon point generates active oxygen radical by photoactivation and makes somatic cells
The permeability of film is changed, and then destroys the metabolism of thallus normal physiological, is led to the death of thallus, is further demonstrated made
Standby carbon dots have bactericidal effect.
Embodiment 7
Bactericidal effect detection is carried out using protoporphyrin fluorescent carbon point, particular content is as follows:
1. the culture of bacterium: taking out the cryopreservation tube that bacterial strain is housed from -20 DEG C of refrigerators, be allowed to melt, be then inoculated in pancreas
It is spare in tryptone soya broth (Tryptone soya broth, TSB) culture medium, and in 37 DEG C of shaking table cultures.Generally mention
The previous day culture.
2. growth curve of bacteria: growth curve of bacteria is the liquid that a small amount of unicellular microorganism is inoculated into a constant volume
It after culture medium, cultivates under appropriate conditions, timing sampling measures cell quantity.Using the time as abscissa, with pair of viable count
Number is ordinate, can obtain a growth curve, and curve shows four periods of bacterial growth breeding: lag phase, logarithmic phase,
Stationary phase, decline phase.The specific steps are (following equipment used and liquid sterilize in advance):
(1) bacterial strain phosphate buffered saline solution (Phosphate buffer saline, PBS) is first diluted to 1 × 105；
(2) it takes the centrifuge tube of two 4mL to be designated as No. 1 No. 2,1mL bacterial solution and 2mL protoporphyrin is added in No. 1 centrifuge tube
Fluorescent carbon point solution, No. 2 centrifuge tubes are added 1mL bacterial solution and 2mL PBS, are uniformly mixed；
(3) four cuvettes is taken to be denoted as No. 3 No. 4 No. 5 No. 6, No. 3 No. 4 each mixed solutions that No. 1 centrifuge tube of 1mL is added, 5
Numbers No. 6 each mixed solutions that No. 2 centrifuge tubes of 1mL are added；
(4) the laser irradiation 10min for being 635nm with wavelength, wherein No. 3 No. 5 laser intensities with 100mW, No. 4 No. 6 with
120mW；
(5) mixed solution in No. 1 No. 2 No. 3 No. 4 No. 5 No. 6 is put into 37 DEG C of bacterium baking ovens after and cultivates 2h；
(6) centrifuge tube of 6 4mL is taken to be designated as No. 1 No. 2 No. 3 No. 4 No. 5 No. 6 again, it is each that 2mL TSB is added, by above-mentioned culture
Bacterial solution after 2h respectively takes 100 μ L to be added in reference numeral centrifuge tube (such as: No. 1 → No. 1), is uniformly mixed；
(7) bacterial solution of above-mentioned 1-6 centrifuge tube being added in 96 orifice plates with liquid-transfering gun, a sample one arranges, and one
100 μ L of hole；It is then placed in 37 DEG C of bacterium baking ovens and cultivates, interval 2h surveys its OD value, until bacterial growth enters decline phase；
Using the time as abscissa, using the logarithm of viable count (OD) as ordinate, growth curve of bacteria is done.
Fig. 5 is SA, and the growth curve of SE: (a) growth curve of the SA in PBS under different illumination intensity, (b) SA is in former porphin
Growth curve in quinoline carbon dots (C=0.52mg/mL) solution under different illumination intensity, (c) SE is in PBS under different illumination intensity
Growth curve, (d) growth curve of the SE in protoporphyrin carbon dots (C=0.52mg/mL) solution under different illumination intensity.From figure
In 5 as can be seen that compared to blank sample, protoporphyrin fluorescent carbon point is to staphylococcus aureus (S.aureus) and epidermis grape ball
Bacterium (S.epidermidis) has all shown very strong bactericidal effect.
Sterilization test shows: protoporphyrin fluorescent carbon point is to staphylococcus aureus (S.aureus) and staphylococcus epidermis
(S.epidermidis) there is apparent bactericidal effect.
Finally it is worth noting that, preferred embodiment above is only used to illustrate the technical scheme of the present invention and not to limit it, to the greatest extent
Pipe has been described in detail the present invention by above preferred embodiment, however, those skilled in the art should understand that, can
To make various changes to it in the form and details, without departing from model defined by claims of the present invention
It encloses.
Claims (3)
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| CN108373472B (en) * | 2018-04-25 | 2021-03-16 | 西南大学 | A kind of bactericidal material containing protoporphyrin and its preparation method and application |
| CN108904801A (en) * | 2018-07-20 | 2018-11-30 | 中山大学 | A kind of multifunctional nano vesica and preparation method thereof |
| CN109468130B (en) * | 2018-12-27 | 2021-12-03 | 武汉工程大学 | Preparation method of metal-doped fluorescent carbon quantum dots |
| CN109943326A (en) * | 2019-04-23 | 2019-06-28 | 中国科学院理化技术研究所 | Biomass-based fluorescent carbon quantum dots and their preparation methods and applications |
| CN111004623B (en) * | 2019-12-20 | 2023-07-18 | 河北科技大学 | A kind of porphyrin fluorescent material and preparation method thereof |
| CN113122245B (en) * | 2019-12-30 | 2023-02-17 | 中国科学院理化技术研究所 | A fluorescent carbon dot with narrow half width of fluorescence emission peak and preparation method thereof |
| CN111848656B (en) * | 2020-06-24 | 2023-03-14 | 天津大学 | Ion-modified protoporphyrin gallium compound and preparation method and application thereof |
| CN111747398B (en) * | 2020-07-17 | 2022-05-24 | 江南大学 | A kind of red carbon dot material and its preparation method and application |
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