CN103421091B - Anti-caries enamel matrix protein functional polypeptide and preparation method and application thereof - Google Patents
Anti-caries enamel matrix protein functional polypeptide and preparation method and application thereof Download PDFInfo
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Abstract
The invention discloses anti-caries enamel matrix protein functional polypeptide and a preparation method and application thereof. The anti-caries polypeptide comprises amino acid sequences as shown in SEQ IDNO.1 or SEQ IDNO.2 and salts or esters of the amino acid sequences. The polypeptide mainly comprises an amino acid sequence of 'QPX' inducing remineralization of early caries and further can comprise an amino acid sequence 'TKREEVD' which can act with calcium ions to induce HA nucleation. The polypeptide is low in molecular weight and has the advantages that the polypeptide can be better adsorbed by the surface of tooth enamel so as to promote remineralization of early caries; the polypeptide is convenient to synthesize, economical, effective and safe and reliable.
Description
Technical field
The present invention relates to a kind of preventing decayed tooth technology, particularly a kind of preventing decayed tooth ENAMELIN functional polypeptide and its production and use.
Background technology
Dental caries disease is the modal oral diseases of the mankind.Because Incidence of caries is high, Endemic Area is wide, has a strong impact on oral cavity and whole body health, and the World Health Organization has been classified as one of three large Non Communicable Diseases (NCD) of mankind's keypoint control, is only second to cardiovascular disorder and tumour.
Fluorochemical is as a kind of preventing decayed tooth preparation of classics, four ten years in the past, be utilized with various form, as fluoridation of drinking water, containing fluorine-added milk or fluorine-containing salt, local painting fluorine (toothpaste with fluoride, fluoride gel, fluorine-containing collutory) etc., thereby the caries prevalence rate in reduction crowd to some extent, is acknowledged as the most effective preventing decayed tooth measure on our times.But the popularization using along with multiple fluorochemical preparation, the increase of working concentration and frequency, the appearance of the bacterial strain of resistance to fluorine, dental fluorosis, skeletal fluorosis highlights fluorochemical preventing decayed tooth limitation day by day.
Anti-microbial agents, as Tubulicid, tsiklomitsin etc., can directly act on bacterium and anticaries, but life-time service easily causes oral cavity flora imbalance, makes bacterium produce resistance, has obvious toxic side effect.
Immune anticaries has certain effect, strengthens immunogenicity and human body application security problem but exist, and also letter is to be solved to affect in addition the problem of oral cavity flora ecology.
Chinese medicine has the bacterial metabolism of interference, suppresses the effects such as Dental plaque biofilm formation as catechu, rheum officinale, the root of large-flowered skullcap, honeycomb, betel nut, pseudo-ginseng, tea-polyphenol etc. have been proved, but has the problems such as the dyeing of liquid tooth body, resistance.
Substitute Xylitol and sorbyl alcohol, Chinese medicine Turkey-galls and the remineralization effect every the mountain that disappears, Nano-hydroxyapatite, phosphopeptide caseinate, trace element, sweet oil, resin etc. of unsetting calcium phosphate, sugar are successively reported, but because DeGrain or experimental result differ, conclusion is not yet unified at present.
For the problems referred to above, other anticariogenic agent and method actively sought in this area.
ENAMELIN (EMP) is one group of protein from epithelial root sheath, be the enameloblast secretion of tooth development phase Hertwig epithelial root sheath internal layer a kind of regulate and control the stromatin of tooth mineralising, before dentine just starts mineralising, express, stop expressing in the early stage stage of maturity of dentine.ENAMELIN contains the protein components such as amelogenin, ameloblastin, glaze albumen, and wherein amelogenin accounts for the more than 90% of growth period Enamel Proteins extract.Amelogenin plays decisive role in enamel matrix biomineralization process.After enameloblast secretion amelogenin, under Dentinal induction, enamel carries out biomineralization very soon.Amelogenin plays an important role to the factors such as formation and arrangement initial, nucleus of enamel mineralising.Amelogenin can be enamel biomineralization necessary support is provided, and the speed of controlled combinations bulk-growth, maintains crystal growth, is the key of enamel biomineralization.
In recent years, the biomineralization function based on ENAMELIN, the external synthetic artificial hydroxylapatite of ENAMELIN that utilizes succeeds.Chen etc. simulation enamel mineralisation process, utilize ENAMELIN control synthesized in chemical constitution and crystalline size on all with the closely similar nano bar-shape hydroxylapatite of natural enamel.Yamagish etc. have formed the fluorapatite with enamel structure at enamel surface, these fluorapatites are arranged fine and close, are arranged in parallel, perpendicular to enamel surfaces.Domestic scholars Wang Zhiweis etc. are placed on enamel containing in phosphoric acid salt agar-calcium acetate solution system of SD rat tooth ENAMELIN 7 days, found that crystal zonal structure appears in the enamel surface that adds ENAMELIN.The powerful potentiality that these experimental results all point out ENAMELIN to have induction Enamel remineralizations, thus utilize this potentiality of ENAMELIN to promote incipient dental caries remineralization, most probably for the sick control of dental caries provides a brand-new thinking.
But ENAMELIN is not yet directly used in preventing decayed tooth at present.ENAMELIN mainly obtains by following approach at present: 1. from tooth bud, extract ENAMELIN.2. according to the gene order of amelogenin, non-ameloblastin, the artificial gene that utilizes biotechnology to realize amelogenin is recombinated, as amelogenin Mr179, the Mrl66 of recombinant rat.3. commercial enamel matrix derivative.Within 1999, Sweden Biora has developed
(trade(brand)name of amelogenin) product, the treatment through U.S. FDA approval as periodontal intrabony defects and root planing region obtains very widespread use subsequently in periodontal disease therapeutic and paradental defect reparation.In above-mentioned ENAMELIN source, extraction method needs organization material more, and what obtain is the mixing element of different molecular weight, is difficult to obtain high-purity product; Gene recombinant protein program complexity, and translation post-treatment modification system imperfection, renaturation and modification are very difficult, the normal imperfection of protein function; Sweden
for the ENAMELIN purifying that pig tooth bud extracts, get 3 relative molecular weight peak value freeze-drying of typical amelogenin and preserve acquisition, although there is obvious promoting regeneration of periodontal tissue effect, may lose effective preventing decayed tooth function fragment.To sum up state, at present the preparation method of ENAMELIN is complicated and may lose effective preventing decayed tooth fragment, and how utilizing ENAMELIN to carry out effective preventing decayed tooth becomes this area and want to solve but a unsolved difficult problem always.
Summary of the invention
One of goal of the invention of the present invention is: for the problem of above-mentioned existence, novelty proposes to utilize the thought of biomimetic mineralization preventing decayed tooth, builds a kind of effectively polypeptide of preventing decayed tooth.
The technical solution used in the present invention is such: a kind of preventing decayed tooth ENAMELIN functional polypeptide, comprise the aminoacid sequence as shown in SEQIDNO.1, and the salt that comprises the aminoacid sequence shown in SEQIDNO.1 or ester;
SEQIDNO.1：QPYQPVQPHQPMQPQ
Amelogenin is made up of a lot of different amino acid, contriver binds up one's hair existing by analyzing total: amelogenin contains a lot of repeating units, as " QPX " tumor-necrosis factor glycoproteins, contriver further draws by great many of experiments: " QPX " sequence can be induced the remineralization effect of enamel, therefore, " QPX " sequence that the present invention chooses in amelogenin combines, thereby build preventing decayed tooth polypeptide of the present invention, this polypeptide molecular weight is less, can improve the absorption at enamel surface, and then bring into play better its effect, promote the adamantine remineralization of demineralization, thereby reach preventing decayed tooth object.
A kind of preventing decayed tooth ENAMELIN functional polypeptide, comprises the aminoacid sequence as shown in SEQIDNO.2;
SEQIDNO.2：QPYQPVQPHQPMQPQTKREEVD
On the basis of " QPX " sequence in amelogenin, add water-wet side " TKREEVD ", this water-wet side can and cause HA (hydroxy phosphorus Calx) nucleation with calcium ion effect, thereby produces better anti-caries effect.
Two of object of the present invention, is to provide a kind of pharmaceutical composition/preparation that comprises aforementioned polypeptides, its pharmaceutically-acceptable salts or ester; Described pharmaceutical composition/preparation, except comprising aforementioned polypeptides, its pharmaceutically-acceptable salts or ester, also can comprise suitable pharmaceutically acceptable carrier and/or auxiliary material.
As optimal technical scheme, the preferred gelifying agent of described pharmaceutical composition/preparation.
Three of object of the present invention, be to provide a kind of preparation method of aforementioned polypeptides, the technical scheme adopting is: comprise the following steps: according to the aminoacid sequence shown in SEQIDNO.1 or SEQIDNO.2, the amino acid chain that first amino is protected by Fmoc is received on solid phase carrier Wang resin, then desamidizate protecting group; Then second amino acid of amino being protected by Fmoc reacts with first the amino acid whose amino that is connected to solid phase carrier and forms peptide bond under the activation of condensing agent; Repeat above-mentioned peptide bond and form reaction, make peptide chain from C end to the growth of N end, until last amino acid access; Cutting obtains target polypeptides.This synthetic method is simple, and production cost is low.
Four of object of the present invention, is to provide the application of aforementioned polypeptides in the medicine for the preparation of preventing decayed tooth.
The preferred gelifying agent of the present invention directly acts on early-stage caries position, thereby reaches result for the treatment of.The most frequently used preventing decayed tooth preparation is Sodium Fluoride now, its main scheme for implementing said method is fluoridation of drinking water, containing fluorine-added milk or fluorine-containing salt, the local fluorine (toothpaste with fluoride, fluoride gel, fluorine-containing collutory) etc. that is coated with, other some preventing decayed tooth preparations are generally all configured to liquid preparation, act locally on dental caries and damage position.The further preferred aqueous gel of gelifying agent of the present invention, auxiliary material used, by functional classification, can comprise: thickening material, wetting Agent for Printing Inks, sanitas, stablizer, pH adjusting agent etc.Particularly, conventional gel matrix has water, glycerine, propylene glycol, derivatived cellulose, carbomer, alginates, alginic acid ester, tragakanta, gelatin, starch etc.
Compared with the embodiment of existing preventing decayed tooth preparation, the present invention, by this polypeptide preparation gel state, reduces its mobility, thereby has increased the local action time, can make this polypeptide bring into play maximum effect, thereby well treats incipient enamel caries.In addition, this polypeptide fragment of structure derives from human amelogenin aminoacid sequence, therefore, with current existing chemistry or Chinese medicine preventing decayed tooth preparation ratio, has better security and biocompatibility.
In sum, owing to having adopted technique scheme, the invention has the beneficial effects as follows: polypeptide of the present invention consists predominantly of the aminoacid sequence of the induction incipient dental caries remineralization of " QPX ", comprise again and can and cause the aminoacid sequence " TKREEVD " of HA nucleation with calcium ion effect, and through synthetic this polypeptide molecular weight is less again, can improve the absorption at enamel surface, and then bring into play better its effect, promote the adamantine remineralization of demineralization; The present invention can promote enamel (incipient dental caries) remineralization of early stage demineralization well, and it is synthetic convenient, and economical and practical, effect is better and safe and reliable.
Brief description of the drawings
Fig. 1 is the microradiography figure before and after the classical preventing decayed tooth chemicals of positive control NaF group remineralization;
Fig. 2 is the polarisation figure before and after the classical preventing decayed tooth chemicals of positive control NaF group remineralization;
Fig. 3 is the microradiography figure before and after negative control group HEPES group remineralization;
Fig. 4 is the polarisation figure before and after negative control group HEPES group remineralization;
Fig. 5 is the microradiography figure of the preventing decayed tooth polypeptide group remineralization front and back of embodiment 1;
Fig. 6 is the polarisation figure of the preventing decayed tooth polypeptide group remineralization front and back of embodiment 1;
Fig. 7 is the microradiography figure of the preventing decayed tooth polypeptide group remineralization front and back of embodiment 2;
Fig. 8 is the polarisation figure of the preventing decayed tooth polypeptide group remineralization front and back of embodiment 2.
Embodiment
The present invention is described in detail below.
In order to make object of the present invention, technical scheme and advantage clearer, below in conjunction with embodiment, the present invention is further elaborated.Should be appreciated that specific embodiment described herein, only in order to explain the present invention, is not intended to limit the present invention.
Embodiment 1:
A kind of preventing decayed tooth polypeptide, aminoacid sequence is as shown in SEQIDNO.1;
SEQIDNO.1：QPYQPVQPHQPMQPQ
Embodiment 2
A kind of preventing decayed tooth polypeptide, aminoacid sequence is as shown in SEQIDNO.2;
SEQIDNO.2：QPYQPVQPHQPMQPQTKREEVD
The preparation of embodiment 3:SEQIDNO.1 polypeptide
1, selecting Fmoc-Gly(Trt)-WangResin is as resin (carrier);
2, with DCM, resin is fully swelling;
3, use the DBLK(hexahydropyridine+DMF of proper concn), Fmoc-blocking group is deviate from;
4, clean several times with DMF, wash away DBLK;
5, taking applicable condensing agent and activator (HBTU, NMM) and C holds second Fmoc-protected amino acid (Fomc-Val-OH) to carry out coupling;
6, triketohydrindene hydrate detection method detects and guarantees that connection is more complete;
7, clean several times with DMF, wash away residual various residues and activator condensing agent;
8, carry out coupling according to SEQIDNO.1 aminoacid sequence, method is with reference to step 3-7;
9. all amino acid is connected and finishes rear employing step 3,4 methods are sloughed last Fmoc-blocking group;
10. with the cracking of TFA cutting liquid, remove resin and amino acid blocking group, obtain crude product;
11. send mass spectrum to confirm product correct (molecular weight 1803.031 meets theoretical value);
12. crude products send purifies and separates, improve purity.
The preparation of embodiment 4:SEQIDNO.2 polypeptide:
1. select Fmoc-Asp (OtBu)-WangResin as resin (carrier);
2. with DCM, resin is fully swelling, with DMF cleaning several times.
3. use the DBLK(hexahydropyridine+DMF of proper concn), Fmoc-blocking group is deviate from.
4. clean several times with DMF, wash away DBLK.
5. taking applicable condensing agent and activator (HBTU, NMM) and C holds second Fmoc-protected amino acid (Fomc-Val-OH) to carry out coupling.
6. triketohydrindene hydrate detection method detects and guarantees that connection is more complete.
7. clean several times with DMF, wash away residual various residues and activator condensing agent.
8. carry out coupling according to SEQIDNO.2 aminoacid sequence, the same 3-7 of method.
9. all amino acid connections are finished to rear employing 3,4 methods and slough last Fmoc-blocking group.
10. with the cracking of TFA cutting liquid, remove resin and amino acid blocking group, obtain crude product.
11. send mass spectrum to confirm product correct (molecular weight 2660.951 meets theoretical value).
12. crude products send purifies and separates, improve purity.
Embodiment 5: the preparation of gelifying agent
Propylene glycol alginate is formulated as to 6%(w/w), pH=4, the aseptic aqueous solution that viscosity is 400mPas.The ENAMELIN functional polypeptide solution 0.1ml of 0.25um/ml is joined to the propylene glycol alginate 6%w/w of 0.9ml, mix rear formation respectively and contain high viscosity (1000mPas) acidic sol that ENAMELIN functional polypeptide concentration is 0.025um/ml.
Embodiment 6: remineralization experiment
The fresh ox incisor of pulling out of this experimental selection, separate crown root, bizet ultrasonic cleaning, dry, the lower observation of stereoscopic microscope (amplifying 10 times) damaged without dental caries, fluorine spot, the corona of slight crack is further cut into corona with high speed sclerous tissues cutting machine the enamel piece of 5 × 5 × 2mm size, with polishing machine and 800#-1200#-2400# carborundum paper, paper under flowing water polishes labial enamel successively, polishing, remove top layer approximately 150 μ m, seasoning, with self-curing plastic by tooth embedding, enamel piece labial surface central authorities retain the district of windowing of 4mm × 4mm, the two-layer antiacid nail varnish of all the other position coatings,
Baurodont enamel sample is surveyed 5 points by microhardness tester surface measurements microhardness value in the window central vertical in district of each enamel sample, and each point at a distance of 100 μ m, calculates its mean value.Select the enamel piece that 120 hardness value scopes are 320-400KHN (Knoophardnessnumber, KHN) to enter further experiment;
Enamel sample is fixed on homemade annular glass rod, put into the glassware that fills artificial demineralization liquid, add demineralization liquid by each sample 8ml solution, magnetic agitation instrument stirs (100 revs/min), demineralization 72 hours at 37 DEG C, enamel window district form artificial caries;
After demineralization, again measure its surface microhardness, put 5 points of the parallel survey of a side in base measurement, select enamel piece that 40 hardness value scopes are 160-220KHN to enter next step remineralization experiment.The half of each sample institute windowing covers as morphology contrast before and after remineralization experiment with antiacid nail varnish;
Be divided at random 4 groups (every group of 10 samples), be respectively by processing medicine difference: A.1g/L Sodium Fluoride (NaF) group (positive controls), B.4-hydroxyethyl piperazine ethanesulfonic acid (HEPES) group (negative control group) C.25 μ mol/L preventing decayed tooth polypeptide group 1(be dissolved in 4-hydroxyethyl piperazine ethanesulfonic acid (HEPES), the preventing decayed tooth polypeptide of embodiment 1) D.25 μ mol/L preventing decayed tooth polypeptide group 2(be dissolved in 4-hydroxyethyl piperazine ethanesulfonic acid (HEPES), the preventing decayed tooth polypeptide of embodiment 2).
PH circulation every day comprises the demineralization of 2 hours, and the drug treating time of 4 times 5 minutes, all the other times are immersed in remineralization solution, and magnetic stirs instrument and stirs (100 revs/min), circulates 12 days at 37 DEG C.
Polarized light microscope observing
By every group of 10 samples, sclerous tissues's cutting machine is windowed perpendicular to enamel, and district is surperficial cuts into slices, each section comprises demineralization enamel, remineralization enamel two portions, the approximately thick 300 μ m that cut into slices then further grind into about 100 μ m thick thin slice under polishing machine flowing water, adopt and attach preparation method, after water retting, use again polarized light microscope observing, digital image obtains (NikonACT-1forL-1, Nikon, Japan) by system-specific software.
The quantitative analysis of gold standard microradiography
Section is fixed on microradiographic special carrier to 20KV, 20mA, the micro-radiation roentgen radiation x of exposure 30s.The supporting analysis software of computer provides total mineral amount lost, dental caries to damage the degree of depth and mineral distribute three indexs to evaluate the remineralization state of the rear sample of pH circulation;
Result data is as follows:
before and after pH circulation, total mineral amount lost of each group and dental caries damage the degree of depth
Statistical study
Statistical analysis all adopts software SPSS17.0 to process, and what before and after circulation, each group mineral content, dental caries damaged the degree of depth relatively selects paired t-test (Student ' spairedt-test).After circulation, the average mineral content of each group, dental caries damage relatively selecting one-way analysis of variance (ANOVA) and comparing between two (Student-Newman-Keulstest), α=0.05 of the degree of depth.
Experimental result
Polarized light microscopy mirror: the artificial caries of respectively organizing preparation before remineralization all shows as typical subsurface demineralization, has the birefringent complete top layer of negativity and is positioned at the birefringent disease damage body that is positive under top layer.After remineralization, Sodium Fluoride group and preventing decayed tooth polypeptide group 1 and preventing decayed tooth polypeptide group 2 sample dental caries damage top layers and obviously thicken, and dental caries damage the degree of depth and shoal, the top layer of HEPES group sample and dental caries damage the degree of depth before and after remineralization without obviously changing.
Microradiography shows, the micro-radiation result of gained is as shown in Fig. 1-8, after remineralization, preventing decayed tooth polypeptide group 1 and preventing decayed tooth polypeptide group 2 thicken compared with HEPES group Zu She district, top layer with Sodium Fluoride group, and the transmission area under top layer is also more shallow, after pH circulation, the mineral amount lost of each group and dental caries damage depth ratio show, the mineral amount lost of Sodium Fluoride group and two groups of preventing decayed tooth polypeptide and dental caries damage the difference not statistically significant (p>0.05) of the degree of depth, all significantly lower than HEPES group (p<0.05), but preventing decayed tooth functional polypeptide 1 has these results of statistical significance (p<0.05) all to show that these two kinds of preventing decayed tooth polypeptide have the enamel white spot of promotion remineralization with mineral amount lost and the dental caries damage degree of depth of preventing decayed tooth functional polypeptide 2, suppress the effect that dental caries damage process, there is significant anticaries action, and, the promotion enamel white spot remineralization of the polypeptide that the sequence that has increased water-wet side is SEQIDNO.2, the polypeptide that the effect that suppresses dental caries damage process is SEQIDNO.1 than sequence is better.
<110> Sichuan University
<120> preventing decayed tooth ENAMELIN functional polypeptide and its production and use
<160> 2
<170> PatentInversion3.3
<210> 1
<211> 15
<212> PRT
<213> artificial sequence
<220>
<222> (1)...(15)
<400> 1
<210> 2
<211> 22
<212> PRT
<213> artificial sequence
<220>
<222> (1)...(22)
<400> 2
Claims (6)
1. a preventing decayed tooth ENAMELIN functional polypeptide, is characterized in that: the aminoacid sequence of described polypeptide is as shown in SEQ ID NO.1.
2. a preventing decayed tooth ENAMELIN functional polypeptide, is characterized in that: the aminoacid sequence of described polypeptide is as shown in SEQ ID NO.2.
3. an anticariogenic agent composition, is characterized in that: described pharmaceutical composition comprise preventing decayed tooth ENAMELIN functional polypeptide as claimed in claim 1 or 2 with and pharmaceutically acceptable carrier and/or auxiliary material.
4. pharmaceutical composition as claimed in claim 3, is characterized in that: described pharmaceutical composition is gelifying agent.
5. the preparation method of preventing decayed tooth ENAMELIN functional polypeptide described in claim 1 or 2, it is characterized in that comprising the following steps: according to the aminoacid sequence shown in SEQ ID NO.1 or SEQ ID NO.2, first amino acid chain that amino is protected by Fmoc is received on solid phase carrier Wang resin, then desamidizate protecting group; Then second amino acid of amino being protected by Fmoc reacts with first the amino acid whose amino that is connected to solid phase carrier and forms peptide bond under the activation of condensing agent; Repeat above-mentioned peptide bond and form reaction, make peptide chain from C end to the growth of N end, until last amino acid access; Cutting obtains target polypeptides.
6. the application of the preventing decayed tooth ENAMELIN functional polypeptide described in claim 1 or 2 in the medicine for the preparation of preventing decayed tooth.
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| CN103830145B (en) * | 2014-03-18 | 2015-10-28 | 林彤 | A kind of toothpaste containing biological peptide and Chinese medicine |
| CN104774250B (en) * | 2015-04-28 | 2018-01-16 | 四川大学 | A kind of antibacterial functions polypeptide and its preparation method and application |
| CN110236958B (en) * | 2019-06-28 | 2020-12-29 | 武汉大学 | Material for promoting repair of defective and missing tooth tissues and preparation method thereof |
| CN112957451B (en) * | 2021-02-26 | 2021-12-17 | 四川大学 | Bioactive glass/bionic functional polypeptide complex, preparation method and application |
| CN113209358A (en) * | 2021-05-21 | 2021-08-06 | 上海交通大学医学院附属第九人民医院 | Tissue adhesive, preparation method and application thereof |
| CN114133441B (en) * | 2021-11-15 | 2024-02-06 | 同济大学 | Active short peptide for promoting dentin mineralization and application thereof |
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