CN109553657A - A kind of non-perfect peptide amphiphile W4 and its preparation method and application - Google Patents
A kind of non-perfect peptide amphiphile W4 and its preparation method and application Download PDFInfo
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- CN109553657A CN109553657A CN201811452528.7A CN201811452528A CN109553657A CN 109553657 A CN109553657 A CN 109553657A CN 201811452528 A CN201811452528 A CN 201811452528A CN 109553657 A CN109553657 A CN 109553657A
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- peptide
- perfect
- antibacterial peptide
- arginine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/06—Linear peptides containing only normal peptide links having 5 to 11 amino acids
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Abstract
The present invention provides a kind of non-perfect peptide amphiphile W4 and its preparation method and application.The sequence of non-perfect peptide amphiphile W4 is as shown in SEQ ID No.1.Preparation method: select 4 arginine as positive charge amino acid and 5 tryptophans as hydrophobic amino acid, two arginine are inserted into tryptophan as a unit, helical wheel projects to form " four sides " conformation, that is two hydrophobic surfaces and two hydrophilic surfaces, and four arginine form two pairs of intramolecular hydrogen bonds, the derived peptide is named as W4, the present invention is in the case where improving antibacterial peptide bactericidal activity, greatly reduce the hemolytic activity of antibacterial peptide, improve selectivity of the antibacterial peptide between bacterial cell and mammalian cell, improving it becomes the development potentiality of antibiotic substitute.
Description
Technical field
The invention belongs to field of biotechnology, and in particular to a kind of non-perfect peptide amphiphile W4 and preparation method thereof and answer
With.
Background technique
Antibiotic will trace back to nineteen forty-three as the application of feed addictive, some antibiotic fermentations of American's first discovery
Residue can promote the growth of pig.American Cunha and Stokstad apply penicillin to carry out system in animal for the first time within 1949
Comparative experiments,
As a result confirm there is preferable diseases prevention and growth promoting function to animal using antibiotic.Nineteen fifty U.S.'s food and drug
The antibiotic such as management board's official approval penicillin are applied in feed.Because having the growth for promoting animal, rate of body weight gain is improved；It mentions
The reproductive performance of high animal；Survival rate is improved, morbidity is reduced；The effects of utilization rate of raising feed, save the cost, antibiotic is made
For a kind of non-nutritive feed addictive and obtain rapidly, be widely applied.Antibiotic is applied to bring people greatly sharp
While beneficial, its abuse also brings increasing trouble to the mankind.Currently, all there is phase in all Conventional antibiotics
The pathogenic strain of the drug resistance answered, the resistance problems of pathogenic bacteria threaten people's health with having got worse.It finds completely new
The antibacterial of type is an effective way for solving resistance problems.
Antibacterial peptide is that animal body resists external microbe infringement and removes the small molecule polypeptide of vivo mutations cell,
Have many advantages, such as broad-spectrum antiseptic, nontoxicity, have no drug resistance, noresidue with it is pollution-free, and its thermal stability is good, additive capacity
It is small, the needs of livestock product safety are complied fully with, are suitble to use in feed preparation, it is great to have as feed addition of new generation
The potential quality of agent.And the antifungal mechanism of antibacterial peptide is different from antibiotic, and antibacterial peptide is to make cell by destroying the cell membrane of bacterium
Dissolve things inside leaks to kill cell, so bacterium is not likely to produce drug resistance.More importantly, antibacterial peptide is several to eukaryocyte
It does not act on, act only on prokaryotic cell and the eukaryocyte of lesion occurs.It is entirely possible to take according to above-mentioned reason antibacterial peptide
Become a kind of novel, efficient, less toxic, noresidue antibacterial material for antibiotic, has broad application prospects.But it is natural
Cationic antibacterial peptide it is not flawless, most of natural antibacterial peptide there are antibacterial activities not strong, antimicrobial spectrum relative narrower is closed
There is certain toxicity to eucaryote at higher cost, part antibacterial peptide, have to the same of the high killing activity of pathogenic microorganism
When the deficiencies of being usually associated with to Eukaryotic haemocylolysis and to protease-sensitive.Therefore its activity and maximum how to be improved
Degree reduce its toxicity become antibacterial peptide molecular modification purpose, and at present antimicrobial peptide medicaments exploitation difficult point and wish institute
?.So making it have higher bacteriostatic activity by the way that antibacterial peptide is transformed, reduces its toxicity and have become the hot spot studied now.
Summary of the invention
The purpose of the present invention is to provide a kind of non-perfect peptide amphiphile W4 and its preparation method and application；The antibacterial peptide pair
Gram-negative bacteria activity is higher and cytotoxicity is relatively low.
The purpose of the present invention is realized by following technology: a kind of non-perfect peptide amphiphile W4, sequence such as SEQ ID No.1
It is shown.
The present invention also has following technical characteristic:
1, non-perfect peptide amphiphile as described above a kind of completely new W4's the preparation method is as follows: 4 arginine is selected to make
Charge amino acid and 5 tryptophans be positive as hydrophobic amino acid, two arginine are inserted into tryptophan, spiral shell as a unit
Spinning roller projects to form " four sides " conformation, i.e. two hydrophobic surfaces and two hydrophilic surfaces, and four arginine form two pairs of intramoleculars
Hydrogen bond, the derived peptide are named as W4, and sequence is as shown in SEQ No.1.
2, a kind of non-perfect peptide amphiphile W4 as described above treats gram positive bacterial infection disease medicament in preparation
In application.
Beneficial effects of the present invention and advantage are as follows: it is simple by this method experimental technique, obtained antibacterial peptide is carried out
Antibacterial and hemolytic activity detection, find W4 to 3 kinds of Gram-negative bacterias such as Escherichia coli, salmonella typhimurium, Pseudomonas aeruginosa
The positive bacterias such as strain and staphylococcus aureus, staphylococcus epidermis, methicillin-resistant staphylococcus aureus have significantly
Inhibiting effect, the therapeutic index of W4 is up to 80.76, and has very low hemolytic activity, improves antibacterial peptide in bacterial cell
Selectivity between mammalian cell, improving it becomes the development potentiality of antibiotic substitute.In conclusion W4 is one
Kind has the antibacterial peptide of higher application value.
Detailed description of the invention
Fig. 1 is the mass spectrogram of antibacterial peptide W4.
Fig. 2 is the helical wheel perspective view of antibacterial peptide W4.
Specific embodiment
Present invention will now be described in further detail with reference to the embodiments and the accompanying drawings, but embodiments of the present invention are unlimited
In this.
Embodiment 1
The design of antibacterial peptide
Select 4 arginine as positive charge amino acid and 5 tryptophans as hydrophobic amino acid, two arginine are made
It is inserted into tryptophan for a unit, helical wheel projects to form " four sides " conformation, i.e. two hydrophobic surfaces and two hydrophilic surfaces, and four
A arginine forms two pairs of intramolecular hydrogen bonds, which is named as W4, and sequence is as shown in the table.
The amino acid sequence of 1 derived peptide of table
The charge number of W4 is respectively+4, and hydrophobic value is 0.801.By the terminal-carboxy amidation of W4 to improve a positive electricity
Lotus and the stability for increasing peptide.Through this method in the case where improving antibacterial peptide bactericidal activity, the haemolysis of antibacterial peptide is reduced
Activity improves selectivity of the antibacterial peptide between bacterial cell and mammalian cell, improves it and substitutes as antibiotic
The development potentiality of object.
Embodiment 2
Solid-state chemical reaction method method synthesizes W4 antibacterial peptide
1, the preparation of antibacterial peptide carries out one by one from C-terminal to N-terminal, is completed by Peptide synthesizer.First by Fmoc-X (X
It is first amino acid of C-terminal of each antibacterial peptide) it is linked into Wang resin, X-Wang tree is obtained after then sloughing Fmoc group
Rouge；Again by Fmoc-Y-Trt-OH (9- fluorenes methoxy carboxyl-trimethyl-Y, Y is second amino acid of each antibacterial peptide C-terminal)；According to
This program is successively synthesized to N-terminal from C-terminal, until synthesis finishes, obtains the resin for sloughing the side chain protection of Fmoc group；
2, in peptide resin obtained above, cutting reagent is added, 20 DEG C are protected from light lower reaction 2h, filtering；Precipitate TFA (three
Fluoroacetic acid) washing, washing lotion is mixed with above-mentioned filtrate, Rotary Evaporators concentration, the pre-cooling for adding 10 times or so volumes is anhydrous
White powder object is precipitated in ether, -20 DEG C of precipitating 3h, is centrifuged 10min with 2500g, collects precipitating, then washed and sunk with anhydrous ether
It forms sediment, vacuum drying obtains polypeptide, wherein cutting reagent is by TFA, water and TIS (tri isopropyl chlorosilane) according to mass ratio 95:
2.5:2.5 mixing；
3, column equilibration 30min is carried out using 0.2mol/L sodium sulphate (phosphoric acid is adjusted to pH7.5), with 90% acetonitrile solution
Polypeptide is dissolved, filtering, C18 reverse phase normal pressure column, using gradient elution, (eluant, eluent is methanol and aqueous sodium persulfate solution according to volume ratio
For 30:70~70:30 mixing), flow velocity 1mL/min, detection wave is 220nm, collects main peak, freeze-drying；Recycle reverse phase C18
Column is further purified, and eluent A is 0.1%TFA/ aqueous solution；Eluent B is 0.1%TFA/ acetonitrile solution, and wash-out concentration is
25%B~40%B, elution time 12min, flow velocity 1mL/min, then main peak is ibid collected, freeze-drying；
4, the identification of antibacterial peptide: antibacterial peptide obtained above is analyzed by electron spray mass spectrometry, is shown in mass spectrogram
Molecular weight (as shown in Figure 1) and the theoretical molecular weight in table 1 are almost the same, and the purity of antibacterial peptide is greater than 95%.
Sample information parameter is as follows in Fig. 1:
Interface: electric spray ion source voltage :+4.5kv
Dissolution method :+85% water of 15% acetonitrile sprays gas flow: 1.50L/min detector: -0.2kv
Radio frequency temperature: 250 DEG C of flow velocitys: 0.2ml/min
Sample volume: 1 μ l radio-frequency voltage: 0v
The ratio of mobile phase: 50% water/50% methanol
Blocking temperature: 200
Sequence: RWRWRWRWW-NH2
Modification: C- is terminus amidated
Theoretical value: 1572.85
Detected value: 1572.00
Embodiment 3: the measurement of antibacterial peptide antibacterial activity
1, peptide the measurement of antibacterial activity: is configured as certain storing liquid in case using.It is surveyed using micro broth dilution method
The minimal inhibitory concentration of fixed several antibacterial peptides.Using 0.01% acetic acid (containing 0.2%BSA) as dilution, doubling dilution is used
Configure in order the antibacterial peptide solution of graded series.It takes above-mentioned 100 μ L of solution to be placed in 96 porocyte culture plates, then adds respectively
Add isometric bacterium solution to be measured (~105A/mL) in each hole.Positive control is respectively set (containing bacterium solution without containing antibacterial
Peptide) and negative control (be both free of bacterium solution or be free of peptide).37 DEG C of constant temperature incubation 20h, visually to have no that research of chaotic phenomenon is arranged at hole bottom
Be minimal inhibitory concentration.Testing result is shown in Table 2.
The bacteriostatic activity of 2 W4 of table
It can be seen from Table 2 that W4 bacteriostatic activity is higher, it is blue to be slightly better than leather for the bactericidal activity of gram-positive bacteria
Family name's negative bacterium shows that W4 has the potentiality for becoming antibacterials of new generation.
2, the measurement of hemolytic activity: acquiring the new blood 1mL of people, be dissolved into 2mLPBS solution after anticoagulant heparin,
1000g is centrifuged 5min, collects red blood cell；It is washed 3 times with PBS, then is resuspended with 10mL PBS；Take 50 μ L red cell suspensions and 50 μ L
It is uniformly mixed with the antibacterial peptide solution of the various concentration of PBS dissolution, the constant-temperature incubation 1h in 37 DEG C of incubators；It is taken out after 1h, 4
DEG C, 1000g be centrifuged 5min；It takes out supernatant microplate reader and surveys absorbance value at 570nm；Every group is averaged, and compares point
Analysis.Wherein 50 μ L red blood cells add 50 μ LPBS as negative control；50 μ L red blood cells add 50 μ L0.1%Tritonx-100 conducts
Positive control.Minimum hemolytic concentration is antibacterial peptide concentration when antibacterial peptide causes 10% hemolysis rate.Testing result is shown in Table 3.
The measurement of 3 antibacterial peptide hemolytic activity of table
It can be seen from Table 3 that W4 does not show hemolytic activity in detection range.
The above results show that forming " four sides " structure, while four arginine form the W4 of two pairs of hydrogen bonds, antibacterial activity
It significantly improves.The antibacterial and hemolytic activity of comprehensive analysis antibacterial peptide, can by therapeutic index (hemolytic concentration and Mlc
Ratio) more fully evaluate the biological activity of each antibacterial peptide.W4 treatment with higher refers to it can be seen from table 3
Number shows the development potentiality for the W4 antibacterial peptide substitute antibiotics with higher that design obtains.
Sequence table
<110>Northeast Agricultural University
<120>a kind of non-perfect peptide amphiphile W4 and its preparation method and application
<160> 1
<170> SIPOSequenceListing 1.0
<210> 1
<211> 9
<212> PRT
<213> Artificial sequence
<400> 1
Arg Trp Arg Trp Arg Trp Arg Trp Trp
1 5
Claims (3)
1. a kind of non-perfect peptide amphiphile W4, which is characterized in that its sequence is as shown in SEQ ID No.1.
2. the preparation method of non-perfect peptide amphiphile W4 according to claim 1 a kind of, which is characterized in that method is as follows:
Select 4 arginine as positive charge amino acid and 5 tryptophans as hydrophobic amino acid, two arginine are as a list
Member insertion tryptophan, helical wheel project to form " four sides " conformation, i.e. two hydrophobic surfaces and two hydrophilic surfaces, and four arginine
Two pairs of intramolecular hydrogen bonds are formed, which is named as W4, and sequence is as shown in SEQ No.1.
3. a kind of non-perfect peptide amphiphile W4 according to claim 1 treats gram positive bacterial infection disease in preparation
Application in drug.
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Cited By (4)
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| CN110283252A (en) * | 2019-07-12 | 2019-09-27 | 东北农业大学 | Pig source heterozygous antibacterial peptide PP-1 and its preparation method and application |
| WO2022263695A1 (en) * | 2021-06-16 | 2022-12-22 | Consejo Superior De Investigaciones Científicas (Csic) | Peptides with antimicrobial activity and uses thereof |
| CN116041422A (en) * | 2023-03-31 | 2023-05-02 | 四川大学 | Self-assembled antibacterial peptide and composition, drug carrier, drug carrying system and application thereof |
| CN116332777A (en) * | 2023-02-20 | 2023-06-27 | 华中科技大学 | Diaryl benzyl methylamine compound, preparation and application as carrier in synthesizing polypeptide |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110283252A (en) * | 2019-07-12 | 2019-09-27 | 东北农业大学 | Pig source heterozygous antibacterial peptide PP-1 and its preparation method and application |
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| WO2022263695A1 (en) * | 2021-06-16 | 2022-12-22 | Consejo Superior De Investigaciones Científicas (Csic) | Peptides with antimicrobial activity and uses thereof |
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| CN116332777A (en) * | 2023-02-20 | 2023-06-27 | 华中科技大学 | Diaryl benzyl methylamine compound, preparation and application as carrier in synthesizing polypeptide |
| CN116041422A (en) * | 2023-03-31 | 2023-05-02 | 四川大学 | Self-assembled antibacterial peptide and composition, drug carrier, drug carrying system and application thereof |
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