CN103805588A - Method for modifying superoxide dismutase by using lauric acid - Google Patents
Method for modifying superoxide dismutase by using lauric acid Download PDFInfo
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- CN103805588A CN103805588A CN201410062990.1A CN201410062990A CN103805588A CN 103805588 A CN103805588 A CN 103805588A CN 201410062990 A CN201410062990 A CN 201410062990A CN 103805588 A CN103805588 A CN 103805588A
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/96—Stabilising an enzyme by forming an adduct or a composition; Forming enzyme conjugates
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- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
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- C12N9/0089—Oxidoreductases (1.) acting on superoxide as acceptor (1.15)
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- C12Y115/00—Oxidoreductases acting on superoxide as acceptor (1.15)
- C12Y115/01—Oxidoreductases acting on superoxide as acceptor (1.15) with NAD or NADP as acceptor (1.15.1)
- C12Y115/01001—Superoxide dismutase (1.15.1.1)
Abstract
The invention discloses a method for modifying superoxide dismutase (SOD) by using lauric acid. The method comprises the following steps: putting lauric acid, thionyl chloride and a catalyst in a reactor, heating and reacting, and after ending reaction, distilling so as to obtain activated lauric acid; dissolving ox blood Cu/Zn-SOD in an alkalescence buffer solution, then adding activated lauric acid, heating, stirring for 60 minutes, concentrating, cooling, then adding absolute ethyl alcohol, centrifuging, washing, centrifuging again, dialyzing by using a dialyzer, collecting an enzymatic activity part, dialyzing, and carrying out ultrafiltration and freeze-drying so as to obtain the lauric acid modified superoxide dismutase. The lauric acid modified superoxide dismutase has the advantages that the enzyme recovery rate reaches above 90%, no harmful substances are remained, and the lauric acid modified superoxide dismutase is high in stability.
Description
Technical field
The present invention relates to proteolytic enzyme chemical modification technology field, relate in particular to a kind of method of La-SOD.
Background technology
Superoxide-dismutase (Superoxide dismutase, be called for short SOD), it is a kind of metalloenzyme being extensively present in nature animals and plants and some microbies, be the important member of biological antioxidant enzyme, it can remove the ultra-oxygen anion free radical (O producing in biological oxidation process
2 -), be one of important enzyme of the effective Scavenger of ROS of organism, be called as the first line of defence of organism antioxidant system.It using superoxide anion as substrate and catalysis its there is disproportionation reaction, thereby remove the superoxide radical harmful to body.Its catalytic mechanism is as follows:
SOD(oxidized form)+O
2 ----SOD
-(reduced form)+O
2
SOD
-(reduced form)+O
2 ----SOD(oxidized form)+H
2o
2
Total reaction: 2O
2 -+ 2H
+ sOD enzymeo
2+ H
2o
2
In the time that body produces unnecessary superoxide radical and can not be removed in time, will cause organism fatigue, accelerate aging and bring out various diseases simultaneously.Free radical theory is thought: free radical has the chemically reactive of height, is human homergy's intermediate product, can damage microbial film, is the root of various diseases Emergence and Development.SOD, as one of most important antioxidase body in body, can directly remove excessive superoxide radical, stops the peroxidation of body, has higher protective effect and health care to be worth to body.Due to the antioxygenation of superoxide-dismutase, it has been widely used in medical treatment, makeup and other chemical field.
Due to SOD be subject to short, relative molecular mass of transformation period large, be difficult for permeate through cell membranes, be subject to the restriction of the factors such as stomach en-decompositions, body internal specific when oral, very difficult widespread use, therefore must carry out chemically modified to albumen.General using water-soluble macromolecule carries out covalent modification as polyoxyethylene glycol, sucrose, dextrose liver and polyene belong to hydrocarbyl oxide etc. to SOD.But because the molecular weight of above-mentioned substance is larger, the albumen after modification has very strong immunogenicity, although zymetology stability is greatly improved, be still difficult to be utilized by human body.The superoxide-dismutase (LA-SOD) that lauric acid is modified overcomes above-mentioned problem, the amino effect of lauric acid and SOD molecular surface, the introducing of lauric acid surface hydrophobicity group, increase the hydrophobicity on enzyme surface, hide the easy stretching, extension site of enzyme to heat, acid, alkali, organic solvent and proteolytic ferment sensitivity, thereby strengthened widely the stability of enzyme.Simultaneously, the introducing of micromolecular lauric acid hydrophobic grouping can also be covered the antigenic determinant of enzyme molecule, remove its immunogenicity, the more important thing is that hydrophobic grouping cell membrane and lipid bilayer have the affinity of height, make the Transdermal absorption of macromole enzyme have theoretical basis.
But the technology of existing La-SOD but mostly exists that the rate of recovery is low, objectionable impurities is residual and the series of problems such as poor stability, seriously limit the industrial application of La-SOD.
Summary of the invention
Object of the present invention is exactly to solve that the technology rate of recovery of La-SOD is low in prior art, objectionable impurities is residual and the problem such as poor stability, and a kind of method of La-SOD is provided.
For realizing this technique effect, the invention provides following technical scheme:
A method for La-SOD, the method comprises the following steps:
(1) the catalyzer pyridine DMF of 100～200ml lauric acid, 5～15g sulfur oxychloride and 5～10ml is joined in reactor, be heated to 90～95 ℃, stirring reaction 1～3 hour, then reflux 1～3 hour,
(2) reflux and finish, allow reactant carry out fractionation, decompression, removes excessive sulfur oxychloride, collects the cut of 146～150 ℃, obtains the lauric acid that activates, and then dialysis, freeze-drying be white powder, and be placed in refrigerator and preserve,
(3) getting 150～250g concentration is that the ox blood Cu/Zn-SOD of 4500U/mg is dissolved in 15-20L weakly alkaline damping fluid, stirring and dissolving at 20 ℃, add while stirring the lauric acid of 40～60ml activation, then be warming up to 40 ℃, stir after 60min, solution is concentrated into 2000～3000ml, is then cooled to rapidly room temperature
(4) add the dehydrated alcohol of-18 ℃ of 3 times of volumes, be with rotating speed that 4000r/min carries out centrifugal, collecting precipitation, the bi-distilled water of 1500～2500ml will be precipitated and dissolved in, carry out centrifugal with the rotating speed of 4500r/min again, remove insolubles, get supernatant liquor by tubular fibre dialyzer, convert distill water dialysis, dialyzate is used the chromatography column chromatography 1.5-2.5 hour that damping fluid balance is good in advance, finally collect enzymic activity part, dialysis, ultrafiltration, freeze-drying, obtain the superoxide-dismutase (LA-SOD) that lauric acid is modified.
Wherein, in step (3), weakly alkaline damping fluid is the solution with the pH=9 of Sodium phosphate dibasic allotment, in step (4), damping fluid is that concentration is 2.5mmol/L, the potassium sulfate damping fluid of pH=7.6, and in step (4), chromatography column is the Sephacryl S-200 chromatography column of 5cm × 73cm.
The present invention also provides following technical scheme:
A method for La-SOD, comprises the following steps:
A. lauric acid, sulfur oxychloride and catalyzer are joined in reactor, stir, heat;
B. vacuum fractionation, obtains activation lauric acid;
C. Cu/Zn-SOD is dissolved in weakly alkaline damping fluid and is dissolved, add activation lauric acid stirring heating, subsequently by the concentrated solution room temperature that is then cooled to rapidly;
D. add dehydrated alcohol, centrifugal, collecting precipitation, will be precipitated and dissolved in bi-distilled water, again carry out centrifugally, remove insolubles, get supernatant liquor and convert distill water dialysis, collect enzymic activity part, obtain the superoxide-dismutase LA-SOD that lauric acid is modified.
Adopt present method Modified Superoxide Dismutase to have the following advantages: the enzyme rate of recovery reaches more than 90%, residual without any objectionable impurities, and normal temperature stability inferior is high.
Accompanying drawing explanation
Fig. 1. natural SOD and LA-SOD ultra-violet absorption spectrum comparison diagram;
The stability influence comparison diagram of Fig. 2 .pH to natural SOD and LA-SOD enzyme;
Fig. 3. the stability influence comparison diagram of temperature to natural SOD and LA-SOD enzyme;
Fig. 4. the stability influence comparison diagram (37 ℃) of mankind's gastric juice to natural SOD and LA-SOD enzyme.
Embodiment
For clearer explanation technical characterstic of the present invention, below by embodiment, the present invention will be described in detail.
Embodiment mono-
A method for La-SOD, step is as follows:
(1) the catalyzer pyridine DMF of 150ml lauric acid, 9g sulfur oxychloride and 8ml is joined in reactor, be heated to 92 ℃, stirring reaction 2 hours, then reflux 2 hours,
(2) reflux and finish, allow reactant carry out fractionation, decompression, removes excessive sulfur oxychloride, collects the cut of 146～150 ℃, obtains the lauric acid that activates, and then dialysis, freeze-drying be white powder, and be placed in refrigerator and preserve,
(3) getting 200g concentration is that the ox blood Cu/Zn-SOD of 4500U/mg is dissolved in 18L weakly alkaline damping fluid (solution of the pH=9 of Sodium phosphate dibasic allotment), stirring and dissolving at 20 ℃, add while stirring the lauric acid of 50ml activation, then be warming up to 40 ℃, stir after 60min, solution is concentrated into 2500ml, is then cooled to rapidly room temperature
(4) add the dehydrated alcohol of-18 ℃ of 3 times of volumes, be with rotating speed that 4000r/min carries out centrifugal, collecting precipitation, the bi-distilled water of 2000ml will be precipitated and dissolved in, carry out centrifugal with the rotating speed of 4500r/min again, remove insolubles, get supernatant liquor by tubular fibre dialyzer, convert distill water dialysis, dialyzate is used damping fluid in advance, and (concentration is 2.5mmol/L, the potassium sulfate damping fluid of pH=7.6) chromatography column (the Sephacryl S-200 of 5cm × 73cm) chromatography that balance is good 2 hours, finally collect enzymic activity part, dialysis, ultrafiltration, freeze-drying, obtain the superoxide-dismutase (LA-SOD) that lauric acid is modified.
Embodiment bis-
A method for La-SOD, step is as follows:
(1) the catalyzer pyridine DMF of 100ml lauric acid, 5g sulfur oxychloride and 5ml is joined in reactor, be heated to 90 ℃, stirring reaction 1 hour, then reflux 1 hour,
(2) reflux and finish, allow reactant carry out fractionation, decompression, removes excessive sulfur oxychloride, collects the cut of 146～150 ℃, obtains the lauric acid that activates, and then dialysis, freeze-drying be white powder, and be placed in refrigerator and preserve,
(3) getting 150g concentration is that the ox blood Cu/Zn-SOD of 4500U/mg is dissolved in 15L weakly alkaline damping fluid (solution of the pH=9 of Sodium phosphate dibasic allotment), stirring and dissolving at 20 ℃, add while stirring the lauric acid of 40ml activation, then be warming up to 40 ℃, stir after 60min, solution is concentrated into 2000ml, is then cooled to rapidly room temperature
(4) add the dehydrated alcohol of-18 ℃ of 3 times of volumes, be with rotating speed that 4000r/min carries out centrifugal, collecting precipitation, the bi-distilled water of 1500ml will be precipitated and dissolved in, carry out centrifugal with the rotating speed of 4500r/min again, remove insolubles, get supernatant liquor by tubular fibre dialyzer, convert distill water dialysis, dialyzate is used damping fluid in advance, and (concentration is 2.5mmol/L, the potassium sulfate damping fluid of pH=7.6) chromatography column (the Sephacryl S-200 of 5cm × 73cm) chromatography that balance is good 1.5 hours, finally collect enzymic activity part, dialysis, ultrafiltration, freeze-drying, obtain the superoxide-dismutase (LA-SOD) that lauric acid is modified.
Embodiment tri-
A method for La-SOD, step is as follows:
(1) the catalyzer pyridine DMF of 200ml lauric acid, 15g sulfur oxychloride and 10ml is joined in reactor, be heated to 95 ℃, stirring reaction 3 hours, then reflux 3 hours,
(2) reflux and finish, allow reactant carry out fractionation, decompression, removes excessive sulfur oxychloride, collects the cut of 146～150 ℃, obtains the lauric acid that activates, and then dialysis, freeze-drying be white powder, and be placed in refrigerator and preserve,
(3) getting 250g concentration is that the ox blood Cu/Zn-SOD of 4500U/mg is dissolved in 20L weakly alkaline damping fluid (solution of the pH=9 of Sodium phosphate dibasic allotment), stirring and dissolving at 20 ℃, add while stirring the lauric acid of 60ml activation, then be warming up to 40 ℃, stir after 60min, solution is concentrated into 3000ml, is then cooled to rapidly room temperature
(4) add the dehydrated alcohol of-18 ℃ of 3 times of volumes, be with rotating speed that 4000r/min carries out centrifugal, collecting precipitation, the bi-distilled water of 2500ml will be precipitated and dissolved in, carry out centrifugal with the rotating speed of 4500r/min again, remove insolubles, get supernatant liquor by tubular fibre dialyzer, convert distill water dialysis, dialyzate is used damping fluid in advance, and (concentration is 2.5mmol/L, the potassium sulfate damping fluid of pH=7.6) chromatography column (the Sephacryl S-200 of 5cm × 73cm) chromatography that balance is good 2.5 hours, finally collect enzymic activity part, dialysis, ultrafiltration, freeze-drying, obtain the superoxide-dismutase (LA-SOD) that lauric acid is modified.
Adopt the prepared LA-SOD results of performance analysis of present method as follows:
1, the enzyme rate of recovery
Measure the vigor of LA-SOD with pyrogallol Autoxidation Method, result demonstration, adopting the vigor of the prepared LA-SOD of present method is that every milligram of sample contains SOD10650 unit of enzyme, the enzyme rate of recovery reaches more than 90%.
2, ultra-violet absorption spectrum
Measure with Japanese Shimadzu UV-240 spectrophotometer.
As shown in Figure 1, the ultraviolet absorption peak of LA-SOD is consistent with natural SOD, still at 258nm place, so illustrate in the prepared LA-SOD of employing present method residual without any impurity.
3, stability
3.1pH stability
LA-SOD and natural SOD are placed on respectively in the worth damping fluid of different pH, then at 25 ℃ of insulation 2h, then measure the vigor of SOD and calculate relative activity.
As can be seen from Figure 2, higher than natural SOD by the pH stability of the prepared LA-SOD of present method.
3.2 thermostability
LA-SOD and natural SOD are placed in respectively at different temperature and are incubated 2h, then measure enzyme activity, and calculate relative activity take the enzyme activity at 25 ℃ as benchmark.
As shown in Figure 3, the vigor of two kinds of SOD all declines with temperature rise, but adopts the prepared LA-SOD of present method will be higher than natural SOD to the stability of temperature.
3.3 stability in human gastric juice
Get on an empty stomach gastric juice 10ml of normal people, be diluted to respectively 1:10,1:20,1:30,1:40,1:50, then adds respectively LA-SOD and natural SOD, is incubated 2h at 37 ℃, then measures SOD vigor and calculate relative activity.
As shown in Figure 4, adopt present method prepared LA-SOD and natural SOD vigor in gastric juice all lower, but along with gastric juice extension rate increases, SOD vigor rise.And adopt the prepared LA-SOD of present method more stable than natural SOD.
The stability of depositing under 3.4 room temperatures
Adopt the prepared LA-SOD lyophilized powder of present method to be placed under room temperature and deposit 1 year, measure at regular intervals its vigor and calculate relative activity.
Result shows, adopts the prepared LA-SOD of present method at room temperature to deposit 1 year, and its vigor changes little, so its shelf life at room temperature can reach more than 2 years.
In sum, adopt the stability of the prepared LA-SOD of present method very high.
Claims (10)
1. a method for La-SOD, is characterized in that: the method comprises the following steps:
(1) the catalyzer pyridine DMF of 100～200ml lauric acid, 5～15g sulfur oxychloride and 5～10ml is joined in reactor, be heated to 90～95 ℃, stirring reaction 1～3 hour, then reflux 1～3 hour,
(2) reflux and finish, allow reactant carry out fractionation, decompression, removes excessive sulfur oxychloride, collects the cut of 146～150 ℃, obtains the lauric acid that activates, and then dialysis, freeze-drying be white powder, and be placed in refrigerator and preserve,
(3) getting 150～250g concentration is that the ox blood Cu/Zn-SOD of 4500U/mg is dissolved in 15-20L weakly alkaline damping fluid, stirring and dissolving at 20 ℃, add while stirring the lauric acid of 40～60ml activation, then be warming up to 40 ℃, stir after 60min, solution is concentrated into 2000～3000ml, is then cooled to rapidly room temperature
(4) add the dehydrated alcohol of-18 ℃ of 3 times of volumes, be with rotating speed that 4000r/min carries out centrifugal, collecting precipitation, the bi-distilled water of 1500～2500ml will be precipitated and dissolved in, carry out centrifugal with the rotating speed of 4500r/min again, remove insolubles, get supernatant liquor by tubular fibre dialyzer, convert distill water dialysis, dialyzate is used the chromatography column chromatography 1.5-2.5 hour that damping fluid balance is good in advance, finally collect enzymic activity part, dialysis, ultrafiltration, freeze-drying, obtain the superoxide-dismutase that lauric acid is modified.
2. a method for La-SOD, is characterized in that: the method comprises the following steps:
(1) the catalyzer pyridine DMF of 150ml lauric acid, 9g sulfur oxychloride and 8ml is joined in reactor, be heated to 90～95 ℃, stirring reaction 2 hours, then reflux 2 hours,
(2) reflux and finish, allow reactant carry out fractionation, decompression, removes excessive sulfur oxychloride, collects the cut of 146～150 ℃, obtains the lauric acid that activates, and then dialysis, freeze-drying be white powder, and be placed in refrigerator and preserve,
(3) getting 200g concentration is that the ox blood Cu/Zn-SOD of 4500U/mg is dissolved in 18L weakly alkaline damping fluid, and stirring and dissolving at 20 ℃ adds the lauric acid of 50ml activation while stirring, then be warming up to 40 ℃, stir after 60min, solution is concentrated into 2500ml, then be cooled to rapidly room temperature
(4) add the dehydrated alcohol of-18 ℃ of 3 times of volumes, be with rotating speed that 4000r/min carries out centrifugal, collecting precipitation, will be precipitated and dissolved in the bi-distilled water of 2000ml, then carries out centrifugal with the rotating speed of 4500r/min, remove insolubles, get supernatant liquor by tubular fibre dialyzer, convert distill water dialysis, dialyzate is used the chromatography column chromatography 2 hours that damping fluid balance is good in advance, finally collect enzymic activity part, dialysis, ultrafiltration, freeze-drying, obtain the superoxide-dismutase that lauric acid is modified.
3. the method for a kind of La-SOD as claimed in claim 1 or 2, is characterized in that: in step (3), weakly alkaline damping fluid is the solution with the pH=9 of Sodium phosphate dibasic allotment.
4. the method for a kind of La-SOD as claimed in claim 1 or 2, is characterized in that: in step (4), damping fluid is that concentration is 2.5mmol/L, the potassium sulfate damping fluid of pH=7.6.
5. the method for a kind of La-SOD as claimed in claim 1 or 2, is characterized in that: in step (4), chromatography column is the SephacrylS-200 chromatography column of 5cm × 73cm.
6. a method for La-SOD, comprises the following steps:
A. lauric acid, sulfur oxychloride and catalyzer are joined in reactor, stir, heat;
B. vacuum fractionation, obtains activation lauric acid;
C. Cu/Zn-SOD is dissolved in weakly alkaline damping fluid and is dissolved, add activation lauric acid stirring heating, subsequently by the concentrated solution room temperature that is then cooled to rapidly;
D. add dehydrated alcohol, centrifugal, collecting precipitation, will be precipitated and dissolved in bi-distilled water, again carry out centrifugally, remove insolubles, get supernatant liquor and convert distill water dialysis, collect enzymic activity part, obtain the superoxide-dismutase LA-SOD that lauric acid is modified.
7. the method for a kind of La-SOD according to claim 6, in step a, Heating temperature is 90 ℃～95 ℃, and be 1～3 hour heat-up time, and carry out under the condition refluxing, and described catalyzer is pyridine DMF.
8. the method for a kind of La-SOD according to claim 7, vacuum fractionation in step b, collects the cut of 146～150 ℃, obtains the lauric acid of activation, and then dialysis, freeze-drying are to refrigerate after white powder.
9. the method for a kind of La-SOD according to claim 8, the dehydrated alcohol adding in steps d is 3 times of concentrated solution volume, dehydrated alcohol temperature is-18 ℃.
10. the method for a kind of La-SOD according to claim 8, wherein said dialyzate is used the chromatography column chromatography 1.5-2.5 hour that damping fluid balance is good in advance, and described damping fluid is that concentration 2.5mmol/L, pH are 7.6 potassium sulfate solution.
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| CN104906561A (en) * | 2014-05-30 | 2015-09-16 | 中国石油化工股份有限公司 | Application of lauric acid modified SOD on labor protection of chemical industry |
| CN104906562A (en) * | 2014-05-30 | 2015-09-16 | 中国石油化工股份有限公司 | Application of lauric acid modified SOD on prevention of chronic radiation skin lesion |
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| CN104906561B (en) * | 2014-05-30 | 2017-12-26 | 中国石油化工股份有限公司青岛安全工程研究院 | Application of the laurate modification SOD in terms of chemical industry labour protection |
| CN104404020A (en) * | 2014-11-05 | 2015-03-11 | 岭南师范学院 | Preparation method of lyophilized agave SOD modifier mPEG-SOD powder |
| CN104404020B (en) * | 2014-11-05 | 2017-04-26 | 岭南师范学院 | Preparation method of lyophilized agave SOD modifier mPEG-SOD powder |
| CN104357410B (en) * | 2014-11-05 | 2017-04-05 | 岭南师范学院 | A kind of preparation method of modification ixtle SOD lyophilized powder |
| CN104357410A (en) * | 2014-11-05 | 2015-02-18 | 岭南师范学院 | Preparation method of freeze-dried powder for modifying ixtle SOD |
| CN105087509A (en) * | 2015-08-27 | 2015-11-25 | 江苏奥晟生物医疗科技有限公司 | Preparation method of lauric acid modified superoxide dismutase |
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Application publication date: 20140521 |