CN103333270B - Collagen peptide grafted sodium alginate sulfuric ester, preparation method and its usage - Google Patents
Collagen peptide grafted sodium alginate sulfuric ester, preparation method and its usage Download PDFInfo
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- CN103333270B CN103333270B CN201310275413.6A CN201310275413A CN103333270B CN 103333270 B CN103333270 B CN 103333270B CN 201310275413 A CN201310275413 A CN 201310275413A CN 103333270 B CN103333270 B CN 103333270B
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Abstract
The invention belongs to macromolecule chemical material field, be specifically related to a kind of collagen peptide grafted sodium alginate sulfuric ester, preparation method and its usage. Collagen peptide grafted sodium alginate sulfuric ester, it is to carry out graft reaction and obtain with collagen peptide 25-65 DEG C again after the carboxyl sodium group of sodium alginate sulfuric ester is activated. The method preparation technology is simple, and the collagen peptide grafted sodium alginate sulfuric ester making has good removing hydrogen peroxide, promotes the performance of fibroblast proliferation, can significantly promote the healing of wound surface.
Description
Technical field
The invention belongs to macromolecule chemical material field, be specifically related to a kind of collagen peptide grafted sodium alginate sulfuric ester,Preparation method and its usage.
Background technology
On sodium alginate skeleton, being distributed with many free hydroxyl and carboxyl sodium group, is desirable chemical modification material. SeaMosanom sulfuric ester is that the hydroxyl of sodium alginate is carried out to the product after sulfonation modifying. Compared with sodium alginate, sodium alginate sulphurAcid esters has not only retained the character such as the biocompatibility of sodium alginate, nontoxic, non-immunogenic, also have good water-soluble,Blood sugar reducing function, anticoagulant property, anti-oxidant, antitumor action, the performances such as antiinflammatory action and promotion cell proliferation. Sodium alginate sulfuric acidEster structure is similar to heparin, has certain anticoagulant active, can promote wound healing in the mode that is similar to heparin. Due to moltenThe improvement of solution property, makes the range of application of sodium alginate sulfuric ester more extensive, and at food, there are a lot of application the aspects such as medicine.Collagen peptide is the hydrolysate of collagen, is easily absorbed by the body, and has fabulous hydrophily, moisture absorbability and moisture retentivity. As can be byOn collagen peptide grafting and sodium alginate sulfuric ester, it will bring into play effect better in wound healing. .
Summary of the invention
Technical problem to be solved by this invention be to provide collagen peptide grafted sodium alginate sulfuric ester, preparation method andIts purposes. The method preparation technology is simple, and the collagen peptide grafted sodium alginate sulfuric ester making has good removingThe performance of hydrogen oxide, promotion fibroblast proliferation, can significantly promote the healing of wound surface.
For solving the problems of the technologies described above, technical scheme provided by the invention is:
Collagen peptide grafted sodium alginate sulfuric ester, is characterized in that: it is by the carboxyl sodium of sodium alginate sulfuric esterAfter activating, group carries out with collagen peptide 25-65 DEG C that graft reaction obtains again.
Press such scheme, in described collagen peptide grafted sodium alginate sulfuric ester, carboxyl sodium group is got by collagen peptideThe substitution value in generation is 0.062-0.469, is preferably 0.124-0.469, more preferably 0.228-0.469.
The present invention also provides the preparation method of above-mentioned collagen peptide grafted sodium alginate sulfuric ester.
The preparation method of collagen peptide grafted sodium alginate sulfuric ester, is characterized in that: it is first by sodium alginate sulphurAfter the carboxyl sodium group of acid esters reacts with carboxyl activator is activated, then with collagen peptide 25-65 DEG C carry out graft reaction, afterProcess.
Press such scheme, under the condition that described priming reaction is is 5-7 at pH, sodium alginate sulfuric ester and carboxyl are livedAgent is reacted 12-28 hour at 25-65 DEG C, and described carboxyl activator is 1-(3-dimethylaminopropyl)-3-ethyl carbonThe mixture of diimmonium salt hydrochlorate (EDC) and N-hydroxy-succinamide (NHS).
Press such scheme, in described priming reaction, sodium alginate sulfuric ester is the 2-(N-morpholino) that is first 5-7 with pHAfter ethyl sulfonic acid (MES) cushioning liquid dissolves, then add carboxyl activator to react.
Press such scheme, 1-in described carboxyl activator (3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride(EDC) and the mass ratio of N-hydroxy-succinamide (NHS) be 3.3:1-6.7:1; Described N-hydroxy-succinamide (NHS) withThe mass ratio of sodium alginate sulfuric ester is 0.2:1-0.6:1.
Press such scheme, the sulfuric ester (SO of described sodium alginate sulfuric ester3Na) substitution value is 1-1.8.
Press such scheme, the mass ratio of described collagen peptide and sodium alginate sulfuric ester is 0.4:1-2.0:1.
Press such scheme, described in to add the reaction time of carrying out graft reaction after collagen peptide be 10-30min.
Press such scheme, described post processing is dialysis after adding collagen reactive polypeptide to complete, and purifying is dry.
Press such scheme, the application of described collagen peptide grafted sodium alginate sulfuric ester in wound surface healing.
Beneficial effect of the present invention: preparation technology of the present invention is simple, with low cost, environmental friendliness, function is remarkable; PreparationCollagen peptide grafted sodium alginate sulfuric ester good water solubility, can remove hydrogen peroxide and can promote fibroblast proliferation, energyPromote significantly the healing of wound surface.
Brief description of the drawings
Fig. 1 is the infrared spectrogram of the collagen peptide grafted sodium alginate sulfuric ester prepared of embodiment 1;
Fig. 2 is the clearance rate of the collagen peptide grafted sodium alginate sulfuric ester prepared of embodiment 1-6 to hydrogen peroxide;
Fig. 3 is the collagen peptide grafted sodium alginate sulfuric ester of embodiment 1,2,6 preparation and grafting collagen peptide notSodium alginate sulfuric ester to fibroblastic cell survival rate;
Fig. 4 is the observation to effect of burn healing of the collagen peptide grafted sodium alginate sulfuric ester of embodiment 1;
Fig. 5 is that the collagen peptide grafted sodium alginate sulfuric ester of embodiment 2 is aobvious to the optics of effect of burn healingMicro mirror is observed.
Detailed description of the invention
Further illustrate the present invention below in conjunction with concrete example.
Embodiment 1
2-(N-morpholino) ethyl sulfonic acid (MES) cushioning liquid of preparation 0.2mol/l, and molten with the sodium chloride of 0.3mol/lLiquid regulates its pH value to 6.5. Measure MES cushioning liquid 50ml to there-necked flask, add 0.6g sodium alginate sulfuric ester, make itFully dissolve. Add successively subsequently 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC) 0.40g and N-HOSu NHS (NHS) 0.12g. Stir after 20 hours at 55 DEG C of lower magnetic forces, add 0.48g collagen peptide, and continueMagnetic agitation 10min. By three days purifying of reacted solution dialysis, after freeze drying, obtain collagen peptide grafted sodium alginateSulfuric ester, after measured: what in this collagen peptide grafted sodium alginate sulfuric ester, carboxyl sodium group was replaced by collagen peptide getsDai Du is 0.436. This collagen peptide grafted sodium alginate sulfuric ester is shown in Fig. 1 through the infared spectrum of IR Characterization. In figure:1651cm-1And 1555cm-1The absworption peak that place occurs, they belong to respectively amide Ⅰ and acid amides II band; At 1245cm-1With875cm-1The absworption peak that place occurs belongs to respectively the stretching vibration absworption peak of S=O key and the vibration absorption peak of C-O-S.
Embodiment 2
2-(N-morpholino) ethyl sulfonic acid (MES) cushioning liquid of preparation 0.2mol/l, and molten with the sodium chloride of 0.3mol/lLiquid regulates its pH value to 6.5. Measure MES cushioning liquid 50ml to there-necked flask, add 0.6g sodium alginate sulfuric ester, make itFully dissolve. Add successively subsequently 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC) 0.60g and N-HOSu NHS (NHS) 0.18g. Stir after 20 hours at 45 DEG C of lower magnetic forces, add 1.2g collagen peptide, and continue magneticPower stirs 10min. By three days purifying of reacted solution dialysis, after freeze drying, obtain collagen peptide grafted sodium alginate sulphurAcid esters, after measured: the replacement that in this collagen peptide grafted sodium alginate sulfuric ester, carboxyl sodium group is replaced by collagen peptideDegree is for being 0.310.
Embodiment 3
2-(N-morpholino) ethyl sulfonic acid (MES) cushioning liquid of preparation pH6.5, then measures appropriate this MES cushioning liquidTo there-necked flask, add 0.6g sodium alginate sulfuric ester, it is fully dissolved. Add successively subsequently 1-(3-dimethylaminoPropyl group)-3-ethyl-carbodiimide hydrochloride (EDC) 1.19g and N-hydroxy-succinamide (NHS) 0.36g. At 35 DEG C of lower magnetic forcesStir after 12 hours, add 0.48g collagen peptide, and continue magnetic agitation reaction. By reacted solution dialysis, purifying,After dry, obtain collagen peptide grafted sodium alginate sulfuric ester, after measured: this collagen peptide grafted sodium alginate sulfuric esterThe substitution value that middle carboxyl sodium group is replaced by collagen peptide is for being 0.062.
Embodiment 4
2-(N-morpholino) ethyl sulfonic acid (MES) cushioning liquid of preparation 0.2mol/l, and molten with the sodium chloride of 0.3mol/lLiquid regulates its pH value to 6.5. Measure MES cushioning liquid to there-necked flask, add 0.6g sodium alginate sulfuric ester, make it abundantDissolve. Add successively subsequently 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC) 0.40g and N-hydroxylSuccinimide (NHS) 0.12g. Stir after 24 hours at 35 DEG C of lower magnetic forces, add 0.48g collagen peptide, and continue magnetic forceStir 30min. By three days purifying of reacted solution dialysis, after freeze drying, obtain collagen peptide grafted sodium alginate sulfuric acidEster, after measured: the substitution value that in this collagen peptide grafted sodium alginate sulfuric ester, carboxyl sodium group is replaced by collagen peptideFor being 0.359.
Embodiment 5
2-(N-morpholino) ethyl sulfonic acid (MES) cushioning liquid of secure ph 5.5. Measure appropriate MES cushioning liquid to threeIn mouth flask, add 0.6g sodium alginate sulfuric ester, it is fully dissolved. Add successively subsequently 1-(3-dimethylamino thirdBase)-3-ethyl-carbodiimide hydrochloride (EDC) 0.80g and N-hydroxy-succinamide (NHS) 0.12g. Stir at 35 DEG C of lower magnetic forcesMix after 28 hours, add 0.24g collagen peptide, and continue magnetic agitation 20min. By pure reacted solution dialysis three daysChange, after freeze drying, obtain collagen peptide grafted sodium alginate sulfuric ester, after measured: this collagen peptide grafted sodium alginateThe substitution value that in sulfuric ester, carboxyl sodium group is replaced by collagen peptide is for being 0.228.
Embodiment 6
2-(N-morpholino) ethyl sulfonic acid (MES) cushioning liquid of preparation 0.2mol/l, and molten with the sodium chloride of 0.3mol/lLiquid regulates its pH value to 6.5. Measure MES cushioning liquid 50ml to there-necked flask, add 0.6g sodium alginate sulfuric ester, make itFully dissolve. Add successively subsequently 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDC) 1.19g and N-HOSu NHS (NHS) 0.36g. Stir after 20 hours at 35 DEG C of lower magnetic forces, add 0.24g collagen peptide, and continueMagnetic agitation 10min. By three days purifying of reacted solution dialysis, after freeze drying, obtain collagen peptide grafted sodium alginateSulfuric ester, after measured: what in this collagen peptide grafted sodium alginate sulfuric ester, carboxyl sodium group was replaced by collagen peptide getsDai Du is for being 0.124.
Collagen peptide grafted sodium alginate sulfuric ester prepared by the various embodiments described above carries out following performance characterization:
(1) the collagen peptide grafted sodium alginate sulfuric ester of being prepared by embodiment 1-6 is mixed with respectively the molten of 1mg/mlLiquid, makes test sample, then mixes with the PBS (PBS, 0.1mol/l, pH7.4) of 6.0ml, adds 1.0ml'sHydrogen peroxide (H2O2, 40mmol/l) and in above-mentioned mixed liquor, obtain each test sample solution. After 10min, use ultraviolet specrophotometerSurvey the absorbance of each test sample solution at 230nm place, calculate as follows collagen peptide grafting prepared by each embodimentThe hydrogen peroxide clearance rate of sodium alginate sulfuric ester, the results are shown in Figure 2, wherein AsFor the absorbance of test sample solution, AbFor not addingThe absorbance of the test sample solution of hydrogen peroxide, AcFor not adding the absorbance of the sample solution of testing sample.
As shown in Figure 2: sodium alginate sulfuric ester after collagen peptide graft modification hydrogen peroxide clearance rate increase, andIncrease along with the increase of substitution value. Suitably remove oxygen radical and can improve vasopermeability, reduce diffusate, alleviate tissueOedema and cellular damage, thereby promote the healing acceleration of the surface of a wound, and hydrogen peroxide can change oxygen radical in vivo into, thereforeGood hydrogen peroxide clearance rate will be conducive to the healing of wound surface.
(2) the collagen peptide grafted sodium alginate sulfuric ester of being prepared by embodiment 1,2,6 and not grafting collagen peptideSodium alginate sulfuric ester be used for measuring it to fibroblastic facilitation, experimental procedure is as follows:
Under aseptic condition, rat dermal fibroblasts is inserted in blake bottle, with the DMEM culture medium containing 10%FBSAt 37 DEG C, 5%CO2Incubator in cultivate. The fibroblast of going down to posterity after 3 times is inoculated in 96 porocyte culture plates to (6000Cells/well), the DMEM medium culture 24h with 200 μ l containing 10%FBS. Add the collagen peptide grafting marine alga of each embodimentAcid sodium sulfuric ester (test specimens) or the not sodium alginate sulfuric ester of grafting collagen peptide (contrast sample) are cultivated after 48h, with containing 10%The DMEM culture medium of FBS is replaced the MTT solution that adds subsequently 20 μ l, lucifuge reaction 4h. After sucking culture medium, add 150 μ l diformazansBase sulfoxide (DMSO), reaction 10min, makes MTT first a ceremonial jade-ladle, used in libation dissolution of crystals. Survey its absorbance at 492nm place with ELIASA, by formulaCalculate cell survival rate, the results are shown in Figure 3, wherein AsFor the absorbance of test specimens or contrast sample, AcFor blank.
As shown in Figure 3: the glue in each embodiment that sodium alginate sulfuric ester obtains after collagen peptide graft modificationFormer protein peptides grafted sodium alginate sulfuric ester has all shown good cell survival rate, and apparently higher than grafting collagen notThe sodium alginate sulfuric ester of peptide, and along with the increase of substitution value, cell survival rate has the trend of rising. Fibroblast is at the surface of a woundPropagation in agglutination and differentiation play an important role to wound healing, and fibroblast survival rate is larger, and the surface of a wound moreClose faster.
(3) healing for deepⅱdegreeburnwound by the collagen peptide grafted sodium alginate sulfuric ester of embodiment 1.
By 3% yellow Jackets of SD rats by intraperitoneal injection 0.8ml, make its anesthesia. Back is de-with 8% sodium sulfide solutionHair. With constant temperature and pressure electric pressing instrument, at the boiling hot 15s of SD rat back, temperature is 75 DEG C, and causing area is 3.14cm2DeepⅱdegreeburnThe surface of a wound. Burn wound connects with soaking collagen peptide after being 1 PVP-I of ︰ 4 and the iodophor disinfection of normal saline dilution by volume ratioThe oily yarn wrapping surface of a wound of branch sodium alginate sulfuric ester, suture suture needle is fixed, and wraps up eight layers of sterile gauze, self-adhesive elastic bandageFixing. Every other day change a dressing. Then scalding the same day, the 3rd day, within the 7th day and the 14th day, observe respectively, scaldThe wound healing photo on the same day, the 3rd day, the 7th day and the 14th day the results are shown in Figure 4, scalds the light microscope of the 7th day and the 14th dayThe results are shown in Figure 5.
As seen from Figure 4: scald the same day, naked eyes can obviously be distinguished the surface of a wound and normal region, and the surface of a wound is all rounded, and edge of wound is wholeBody, sharpness of border, the surface of a wound is pale without life, gloss difference, mild swelling; Latter the 3rd day of wound, surface of a wound area diminishes, and the surface of a wound is dry redProfit, the thin scab of skin is thin, and crust is close to basalis, the skin of local visible a little healing; Latter the 7th day of wound, the surface of a wound obviously dwindles, the surface of a woundDry ruddy, without oozing out, crust separates, comes off with the surface of a wound, has as seen newborn skin to grow, and climbs skin speed; Wound the rear the 14thMy god, surface of a wound well-grown, is covered completely by newborn epithelial tissue, without infecting, and Sutureless reaction, without red and swollen, burn woundHealing completely.
As seen from Figure 5: latter the 7th day of wound, capillary quantity, fibrocyte, fibroblast, epidermal cell, inflammationCell showed increased, surface of a wound part is covered by epidermis; Latter the 14th day of wound, the surface of a wound is covered by epidermal cell, and epidermis healing is complete, glueFibrillation marshalling and parallel with epidermis, the connective fiber densification of arranging. This illustrates collagen peptide grafting of the present inventionSodium alginate sulfuric ester has good healing effect to deepⅱdegreeburnwound.
Claims (6)
1. collagen peptide grafted sodium alginate sulfuric ester, is characterized in that: it is by the carboxyl sodium base of sodium alginate sulfuric esterAfter activating, group carries out with collagen peptide 25-65 DEG C that graft reaction obtains again, described collagen peptide grafting alginic acidThe substitution value that in sodium sulfuric ester, carboxyl sodium group is replaced by collagen peptide is 0.310-0.469; Described sodium alginate sulfuric esterSulfuric ester substitution value be 1-1.8; Collagen peptide grafted sodium alginate sulfuric ester is prepared by following methods: by alginic acidAfter the carboxyl sodium group of sodium sulfuric ester reacts with carboxyl activator is activated, then with collagen peptide 25-65 DEG C to carry out grafting anti-Should, post processing, in described priming reaction, sodium alginate sulfuric ester is to be first 5-7 with pH 2-(N-morpholino) ethyl sulfonic acid cushionsAfter solution dissolves, then add carboxyl activator to react, the mass ratio of described collagen peptide and sodium alginate sulfuric ester is0.4:1-2.0:1。
2. the preparation method of collagen peptide grafted sodium alginate sulfuric ester claimed in claim 1, is characterized in that: it is firstAfter the carboxyl sodium group of sodium alginate sulfuric ester is reacted with carboxyl activator is activated, then enter with collagen peptide 25-65 DEG CRow graft reaction, post processing, in described priming reaction, sodium alginate sulfuric ester is 2-(N-morpholino) second that is first 5-7 with pHAfter sulfonic acid cushioning liquid dissolves, then add carboxyl activator to react, described collagen peptide and sodium alginate sulfuric esterMass ratio is 0.4:1-2.0:1.
3. the preparation method of collagen peptide grafted sodium alginate sulfuric ester according to claim 2, is characterized in that: instituteUnder the condition that the priming reaction of stating is is 5-7 at pH, sodium alginate sulfuric ester is reacted to 12-with carboxyl activator at 25-65 DEG C28 hours, described carboxyl activator was 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride and N-hydroxyl amberThe imido mixture of amber.
4. the preparation method of collagen peptide grafted sodium alginate sulfuric ester according to claim 3, is characterized in that: instituteState the matter of 1-in carboxyl activator (3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride and N-hydroxy-succinamideAmount is than being 3.3:1-6.7:1; The mass ratio of described N-hydroxy-succinamide and sodium alginate sulfuric ester is 0.2:1-0.6:1.
5. the preparation method of collagen peptide grafted sodium alginate sulfuric ester according to claim 2, is characterized in that: instituteThe reaction time of stating graft reaction is 10-30min.
6. collagen peptide grafted sodium alginate sulfuric ester according to claim 1 is preparing in wound surface healing medicineApplication.
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1542021A (en) * | 2003-11-04 | 2004-11-03 | 武汉大学 | Sodium alginate sulfuric ester and preparation method and use thereof |
| CN101018513A (en) * | 2004-08-13 | 2007-08-15 | 渥太华健康研究所 | Vision enhancing ophthalmic devices and related methods and compositions |
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| CN1542021A (en) * | 2003-11-04 | 2004-11-03 | 武汉大学 | Sodium alginate sulfuric ester and preparation method and use thereof |
| CN101018513A (en) * | 2004-08-13 | 2007-08-15 | 渥太华健康研究所 | Vision enhancing ophthalmic devices and related methods and compositions |
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| Title |
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| "Study on gelatin-containing artificial skin:Ⅰ.Preparation and characteristics of novel gelatin-alginate sponge";Young Seon Choi et al.;《Biomaterials》;19990331;第20卷(第5期);第409-412,414-415页 * |
| "褐藻酸钠硫酸酯的抗凝血及抗血栓作用";许实波等;《热带海洋》;19980630;第17卷(第2期);第32-37页 * |
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