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RGD cyclopeptide for cancer cell integrin and application of RGD cyclopeptide in preparation of tumor drugs

A technology for integrins and cancer cells, applied in the field of RGD cyclic peptide and its application in the preparation of tumor drugs, can solve the problems of poor selectivity, achieve good metastasis and proliferation, and inhibit metastasis and proliferation

Pending Publication Date: 2022-06-24
HEFEI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The application provides a RGD cyclic peptide used in cancer cell integrins and its application in the preparation of tumor drugs, in order to solve the problem of existing polypeptides on α v beta 3 and alpha v beta 5 A technical problem with the poor selectivity of these two integrins

Method used

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  • RGD cyclopeptide for cancer cell integrin and application of RGD cyclopeptide in preparation of tumor drugs
  • RGD cyclopeptide for cancer cell integrin and application of RGD cyclopeptide in preparation of tumor drugs
  • RGD cyclopeptide for cancer cell integrin and application of RGD cyclopeptide in preparation of tumor drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Synthesis of RGD Linear Peptide on Wang Resin: GGGCRGDfVCLPXTGGS

[0048] (1) Resin swelling: Fmoc-Ser(otBu)-Wang resin (loaded at 0.564 mmol / g) was weighed and placed in a peptide solid-phase synthesis tube, and DMF was added to immerse the resin, and swelled for 3 hours. The resin was washed 3 times with MeOH, dichloromethane (DCM) and N,N-dimethylformamide (DMF) successively, and drained for use.

[0049] (2) Removal of fluorene methoxycarbonyl (Fmoc): add 5 mL of 20% piperidine DMF solution to the resin, shake the reaction for 15 min, repeat once, and finally wash the resin with DMF three times.

[0050] (3) Condensation of the remaining amino acids: The above resin was transferred to a polypeptide synthesizer (CEM) to complete the condensation of the remaining amino acids. The condensing agent is O-benzotriazole-tetramethylurea hexafluorophosphate (HBTU), and the organic base is N,N-diisopropylethylamine (DIPEA).

[0051] (4) Deprotection of the side chain: the a...

Embodiment 2

[0055] GnCRGDfVCRGDfVCLPXT (N-terminal G forms amide bond with C-segment T, n=3, y=1, m=2) cyclic peptide synthesis

[0056] The difference between the examples of this application and Example 1 is that the three cysteines in the GnCRGDfVCRGDfVCLPXT cyclic peptide form a disulfide bond mediated by 1,3,5-tribromomethylbenzene (TBMB). The amino acid reacts with TBMB to form a tricyclic peptide structure ( figure 2A). In the reaction system of 600 μL, the concentration of linear peptide GGGCRGDfVCRGDfVCLPKTGGS was 0.5 mM, the reaction concentration of Srt A was 5 μM, and the reaction concentration of TBMB was 1 mM. HPLC liquid phase monitoring and analysis of linear peptide and TBMB reaction 20min, 1h, 3h, 5h and Sortase A enzyme-mediated substrate peptide reaction 0h, 1h, 3h, 6h, 21h, 29h. The HPLC analysis conditions were: the mobile phase was water and acetonitrile, both containing 0.1% TFA; the flow rate was 0.5 mL / min; the detection wavelength was 220 nm; the gradient elu...

example 3

[0058] GnCCRGDfVCRGDfVCLPXT (N-terminal G and C-segment T form an amide bond, n=2, y=2, m=2) cyclic peptide synthesis

[0059] The difference between the examples of this application and Example 1 is: 4 cysteines in the GGCCRGDfVCRGDfVCLPXT cyclic peptide are selected to form disulfide bonds, the first and third cysteines form disulfide bonds, and the second and fourth cysteines form disulfide bonds. disulfide bonds. During solid-phase synthesis of linear peptides, the thiol groups of the 1st and 3rd cysteines are deprotected by trityl (trt), and the thiols of the 1st and 3rd cysteines are protected by Acm ( image 3 A). In a reaction system of 600 μL, the concentration of linear peptide GGCCRGDfVCRGDfVCLPXTLPKTGGS was 0.5 mM, and the reaction concentration of Srt A was 5 μM, and the reaction was carried out at 37 °C for 24 h to cyclize and form the first pair of disulfide bonds (Cys 3 -Cys 10 ), then add an equal volume of 10eq (relative to Acm) iodoacetic acid solution (t...

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Abstract

The invention belongs to the technical field of biology, and particularly relates to RGD cyclopeptide for cancer cell integrin and application of the RGD cyclopeptide in preparation of tumor drugs. The RGD cyclic peptide is rich in disulfide bonds formed by cysteine sulfydryl, the amino acid sequence of the RGD cyclic peptide is as follows: Gn (CyRGDfV) mCLPXT, n is a positive integer from 1 to 3, y is 1 or 2, m is 1 or 2, and n is a positive integer from 1 to 3. X is any one of glycine, alanine, valine, leucine, isoleucine, methionine, proline, tryptophan, serine, tyrosine, phenylalanine, asparagine, glutamine, threonine, aspartic acid, glutamic acid, lysine, arginine, histidine, selenocysteine and pyrrole lysine. The RGD cyclopeptide has relatively strong selective binding capacity on two integrin alpha v beta 3 and alpha v beta 5 in cancer cells, and metastasis and proliferation of the cancer cells can be better inhibited through selective binding of the RGD cyclopeptide and the integrin.

Description

technical field [0001] The invention belongs to the field of biotechnology, and in particular relates to an RGD cyclic peptide for cancer cell integrin and its application in preparing tumor medicine. Background technique [0002] RGD is a short peptide containing arginine-glycine-aspartic acid (Arg-Gly-Asp), which is mainly present in the extracellular matrix (ECM) and blood cohesins, such as fibrin (Fibrinogen, FB), Fibronectin (FN), laminin (Vitronectin, VN) and collagen (Collagen) all contain RGD sequences. As a conserved sequence of these proteins, RGD interacts with integrin receptors on cell membranes (eg, α v beta 3 and α v beta 5 ) interact to mediate cell adhesion to the extracellular matrix. The cell membranes of many cancer cells overexpress related integrin receptors, which play an important role in cancer cell metastasis, proliferation, and signal transmission. Among various integrin molecules, α v beta 3 and α v beta 5 The high expression of is a spe...

Claims

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Application Information

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IPC IPC(8): C07K7/08A61K38/10A61P35/00
CPCC07K7/08A61P35/00A61K38/00
Inventor 程孝中汪亦鸣荚李璇陈晗庞习习
Owner HEFEI NORMAL UNIV
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