CN101293101A - Gamma-polyglutamic acid-vanadyl complexes, preparation and application thereof - Google Patents
Gamma-polyglutamic acid-vanadyl complexes, preparation and application thereof Download PDFInfo
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- CN101293101A CN101293101A CNA2008100393255A CN200810039325A CN101293101A CN 101293101 A CN101293101 A CN 101293101A CN A2008100393255 A CNA2008100393255 A CN A2008100393255A CN 200810039325 A CN200810039325 A CN 200810039325A CN 101293101 A CN101293101 A CN 101293101A
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Abstract
The invention relates to a Gamma-PGA-vanadyl complex, a preparation thereof and application, which pertains to the organic vanadium compounds and the technical field of the preparation and the application. The composite is formed by connecting the carboxyl group of the Gamma-PGA and the coordination bond on VOSO4 formed by VO<2 +>, and the molecular structural general formula is: (VO<2 +>) m-(Gamma-PGA), wherein, m is a positive integer ranging from 2500 to 6000. The commercial bacteria is utilized to carry out the fermentation, the separation and the purification of the Gamma-PGA, the Gamma-PGA and the VOSO4 are carried out the modification reaction, thus obtaining a crude product of the VO-Gamma-PGA composite, and the VO-Gamma-PGA composite is further obtained by centrifugalization and vacuum drying. The Gamma-PGA-vanadyl composite has the advantages that: the Gamma-PGA is taken as a carrier, the molecular weight thereof is large, thus playing the role of realizing the sustained release of the carrying drug, the biocompatibility is great, and the Gamma-PGA-vanadyl composite is non-toxic. The carrier Gamma-PGA is obtained by the microbial fermentation and preparation, the structure is homogeneous, the molecular weight is larger and the cost is low.
Description
Technical field
The present invention relates to a kind of gamma-polyglutamic acid-vanadyl complexes and preparation thereof and application, definitely say, relate to a kind of VO-γ-PGA complex and preparation and application, belong to the technical field of organic vanadium chemical compound and preparation and application.
Background technology
Diabetes be one group because defect of insulin secretion and biological action obstacle thereof cause is the metabolic disease of feature with the hyperglycemia.It can cause a series of severe complications and cause long-term damage, functional defect and the depletion of various internal organs, be worldwide commonly encountered diseases and frequently-occurring disease.In in the past 20 years, diabetics quantity is explosive increase in the world wide, has almost turned over 3 times.At present diabetics sum in the whole world is nearly 200,000,000, and estimating 2010 and will rise to 2.2 hundred million, 2025 will be above 300,000,000.Along with the variation of expanding economy and people life style, the prevalence and the case fatality rate of China's diabetes also are being fast rise trend at present, become the third-largest noninfectious of the serious harm people ' s health after cardiovascular and cerebrovascular disease, tumor.Diabetics has increased nearly 5 times in nearest 25 years.China's diabetics number is more than 4,000 ten thousand at present, is only second to India and occupies the second place of the world, estimates that annual morbidity rate of increase surpasses 6%, and therefore, the market potential of the antidiabetic medicine of efficient and cheap is huge.
Vanadium is the trace element of needed by human, plays an important role in the metabolic process of glucose.Just find that as far back as French scientist Lynnet in 1899 vanadium can reduce glucose in urine.The eighties in last century, people have just found the para-insulin effect and the antidiabetic effect of vanadium, and to vanadium oxysulfate (VOSO
4) wait the hypoglycemic activity of inorganic matter to do systematic research.The result shows the level of this chemical compound energy blood sugar lowering.
But the inorganic vanadium chemical compound fat-soluble little, bioavailability is low, activity is not high, required dosage is big, and often with side effect such as gastrointestinal upset, nausea,vomiting,diarrheas.In order to reduce the absorption of side effect and promotion vfanadium compound, the organic coordination compound of vanadium is subjected to extensive concern, and it has become the research focus of domestic and international researcher.Domestic and international a series of result of study shows that the hypoglycemic activity of organic vanadium chemical compound generally is higher than the inorganic vanadium chemical compound, fat-soluble height, and Premeabilisation of cells power is strong, and does not have tangible digestive tract side effects.And the part that they select mainly comprises: biological micromolecule aminoacid and derivant thereof; The organic carboxyl acid class of low toxicity and contain hetero atom tripod type organic compound.But these ligand molecular amounts are all less, enter and do not have slow release effect in the body, bioavailability is low, activity is not high.In addition, the organic carboxyl acid class also has certain toxicity.
Summary of the invention
First technical problem that the present invention will solve is to propose a kind of VO-γ-PGA complex, it is characterized in that this complex is by γ-PGA and VOSO
4By carboxyl on the former and the VO on the latter
2+The coordinate bond that forms is formed by connecting, and its general formula of molecular structure and structural formula are respectively: (VO
2+)
m-(γ-PGA), wherein, m be between 2500～6000 positive integer and
Its molecular weight is between 1000kD～2000kD.
The advantage of this complex is that bioavailability height, activity are strong, toxic and side effects is little.
Second technical problem that the present invention will solve provides the preparation method of VO-γ-PGA complex.
The scheme that the present invention solves the problems of the technologies described above is: utilize commercially available strain to carry out the fermentation of γ-PGA and it is carried out separation and purification, with γ-PGA and VOSO
4Carry out modification reaction, obtain VO-γ-PGA complex crude product, obtain VO-γ-PGA complex through centrifugal, vacuum drying again.
Now describe technical scheme of the present invention in detail.The preparation method of this complex is characterized in that, the concrete operations step:
The preparation of first step γ-PGA-Na
Inoculum concentration by 3%～7% inserts the LB fluid medium with purchasing in the B.Subtils.sp at Chinese microorganism strain preservation center activation back, add maltose 30g～70g, yeast extract 5g～15g, sodium glutamate 10g～50g in every liter of LB fluid medium, NaCl 5g～15g, KH
2PO
41g～9g, MgSO
47H
2O 0.1g～0.9g, the pH value of culture medium is 5.0～7.0,20 ℃～50 ℃ following shake flask fermentation 24h～72h, gets fermentation liquid, 1～7 times of fermentation liquid adding distil water dilution, 8000r/min～15000r/min is centrifugal, and 10min～20min removes thalline, and dehydrated alcohol is added in the supernatant, and the volume ratio of supernatant and dehydrated alcohol is 1: 1～5, stir to such an extent that precipitate, vacuum drying gets γ-PGA-Na crude product, and this crude product is dissolved in distilled water, concentration is 0.5%～1.5%, with the distilled water is the dialysis solution dialysis, filters, and gets filtrate, the filtrate lyophilization, get γ-PGA-Na, its molecular weight is between 1000kD～2000kD, and every liter of culture medium makes γ-PGA-Na20.0g～30.26g;
The preparation of second step VO-γ-PGA complex
γ-the PGA-Na of 1.5g～15g first step preparation is dissolved in the 450ml distilled water, is stirred to dissolving fully, get γ-PGA-Na solution, 2.62gVOSO
4Be dissolved in the 200ml distilled water, be stirred to dissolving fully, get VOSO
4Solution stirs down VOSO
4Solution adds γ-PGA-Na solution, γ-PGA-Na solution-COOH and VOSO
4The VO of solution
2+Mol ratio be under 1～10: 1,30 ℃～70 ℃, stirring reaction 0.5h～5h, under 20 ℃～30 ℃, the centrifugal 20min～40min of 10000r/min～15000r/min abandons supernatant, precipitation is dissolved in the distilled water of 5～20 times of volumes, under 20 ℃～30 ℃, and the centrifugal 20min～40min of 10000r/min～15000r/min, abandon supernatant, obtain VO-γ-PGA complex crude product, distillation water washing and precipitating 1 time～5 times, filter, abandon filtrate, vacuum drying, VO-γ-PGA complex of 1.42g～14.2g.
The 3rd technical problem that the present invention will solve provides a kind of method that reduces the blood glucose of type i diabetes mice with VO-γ-PGA complex.
For solving the problems of the technologies described above, the present invention adopts following technical scheme.
A kind of method that reduces the blood glucose of type i diabetes mice with VO-γ-PGA complex, it is characterized in that, with concentration is that VO-γ-PGA complex of 20mmol/mL is dissolved in 0.1% agarose solution and gives the type i diabetes mice oral to irritate the stomach mode, and dosage is between 0.1mmolV/kg/day～0.4mmol V/kg/day.
Advantage of the present invention is: with γ-PGA is carrier, and its molecular weight is big, can play the effect of the contained medicine of slow release, and good biocompatibility is nontoxic.With itself and VOSO
4In conjunction with generating more stable VO-γ-PGA complex.This complex will slowly release medicine after entering in the body, and carrier γ-PGA then can be degraded to endogenous glutamic acid by lysosome, and catabolite does not have toxicity.The bioavailability specific ionization VOSO of VO-γ-PGA complex
4Want high, required dosage is little, and toxic side effects is lower, and carrier γ-PGA is prepared by microbial fermentation, the structure homogeneous, and molecular weight is bigger, and is with low cost.
Description of drawings
Fig. 1 is for showing the figure line of VO-γ of the present invention-PGA complex to the influence of type i diabetes mouse blood sugar.
Fig. 2 is for showing the figure line of VO-γ of the present invention-PGA complex to the influence of type i diabetes mice drinking-water.
Fig. 3 is for showing the figure line of VO-γ of the present invention-PGA complex to the influence of type i diabetes mice oral glucose tolerance.
The specific embodiment
The present invention is further illustrated below in conjunction with embodiment.Embodiment 1～6 operates according to the concrete operations step of above preparation method or application process fully, and their each step is only enumerated crucial technical data.
One of preparation of embodiment 1 gamma-polyglutamic acid-vanadyl complexes
In the first step, the inoculum concentration of B.Subtils.sp is 3%, adds maltose 30g, yeast extract 5g, sodium glutamate 10g, NaCl 5g, KH in every liter of LB fluid medium
2PO
41g, MgSO
47H
2O 0.1g, the pH value of culture medium are 5.0,20 ℃ of following shake flask fermentation 24h, 1 times of fermentation liquid adding distil water dilution, the centrifugal 10min of 8000r/min, the volume ratio of supernatant and dehydrated alcohol is 1: 1, the concentration of γ-PGA-Na crude product aqueous solution is 0.5%, and every liter of culture medium makes γ-PGA-Na 20.0g; In second step, the γ-PGA-Na and the VOSO of first step preparation
4Consumption be respectively 1.5g and 2.62g, γ-PGA-Na solution-COOH and VOSO
4The VO of solution
2+Mol ratio be 1: 1, under 30 ℃, stirring reaction 0.5h is under 20 ℃, the centrifugal 20min of 10000r/min, precipitation is dissolved in the distilled water of 5 times of volumes, under 20 ℃, the centrifugal 20min of 10000r/min, obtain VO-γ-PGA complex crude product, distill water washing and precipitating 1 time, get VO-γ-PGA complex of 1.42g.
Two of the preparation of embodiment 2 gamma-polyglutamic acid-vanadyl complexes
In the first step, the inoculum concentration of B.Subtils.sp is 5%, adds maltose 50g, yeast extract 10g, sodium glutamate 30g, NaCl 10g, KH in every liter of LB fluid medium
2PO
45g, MgSO
47H
2O 0.5g, the pH value of culture medium is 6.0,35 ℃ of following shake flask fermentation 48h, 4 times of fermentation liquid adding distil water dilutions, the centrifugal 15min of 11500r/min, the volume ratio of supernatant and dehydrated alcohol is 1: 3, and the concentration of γ-PGA-Na crude product aqueous solution is 1.0%, and every liter of culture medium makes γ-PGA-Na 25.12g; In second step, the γ-PGA-Na and the VOSO of first step preparation
4Consumption be respectively 8.5g and 2.62g, γ-PGA-Na solution-COOH and VOSO
4The VO of solution
2+Mol ratio be 5: 1, under 50 ℃, stirring reaction 2.5h, under 25 ℃, the centrifugal 30min of 12500r/min, precipitation is dissolved in the distilled water of 12.5 times of volumes, under 25 ℃, the centrifugal 30min of 12500r/min, distillation water washing and precipitating 3 times, VO-γ-PGA complex of 7.7g.
Three of the preparation of embodiment 3 gamma-polyglutamic acid-vanadyl complexes
In the first step, the inoculum concentration of B.Subtils.sp is 7%, adds maltose 70g, yeast extract 15g, sodium glutamate 50g, NaCl 15g, KH in every liter of LB fluid medium
2PO
49g, MgSO
47H
2O 0.9g, the pH value of culture medium is 7.0,50 ℃ of following shake flask fermentation 72h, 7 times of fermentation liquid adding distil water dilutions, the centrifugal 20min of 15000r/min, the volume ratio of supernatant and dehydrated alcohol is 1: 5, and the concentration of γ-PGA-Na crude product aqueous solution is 1.5%, and every liter of culture medium makes γ-PGA-Na 30.26g; In second step, the γ-PGA-Na and the VOSO of first step preparation
4Consumption be respectively 15g and 2.62g, γ-PGA-Na solution-COOH and VOSO
4The VO of solution
2+Mol ratio be 10: 1, under 70 ℃, stirring reaction 5h, under 30 ℃, the centrifugal 40min of 15000r/min, precipitation is dissolved in the distilled water of 20 times of volumes, under 30 ℃, the centrifugal 40min of 15000r/min, distillation water washing and precipitating 5 times, VO-γ-PGA complex of 14.2g.
Two of the blood glucose of embodiment 5 usefulness VO-γ-PGA complex reduction type i diabetes mice: dosage is 0.25mmol V/kg/day.
Three of the blood glucose of embodiment 6 usefulness VO-γ-PGA complex reduction type i diabetes mice: dosage is 0.4mmol V/kg/day.
Embodiment 7VO-γ-PGA complex is to the influence of type i diabetes mouse blood sugar, drinking-water
Adopt the male and healthy Kunming mouse, injection 200mg/kg alloxan is set up diabetes model, fasting 4h after 7 days, and blood glucose＞11mmol/L person is confirmed as into the mould Mus.Choose 32 body weight and be the I type DM mice of making as stated above about 30g, fasting 4h surveys the initial blood glucose of blood glucose integrated survey and weight average is divided into 3 groups, is made as normal saline matched group, VOSO respectively
4Group and VO-γ-PGA group.Administration mouse stomach dosage is 0.2mmol V/kg/day, and the normal saline matched group gavages the respective volume normal saline.In 2 weeks of administration, drug withdrawal detected for 1 week.Write down the drinking-water situation every day, fasting 3h surveys blood glucose every other day.
Experimental data shows: under the Isodose situation, VO-γ-PGA is than VOSO
4The blood sugar lowering ability is strong.Administration treated animal amount of drinking water is starkly lower than matched group.See Fig. 1 and Fig. 2.
Embodiment 8VO-γ-PGA complex is to the influence of type i diabetes mouse glucose tolerance
Choose 32 body weight and be the type i diabetes mice of making by embodiment 3 methods about 30g, fasting 4h surveys the initial blood glucose of blood glucose integrated survey and weight average is divided into 3 groups, is made as normal saline matched group, VOSO respectively
4Group and VO-γ-PGA group.Administration mouse stomach dosage is 0.2mmol V/kg/day, and the normal saline matched group gavages the respective volume normal saline.2 weeks of administration stop administration overnight fasting on that night (12h), gavage 50% glucose solution by the 1g/kg body weight, measure the blood glucose value of 0min, 45min, 1.5h, 3h, 4h, 6h and 8h with blood glucose meter.
Experimental data shows: diabetic mice oral glucose tolerance obviously improves after the administration.See Fig. 3.
VO-γ-PGA the complex of embodiment 9 various dose is to the influence of some serum biochemistry indexs of type i diabetes mice.
Choose 40 body weight and be the type i diabetes mice of making by embodiment 5 described methods about 30g, fasting 4h surveys blood glucose, and initial blood glucose of integrated survey and weight average are divided into 5 groups, are made as normal saline matched group, 0.2mmol V/kg/day VOSO respectively
4Group, 0.1mmolV/kg/day VO-γ-PGA group (low dose group), 0.2mmol V/kg/day VO-γ-PGA group (middle dosage group) and 0.4mmol V/kg/day VO-γ-PGA organize (high dose group).4 weeks of gastric infusion, stop administration overnight fasting on that night, next day, eye socket was got blood, and centrifuging and taking serum utilizes automatic clinical chemistry analyzer to detect free serum fatty acid (FFA), total triglyceride (TG), glutamate pyruvate transaminase (GPT), glutamic oxaloacetic transaminase, GOT (GOT), serum urea nitrogen (BUN).
Experimental data shows: high dose medicament can obviously reduce FFA, TG, GPT, GOT, the BUN level of type i diabetes mice.See Table 1:
Table 1
| GPT (U/L) | GOT (U/L) | BUN (mg/dL) | TG (mg/dL) | FFA (mEq/L) | |
| Control | 43.17±9.52 | 149.67±23.20 | 15.52±2.88 | 3.83±1.55 | 0.95±0.23 |
| VOSO 4 | 54.80±28.46 | 205.81±25.59 | 13.70±3.17 | 3.19±1.05 | 0.78±0.08 |
| VO-γ-PGA(0.1) | 74.80±71.20 | 168.80±48.01 | 13.87±4.34 | 2.77±1.13 | 0.75±0.09 |
| VO-γ-PGA(0.2) | 26.86±4.1 b | 160.14±67.42 | 16.04±12.43 | 2.14±1.31 | 0.71±0.14 a |
| VO-γ-PGA(0.4) | 26.85±9.43 b | 103.71±28.9 b | 11.61±2.14 a | 1.76±0.92 a | 0.51±0.09 b |
A shows and compares P＜0.05 with Control group, and b shows with the Control group and compares P＜0.01.
Claims (3)
1, a kind of VO-γ-PGA complex is characterized in that this complex is by γ-PGA and VOSO
4By carboxyl on the former and the VO on the latter
2+The coordinate bond that forms is formed by connecting, and its general formula of molecular structure and structural formula are respectively:
(VO
2+)
m-(γ-PGA), wherein, m be between 2500～6000 positive integer and
Its molecular weight is between 1000kD～2000kD.
2, the preparation method of the described VO-γ of claim 1-PGA complex is characterized in that the concrete operations step:
The preparation of first step γ-PGA-Na
Inoculum concentration by 3%～7% inserts the LB fluid medium with purchasing in the B.Subtils.sp at Chinese microorganism strain preservation center activation back, add maltose 30g～70g, yeast extract 5g～15g, sodium glutamate 10g～50g in every liter of LB fluid medium, NaCl 5g～15g, KH
2PO
41g～9g, MgSO
47H
2O 0.1g～0.9g, the pH value of culture medium is 5.0～7.0,20 ℃～50 ℃ following shake flask fermentation 24h～72h, gets fermentation liquid, 1～7 times of fermentation liquid adding distil water dilution, 8000r/min～15000r/min is centrifugal, and 10～20min removes thalline, and dehydrated alcohol is added in the supernatant, and the volume ratio of supernatant and dehydrated alcohol is 1: 1～5, stir to such an extent that precipitate, vacuum drying gets γ-PGA-Na crude product, and this crude product is dissolved in distilled water, concentration is 0.5%～1.5%, with the distilled water is the dialysis solution dialysis, filters, and gets filtrate, the filtrate lyophilization, get γ-PGA-Na, its molecular weight is between 1000kD～2000kD, and every liter of culture medium makes γ-PGA-Na20.0g～30.26g;
The preparation of second step VO-γ-PGA complex
γ-the PGA-Na of 1.5g～15g first step preparation is dissolved in the 450ml distilled water, is stirred to dissolving fully, get γ-PGA-Na solution, 2.62gVOSO
4Be dissolved in the 200ml distilled water, be stirred to dissolving fully, get VOSO
4Solution stirs down VOSO
4Solution adds γ-PGA-Na solution, γ-PGA-Na solution-COOH and VOSO
4The VO of solution
2+Mol ratio be under 1～10: 1,30 ℃～70 ℃, stirring reaction 0.5h～5h, under 20 ℃～30 ℃, the centrifugal 20min～40min of 10000r/min～15000r/min abandons supernatant, precipitation is dissolved in the distilled water of 5～20 times of volumes, under 20 ℃～30 ℃, and the centrifugal 20min～40min of 10000r/min～15000r/min, abandon supernatant, obtain VO-γ-PGA complex crude product, distillation water washing and precipitating 1 time～5 times, filter, abandon filtrate, vacuum drying, VO-γ-PGA complex of 1.42g～14.2g.
3, reduce the method for the blood glucose of type i diabetes mice with the described VO-γ of claim 1-PGA complex, it is characterized in that, with concentration is that VO-γ-PGA complex of 20mmol/mL is dissolved in 0.1% agarose solution and gives the type i diabetes mice oral to irritate the stomach mode, and dosage is between 0.1mmol V/kg/day～0.4mmol V/kg/day.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107088202A (en) * | 2011-03-07 | 2017-08-25 | Cfm医药控股有限公司 | Purposes for maintaining normoglycemic vfanadium compound in mammal body |
| CN117224690A (en) * | 2023-11-10 | 2023-12-15 | 江苏海王健康生物科技有限公司 | Gamma-polyglutamic acid mixture, composition and preparation method as auxiliary agent |
-
2008
- 2008-06-20 CN CNA2008100393255A patent/CN101293101A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107088202A (en) * | 2011-03-07 | 2017-08-25 | Cfm医药控股有限公司 | Purposes for maintaining normoglycemic vfanadium compound in mammal body |
| CN107088202B (en) * | 2011-03-07 | 2021-11-30 | Cfm医药控股有限公司 | Use of vanadium compounds for maintaining normoglycemia in a mammal |
| CN117224690A (en) * | 2023-11-10 | 2023-12-15 | 江苏海王健康生物科技有限公司 | Gamma-polyglutamic acid mixture, composition and preparation method as auxiliary agent |
| CN117224690B (en) * | 2023-11-10 | 2024-01-30 | 江苏海王健康生物科技有限公司 | Gamma-polyglutamic acid mixture, composition and preparation method as auxiliary agent |
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Open date: 20081029 |