CN105606602A - Method for measuring PEG-dithiol residues in cross-linked sodium hyaluronate gel - Google Patents
Method for measuring PEG-dithiol residues in cross-linked sodium hyaluronate gel Download PDFInfo
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- CN105606602A CN105606602A CN201510979778.6A CN201510979778A CN105606602A CN 105606602 A CN105606602 A CN 105606602A CN 201510979778 A CN201510979778 A CN 201510979778A CN 105606602 A CN105606602 A CN 105606602A
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Abstract
The invention relates to a detection method for measuring PEG-dithiol residues in cross-linked sodium hyaluronate gel. The detection method which is simple to operate and used for measuring the PEG-diothiol residues in the cross-linked gel quickly is established according to the principle that a compound produced by reacting an Ellman's reagent with thiol is in linear relation with the content of PEG-dithiol in the 412 nm position. The detection method has the good linear relation within 40-200 mu g/ml and can be particularly applied to detection of macromolecular cross-linked gel.
Description
Technical field:
The present invention relates to biochemistry, pharmaceutical chemistry and Pharmaceutical Analysis technical field, be specifically related to a kind of surveyDetermine the residual method of dimercapto polyethylene glycol in cross-linking sodium hyaluronate gel.
Background technology:
Dimercapto polyethylene glycol, in current disclosed document, there is no its toxicity data. In view of productSafety in utilization is considered, is necessary PEG-dithiol residual in product to carry out the detection of residual quantity limit.There is not at present the detection method of this content of material of bibliographical information or residual volume.
Summary of the invention:
The object of this invention is to provide a kind of dimercapto polyethylene glycol of measuring in cross-linking sodium hyaluronate gel residualThe detection method of staying, to solve the residual safety issue being caused of dimercapto polyethylene glycol, the method inspectionSurvey accurately, inspection cost, checkability are high, inspection work is carried out conveniently.
For realizing object of the present invention, the technical solution adopted in the present invention is:
A method of measuring dimercapto polyethylene glycol in cross-linking sodium hyaluronate gel, is characterized in that,Comprise the following steps:
(1) preparation of phosphate buffer: get ADSP 912mg, a hypophosphite monohydrate dihydroSodium 300mg, adds water and makes to be dissolved into 500ml, obtains pH value and be 7.4 phosphate buffer;
(2) preparation of PEG-dithiol reference substance solution: precision takes dimercapto polyethylene glycol reference substance40mg, puts in 20ml measuring bottle, and add pH value and be 7.4 phosphate buffer and dissolve and be diluted to scale,Shake up; Precision measures 5ml, puts in 25ml measuring bottle, adds pH value and is 7.4 phosphate buffer and be diluted toScale, making concentration is the PEG-dithiol reference substance solution of 0.4mg/ml;
(3) preparation of acetate buffer: get 11.55ml glacial acetic acid, be settled to 1000ml, obtain denseDegree is 0.2mol/L acetic acid; Take 16.4g anhydrous sodium acetate or 27.2g sodium acetate trihydrate is dissolved inIn 1000ml water, obtaining concentration is 0.2mol/L sodium acetate; Getting 148ml concentration is 0.2mol/L acetic acidSolution and 352ml concentration are that 0.2mol/L SAS mixes, and obtain pH and be 5.0, concentration is0.2mol/L acetate buffer;
(4) preparation of enzyme solutions: take the 809U/mg hyaluronidase 30mg that simga company produces,Add pH value and be 5.0, concentration is that 0.2mol/L acetate buffer dissolves and makes 10ml enzyme solutions;
(5) sample solution preparation: get cross-linking sodium hyaluronate gel 1.0g, add 1.0ml step (4)The enzyme solutions of preparation, puts 37 DEG C of degraded 2.0h, makes gel degradation become sample solution for subsequent use;
(6) reaction buffer preparation: take 35.814g disodium hydrogen phosphate dodecahydrate, be dissolved in water and makeBecome 100ml, obtaining concentration is 1mol/L disodium phosphate soln; Take 15.601g bis-hypophosphite monohydrates twoHydrogen sodium, is dissolved in water and makes into 100ml, obtains the sodium dihydrogen phosphate that concentration is 1mol/L; DrawThe concentration of 9.32ml is the di(2-ethylhexyl)phosphate that the concentration of 1mol/L disodium phosphate soln and 0.68ml is 1mol/LHydrogen sodium solution is diluted with water to 90ml, mixes, and with sodium hydroxide test solution adjust pH to 8.0, adds water and determines extremely100ml, obtains pH value and is 8.0, concentration is 0.1mol/L sodium radio-phosphate,P-32 solution; Take 0.03724gEDTATo pH value be 8.0, concentration is in 0.1mol/L sodium radio-phosphate,P-32 solution, mixes, obtain pH value and be 8.0,Concentration is 0.1mol/L reaction buffer;
(7) preparation of DTNB solution: take 40mgDTNB, add reaction buffering prepared by step (6)Liquid dissolves makes DTNB solution for standby;
(8) preparation of calibration curve: precision measures PEG-dithiol reference substance prepared by step (2)Solution 0,0.2,0.4,0.6,0.8ml, 1.0ml put in 1.5ml centrifuge tube, add successively pH valueBe 7.4 phosphate buffers to 1.0ml, mix; Divide and get the each 0.5ml of above-mentioned solution, add 0.5ml step(4) enzyme solutions of preparing, mixes, and places about 2.0h for 37 DEG C, then the reaction that respectively prepared by step (6)Buffer solution 5.0ml, vortex mixes, and the DTNB solution 0.2ml that adds step (7) to prepare, mixes chamberTemperature is placed 15 minutes; The solution of preparing through said method taking reference substance solution 0ml is as blank, at 412nmWavelength place measure absorbance, with the concentration of reference substance solution, corresponding absorbance is calculated to regression equation;
(9) the residual mensuration of cross-linking sodium hyaluronate gel PEG-dithiol: get step (5) preparationThe sample solution 1.0ml of gained, the reaction buffer and the step that add step (6) to prepare by step (8)(7) the DTNB solution reaction of preparing 15 minutes, measures absorbance at the wavelength place of 412nm, according to returningReturn equation to calculate the residual of PEG-dithiol in cross-linking sodium hyaluronate gel.
In a preferred embodiment of the invention, in described step (4), the enzyme solutions of preparation is 2400U/mlEnzyme solutions.
In a preferred embodiment of the invention, the molecular weight of measurable PEG-dithiol is 3400Da。
The detection principle of the detection method of dimercapto polyethylene glycol of the present invention is according in dimercapto polyethylene glycolThe sulfydryl containing and DTNB solution react, and produce yellow compound, and this compound is in the meeting of 412nm placeProduce absorption maximum.
Utilize in method detection assay cross-linking sodium hyaluronate gel of the present invention dimercapto polyethylene glycol residualStay, make up current dimercapto polyethylene glycol and cannot monitor as crosslinking agent the shortcoming of its residual quantity, suitable especiallyClose the residual detection of macromolecules cross-linking gel.
Detailed description of the invention
Can further be well understood to the present invention by specific embodiments of the invention given below, butThey are not limitation of the invention.
Embodiment 1
(1) preparation of phosphate buffer: get ADSP 912mg, a hypophosphite monohydrate dihydroSodium 300mg, adds water and makes to be dissolved into 500ml, obtains the phosphate buffer of pH7.4.
(2) preparation of PEG-dithiol reference substance solution: precision takes dimercapto polyethylene glycol reference substance40mg, puts in 20ml measuring bottle, adds phosphate buffer (pH7.4) and dissolves and be diluted to scale, shakes up.Precision measures 5ml, puts in 25ml measuring bottle, adds phosphate buffer (pH7.4) and is diluted to scale, makesThe reference substance solution of about 0.4mg/ml.
(3) preparation of acetate buffer: get 11.55ml glacial acetic acid, be settled to 1000ml, obtain0.2mol/L acetic acid; Take 16.4g anhydrous sodium acetate and be dissolved in 1000ml water, obtain 0.2mol/L vinegarAcid sodium; Get 148ml0.2mol/L acetum and 352ml0.2mol/L SAS mixes,To 0.2mol/L acetate buffer (pH5.0).
(4) preparation of enzyme solutions: take the about 30mg of hyaluronidase (809U/mg of simga company),Adding 0.2mol/L acetate buffer (pH5.0) dissolves and makes into 10ml.
(5) sample solution preparation: get the about 1.0g of cross-linking sodium hyaluronate gel, add 1.0ml enzyme liquid, put37 DEG C of about 2.0h of degraded, make gel degradation become solution for standby.
(6) reaction buffer preparation: take 35.814g disodium hydrogen phosphate dodecahydrate, be dissolved in water and makeBecome 100ml, obtain 1mol/L disodium phosphate soln; Take 15.601g bis-hypophosphite monohydrate sodium dihydrogens,Be dissolved in water and make into 100ml, obtain the sodium dihydrogen phosphate of 1mol/L; Draw the 1mol/L of 9.32mlThe sodium dihydrogen phosphate of the 1mol/L of disodium phosphate soln and 0.68ml is diluted with water to about 90ml,Mix, adjust pH to 8.0 with sodium hydroxide test solution, add water fixed to 100ml, obtain 0.1mol/L sodium phosphate(pH8.0) solution; Take in 0.03724gEDTA to 0.1mol/L sodium phosphate (pH8.0) solution, mix,Obtain 0.1mol/L sodium phosphate (pH8.0) 1mmol/LEDTA reaction buffer.
(7) DTNB[5,5 '-bis-thiobis (2-nitrobenzoic acid)] preparation of solution: take 40mgDTNB, adds the dissolving of 0.1mol/L sodium phosphate (pH8.0) 1mmol/LEDTA reaction buffer and makes into 10ml,Face with now joining.
(8) preparation of calibration curve: precision measure reference substance solution 0,0.2,0.4,0.6,0.8ml,1.0ml puts in 1.5ml centrifuge tube, adds successively phosphate buffer (pH7.4) to 1.0ml, mixes.Divide and get the each 0.5ml of above-mentioned solution, add 0.5ml enzyme liquid, mix, place about 2.0h, then add respectively for 37 DEG CEnter 0.1mol/L sodium phosphate (pH8.0) 1mmol/LEDTA reaction buffer 5.0ml, vortex mixes, and addsEnter DTNB solution 0.2ml, mix, room temperature is placed 15 minutes. With reference substance solution 0ml through said methodThe solution of preparation is blank, measures absorbance, with the concentration pair of reference substance solution at the wavelength place of 412nmCorresponding absorbance is calculated regression equation.
(9) mensuration of cross-linking sodium hyaluronate gel PEG-dithiol residual quantity: get step (5) systemThe sample solution 1.0ml of standby gained, adds reaction buffer and DTNB solution reaction 15 by step (8)Minute, measure absorbance at the wavelength place of 412nm, solidifying according to regression equation calculation cross-linking hyaluronic acid sodiumThe residual quantity of PEG-dithiol in glue.
The absorbance obtaining by detection is brought linear regression equation into and is conversed concentration.
Equation is: y=0.00099x-0.00539
The wherein concentration of x:PEG-dithiol (μ g/ml)
Y: absorbance
But this equation records during because of each test again, and the equation that this example provides is only for referenceResult of the test:
To the residual testing result of carrying out of dimercapto polyethylene glycol in three batches of cross-linking sodium hyaluronate gels in Table1。
Table 1
As known from Table 1, method of the present invention is to the poly-second two of dimercapto in three batches of cross-linking sodium hyaluronate gelsThe residual of alcohol detects, and made up the blank that there is no at present the method, ensured the safety of medicine.
Claims (3)
1. measure a method for dimercapto polyethylene glycol in cross-linking sodium hyaluronate gel, its feature existsIn, comprise the following steps:
(1) preparation of phosphate buffer: get ADSP 912mg, a hypophosphite monohydrate dihydroSodium 300mg, adds water and makes to be dissolved into 500ml, obtains pH value and be 7.4 phosphate buffer;
(2) preparation of PEG-dithiol reference substance solution: precision takes dimercapto polyethylene glycol reference substance40mg, puts in 20ml measuring bottle, and add pH value and be 7.4 phosphate buffer and dissolve and be diluted to scale,Shake up; Precision measures 5ml, puts in 25ml measuring bottle, adds pH value and is 7.4 phosphate buffer and be diluted toScale, making concentration is the PEG-dithiol reference substance solution of 0.4mg/ml;
(3) preparation of acetate buffer: get 11.55ml glacial acetic acid, be settled to 1000ml, obtain denseDegree is 0.2mol/L acetic acid; Take 16.4g anhydrous sodium acetate or 27.2g sodium acetate trihydrate is dissolved inIn 1000ml water, obtaining concentration is 0.2mol/L sodium acetate; Getting 148ml concentration is 0.2mol/L acetic acidSolution and 352ml concentration are that 0.2mol/L SAS mixes, and obtain pH and be 5.0, concentration is0.2mol/L acetate buffer;
(4) preparation of enzyme solutions: take the 809U/mg hyaluronidase 30mg that simga company produces,Add pH value and be 5.0, concentration is that 0.2mol/L acetate buffer dissolves and makes 10ml enzyme solutions;
(5) sample solution preparation: get cross-linking sodium hyaluronate gel 1.0g, add 1.0ml step (4)The enzyme solutions of preparation, puts 37 DEG C of degraded 2.0h, makes gel degradation become sample solution for subsequent use;
(6) reaction buffer preparation: take 35.814g disodium hydrogen phosphate dodecahydrate, be dissolved in water and makeBecome 100ml, obtaining concentration is 1mol/L disodium phosphate soln; Take 15.601g bis-hypophosphite monohydrates twoHydrogen sodium, is dissolved in water and makes into 100ml, obtains the sodium dihydrogen phosphate that concentration is 1mol/L; DrawThe concentration of 9.32ml is the di(2-ethylhexyl)phosphate that the concentration of 1mol/L disodium phosphate soln and 0.68ml is 1mol/LHydrogen sodium solution is diluted with water to 90ml, mixes, and with sodium hydroxide test solution adjust pH to 8.0, adds water and determines extremely100ml, obtains pH value and is 8.0, concentration is 0.1mol/L sodium radio-phosphate,P-32 solution; Take 0.03724gEDTATo pH value be 8.0, concentration is in 0.1mol/L sodium radio-phosphate,P-32 solution, mixes, obtain pH value and be 8.0,Concentration is 0.1mol/L reaction buffer;
(7) preparation of DTNB solution: take 40mgDTNB, add reaction buffering prepared by step (6)Liquid dissolves makes DTNB solution for standby;
(8) preparation of calibration curve: precision measures PEG-dithiol reference substance prepared by step (2)Solution 0,0.2,0.4,0.6,0.8ml, 1.0ml put in 1.5ml centrifuge tube, add successively pH valueBe 7.4 phosphate buffers to 1.0ml, mix; Divide and get the each 0.5ml of above-mentioned solution, add 0.5ml step(4) enzyme solutions of preparing, mixes, and places about 2.0h for 37 DEG C, then the reaction that respectively prepared by step (6)Buffer solution 5.0ml, vortex mixes, and the DTNB solution 0.2ml that adds step (7) to prepare, mixes chamberTemperature is placed 15 minutes; The solution of preparing through said method taking reference substance solution 0ml is as blank, at 412nmWavelength place measure absorbance, with the concentration of reference substance solution, corresponding absorbance is calculated to regression equation;
(9) the residual mensuration of cross-linking sodium hyaluronate gel PEG-dithiol: get step (5) preparationThe sample solution 1.0ml of gained, the reaction buffer and the step that add step (6) to prepare by step (8)(7) the DTNB solution reaction of preparing 15 minutes, measures absorbance at the wavelength place of 412nm, according to returningReturn equation to calculate the residual of PEG-dithiol in cross-linking sodium hyaluronate gel.
2. the side of dimercapto polyethylene glycol in mensuration cross-linking sodium hyaluronate gel as claimed in claim 1Method, is characterized in that, in described step (4), the enzyme solutions of preparation is 2400U/ml enzyme solutions.
3. in mensuration cross-linking sodium hyaluronate gel as claimed in claim 1, dimercapto polyethylene glycol is residualMethod, it is characterized in that: the molecular weight of measurable PEG-dithiol is 3400Da.
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Cited By (4)
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| CN106248819A (en) * | 2016-07-13 | 2016-12-21 | 浙江景嘉医疗科技有限公司 | The detection method of lidocaine hydrochloride content in a kind of medical cross-linking sodium hyaluronate gel |
| CN109223708A (en) * | 2018-10-24 | 2019-01-18 | 上海景峰制药有限公司 | A kind of antineoplastic pharmaceutical compositions and its preparation method and application being crosslinked sodium hyaluronate |
| CN111122742A (en) * | 2020-01-07 | 2020-05-08 | 上海景峰制药有限公司 | Method for detecting residual quantity of dimercaptopolyethylene glycol in sample to be detected |
| CN115406885A (en) * | 2022-11-01 | 2022-11-29 | 常州百瑞吉生物医药有限公司 | Method for detecting residual cross-linking agent in disulfide bond cross-linked hyaluronic acid gel |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106248819A (en) * | 2016-07-13 | 2016-12-21 | 浙江景嘉医疗科技有限公司 | The detection method of lidocaine hydrochloride content in a kind of medical cross-linking sodium hyaluronate gel |
| CN109223708A (en) * | 2018-10-24 | 2019-01-18 | 上海景峰制药有限公司 | A kind of antineoplastic pharmaceutical compositions and its preparation method and application being crosslinked sodium hyaluronate |
| CN111122742A (en) * | 2020-01-07 | 2020-05-08 | 上海景峰制药有限公司 | Method for detecting residual quantity of dimercaptopolyethylene glycol in sample to be detected |
| CN115406885A (en) * | 2022-11-01 | 2022-11-29 | 常州百瑞吉生物医药有限公司 | Method for detecting residual cross-linking agent in disulfide bond cross-linked hyaluronic acid gel |
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