CN105030819B - A kind of purposes of 3- hydroxyl -4- pyridinone macromolecule iron chelating agent - Google Patents
A kind of purposes of 3- hydroxyl -4- pyridinone macromolecule iron chelating agent Download PDFInfo
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- CN105030819B CN105030819B CN201510395542.8A CN201510395542A CN105030819B CN 105030819 B CN105030819 B CN 105030819B CN 201510395542 A CN201510395542 A CN 201510395542A CN 105030819 B CN105030819 B CN 105030819B
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Abstract
The invention discloses a kind of purposes of 3- hydroxyl -4- pyridinone macromolecule iron chelating agent, the macromolecule iron chelating agent has antibacterial action, can be used as anti-biotic material use, wherein especially having excellent antibacterial effect to methicillin-resistant staphylococcus aureus.The present invention utilizes the tertiary amine in macromolecule iron chelating agent or the cation simulation antibacterial peptide mechanism of secondary amine cation structure formation, negative electrical charge regional interaction on positive charge region and cell membrane, herein in connection with iron chelating agent for the chelation of ferro element, destroy bacterium surrounding normal growing environment, the growth of bacterium is caused to be suppressed, make it can not growth and breeding, its macromolecular characteristic of 3- hydroxyl -4- pyridinone macromolecule iron chelating agent of the invention is not absorbed by the skin, toxic side effect is not generated, can be used as a kind of anti-biotic material of dual antibacterial action.
Description
One, technical field
The present invention relates to a kind of purposes of chelating agent, specifically a kind of 3- hydroxyl -4- pyridinone macromolecule iron chela
The purposes of mixture.
Two, background technique
Anti-biotic material refer to itself have kill or inhibit microbial function a kind of new function material, medical field,
There is extremely wide application prospect in the fields such as household supplies, household electrical appliance, food packaging, require increasingly in people environmental sanitation
Today of raising, the application of anti-biotic material is by more extensive concern.Country's antibacterial, sterilization material generally use antibiosis at present
Element, such as o-phenyl phenol, methylisothiazolinone and triclosan, although antibiotic have for wildtype bacterium it is higher
Antibacterial activity, but it does not have any effect for the strain of drug resistance.Now, the abuse of antibiotic has reached very seriously
Step, the abuse of antibiotic will lead to the extremely strong superbacteria of drug resistance and generate, if such case continues to deteriorate, it is likely that
Make facing mankind when infecting without the available condition of medicine.In addition for antibiotic due to being small molecule, it can be with blood circulation to human body
Some positions not being infected by bacterial, to bring biggish toxic side effect.Antibiotic is for idiosyncrasy
The person is easy to produce allergic reaction, may be fatal when allergic reaction is serious.And used antibiotics fungicide enters
Water circulation system is also secondary pollution.After being inhibited with antibacterials or killing sensitive bacterium, some insensitive bacteriums or
Mould but breed by continued growth, causes new infection, i.e. " suprainfection ", this is many in the patient of long-term Domain of Abuse Antibiotics
See, it is high to will lead to treatment difficulty, case fatality rate.
Microorganism needs to absorb the iron ion in environment to ensure a series of progress of its intracorporal physiological activity, such as
The reduction of oxygen in ATP synthesis process, the reduction of DNA premise substance nucleotide, the synthesis of ferroheme and other a series of heavy
The reaction wanted requires the participation of iron.Meanwhile iron is also a kind of important nutrient of microorganism, it is permitted for keeping intracellular
The activity of multienzyme is essential.In order to obtain ferro element necessary to the activity of sustaining life, microbes synthesize in vivo and divide
One kind is secreted to Fe3+With relatively organic micromolecule compound --- the siderophore of complexing power by force, so if having in ambient enviroment pair
The very high chelating agent of iron compatibility and the siderophore of microorganism compete iron, prevent bacterium from accessing enough ferro elements, give birth to
Length will be suppressed, just can not growth and breeding.So synthesize it is a kind of with it is not being absorbed by the body, there is high affine iron energy
Power, macromolecule iron chelating agent that iron capacity is big will have certain application prospect to treatment microbial infectious diseases.From 20
The sixties in century, it was golden yellow since American-European first discovery methicillin-resistant staphylococcus aureus (MRSA) nosocomial infection
Shared ratio is higher and higher in color staphy lococcus infection, it has also become important one of the pathogenic bacteria of nosocomial infection.Because it propagates way
Diameter is extensive, outbreak of epidemic in Yi Zhi institute；Again since its is pathogenic strong, become the difficult point of clinical treatment in multidrug resistant.Cause
This, the infection for preventing and treating MRSA is important topic that Nosocomiology is faced.
Antibacterial peptide is a kind of polypeptide generated through biological Immune inducing in vivo, is the component part of congenital immunity response.It has
Thermal stability and high-efficiency antimicrobial activity.Start within 2003, the states such as the U.S., Japan begin with seminar successively and are engaged in poly- polypeptide people
The research of work antibacterial peptide；2005, the Wong professor seminar of UCLA university, the U.S. took to polymer electrolyte artificial antimicrobial peptide and grinds
Study carefully；2009, Univ Michigan-Ann Arbor USA Kuroda seminar started from molecular biology angle to polymer electrolyte artificial antimicrobial peptide
Research, and inquired into influence of the chemical environment for antibacterial effect of functional groups in detail.Utilize the hand of Polymer Synthesizing
Section, simulates the molecular structure of natural antibacterial peptide, can synthesize cheap and be not easy biodegradable artificial synthesized polymer, especially
It is that the cation type polymer designed by structure can interact with cell membrane surface, makes the permeability of bacterial membrane
Change, the negative electrical charge regional interaction on positive charge region therein and cell membrane, makes high molecular hydrophobic side insertion cell
In the lipid film of film, and then change lipid membrane structure, form membrane potential after acting on cell membrane, break acid-base balance, influences
Osmotic balance inhibits respiration, then plays good antibacterial action.
Either gram-positive bacteria or Gram-negative bacteria, their growth require iron, if in conjunction with macromolecule
The characteristic that the iron affinity and macromolecular of iron chelating agent are not absorbed by human skin, in addition utilizing the positive charge antibacterial of antibacterial peptide
The mechanism of action, it will obtain a kind of very effective dual anti-biotic material.
Three, summary of the invention
The present invention is intended to provide a kind of purposes of 3- hydroxyl -4- pyridinone macromolecule iron chelating agent, wherein 3- hydroxyl -4-
Pyridinone macromolecule iron chelating agent is by polymethylacrylic acid glycidol ether-ether and the 3- hydroxyl -4- pyridine containing amido
Ketone compounds occur ring-opening reaction and are made, and utilize the tertiary amine or secondary amine in 3- hydroxyl -4- pyridinone macromolecule iron chelating agent
Positive electricity minor structure, the negative electrical charge regional interaction on positive charge region and bacterial cell membrane inserts high molecular hydrophobic side
Enter in the lipid film of cell membrane, and then change lipid membrane structure, form membrane potential after acting on cell membrane, it is flat to break soda acid
Weighing apparatus influences osmotic balance, inhibits respiration, in addition the high-speed rail affinity of 3- hydroxyl -4- pyridine compounds, absorbs
The microelement of bacterium surface, especially trivalent ferro element are suppressed its growth.
The structural formula of 3- hydroxyl -4- pyridinone macromolecule iron chelating agent of the present invention is as follows:
The value range 20-200 of n.
3- hydroxyl -4- pyridinone macromolecule iron chelating agent of the present invention be by polymethylacrylic acid glycidol ether-ether with contain
Ring-opening reaction occurs for the 3- hydroxyl -4- pyridine compounds and epoxy group for having amido, by 3- hydroxyl -4- pyridinone chemical combination
Object is covalently attached to macromolecule iron (III) chelating agent that polymethylacrylic acid glycidol ether ester side chain obtains, and specifically prepares
Journey is as follows:
By the polymethylacrylic acid glycidol ether-ether (M of 100 mass partsn=1000-10000) it is added in single port bottle,
Then the anhydrous n,N-Dimethylformamide dissolution of 200-300 mass parts is added, adds 50-100 mass parts triethylamine and 100-
1000 mass parts contain the 3- hydroxyl -4- pyridine compounds of amido, are kept for 55-80 DEG C reaction 2-36 hours, to reaction solution
The middle ether sedimentation products that 2000-3000 mass parts are added, filtering is dry after precipitating, and it is anhydrous that 200-300 mass parts are then added
N,N-Dimethylformamide dissolution is then placed in bag filter to dialyse 3-5 days and (changes four distilled water, bag filter retention point daily
Son amount obtains macromolecule iron (III) chelating 3000) to remove the excessive 3- hydroxyl -4- pyridine compounds containing amido
Agent.
3- hydroxyl -4- the pyridine compounds containing amido are selected from 1- (three oxygen tridecane of amino -4,7,10-
Base) -2- methyl -3- hydroxyl -4- (1H)-pyridone (1), 1- amino-ethyl -2- methyl -3- hydroxyl -4- (1H)-pyridone (2),
1- methylaminopropyl -2- methyl -3- hydroxyl -4- (1H)-pyridone (3) or 2- methyl -3- hydroxyl -4- (1H) -5- methylamino first
Base-pyridone (4), structural formula is as follows:
3- hydroxyl -4- pyridinone macromolecule iron chelating agent of the present invention has antibacterial action, can be used as anti-biotic material use,
Especially wherein there is excellent antibacterial effect to methicillin-resistant staphylococcus aureus.
Compared with the prior art, the present invention has the following advantages:
1,3- hydroxyl -4- pyridinone macromolecule iron chelating agent of the present invention, not only combines the cation of natural antibacterial peptide
Antibacterial Mechanism destroys bacterium surrounding normal growing environment, can be used as herein in connection with iron chelating agent for the chelation of ferro element
A kind of anti-biotic material of double action.
2, present invention incorporates good, the obtained materials nontoxic, with material compatibility of polymethylacrylic acid glycidol ether-ether
Material iron chelating capacity greatly promotes, and is up to 1196 μm of ol/g, bacterium can be effectively absorbed when using as anti-biotic material
Ferro element necessary to growing, causes the growth of bacterium to be suppressed, makes it can not growth and breeding.
3,3- hydroxyl -4- pyridinone macromolecule iron chelating agent of the present invention utilizes the tertiary amine or secondary amine cation in structure
Structure is adsorbed on the bacterial cell membrane with negative electrical charge, is covered on film just as carpet when quantity is reached a certain level
Surface with the mode of action targeting attack of " detergent ", destroys bacterial cell membrane and causes cell death, utilizes carpet model
(carpet-like) function cells film.The model mechanism of action will not have any effect to the human cell membrane close to electroneutral,
It tests through hemolytic experiment, has no toxic side effect to epithelial cell, and good water solubility, can be configured to antiseptic solution and be widely used,
Its macromolecular characteristic is not absorbed by the skin, and does not generate toxic side effect, if being added in material with antibacterial additives can solve
Small molecule antibacterial agent is added to the problem of high molecular material resistance to migration difference at present.
Four, Detailed description of the invention
Fig. 1 is that height prepared by ferric ion content and the embodiment of the present invention 1 is measured using UV-VIS spectrophotometry
The absorbance relational graph of molecule iron chelating agent 8K21 aqueous solution.
Fig. 2 is the macromolecule iron chelating agent 7K21 and 7TD of Example 1 and Example 2 of the present invention preparation in air incubator
To the histogram of methicillin-resistant staphylococcus aureus sterilizing rate and concentration relationship after hatching 24 hours.
The epithelial cell poison that Fig. 3 is macromolecule the iron chelating agent 7K21 and 7TD of Example 1 and Example 2 of the present invention preparation
Property test result figure.
Five, specific embodiment
Embodiment 1:
By 0.2g polymethylacrylic acid glycidol ether-ether PGMA1 (Mn=12800gmol-1) and 1.3g 1- (amino-
4,7,10- tri- oxygen tridecyls) -2- methyl -3- hydroxyl -4- (1H)-pyridone is added in single port bottle, be then added 8mL without
The dissolution of water n,N-Dimethylformamide, adds 1mL triethylamine, is kept for 55 DEG C react 36 hours, 80mL is added into reaction solution
Ether sedimentation products, filtering is dry after precipitating, and is put into dialyse 3 days in bag filter and (changes four water, dialysis bag retention molecular weight daily
Macromolecule iron chelating agent 7K21 is obtained 3000) to remove excessive monomer, wherein small molecule chelators are in macromolecule iron chelating agent
In content be about 70wt%.0.1 gram of 7K21 is taken to be dissolved separately in 1mL water and acetone, butanone, N,N-dimethylformamide, two
In first sulfoxide, solution can be formed, is left in the solution without any insoluble matter.Poly- methyl-prop is calculated by nuclear magnetic resonance spectroscopy
The number-average molecular weight M of macromolecule iron chelating agent is calculated in repetitive unit number in olefin(e) acid glycidol ether-ethern=50100.
If keeping other conditions constant, 0.2g PGMA1 in reactant is replaced by 0.2g polymethyl acid glycidyl
Ether-ether PGMA2 (Mn=10300g mol-1), macromolecule iron chelating agent 8K21 can be obtained, wherein small molecule chelators are in macromolecule
Content in iron chelating agent is about 70wt%.
Embodiment 2:
By 0.2g polymethylacrylic acid glycidol ether-ether PGMA2 (Mn=10300gmol-1) and 0.29g1- methylamino
Propyl -2- methyl -3- hydroxyl -4- (1H)-pyridone is added in single port bottle, and the anhydrous N of 8mL, N- dimethyl formyl is then added
Amine dissolution, is then added 1mL triethylamine, is kept for 80 DEG C react 2 hours, 80mL ether sedimentation products, mistake are added into reaction solution
It is dry after filter precipitating, removal in 3 days (changing four distilled water, dialysis bag retention molecular weight 3000 daily) of dialysing is put into bag filter
Excessive monomer obtains macromolecule iron chelating agent 8K41, and wherein content of the small molecule chelators in macromolecule iron chelating agent is about
58wt%.
If keeping other conditions constant, by 0.2g PGMA2,0.29g1- methylaminopropyl -2- methyl -3- hydroxyl in reactant
Base -4- (1H)-pyridone is replaced by 0.2g polymethylacrylic acid glycidol ether-ether PGMA1,0.24g 2- methyl -3- hydroxyl respectively
Base -4- (1H) -5- Methyaminomethyl-pyridone, can be obtained macromolecule iron chelating agent 7TD, wherein small molecule chelators are in high score
Content in sub- iron chelating agent is about 70wt%.Weight in polymethylacrylic acid glycidol ether-ether is calculated by nuclear magnetic resonance spectroscopy
Multiple unit number, is calculated the number-average molecular weight M of macromolecule iron chelating agentn=33100.
Application Example:
Selection above-described embodiment 1 synthesizes the measurement that obtained 8K21 carries out iron chelating capacity, long to probe into different molecular weight
The chelated iron macromolecule of degree, iron ion (III) chelating capacity for the macromolecule iron chelating agent that different ligands are formed.Concrete operations are such as
Under: it takes dried chelated iron macromolecule to weigh respectively (5.39mg 8K21), 0.4mL dimethyl sulfoxide is added and forms solution,
It takes the 5 above-mentioned solution of μ L to be added to 1.4mL water again and forms the high molecular aqueous solution of chelated iron (amount of dimethyl sulfoxide is ignored),
The concentration that high-molecular compound 8K21 is obtained by calculation is 48.13 μ g/mL.This experiment uses ferric chloride in aqueous solution
(0.8953mM,FeCl3) titrated, the 5 microlitres of ferric chloride in aqueous solution of titration in every 5 minutes pass through ultraviolet-visible absorption spectroscopy
(250-600nm) measures the iron chelating capacity of compound, because after high-molecular compound and iron ion chelating, visible
There is absorption in optical range, with the increase of iron chelating agent concentration, UV-visible absorbance increases, when iron ion and macromolecule shape
At chelating agent saturation when, absorbance will no longer change, and can be calculated at this time according to the content of iron ion in ferrous solution is added dropwise
High molecular iron chelating capacity, the iron chelating capacity for finally measuring 8K21 is 1196 μm of ol/g.Fig. 1 is using ultraviolet-visible point
Light photometry measures the extinction of macromolecule iron chelating agent 8K21 aqueous solution prepared by ferric ion content and the embodiment of the present invention 1
Spend relational graph.
Strain inoculated is frozen in (TSB, 2.5mL) in fresh soybean protein, is trained in 37 DEG C of constant incubator later
It supports 18 hours.40 μ L culture solutions are therefrom taken, are diluted to (4mL) in the TSB containing 100 μ g/mL ampicillins, then at 37 DEG C
It is cultivated in constant incubator about 3 hours.Centrifugation makes bacterial strain settle (staphylococcus aureus revolving speed 10000rpm, other strains
For 5000rpm, it is centrifuged 5min), supernatant is removed, utilizes 2- [4- (2- ethoxy) -1- piperazinyl] esilate later
(HEPES) buffer (10mM HEPES, 150mM NaCl, pH 7.4) washes remaining bacterial strain twice.Obtained bacterium solution is put into 96
Sterilization experiment is carried out in microwell plate, using the method for doubling dilution, by 3- hydroxyl -4- pyridinone macromolecule iron chelating agent
HEPES buffer solution is added in 96 microwell plates.Macromolecule iron chelating agent is diluted to 150 μ L using HEPES, 50 μ L bacterium are being added
Liquid.Microwell plate is placed in 3 hours of culture in 37 DEG C of constant incubator, it will be thin in 96 microwell plates by 10 times of dilution methods
Bacterium dilution, is cultivated 12 hours in M ü eller-Hinton (MH) agar plate later, and the number of strains of control reference (PC) exists
Between 80~120.Table 1 is the macromolecule iron chelating agent concentration data table that the antibacterial experiment uses.Fig. 2 is the embodiment of the present invention 1
The macromolecule iron chelating agent 7K21 and 7TD prepared with embodiment 2 is after air incubator is hatched 24 hours to methicillin-resistant gold
The histogram of staphylococcus aureus sterilizing rate and concentration relationship.
Table 1
Table 2 be various concentration macromolecule iron chelating agent 7K21 and 7TD air incubator hatch 24 hours after to resistance to first
Oxygen XiLin staphylococcus aureus sterilizing rate tables of data.As can be seen from the table, macromolecule iron chelating agent 7K21 and 7TD exists respectively
There can be 99.9% sterilizing rate under the concentration of 6 μM (0.301mg/mL) and 12 μM (0.397mg/mL).
Table 2
Using 2 times of dilution methods, the PBS that 3- hydroxyl -4- pyridinone macromolecule iron chelating agent is prepared in 96 microwell plates is slow
Rush solution.0.1mL mouse epithelial cells liquid is taken later, washs mouse haemocyte using phosphate buffered saline (PBS) (PBS) buffer.
Mouse haemocyte is diluted using PBS later, guarantees that mouse hematocrite concentration is about 2.5 × 104cells/μL.160 μ L are small
The mixing of the PBS buffer solution of mouse haemocyte dispersion liquid and 40 μ L3- hydroxyl -4- pyridinone macromolecule iron chelating agents, reference are used
50% Qula pine mixes with mouse cell, cultivates 1 hour in 37 DEG C of constant incubator, and control shaking table shakes rate and is
200rpm.Then the mixed liquor in microwell plate is centrifuged 5min with the revolving speed of 800rcf, 50 μ L is taken to be added in 96 microwell plates,
Its absorbance is surveyed under 414nm wavelength, and is defined as 100% with the absorbance of mouse cell mixing sample with 50% Qula pine.Fig. 3
For the epithelial cell Toxic test results figure of macromolecule iron chelating agent 7K21 and 7TD prepared by the embodiment of the present invention 1 and 2.The figure
Show that macromolecule iron chelating agent 7TD has smaller cytotoxicity compared with 7K21,7TD is substantially without cytotoxicity.
Claims (3)
1. a kind of 3- hydroxyl -4- pyridinone macromolecule iron chelating agent is preparing the application in anti-biotic material, it is characterised in that: institute
Macromolecule iron chelating agent is stated to use as anti-biotic material；
The macromolecule iron chelating agent are as follows:
The value range 20-200 of n.
2. application according to claim 1, it is characterised in that: the macromolecule iron chelating agent has dual antibacterial action,
On the one hand inhibit bacterium respiration, on the other hand by absorption bacterium surface trivalent ferro element make the growth of bacterium by
Inhibit.
3. application according to claim 1 or 2, it is characterised in that:
The macromolecule iron chelating agent has excellent antibacterial effect to methicillin-resistant staphylococcus aureus.
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| CN1926135A (en) * | 2003-11-20 | 2007-03-07 | 阿普泰克斯公司 | Cycloalkyl derivatives of 3-hydroxy-4-pyridinones |
| CN103228653A (en) * | 2010-09-24 | 2013-07-31 | 盐野义制药株式会社 | Substituted polycyclic carbamoyl pyridone derivative prodrug |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1926135A (en) * | 2003-11-20 | 2007-03-07 | 阿普泰克斯公司 | Cycloalkyl derivatives of 3-hydroxy-4-pyridinones |
| CN103228653A (en) * | 2010-09-24 | 2013-07-31 | 盐野义制药株式会社 | Substituted polycyclic carbamoyl pyridone derivative prodrug |
Non-Patent Citations (1)
| Title |
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| 3-羟基-4-吡啶酮衍生物的合成及与Fe3+螯合性能;马越等;《精细化工》;20140315;第31卷(第3期);第294-298页 |
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