Cyclo(Arg-Gly-Asp-D-Phe-Val)

CAS

137813-35-5

Catalog Number

ACM137813355-1

Category

Inhibitors

Molecular Weight

574.63

Molecular Formula

C26H38N8O7

MSDS COA Spec Sheet

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Specification

Description

Cyclo(Arg-Gly-Asp-D-Phe-Val) is an integrin αvβ3 inhibitor. Cyclo(Arg-Gly-Asp-D-Phe-Val) has antitumor activity. Cyclo(Arg-Gly-Asp-D-Phe-Val) can be used for the research of acute myeloid leukemia.

Appearance

Solid

Storage

Please store the product under the recommended conditions in the Certificate of Analysis.

Shipping

Can be shipped at room temperature, where not in use may vary.

Cyclo (Arg-Gly-Asp-D-Phe-Val) with Integrin Inhibitors

The molecular structures of the obtained five lowest energy conformers of Cyclo (Arg-Gly-Asp-D-Phe-Val) by conformational analysis

Çelik, Sefa, et al. Open Journal of Nano 6.2 (2021): 1-6.

Using the program, all possible conformations of Cyclo (Arg-Gly-Asp-D-Phe-Val) (C26H38N8O7) with antitumor activity were determined, and the most stable conformer was elucidated by the MMFF method. The energy differences between the conformers were determined, and the low-energy conformers required for the determination of biological activity were characterized. Since the studied molecules are expected to be integrin inhibitors as anticancer drug candidates, molecular docking studies with αβ integrins were performed to determine the mechanism of interaction. As a result of the docking simulations, the binding affinity and interaction between the studied peptides and the target integrin were determined.
Conformational analysis was performed using Spartan06 software and MMFF technology. To determine the possible binding sites on the receptor surface, CAVER software was used. Molecular docking studies of the identified active sites were performed using AutoDock-Vina software. Molecular docking simulation of target protein αβ integrin to evaluate the proliferative effect of Cyclo (Arg-Gly-Asp-D-Phe-Val) with anticancer activity. αβ integrin was prepared for molecular docking, and docking simulation of Cyclo (ArgGly-Asp-D-Phe-Val) with the most active site of αβ integrin was performed with a binding affinity of -10.5 kcal/mol.

Cyclic pentapeptide cyclo(Arg-Gly-Asp-D-Phe-Val) emerges as a promising anticancer agent

Schematic overview of all examined conformations of the cyclic RGD pentapeptides in comparison to cyclopentaalanine model peptides.

Wermuth, J., et al. Journal of the American Chemical Society 119.6 (1997): 1328-1335.

Cyclic pentapeptide Cyclo(Arg-Gly-Asp-D-Phe-Val) is a highly potent and selective Rβ3 integrin inhibitor and emerges as a promising anticancer agent by inhibiting angiogenesis and inducing apoptosis in vascular cells. Cyclic retro-inverso peptides as well as retro-inverso peptides and cyclic retro-inverso peptide analogs of four cyclic Arg-Gly-Asp-Phe-Val peptides with one amino acid in the configuration and the corresponding full peptides have been synthesized. Eighteen compounds have been tested for their inhibitory activity against isolated integrin R IIbβ3 and Rβ receptors. The conformations of the cyclic retro-inverso pentapeptides have been studied by NMR spectroscopy using NOE, ROE, and coupling constants and determined by distance geometry (DG) calculations. These structures are compared with their parent analogs and the relationship between their conformation and biological activity is discussed. Due to the inversion of peptide bonds in the retro-inverso peptide, the hydrogen bonding pattern was changed and the spatial structure was different from that of its parent compound. These conformational changes resulted in a drastic decrease in activity compared to the highly active parent peptide. On the other hand, the retro-inverso peptide analog of the less active parent peptide cyclo(-D-Arg-Gly-Asp-Phe-Val-) was found to be highly active and selective for the Rβ receptor. In addition, the almost complete similarity of the side chain orientation between the highly active peptide cyclo(Arg-Gly-Asp-D-Phe-Val) and the inactive retro-inverso peptide cyclo(-Val-D-Phe-D-Asp-Gly-Arg-) indicated a significant interaction of at least one peptide bond of the backbone with the Rβ3 receptor.
TOCSY with short (20 ms) and long (80 ms) mixing times was used for proton assignments, and HMQC and HMQC-TOCSY were used for carbon assignments. The sequential assignment of proton resonances was achieved by NOESY (500 MHz) and HMBC, which also confirmed the cyclization. The J coupling constants were extracted from 1D or PE-COSY spectra. NOE effects were quantified by NOESY experiments at 500 MHz with a mixing time of 150 ms. All compounds examined showed only one conformation on the NMR time scale, as expected without the incorporation of secondary amines (e.g., proline). The retro and retro-inverse compounds showed exactly the same H and C spectra as their parent and retro compounds, respectively.

What is the molecular formula of Cyclo(Arg-Gly-Asp-D-Phe-Val)?

The molecular formula of Cyclo(Arg-Gly-Asp-D-Phe-Val) is C26H38N8O7.

What are the synonyms of Cyclo(Arg-Gly-Asp-D-Phe-Val)?

The synonyms of Cyclo(Arg-Gly-Asp-D-Phe-Val) are CYCLORGDFV, 137813-35-5, and CHEMBL411941.

What is the molecular weight of Cyclo(Arg-Gly-Asp-D-Phe-Val)?

The molecular weight of Cyclo(Arg-Gly-Asp-D-Phe-Val) is 574.6 g/mol.

How was the molecular weight computed?

The molecular weight was computed by PubChem 2.1.

When was Cyclo(Arg-Gly-Asp-D-Phe-Val) created?

Cyclo(Arg-Gly-Asp-D-Phe-Val) was created on October 25, 2006.

When was Cyclo(Arg-Gly-Asp-D-Phe-Val) last modified?

Cyclo(Arg-Gly-Asp-D-Phe-Val) was last modified on October 21, 2023.

What is the IUPAC Name of Cyclo(Arg-Gly-Asp-D-Phe-Val)?

The IUPAC Name of Cyclo(Arg-Gly-Asp-D-Phe-Val) is 2-[(2S,5R,8S,11S)-5-benzyl-11-[3-(diaminomethylideneamino)propyl]-3,6,9,12,15-pentaoxo-8-propan-2-yl-1,4,7,10,13-pentazacyclopentadec-2-yl]acetic acid.

What is the InChI of Cyclo(Arg-Gly-Asp-D-Phe-Val)?

The InChI of Cyclo(Arg-Gly-Asp-D-Phe-Val) is InChI=1S/C26H38N8O7/c1-14(2)21-25(41)32-16(9-6-10-29-26(27)28)22(38)30-13-19(35)31-18(12-20(36)37)23(39)33-17(24(40)34-21)11-15-7-4-3-5-8-15/h3-5,7-8,14,16-18,21H,6,9-13H2,1-2H3,(H,30,38)(H,31,35)(H,32,41)(H,33,39)(H,34,40)(H,36,37)(H4,27,28,29)/t16-,17+,18-,21-/m0/s1.

What is the InChIKey of Cyclo(Arg-Gly-Asp-D-Phe-Val)?

The InChIKey of Cyclo(Arg-Gly-Asp-D-Phe-Val) is YYQUWEHEBOMRPH-NYUBLWNDSA-N.

What are the computed properties of Cyclo(Arg-Gly-Asp-D-Phe-Val)?

The computed properties of Cyclo(Arg-Gly-Asp-D-Phe-Val) include XLogP3-AA (-1.2), Hydrogen Bond Donor Count (8), Hydrogen Bond Acceptor Count, Rotatable Bond Count (9), Exact Mass (574.28634558 g/mol), Topological Polar Surface Area (247Å²), Heavy Atom Count (41), Formal Charge (0), Complexity (992), Isotope Atom Count, Defined Atom Stereocenter Count (4), Undefined Atom Stereocenter Count, Defined Bond Stereocenter Count, Undefined Bond Stereocenter Count, Covalently-Bonded Unit Count (1), and Compound Is Canonicalized (Yes).