Cyclo(-Arg-Gly-Asp-D-Phe-Lys) CAS 161552-03-0

CYCLO (RGDFK) is a cyclic pentapeptide formed by connecting arginine (R), glycine (G), aspartic acid (D), D-phenylalanine (f), and lysine (K) through peptide bonds to create a cyclic structure. Research indicates that the cyclic structure enhances its stability, making it less susceptible to protease degradation in both in vivo and in vitro environments. The Cyclo(-Arg-Gly-Asp-D-Phe-Lys) provided by our company is a white or almost white crystalline powder that is extremely soluble in water. The core cyclic peptide within it is the RGD sequence, which can specifically bind to receptors such as integrin αvβ3 and αvβ5, playing a crucial role in physiological and pathological processes such as cell adhesion, migration, and angiogenesis.

What is the pharmacological mechanism of action of Cyclo(-Arg-Gly-Asp-D-Phe-Lys)?

CYCLO (ARG-GLY-ASP-D-PHE-LYS) is an effective and selective integrin αvβ3 inhibitor with an IC50 value of 0.94 nM. It specifically binds to integrin receptors on the cell surface through the RGD sequence, blocking the interaction between integrin and its natural ligands, thereby inhibiting tumor angiogenesis, tumor cell proliferation, migration, and invasion. Compared to linear RGD peptides, the cyclic structure makes its conformation more rigid, enhancing its affinity and selectivity for integrin receptors. Biological experiments have shown that the CYCLO (RGDFK) cyclic peptide possesses the following biological functions: 1) specific binding to integrin αvβ3 and αvβ5 with high affinity (Kd approximately 10⁻⁹ M); 2) inhibition of tumor angiogenesis and tumor cell invasion and metastasis; 3) promotion of drug accumulation at tumor sites through receptor-mediated endocytosis; 4) the cyclic structure provides higher in vivo stability and resistance to protease degradation.

Where is the application field of CYCLO (ARG-GLY-ASP-D-PHE-LYS)?

Cyclo(-RGDfK) is a highly selective cyclic peptide inhibitor of integrin_alpha_v_beta_3, which can be used not only in scientific research experiments but also holds its own in the pharmaceutical field.
1. The application of CYCLO (RGDFK) in targeted tumor therapy.
1) Targeted Drug Delivery: When coupled with anti-tumor pharmaceutical ingredients as a targeting ligand, c(RGDfK) at an appropriate concentration enables the precise accumulation of anti-tumor active factors at the tumor site, thereby enhancing therapeutic efficacy and reducing toxic side effects. 2) Molecular Imaging: High-grade Cyclo (-RGDfK) TFA can label radioactive isotopes (such as Ga-68, Cu-64) or fluorescent substances for use in imaging techniques like PET and SPECT, facilitating early diagnosis and precise monitoring of tumor treatment. 3) Drug Carrier Modification: API powder CYCLO (ARG-GLY-ASP-D-PHE-LYS) can modify the surface of carriers like liposomes and nanoparticles, enhancing the targeting ability of drugs towards tumor cells. 4) Anti-angiogenesis Research: In medicine, anti-angiogenic inhibitors or anti-tumor strategies are often studied by competing for integrin binding sites. Cyclo(-Arg-Gly-Asp-D-Phe-Lys) is currently the latest research topic.
2. The application of CYCLO (RGDFK) in the field of tissue engineering.
It can be used to modify the surface of biomaterials, regulate the interaction between cells and materials, and promote tissue repair and regeneration. In biomaterial science, high-quality Cyclo(-Arg-Gly-Asp-D-Phe-Lys) can bind to integrin receptors through the RGD sequence, guiding cell adhesion, proliferation, and differentiation on the material surface. This has potential applications in fields such as bone tissue engineering, cartilage repair, and nerve regeneration.

What are the advantages of Cyclo(-Arg-Gly-Asp-D-Phe-Lys)?

Compared to linear RGD peptides, CYCLO (RGDFK) possesses the following advantages:
1) High stability: The cyclic structure reduces the reactivity of the terminal groups of the peptide chain, making it less susceptible to protease degradation in both in vivo and in vitro environments, significantly extending its half-life; 2) High affinity: The cyclic conformation enables the RGD sequence to adopt a specific angle in space, enhancing its affinity and selectivity for integrin receptors; 3) Multifunctionality: The amino group of the lysine side chain provides active sites for subsequent modifications, allowing for the attachment of fluorescent dyes, radioactive isotopes, drug molecules, or carrier systems; 4) High selectivity: It exhibits high specificity for integrin αvβ3 and αvβ5, reducing non-specific binding. According to current peptide research findings, compared to natural L-amino acids, D-amino acids can significantly enhance the stability of peptides in body fluids and reduce the rate of enzyme degradation, thereby extending the effective action time of peptides. The phenyl ring of D-phenylalanine also increases the hydrophobicity of the molecule, maintains the stability of the ring, and affects the hydrophobic interaction with receptors. The introduction of D-phenylalanine (f) to c(RGDfK) peptide powder retains the above characteristics, makes the peptide conformation more rigid, and enhances its selectivity for αvβ3 integrin.

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FAQ:

Q1: How secure is it? ​
The Cyclo(-Arg-Gly-Asp-D-Phe-Lys) peptide has good biocompatibility and has demonstrated good safety in vitro and animal experiments. However, due to its targeting of integrin receptors, it may affect normal cell adhesion and migration processes. In preclinical studies, it is necessary to evaluate its impact on normal tissues, particularly on angiogenesis and wound healing.

Q2: How to store it?
It is recommended to place it in a low-temperature refrigeration environment (-20 ℃), avoiding light and moisture, to maintain the activity and stability of CYCLO (RGDFK) peptide. If not used, it should always be stored in its original packaging to avoid being divided into other containers. The packaging should be sealed immediately after each use. Under appropriate storage conditions, the product's shelf life is usually 24 months.

Q3: What are the characteristics of CYCLO (RGDFK) compared to other RGD peptides? ​
Compared with linear RGD peptides, CYCLO (RGDFK) has higher stability and affinity; Compared with other cyclic RGD peptides such as c (RGDyK), the introduction of D-phenylalanine makes its conformation more rigid and has higher selectivity for α v β 3 integrin. In addition, the lysine side chain amino group provides convenient active sites for subsequent modifications, making it more advantageous in functionalization.

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