CN105524142B - Ten hexapeptide QTDDNHSNVLWAGFSR of one kind and its application - Google Patents
Ten hexapeptide QTDDNHSNVLWAGFSR of one kind and its application Download PDFInfo
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- C07K7/00—Peptides having 5 to 20 amino acids in a fully defined sequence; Derivatives thereof
- C07K7/04—Linear peptides containing only normal peptide links
- C07K7/08—Linear peptides containing only normal peptide links having 12 to 20 amino acids
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Abstract
The present invention discloses ten hexapeptide QTDDNHSNVLWAGFSR of one kind and its application, and the amino acid sequence of ten hexapeptide is Gln-Thr-Asp-Asp-Asn-His-Ser-Asn-Val-Leu-Trp-Ala-Gly-Phe- Ser-Arg, molecular weight 1846.8613, purity 95%.Polypeptide of the invention uses Peptide synthesizer, is synthesized using solid-phase synthesis.It is detected by anti tumor activity in vitro, in 100-500 μ g/mL gradient scope, polypeptide of the invention presents inhibitory effect to breast cancer cell MCF-7 and HepG-2 cell.In 500 μ g/mL, the in-vitro multiplication inhibiting rate to MCF-7 and HepG-2 is respectively 54.52% and 61.36%.Synthesis polypeptide of the invention has anti tumor activity in vitro, can be applied to field of biological pharmacy.
Description
Technical field
The invention belongs to field of biological pharmacy, and in particular to a kind of ten hexapeptide QTDDNHSNVLWAGFSR of synthesis and its answer
With.
Background technique
Biologically active peptide (Bioactivity peptides) is also known as Functional Polypeptides (Functional peptides), cares for name
Thinking justice, it is a kind of peptide with certain physiological active functions, can inhibit growth of tumour cell, destroy, killing tumor cell or
The important function such as antibacterial, antiviral, blood pressure lowering, hypoglycemic.Since its molecular weight is small, is easy to absorb, can be widely used in
The exploitation of health care product and drug, therefore, biologically active peptide has become one of hot spot of protein research.
Tumour is the Health Killer of 21 century, and morbidity and mortality are still soaring.At present to the treatment of tumor patient
Method is mainly chemotherapy and radiation means, causes greatly to damage to human body, and no matter tumour occurs after pernicious transfer with which kind of mode
All it is difficult thoroughly to cure.So finding a kind of can thoroughly remove cancer cell and become complete without damageeing the treatment method of other cells
The research hotspot of ball medical oncology field.Several Active Peptides are found to have anti-tumor activity one by one, this becomes anti-
The new direction of tumour medicine research and development.Japanese scholars Yamaguchi etc. is once with casein and the common feeding of corn peptide through 7,12-
The rat with tumor of breast of dimethylbiphenyl [a] anthracene induction.Corn peptide has certain anti-breast cancer effect as the result is shown,
And with the increase of corn peptide dosage, antitumous effect is more obvious.Yang Yongfang etc. has studied the external of Mytilus galloprovincialis enzymolysis polypeptide
Anti-tumor activity finds that the peptide has anti-tumor activity, can lower the expression of Bc1-2 in tumour cell.
The present invention provides a kind of synthesis polypeptide with anti tumor activity in vitro, can be applied to field of biological pharmacy.
Summary of the invention
It is research object that the present invention, which chooses a kind of two kinds of tumour cell MCF-7 and HepG-2 and normal liver cell LO2, is made
With the external inhibitory activity of mtt assay measurement synthetic peptide.The object of the present invention is to provide a kind of conjunctions with anti tumor activity in vitro
At polypeptide, field of biological pharmacy can be applied to.
The purpose of the present invention is achieved through the following technical solutions:
The molecular weight of ten hexapeptide QTDDNHSNVLWAGFSR of one kind, ten hexapeptide are 1846.8613, and amino acid sequence is
Gln-Thr-Asp-Asp-Asn-His-Ser-Asn-Val-Leu-Trp-Ala-Gly-Phe- Ser-Arg, wherein
Gln indicates that English name is Glutamine, and Chinese is the corresponding residue of the amino acid of glutamine;
Thr indicates that English name is Threonine, and Chinese is the corresponding residue of the amino acid of threonine；
Asp indicates that English name is Aspartic, and Chinese is the corresponding residue of the amino acid of aspartic acid；
Asp indicates that English name is Aspartic, and Chinese is the corresponding residue of the amino acid of aspartic acid；
Asn indicates that English name is Asparagine, and Chinese is the corresponding residue of the amino acid of asparagine；
His indicates that English name is Histidine, and Chinese is the corresponding residue of the amino acid of histidine；
Ser indicates that English name is Serine, and Chinese is the corresponding residue of the amino acid of serine；
Asn indicates that English name is Asparagine, and Chinese is the corresponding residue of the amino acid of asparagine；
Val indicates that English name is Valine, and Chinese is the corresponding residue of the amino acid of valine；
Leu indicates that English name is Leucine, and Chinese is the corresponding residue of the amino acid of leucine；
Trp indicates that English name is Tryptophan, and Chinese is the corresponding residue of the amino acid of tryptophan；
Ala indicates that English name is Alanine, and Chinese is the corresponding residue of the amino acid of alanine；
Gly indicates that English name is Glycine, and Chinese is the corresponding residue of the amino acid of glycine；
Phe indicates that English name is Phenylalanine, and Chinese is the corresponding residue of the amino acid of phenylalanine；
Ser indicates that English name is Serine, and Chinese is the corresponding residue of the amino acid of serine；
Arg indicates that English name is Arginine, and Chinese is the corresponding residue of arginic amino acid.
Further, ten hexapeptide is when concentration is 100-500 μ g/mL, to breast cancer cell MCF-7 and liver cancer cells
The in-vitro multiplication inhibiting rate of HepG-2 is respectively 28.96%-54.52% and 35.33%-61.36%.
Further, ten hexapeptide is when concentration is 500 μ g/mL, to breast cancer cell MCF-7 and liver cancer cells
The in-vitro multiplication inhibiting rate of HepG-2 is respectively 54.52% and 61.36%.
Further, ten hexapeptide is when concentration is 100-500 μ g/mL, to the in-vitro multiplication of Human normal hepatocyte LO2
Inhibiting rate is 5.78%-22.8%.
Further, ten hexapeptide inhibits the in-vitro multiplication of Human normal hepatocyte LO2 when concentration is 500 μ g/mL
Rate is 22.8%.
The amino acid sequence of ten hexapeptides of the invention uses standard Fmoc scheme, by the screening of resin, reasonable polypeptide
Synthetic method.The C- carboxyl end group of target polypeptides is connected in the form of covalent bond with an insoluble macromolecule resin, then with
The amino of this amino acid acts on forming peptide bond as starting point with the carboxyl of another molecule amino acid.This process is constantly repeated,
It can obtain target polypeptides product.After the completion of synthetic reaction, protecting group is removed, peptide chain is separated with resin to get target is arrived
Product.Peptide systhesis is the process that amino acid is added in a repetition, and synthesis in solid state sequence is synthesized from C-terminal to N-terminal.
The present invention mixes the synthesis polypeptide of final concentration of 100-500 μ g/mL and two kinds of tumour cells MCF-7 and HepG-2
It is even, after being incubated for 48 h, detected through mtt assay, 28.96% ~ 54.52% and 35.33% is respectively reached to inhibition rate of tumor cell ~
61.36%.Inhibiting rate is 5.78% ~ 22.8% after handling normal liver cell LO2 with the synthesis polypeptide of 100 ~ 500 μ g/mL, is shown
There is lesser lethal effect to normal liver cell LO2, can be applied in biomedicine field.
Compared with prior art, the invention has the advantages that and technical effect:
The present invention has synthesized the peptide for the first time, and the anti tumor activity in vitro of synthesis polypeptide, institute are had detected using MTT method
Synthesis polypeptide is stated with certain inhibiting tumour cells ability, meanwhile, synthesis polypeptide has lesser killing to make normal liver cell
With.
Detailed description of the invention
Fig. 1 is the HPLC figure for synthesizing ten hexapeptide QTDDNHSNVLWAGFSR.
Fig. 2 is the ESI-MS figure for synthesizing ten hexapeptide QTDDNHSNVLWAGFSR.
Specific embodiment
Below in conjunction with specific example, the invention will be further described, but implementation and protection scope of the invention is not limited to
This.For not specifically specified technological parameter, routine techniques progress can refer to.
Solid-phase synthesis peptides
It selects macromolecule resin (Shanghai Jie Tai Biotechnology Co., Ltd), according to the amino acid sequence Gln- of ten hexapeptides
The feature of Thr-Asp-Asp-Asn-His-Ser-Asn-Val-Leu-Trp-Ala-Gly-Phe-Ser- Arg, first by the carboxylic of Arg
Base is connected in the form of covalent bond with a resin, and then the carboxyl of the amino of Arg and Ser, which shrink, reacts, and after processing, then is added
The carboxyl reaction of the amino and Phe of Phe, Ser, successively adds amino acid from right to left, after having added the last one Gln amino acid,
Resin is cut off again obtains ten hexapeptide QTDDNHSNVLWAGFSR of target.Production to the end is obtained using high-efficient liquid phase chromatogram purification
Product, purification process use kromasil C18- 5(4.6*250mm) chromatographic column, flow velocity is 1.0 mL/min.Liquid phase systems use two
Solvent A: the water of 0.1% (volume) trifluoroacetic acid is contained in a channel；Solvent B: contain the second of 0.1% (volume) trifluoroacetic acid
Nitrile.Gradient elution is as follows: the initial proportion of solvent B is 2%(volume, similarly hereinafter), in 0.01min to 30min, the ratio of solvent B
65% is risen to, in 30min to 33min, the ratio of solvent B rises to 100%, keeps 100% operation to stop to 40min, detects
Wavelength 214nm.Polypeptide solution is collected, then liquid nitrogen quickly cooling is lyophilized.The product of 95% or more purity is obtained, and is reflected through ESI-MS
Determine structure (shown in as shown in Figure 1, Figure 2).
The external inhibitory activity of synthesis polypeptide
By each polypeptide fractions of MTT colorimetrically analysing to breast cancer cell MCF-7, HepG-2 cell and normal hepatocytes
The growth inhibition effect of cell LO2.Specific steps are as follows:
1) cell of logarithmic growth phase, through 0.25%(volume) trypsase-EDTA digestive juice digestion after, be added phase
The complete medium answered, which terminates, digests and is resuspended cell, after blood cell plate count, adjusts the concentration of cell suspension to 5 × 104A/
ML is added in 96 orifice plates, every 100 μ L of hole, in 37 DEG C of constant temperature CO2It is cultivated in incubator；
2) cell is adherent after cultivating 24 h, and waste and old culture solution is sucked out, and final volume is added as 200 μ L and contains various concentration
The DMEM basal medium of sample to be tested, and using DMEM as negative control, in 37 DEG C of constant temperature CO2It is cultivated in incubator；
3) medical fluid is sucked out after 48 h, with PBS board-washing 2 times, 5 mg/mL MTT solution, 20 μ l and fresh basal training is added
Support 180 μ L of base；In 37 DEG C of constant temperature CO2Continue to cultivate in incubator；
4) it after 4 h, discards the culture solution containing MTT, is added after 150 μ L DMSO in vibrating 15 on microoscillator
OD value is measured at min, 490nm wavelength and calculates inhibiting rate:
Growth of cancer cells inhibiting rate (%)=((control group OD- blank group OD)-(administration group OD- blank group OD))/((control
Group OD- blank group OD)) × 100
Application Example 1
Take each 100 μ L cell suspension (5 × 10 of tumour cell MCF-7 and HepG-2 and Human normal hepatocyte LO24A/
ML it) adds in 96 orifice plates, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Cell is adherent after 24 h, and waste and old culture solution is sucked out, adds
Enter the DMEM basal medium that final volume is the ten hexapeptide QTDDNHSNVLWAGFSR samples that 200 μ L contain 100 μ g/mL, and
Using DMEM as negative control, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Medical fluid is sucked out after 48 h, with PBS board-washing 2 times, is added
180 μ L of 5 mg/mL MTT solution, 20 μ l and fresh basal medium；In 37 DEG C of constant temperature CO2Continue to cultivate in incubator；4
After h, the culture solution containing MTT is discarded, be added after 150 μ l DMSO in vibrating 15 min, 490nm wavelength on microoscillator
Place's measurement OD value simultaneously calculates inhibiting rate.As shown in Table 1, ten hexapeptides of 100 μ g/mL are to tumour cell MCF-7 and HepG-2
And the inhibiting rate of Human normal hepatocyte LO2 is 28.96%, 35.33% and 5.78% respectively.
Table 1
| Concentration (μ g/mL) | Negative control | 500 | 400 | 300 | 200 | 100 |
| MCF-7 | 0 | 54.52±1.29 | 50.24±2.44 | 44.85±0.94 | 32.26±2.2 | 28.96±0.27 |
| HepG-2 | 0 | 61.36±0.94 | 58.95±1.99 | 52.21±1.2 | 42.86±0.68 | 35.33±1.18 |
| LO2 | 0 | 22.8±1.14 | 20.22±0.64 | 16.88±1.93 | 10.57±0.45 | 5.78±0.37 |
Application Example 2
Take each 100 μ L cell suspension (5 × 10 of tumour cell MCF-7 and HepG-2 and Human normal hepatocyte LO24A/
ML), add in 96 orifice plates, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Cell is adherent after 24 h, and waste and old culture solution is sucked out, adds
Enter final volume for the DMEM basal medium of 200 μ L, the ten hexapeptide QTDDNHSNVLWAGFSR samples for containing 200 μ g/mL, and with
DMEM is negative control, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Medical fluid is sucked out after 48 h, with PBS board-washing 2 times, is added 5
The 180 μ L of 20 μ l of MTT solution and fresh basal medium of mg/mL；In 37 DEG C of constant temperature CO2Continue to cultivate in incubator；4 h
Afterwards, it discards the culture solution containing MTT, is added after 150 μ l DMSO in vibrating 15 min, 490nm wavelength on microoscillator
Place's measurement OD value simultaneously calculates inhibiting rate.As shown in Table 1, the polypeptide of 200 μ g/mL is to tumour cell MCF-7 and HepG-2
And the inhibiting rate of Human normal hepatocyte LO2 is 32.26%, 42.86% and 10.57% respectively.
Application Example 3
Take each 100 μ L cell suspension (5 × 10 of tumour cell MCF-7 and HepG-2 and Human normal hepatocyte LO24A/
ML it) adds in 96 orifice plates, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Cell is adherent after 24 h, and waste and old culture solution is sucked out, and is added
Final volume is the DMEM basal medium for the ten hexapeptide QTDDNHSNVLWAGFSR samples that 200 μ L contain 300 μ g/mL, and with
DMEM is negative control, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Medical fluid is sucked out after 48 h, with PBS board-washing 2 times, is added 5
The 180 μ L of 20 μ l of MTT solution and fresh basal medium of mg/mL；In 37 DEG C of constant temperature CO2Continue to cultivate in incubator；4 h
Afterwards, it discards the culture solution containing MTT, is added after 150 μ l DMSO in vibrating 15 min, 490nm wavelength on microoscillator
Place's measurement OD value simultaneously calculates inhibiting rate.As shown in Table 1, ten hexapeptides of 300 μ g/mL are to tumour cell MCF-7 and HepG-2
And the inhibiting rate of Human normal hepatocyte LO2 is 44.85%, 52.21% and 16.88% respectively.
Application Example 4
Take each 100 μ L cell suspension (5 × 10 of tumour cell MCF-7 and HepG-2 and Human normal hepatocyte LO24A/
ML it) adds in 96 orifice plates, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Cell is adherent after 24 h, and waste and old culture solution is sucked out, and is added
Final volume is the DMEM basal medium for the ten hexapeptide QTDDNHSNVLWAGFSR samples that 200 μ L contain 400 μ g/mL, and with
DMEM is negative control, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Medical fluid is sucked out after 48 h, with PBS board-washing 2 times, is added 5
The 180 μ L of 20 μ L of MTT solution and fresh basal medium of mg/mL；In 37 DEG C of constant temperature CO2Continue to cultivate in incubator；4 h
Afterwards, it discards the culture solution containing MTT, is added after 150 μ L DMSO in vibrating 15 min, 490nm wavelength on microoscillator
Place's measurement OD value simultaneously calculates inhibiting rate.As shown in Table 1, the polypeptide of 400 μ g/mL to tumour cell MCF-7 and HepG-2 and
The inhibiting rate of Human normal hepatocyte LO2 is 50.24%, 58.95% and 20.22% respectively.
Application Example 5
Take each 100 μ L cell suspension (5 × 10 of tumour cell MCF-7 and HepG-2 and Human normal hepatocyte LO24A/
ML it) adds in 96 orifice plates, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Cell is adherent after 24 h, and waste and old culture solution is sucked out, and is added
Final volume is the DMEM basal medium for the ten hexapeptide QTDDNHSNVLWAGFSR samples that 200 μ L contain 500 μ g/mL, and with
DMEM is negative control, in 37 DEG C of constant temperature CO2It is cultivated in incubator.Medical fluid is sucked out after 48 h, with PBS board-washing 2 times, is added 5
The 180 μ L of 20 μ L of MTT solution and fresh basal medium of mg/mL；In 37 DEG C of constant temperature CO2Continue to cultivate in incubator；4 h
Afterwards, it discards the culture solution containing MTT, is added after 150 μ L DMSO in vibrating 15 min, 490nm wavelength on microoscillator
Place's measurement OD value simultaneously calculates inhibiting rate.As shown in Table 1, the polypeptide of 500 μ g/mL to tumour cell MCF-7 and HepG-2 and
The inhibiting rate of Human normal hepatocyte LO2 is 54.52%, 61.36% and 22.8% respectively.
Claims (3)
1. ten hexapeptide QTDDNHSNVLWAGFSR of one kind, which is characterized in that the molecular weight of ten hexapeptide is 1846.8613, amino
Acid sequence is Gln-Thr-Asp-Asp-Asn-His-Ser-Asn-Val-Leu-Trp-Ala-Gly-Phe- Ser-Arg；It is described
Ten hexapeptides inhibit the in-vitro multiplication of breast cancer cell MCF-7 and HepG-2 cell when concentration is 100-500 μ g/mL
Rate is respectively 28.96%-54.52% and 35.33%-61.36%；Ten hexapeptide is when concentration is 100-500 μ g/mL, just to people
The in-vitro multiplication inhibiting rate of normal liver cell LO2 is 5.78%-22.8%.
2. the ten hexapeptide QTDDNHSNVLWAGFSR of one kind as described in claim 1, which is characterized in that ten hexapeptide is dense
When degree is 500 μ g/mL, the in-vitro multiplication inhibiting rate to breast cancer cell MCF-7 and HepG-2 cell is respectively 54.52%
With 61.36%.
3. the ten hexapeptide QTDDNHSNVLWAGFSR of one kind as described in claim 1, which is characterized in that ten hexapeptide is dense
When degree is 500 μ g/mL, the in-vitro multiplication inhibiting rate to Human normal hepatocyte LO2 is 22.8%.
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| CN109369782B (en) * | 2018-08-31 | 2021-09-21 | 华南理工大学 | Decapeptide for improving diabetes and senile dementia |
| CN109021075B (en) * | 2018-08-31 | 2020-12-22 | 华南理工大学 | Decapeptide for reducing blood sugar |
| CN108976291B (en) * | 2018-08-31 | 2021-06-08 | 华南理工大学 | Sixteen-peptide for improving diabetes and senile dementia |
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