CN107936084A - A kind of production method for the CAP23145 polypeptides based on targeting FMRP for treating glioma - Google Patents
A kind of production method for the CAP23145 polypeptides based on targeting FMRP for treating glioma Download PDFInfo
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- CN107936084A CN107936084A CN201711059913.0A CN201711059913A CN107936084A CN 107936084 A CN107936084 A CN 107936084A CN 201711059913 A CN201711059913 A CN 201711059913A CN 107936084 A CN107936084 A CN 107936084A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/14—Extraction; Separation; Purification
- C07K1/16—Extraction; Separation; Purification by chromatography
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- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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Abstract
The invention discloses a kind of production method for the CAP23145 polypeptides based on targeting FMRP for treating glioma, mainly according to 1 sequence of FMRP, Caprin and interaction feature, using CyberSpace simulation softward, design can specifically bind with FMRP and can block the CAP23145 polypeptides of both interaction；Then designed polypeptide is synthesized；The polypeptide is stronger to the targeting of glioma, does not produce obvious killing to normal spongiocyte while glioma cell is killed, and mitigates the side effect of chemotherapy.
Description
Technical field
The present invention relates to a kind of production method of polypeptide, more particularly to it is a kind of treat glioma based on targeting FMRP's
The production method of CAP23145 polypeptides.
Background technology
Glioma is the most commonly seen primary malignant tumor of nervous system, and wherein more than half is higher for grade malignancy
Glioblastoma, glioma incidence in increasing trend year by year at present, and the death rate is high, and survival rates are low, are to influence
The important malignant tumour of China's residents ' health.
The treatment of glioma at present is aided with chemicotherapy still based on surgical resection therapy, but general effect is not good enough, brain colloid
The complexity of oncocyte component, the wettability of tumour growth and blood-brain barrier to the blocking effect of medicine be cause it is this
The principal element of situation.
The content of the invention
In view of the above-mentioned problems, the present invention proposes a kind of life for the CAP23145 polypeptides based on targeting FMRP for treating glioma
Production method, the polypeptide are stronger to the targeting of glioma, normal spongiocyte are not produced while glioma cell is killed
Obvious killing, mitigates the side effect of chemotherapy.
Technical solution of the present invention comprises the following steps that：
A kind of production method for the CAP23145 polypeptides based on targeting FMRP for treating glioma, includes the following steps：
(1) according to FMRP, Caprin-1 sequence and interaction feature, using CyberSpace simulation softward, design can
Specifically bound with FMRP and the CAP23145 polypeptides of both interaction can be blocked；
(2) the designed polypeptide of synthesis, including flow is produced by below：
A, synthesis material and related reagent, instrument；
A, resin:Substitution value is the 2-Chlorotrityl Chloride Resin of 1.03mmol/g；B, amino acid:
Fmoc-Tyr (Tbu)-OH, Fmoc-Asn (Trt)-OH, Fmoc-Ser (Tbu)-OH etc.；
C, special material:
D-Biotin；
D, synthetic agent:
DMF, DCM, MEOH, DIEA, HBTU；
E, deprotecting regent:Piperidines；
F, detection reagent:Phenol reagent, pyridine reagent, ninhydrin reagent；
G, lytic reagent:
95% cutting liquid:TFA, TIS, EDT, anhydrous ether；
H, nitrogen；
I, instrument:
1. 12 passage semi-automatic polypeptide synthesizers of；
2. .SHIMADZU high performance liquid chromatographs；
3. .LABCONCO freeze dryers；
B, Peptide systhesis step is as follows:Synthesis order:From C-terminal to N-terminal；
A, resin swelling：
2-Chlorotrityl Chloride Resin are put into reaction tube, adds DCM and vibrates；
B, first amino acid is connect：
Solvent is leached out by husky core, adds Fmoc-Tyr (Tbu)-OH amino acid, DMF dissolvings is added, adds DIEA
And vibrate, closed with methanol；
C, it is deprotected：
Remove DMF, add Piperidine/DMF solution, remove and add a Piperidine/DMF solution again；
D, detect:
Take out piperidine solution, if taking resin dry granular, cleaned with ethanol, then add detection reagent detection, become navy blue into
Positive reaction；
E, wash for the first time:
Twice, twice, DMF (10ml/g) is twice by DCM (10ml/g) by DMF (10ml/g)；
F, it is condensed:
Protected amino acid, HBTU are dissolved with DMF, reaction tube is added, is added immediately DIEA and is reacted；
G, detect:
If taking resin dry granular, after being cleaned with ethanol, detection reagent detection is added, is then heated, colourless is negative reaction；
H, wash for the second time:
Once, twice, DMF (10ml/g) is twice by DCM (10ml/g) by DMF (10ml/g)；
I, the operation of three to six steps is repeated, the amino acid being sequentially connected from right to left in sequence, is most followed by D-Biotin；
J, drain, wash resin in following manner:
First DMF is washed, and again with methanol is washed, and is then washed with DMF again, is then washed with DCM, finally drained；
K, polypeptide is cut from resin:
Cutting liquid, water, EDT, TIS are prepared, is then cut；
L, drying washing:
Lysate is dried up with nitrogen, is washed six times with ether, then room temperature volatilizes；
M, analysis purification:
Crude product is purified with high performance liquid chromatography；
N, freeze：
Collection target polypeptides solution, which is put into freeze dryer, to be concentrated, and is lyophilized into white powder.
Preferably as the present invention, in a steps of the step B, the resin swelling is specially：By 2-
Chlorotrityl Chloride Resin are put into reaction tube, add DCM (15ml/g), vibrate 30min.
It is preferably as the present invention, in the b step of the step B, solvent is leached out by husky core, adds 3 times of moles of mistakes
Fmoc-Tyr (Tbu)-OH amino acid of amount, adds DMF dissolvings, adds the DIEA of 10 times of molar excess, vibrates 60min, so
Closed afterwards with methanol.
It is preferably as the present invention, in the step c of the step B, remove DMF, add 20% Piperidine/DMF solution (15ml/
G), 5min, removes and adds 20% Piperidine/DMF solution (15ml/g), 15min again.
It is preferably as the present invention, in the Step d of the step B, piperidine solution is taken out, 10-20 grainy resins is taken, uses ethanol
Wash three times, add detection reagent detection, 105 DEG C of -110 DEG C of heating 5min, change navy blue is positive reaction.
Preferably as the present invention, in the f steps of the step B, protected amino acid three times are excessive, and HBTU three times are excessive,
Dissolved with 10 to 15ml/g DMF, add reaction tube, be added immediately ten times of excess of DIEA, react 30min.
It is preferred as the present invention, in the g steps of the step B, 10-20 grainy resins are taken, is washed three times with ethanol, adds inspection
Test agent detects, and 105 DEG C of -110 DEG C of heating 5min, colourless is negative reaction.
As the present invention it is preferably, in the j steps of the step B, it is described drain, wash resin be specially：DMF(10ml/g)
Twice, twice, twice, DCM (10ml/g) twice, drains 10min to DMF (10ml/g) to methanol (10ml/g).
It is preferably as the present invention, in the k steps of the step B, when polypeptide is cut from resin, prepare cutting liquid (10/
G) TFA95%, water 1%, EDT2%, TIS2%, clipping time 120min.
It is preferably as the present invention, in the l steps of the step B, when drying is washed, first lysate is dried up with nitrogen,
Washed six times with ether, then room temperature volatilizes.
The present invention is a kind of a kind of novel targeted medicine of Treatment for Glioma, experiment in vitro and interior animal experiment confirmation pair
Glioma cell has a specific killing action, and to normal Deiter's cells without obvious lethal effect after, can be to glioma
Treatment play good effect.
Brief description of the drawings
Fig. 1 show glioma cell DBTRG in In vitro cell experiment and adds the design sketch after polypeptide；
Fig. 2 show glioma cell of U251 in In vitro cell experiment and adds the design sketch after polypeptide；
Embodiment
Understand for the ease of those of ordinary skill in the art and implement the present invention, with reference to the accompanying drawings and embodiments to this hair
It is bright to be described in further detail, it will be appreciated that implementation example described herein is merely to illustrate and explain the present invention, not
For limiting the present invention.
(1) according to FMRP, Caprin-1 sequence and interaction feature, using CyberSpace simulation softward, design can
Specifically bound with FMRP and the CAP23145 polypeptides of both interaction can be blocked；
(2) the designed polypeptide of synthesis, including flow is produced by below：
A, synthesis material and related reagent, instrument；
A, resin:Substitution value is 2-Chlorotrityl Chloride Resin (the Tianjin Southern foldings of 1.03mmol/g
Into Science and Technology Ltd.)
B, amino acid:
Fmoc-Tyr (Tbu)-OH (the sincere promise in Chengdu,>99%), Fmoc-Asn (Trt)-OH (the sincere promise in Chengdu,>99%),
Fmoc-Ser (Tbu)-OH (the sincere promise in Chengdu,>99%) etc..
C, special material:
D-Biotin (rich U.S. biology, 99%).
D, synthetic agent:
DMF (original producton location South Korea), DCM (original producton location South Korea), MEOH (original producton location Japan), DIEA (new Dehua work, 99%),
HBTU (vast and boundless sail biotechnology, 99%)；
E, deprotecting regent:Piperidines (Chinese medicines group Solution on Chemical Reagents in Shanghai company, 99%)；
F, detection reagent:Phenol reagent (autogamy), pyridine reagent (autogamy), ninhydrin reagent (autogamy)；
G, lytic reagent:
95% cutting liquid:TFA (J.T.Baker, 99%), TIS (Shanghai reach auspicious fine chemistry industry, 98%), (Shanghai reaches EDT
Auspicious fine chemistry industry, 98%), anhydrous ether (test, and actual measurement is 99.7%) by Shanghai；
H, nitrogen:(newly joining gas)；
I, instrument:
1. 12 passage semi-automatic polypeptide synthesizer Shanghai Qiangyao Biotechnology Co., Ltd.'s autonomous Designs of are simultaneously applied for a patent
Semi-automatic polypeptide synthesizer, Patent No. 201020226529.2
2. .SHIMADZU high performance liquid chromatograph (models:Preparative, analytic type, software:Class-VP.Sevial
System, manufacturer:SHIMADZU)
3. .LABCONCO freeze dryer (models:Freezone.Plus.6, manufacturer:LABCONCO) 4. centrifuge (Town in Shanghai
Booth scientific instrument factory model:TDL-40B)
B, Peptide systhesis step is as follows:Synthesis order:From C-terminal to N-terminal；
A, resin swelling：
2-Chlorotrityl Chloride Resin are put into reaction tube, adds DCM and vibrates；
B, first amino acid is connect：
Solvent is leached out by husky core, adds Fmoc-Tyr (Tbu)-OH amino acid, DMF dissolvings is added, adds DIEA
And vibrate, closed with methanol；
C, it is deprotected：
Remove DMF, add Piperidine/DMF solution, remove and add a Piperidine/DMF solution again；
D, detect:
Take out piperidine solution, if taking resin dry granular, cleaned with ethanol, then add detection reagent detection, become navy blue into
Positive reaction；
E, wash for the first time:
Twice, twice, DMF (10ml/g) is twice by DCM (10ml/g) by DMF (10ml/g)；
F, it is condensed:
Protected amino acid, HBTU are dissolved with DMF, reaction tube is added, is added immediately DIEA and is reacted；
G, detect:
If taking resin dry granular, after being cleaned with ethanol, detection reagent detection is added, is then heated, colourless is negative reaction；
H, wash for the second time:
Once, twice, DMF (10ml/g) is twice by DCM (10ml/g) by DMF (10ml/g)；
Ii, repeat the operation of three to six steps, and the amino acid being sequentially connected from right to left in sequence, is most followed by D-Biotin；
J, drain, wash resin in following manner:
First DMF is washed, and again with methanol is washed, and is then washed with DMF again, is then washed with DCM, finally drained；
K, polypeptide is cut from resin:
Cutting liquid, water, EDT, TIS are prepared, is then cut；
L, drying washing:
Lysate is dried up with nitrogen, is washed six times with ether, then room temperature volatilizes；
M, analysis purification:
Crude product is purified with high performance liquid chromatography；
N, freeze：
Collection target polypeptides solution, which is put into freeze dryer, to be concentrated, and is lyophilized into white powder.
Preferably, in a steps of step B, resin swelling is specially：By 2-Chlorotrityl Chloride
Resin is put into reaction tube, adds DCM (15ml/g), vibrates 30min.
Preferably, in the b step of step B, solvent is leached out by husky core, adds the Fmoc-Tyr of 3 times of molar excess
(Tbu)-OH amino acid, adds DMF dissolvings, adds the DIEA of 10 times of molar excess, vibrates 60min, then closed with methanol.
Preferably, in the step c of step B, remove DMF, add 20% Piperidine/DMF solution (15ml/g), 5min, removes again
Add 20% Piperidine/DMF solution (15ml/g), 15min.
Preferably, in the Step d of step B, piperidine solution is taken out, takes 10-20 grainy resins, is washed three times, added with ethanol
Detection reagent detects, and 105 DEG C of -110 DEG C of heating 5min, change navy blue is positive reaction.
Preferably, in the f steps of step B, protected amino acid three times are excessive, and HBTU three times are excessive, arrive 15ml/ with 10
The DMF dissolvings of g, add reaction tube, are added immediately ten times of excess of DIEA, react 30min.
Preferably, in the g steps of step B, 10-20 grainy resins are taken, are washed three times with ethanol, add detection reagent detection,
105 DEG C of -110 DEG C of heating 5min, colourless is negative reaction, and in practical operation, resin usually takes 12.
Preferably, in the j steps of step B, drain, wash resin and be specially：DMF (10ml/g) twice, methanol (10ml/
G) twice, twice, DCM (10ml/g) twice, drains 10min to DMF (10ml/g).
Preferably, in the k steps of step B, when polypeptide is cut from resin, cutting liquid (10/g) TFA95%, water are prepared
1%, EDT2%, TIS2%, clipping time 120min.
Preferably, in the l steps of step B, when drying is washed, first lysate is dried up with nitrogen, is washed six times with ether,
Then room temperature volatilizes.
In order to further confirm effects of the CAP23145 to treatment glioma, it is as follows now to compare experiment：
1. glioma cell (U251, DBTRG), according to 5000/hole, spreads into 96 orifice plates, replace culture medium daily, respectively
The not homopolypeptide of same concentrations is added, blank control only adds DMEM culture mediums, and every group is done 3 multiple holes.
2. cell growth state is detected with mtt assay daily.
From Fig. 1,2 it is apparent that in glioma cell DBTRG, U251, compared with control group,
CAPRIN23145 polypeptides can significantly inhibit the growth of glioma cell, and GFP, FITC-CAPRIN3608 (1) and Fmr42443
Growth of the polypeptide to glioma cell simultaneously has no significant effect.
The present invention is a kind of a kind of novel targeted medicine of Treatment for Glioma, experiment in vitro and interior animal experiment confirmation pair
Glioma cell has a specific killing action, and to normal Deiter's cells without obvious lethal effect after, can be to glioma
Treatment play good effect.
Claims (10)
1. a kind of production method for the CAP23145 polypeptides based on targeting FMRP for treating glioma, it is characterised in that including such as
Lower step：
(1) according to FMRP, Caprin-1 sequence and interaction feature, using CyberSpace simulation softward, design can be with
FMRP specifically binds and can block the CAP23145 polypeptides of both interaction；
(2) the designed polypeptide of synthesis, including flow is produced by below：
A, synthesis material and related reagent, instrument；
A, resin:Substitution value is the 2-Chlorotrityl Chloride Resin of 1.03mmol/g；
B, amino acid:
Fmoc-Tyr (Tbu)-OH, Fmoc-Asn (Trt)-OH, Fmoc-Ser (Tbu)-OH etc.；
C, special material:
D-Biotin；
D, synthetic agent:
DMF, DCM, MEOH, DIEA, HBTU；
E, deprotecting regent:Piperidines；
F, detection reagent:Phenol reagent, pyridine reagent, ninhydrin reagent；
G, lytic reagent:
95% cutting liquid:TFA, TIS, EDT, anhydrous ether；
H, nitrogen；
I, instrument:
1. 12 passage semi-automatic polypeptide synthesizers of；
2. .SHIMADZU high performance liquid chromatographs；
3. .LABCONCO freeze dryers；
B, Peptide systhesis step is as follows:Synthesis order:From C-terminal to N-terminal；
A, resin swelling：
2-Chlorotrityl Chloride Resin are put into reaction tube, adds DCM and vibrates；
B, first amino acid is connect：
Solvent is leached out by husky core, adds Fmoc-Tyr (Tbu)-OH amino acid, DMF dissolvings is added, adds DIEA and shake
Swing, closed with methanol；
C, it is deprotected：
Remove DMF, add Piperidine/DMF solution, remove and add a Piperidine/DMF solution again；
D, detect:
Piperidine solution is taken out, if taking resin dry granular, is cleaned with ethanol, then adds detection reagent detection, becomes navy blue as the positive
Reaction；
E, wash for the first time:
Twice, twice, DMF (10ml/g) is twice by DCM (10ml/g) by DMF (10ml/g)；
F, it is condensed:
Protected amino acid, HBTU are dissolved with DMF, reaction tube is added, is added immediately DIEA and is reacted；
G, detect:
If taking resin dry granular, after being cleaned with ethanol, detection reagent detection is added, is then heated, colourless is negative reaction；
H, wash for the second time:
Once, twice, DMF (10ml/g) is twice by DCM (10ml/g) by DMF (10ml/g)；
I, the operation of three to six steps is repeated, the amino acid being sequentially connected from right to left in sequence, is most followed by D-Biotin；
J, drain, wash resin in following manner:
First DMF is washed, and again with methanol is washed, and is then washed with DMF again, is then washed with DCM, finally drained；
K, polypeptide is cut from resin:
Cutting liquid, water, EDT, TIS are prepared, is then cut；
L, drying washing:
Lysate is dried up with nitrogen, is washed six times with ether, then room temperature volatilizes；
M, analysis purification:
Crude product is purified with high performance liquid chromatography；
N, freeze：
Collection target polypeptides solution, which is put into freeze dryer, to be concentrated, and is lyophilized into white powder.
2. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in a steps of the step B, the resin swelling is specially：By 2-Chlorotrityl Chloride
Resin is put into reaction tube, adds DCM (15ml/g), vibrates 30min.
3. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in the b step of the step B, solvent is leached out by husky core, adds the Fmoc-Tyr of 3 times of molar excess
(Tbu)-OH amino acid, adds DMF dissolvings, adds the DIEA of 10 times of molar excess, vibrates 60min, then closed with methanol.
4. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in the step c of the step B, remove DMF, add 20% Piperidine/DMF solution (15ml/g), 5min, removes and add again
20% Piperidine/DMF solution (15ml/g), 15min.
5. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in the Step d of the step B, piperidine solution is taken out, takes 10-20 grainy resins, is washed three times with ethanol, adds inspection
Test agent detects, and 105 DEG C of -110 DEG C of heating 5min, change navy blue is positive reaction.
6. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in the f steps of the step B, protected amino acid three times are excessive, and HBTU three times are excessive, with DMF is molten less as far as possible
Solution, adds reaction tube, is added immediately ten times of excess of DIEA, reacts 30min.
7. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in the g steps of the step B, 10-20 grainy resins are taken, are washed three times with ethanol, detection reagent is added and detects, 105
DEG C of -110 DEG C heating 5min, colourless is negative reaction.
8. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in the j steps of the step B, it is described drain, wash resin be specially：DMF (10ml/g) twice, methanol
(10ml/g) twice, twice, DCM (10ml/g) twice, drains 10min to DMF (10ml/g).
9. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in the k steps of the step B, when polypeptide is cut from resin, cutting liquid (10/g) TFA95%, water are prepared
1%；EDT2%, TIS2%, clipping time 120min.
10. a kind of production method of CAP23145 polypeptides based on targeting FMRP for treating glioma as claimed in claim 1,
It is characterized in that, in the l steps of the step B, during drying washing, first lysate is dried up with nitrogen, washes six times with ether, so
Room temperature volatilizes afterwards.
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Cited By (1)
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| CN110467666A (en) * | 2019-09-17 | 2019-11-19 | 湖北强耀生物科技有限公司 | A kind of synthetic method of novel amylin |
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