CN107011511A - A kind of protoporphyrin fluorescent carbon point and preparation method and application - Google Patents
A kind of protoporphyrin fluorescent carbon point and preparation method and application Download PDFInfo
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- CN107011511A CN107011511A CN201710404826.8A CN201710404826A CN107011511A CN 107011511 A CN107011511 A CN 107011511A CN 201710404826 A CN201710404826 A CN 201710404826A CN 107011511 A CN107011511 A CN 107011511A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
- C08G73/0206—Polyalkylene(poly)amines
- C08G73/0213—Preparatory process
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1441—Heterocyclic
- C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
Abstract
It is specially that protoporphyrin and polyethyleneimine PEI are reacted into 7 10h at 170 220 DEG C the present invention relates to a kind of protoporphyrin fluorescent carbon point and preparation method and application, protoporphyrin fluorescent carbon point is obtained after cooling, dialysis, filtering.The protoporphyrin fluorescent carbon point that the present invention is prepared not only has water-soluble well, also intactly remains the property of protoporphyrin, the light power that Porphyrin-Based Sensitizer is produced can effectively inactive yeast cell, play bactericidal action.This method has reactions steps simple, and reaction condition is gentle, dangerous small, the advantages of low toxicity.
Description
Technical field
The invention belongs to synthesis of polymer material and preparing technical field, it is related to a kind of protoporphyrin fluorescent carbon point and its preparation
Method.
Background technology
In recent years, because the abuse of antibiotic result in the appearance and propagation of " superbacteria ".So-called " superbacteria " is
Referring to these bacteriums has the characteristic of multidrug resistant for current antibiotic, and this is added very for the treatment of clinical wound infection
Big difficulty.Therefore new anti-infective strategy is developed extremely urgent.Light power antibacterial therapy method, is exactly wherein most prospect
One of new treatment, for being infected caused by bacterium, fungi and virus, good curative effect is shown especially for drug-fast bacteria infection.
Protoporphyrin is that well-known aromatic macrocyclic compounds are widely present in nature.Protoporphyrin is puce knot
Crystalline substance powder, is soluble in methanol, is insoluble in diluted acid, water insoluble, chloroform, ether and acetone etc..Research shows that porphyrin is photosensitive
The light power that agent is produced can effectively inactive yeast cell.Its action principle is due to that the protoporphyrin in culture medium is lived by light
Change generation active oxygen radical and make it that the permeability of somatic cells film is changed, and then destroy thalline normal physiological and be metabolized,
So as to cause the death of thalline.Protoporphyrin is water insoluble, greatly limit application of the protoporphyrin in biological field.And dissolving or
Well dispersed derivatives of porphyrin can more effectively kill bacterium than hydrophobicity or the derivatives of porphyrin of reunion.
In summary, it is necessary to develop a kind of method of the protoporphyrin antiseptic with good aqueous solubility.
The content of the invention
In view of this, it is an object of the invention to overcome the shortcoming that protoporphyrin is water insoluble, a kind of water miscible original is obtained
Porphyrin fluorescence carbon point, and propose a kind of preparation method and application of protoporphyrin fluorescent carbon point.
To reach above-mentioned purpose, the present invention provides following technical scheme：
1st, a kind of protoporphyrin fluorescent carbon point, it is characterised in that with following structure：
The positive integer of n=13~15
Further, the protoporphyrin fluorescent carbon point has bactericidal action to staphylococcus aureus and MRSE.
2nd, 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, count by weight, 20-33 parts of protoporphyrin, 50-80 parts of polyethyleneimine.
Further, molecular weight Mn=550~650 of the polyethyleneimine.
3rd, application of a kind of protoporphyrin fluorescent carbon point in terms of anti-Staphylococcus aureus and MRSE.
The beneficial effects of the present invention are：The protoporphyrin fluorescent carbon point prepared not only has water solubility well, also
The complete property for remaining protoporphyrin, the light power that Porphyrin-Based Sensitizer is produced can effectively inactive yeast cell, play and kill
Bacterium acts on.This method has reactions steps simple, and reaction condition is gentle, dangerous small, the advantages of low toxicity.
Brief description of the drawings
In order that the purpose of the present invention, technical scheme and beneficial effect are clearer, the present invention provides drawings described below and carried out
Explanation：
Fig. 1 is the reaction schematic diagram for preparing protoporphyrin fluorescent carbon point.
Fig. 2 is the ultra-violet absorption spectrum of the protoporphyrin fluorescent carbon point aqueous solution (C=0.125mg/mL).
Fig. 3 is the fluorogram of the 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 MRSE.
Embodiment
Below in conjunction with accompanying drawing, the preferred embodiments of the present invention are described in detail.
The protoporphyrin fluorescent carbon point of the present invention is made by reaction as shown in Figure 1：With protoporphyrin and PEI (Mn=550~
650) it is reactant, hydrothermal reaction kettle is reaction vessel, hydro-thermal reaction 7-10h is carried out at 170-220 DEG C；Then, product is treated
Room temperature is down to, product is put into 1000D bag filters is dialysed with deionized water, is filtered after the completion of dialysis with 0.22 μm of pin hole
Device filtering just can obtain protoporphyrin fluorescent carbon point.
Light dynamic pasteurization measure of merit is carried out with obtained protoporphyrin fluorescent carbon point.In the method, golden yellow Portugal is chosen
Grape coccus (S.aureus), Escherichia coli (E.coli), Pseudomonas aeruginosa (P.aeruginosa) and MRSE
(S.epidermidis) as the representative of gram-positive bacteria and negative bacterium, the sterilization for studying protoporphyrin fluorescent carbon point is made
With.
Embodiment 1
The preparation method of protoporphyrin fluorescent carbon point 1, comprises the following steps：
1) match somebody with somebody 2mg/mL PEI (Mn=550~650) solution 10mL, weigh 10mg protoporphyrins, hydro-thermal is added to together anti-
Answer in kettle, 10h is reacted at 220 DEG C；
2) after the completion of reacting, room temperature is cooled to, dialysis 3 days is carried out with 1000D bag filters, afterwards again with 0.22 μm of pin hole
Filter is filtered to the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 2
The preparation method of protoporphyrin fluorescent carbon point 2, comprises the following steps：
1) match somebody with somebody 2mg/mL PEI (Mn=550~650) solution 10mL, weigh 10mg protoporphyrins, hydro-thermal is added to together anti-
Answer in kettle, 8h is reacted at 220 DEG C；
2) after the completion of reacting, room temperature is cooled to, dialysis 3 days is carried out with 1000D bag filters, afterwards again with 0.22 μm of pin hole
Filter is filtered to the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 3
The preparation method of protoporphyrin fluorescent carbon point 3, comprises the following steps：
1) match somebody with somebody 2mg/mL PEI (Mn=550~650) solution 10mL, weigh 10mg protoporphyrins, hydro-thermal is added to together anti-
Answer in kettle, 8h is reacted at 180 DEG C；
2) after the completion of reacting, room temperature is cooled to, dialysis 3 days is carried out with 1000D bag filters, afterwards again with 0.22 μm of pin hole
Filter is filtered to the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 4
The preparation method of protoporphyrin fluorescent carbon point 4, comprises the following steps：
1) match somebody with somebody 2mg/mL PEI (Mn=550~650) solution 10mL, weigh 15mg protoporphyrins, hydro-thermal is added to together anti-
Answer in kettle, 10h is reacted at 220 DEG C；
2) after the completion of reacting, room temperature is cooled to, dialysis 3 days is carried out with 1000D bag filters, afterwards again with 0.22 μm of pin hole
Filter is filtered to the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 5
The preparation method of protoporphyrin fluorescent carbon point 5, comprises the following steps：
1) match somebody with somebody 4mg/mL PEI (Mn=550~650) solution 10mL, weigh 10mg protoporphyrins, hydro-thermal is added to together anti-
Answer in kettle, 10h is reacted at 220 DEG C；
2) after the completion of reacting, room temperature is cooled to, dialysis 3 days is carried out with 1000D bag filters, afterwards again with 0.22 μm of pin hole
Filter is filtered to the product after dialysis, and gained filtrate is protoporphyrin fluorescent carbon point.
Embodiment 6
The preparation method of protoporphyrin fluorescent carbon point 6, comprises the following steps：
1) match somebody with somebody 4mg/mL PEI (Mn=550~650) solution 10mL, weigh 20mg protoporphyrins, hydro-thermal is added to together anti-
Answer in kettle, 10h is reacted at 220 DEG C；
2) after the completion of reacting, room temperature is cooled to, dialysis 3 days is carried out with 1000D bag filters, afterwards again with 0.22 μm of pin hole
Filter is filtered to 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 the protoporphyrin fluorescent carbon point aqueous solution (C=0.125mg/mL), can from figure
Go out, the feature ultraviolet absorption peak of protoporphyrin occurred in that in the range 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 the protoporphyrin fluorescent carbon point aqueous solution (C=0.125mg/mL), it can be seen 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 that the protoporphyrin after illumination can be produced
ROS, produced ROS acts on colored indicator.After illumination 2min, ultraviolet peak value is almost unchanged, it was demonstrated that protoporphyrin fluorescent carbon point
It is fastish to produce oxygen radical.Protoporphyrin fluorescent carbon point produces active oxygen radical by photoactivation and causes somatic cells
The permeability of film is changed, and then destroys the metabolism of thalline normal physiological, is caused the death of thalline, is further demonstrated made
Standby carbon point has bactericidal action.
Embodiment 7
Bactericidal effect detection is carried out using protoporphyrin fluorescent carbon point, particular content is as follows：
1. the culture of bacterium：The cryopreservation tube equipped with bacterial strain is taken out from -20 DEG C of refrigerators, is allowed to melt, is then inoculated in pancreas
It is standby in tryptone soya broth (Tryptone soya broth, TSB) culture medium, and in 37 DEG C of shaking table cultures.Typically carry
The previous day cultivates.
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
After culture medium, cultivate under appropriate conditions, timing sampling determines cell quantity.Using the time as abscissa, with pair of viable count
Number is ordinate, can draw a growth curve, and curve shows four periods of bacterial growth breeding：Lag phase, logarithmic phase,
Stationary phase, decline phase.Concretely comprise the following steps (following equipment and liquid used sterilize in advance)：
(1) bacterial strain is first diluted to 1 × 10 with phosphate buffered saline solution (Phosphate buffer saline, PBS)5；
(2) take two 4mL centrifuge tube to be designated as No. 1 No. 2,1mL bacterial solutions and 2mL protoporphyrins are added in No. 1 centrifuge tube
Fluorescent carbon point solution, No. 2 centrifuge tubes add 1mL bacterial solutions and 2mL PBS, are well mixed；
(3) four cuvettes are taken to be designated as No. 3 No. 4 No. 5 No. 6, No. 3 No. 4 each mixed solutions for adding No. 1 centrifuge tube of 1mL, 5
Numbers No. 6 each mixed solutions for adding No. 2 centrifuge tubes of 1mL；
(4) laser for being 635nm with wavelength irradiates 10min, 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) 6 4mL centrifuge tube is taken to be designated as No. 1 No. 2 No. 3 No. 4 No. 5 No. 6 again, it is each to add 2mL TSB, 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), it is well mixed；
(7) bacterial solution of above-mentioned 1-6 centrifuge tubes is added in 96 orifice plates with liquid-transfering gun, a sample one is arranged, one
The μ L of hole 100；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, the logarithm using viable count (OD) does growth curve of bacteria as ordinate.
Fig. 5 is SA, SE growth curve：(a) growth curves of the SA in PBS under different illumination intensity, (b) SA is in former porphin
Growth curve in quinoline carbon point (C=0.52mg/mL) solution under different illumination intensity, (c) SE is in PBS under different illumination intensity
Growth curve, growth curves of (d) SE in protoporphyrin carbon point (C=0.52mg/mL) solution under different illumination intensity.From figure
As can be seen that compared to blank sample, protoporphyrin fluorescent carbon point is to staphylococcus aureus (S.aureus) and epidermis grape ball in 5
Bacterium (S.epidermidis) shows very strong bactericidal effect.
Sterilization test shows：Protoporphyrin fluorescent carbon point is to staphylococcus aureus (S.aureus) and MRSE
(S.epidermidis) there is obvious bactericidal action.
It is last what deserves to be explained is, preferred embodiment above is merely illustrative of the technical solution of the present invention and unrestricted, to the greatest extent
The present invention is described in detail by above preferred embodiment for pipe, it is to be understood by those skilled in the art that can
So that various changes are made to it in the form and details, the model limited without departing from claims of the present invention
Enclose.
Claims (5)
1. a kind of protoporphyrin fluorescent carbon point, it is characterised in that with following structure：
The positive integer of n=13~15.
2. a kind of preparation method of protoporphyrin fluorescent carbon point as claimed in claim 1, it is characterised in that：Using hydro-thermal method by original
Porphyrin and polyethyleneimine react 7-10h at 170-220 DEG C, and protoporphyrin fluorescent carbon point is obtained after cooling, dialysis, filtering.
3. a kind of preparation method of protoporphyrin fluorescent carbon point as claimed in claim 2, it is characterised in that：Count by weight,
20-33 parts of protoporphyrin, 50-80 parts of polyethyleneimine.
4. a kind of preparation method of protoporphyrin fluorescent carbon point as claimed in claim 2, it is characterised in that：The polyethyleneimine
Molecular weight Mn=550~650.
5. a kind of protoporphyrin fluorescent carbon point described in claim 1 is in terms of anti-Staphylococcus aureus and MRSE
Using.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108373472A (en) * | 2018-04-25 | 2018-08-07 | 西南大学 | A kind of sterilization material and its preparation method and application containing protoporphyrin |
| CN108904801A (en) * | 2018-07-20 | 2018-11-30 | 中山大学 | A kind of multifunctional nano vesica and preparation method thereof |
| CN109468130A (en) * | 2018-12-27 | 2019-03-15 | 武汉工程大学 | A kind of preparation method of metal-doped fluorescent carbon quantum dot |
| CN109943326A (en) * | 2019-04-23 | 2019-06-28 | 中国科学院理化技术研究所 | Fluorescent carbon quantum dot and its preparation method and application based on biomass |
| CN111004623A (en) * | 2019-12-20 | 2020-04-14 | 河北科技大学 | Porphyrin fluorescent material and preparation method thereof |
| CN111747398A (en) * | 2020-07-17 | 2020-10-09 | 江南大学 | Red carbon dot material and preparation method and application thereof |
| CN111848656A (en) * | 2020-06-24 | 2020-10-30 | 天津大学 | Ion-modified protoporphyrin gallium compound and preparation method and application thereof |
| CN113122245A (en) * | 2019-12-30 | 2021-07-16 | 中国科学院理化技术研究所 | Fluorescent carbon dot with narrow fluorescence emission peak half-peak width and preparation method thereof |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108373472A (en) * | 2018-04-25 | 2018-08-07 | 西南大学 | A kind of sterilization material and its preparation method and application containing protoporphyrin |
| CN108904801A (en) * | 2018-07-20 | 2018-11-30 | 中山大学 | A kind of multifunctional nano vesica and preparation method thereof |
| CN109468130A (en) * | 2018-12-27 | 2019-03-15 | 武汉工程大学 | A kind of preparation method of metal-doped fluorescent carbon quantum dot |
| 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 | Fluorescent carbon quantum dot and its preparation method and application based on biomass |
| CN111004623A (en) * | 2019-12-20 | 2020-04-14 | 河北科技大学 | Porphyrin fluorescent material and preparation method thereof |
| CN111004623B (en) * | 2019-12-20 | 2023-07-18 | 河北科技大学 | Porphyrin fluorescent material and preparation method thereof |
| CN113122245A (en) * | 2019-12-30 | 2021-07-16 | 中国科学院理化技术研究所 | Fluorescent carbon dot with narrow fluorescence emission peak half-peak width and preparation method thereof |
| CN113122245B (en) * | 2019-12-30 | 2023-02-17 | 中国科学院理化技术研究所 | Fluorescent carbon dot with narrow fluorescence emission peak half-peak width and preparation method thereof |
| CN111848656A (en) * | 2020-06-24 | 2020-10-30 | 天津大学 | Ion-modified protoporphyrin gallium compound and preparation method and application thereof |
| CN111848656B (en) * | 2020-06-24 | 2023-03-14 | 天津大学 | Ion-modified protoporphyrin gallium compound and preparation method and application thereof |
| CN111747398A (en) * | 2020-07-17 | 2020-10-09 | 江南大学 | Red carbon dot material and preparation method and application thereof |
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