cyclo[Asp-Glu-Tyr-Val-Orn-Leu-D-Phe-Pro-Phe-DL-Phe]
[CAS# 1404-88-2]

Identification

• Classification: API >> Antibiotics >> Peptide drug
• Name: cyclo[Asp-Glu-Tyr-Val-Orn-Leu-D-Phe-Pro-Phe-DL-Phe]
• Synonyms: cyclo[Asp-Glu-Tyr-Val-Orn-Leu-D-Phe-Pro-Phe-DL-Phe]; 3-[(3R,6S,9S,12S,15S,18S,21S,27S,30S)-9-(3-aminopropyl)-3,24,27-tribenzyl-21-(carboxymethyl)-15-[(4-hydroxyphenyl)methyl]-6-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29-decaoxo-12-propan-2-yl-1,4,7,10,13,16,19,22,25,28-decazabicyclo[28.3.0]tritriacontan-18-yl]propanoic acid
• Molecular Formula: C₆₆H₈₅N₁₁O₁₅
• Molecular Weight: 1272.45
• CAS Registry Number: 1404-88-2
• EC Number: 215-771-0
• SMILES: CC(C)C[C@H]1C(=O)N[C@@H](C(=O)N2CCC[C@H]2C(=O)N[C@H](C(=O)NC(C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN)C(C)C)CC3=CC=C(C=C3)O)CCC(=O)O)CC(=O)O)CC4=CC=CC=C4)CC5=CC=CC=C5)CC6=CC=CC=C6

Properties

• Density: 1.3±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.635, Calc.^*
• Boiling Point: 1516.6±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 871.0±34.3 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Discovery and Applications

Cyclo [aspartyl-glutamyl-tyrosyl-valyl-ornityl-leucyl-D-phenylalanyl-prolyl-phenylalanyl-DL-phenylalanyl] The discovery stems from the study of microorganisms or the chemical composition of marine biochemistry. Screening of extracts or fermentation broths for biological activity against specific targets led to the identification of this cyclic peptide as a promising product candidate. As a cyclic peptide, it exhibits enhanced stability, bioavailability, and target specificity compared to linear peptides, making it an attractive candidate for drug discovery and development.

Cyclo [aspartyl-glutamyl-tyrosyl-valyl-ornityl-leucyl-D-phenylalanyl-prolyl-phenylalanyl-DL-phenylalanyl] exhibits multiple biological activities, making them promising candidates for therapeutic intervention. Studies have shown its potential in anti-cancer treatments, inhibiting tumor growth or inducing apoptosis in cancer cells. Cyclo [aspartyl-glutamyl-tyrosyl-valyl-ornityl-leucyl-D-phenylalanyl-prolyl-phenylalanyl-DL-phenylalanyl] exhibits antibacterial properties against a variety of pathogens, including bacteria, fungi and viruses. Its mechanism of action involves disrupting microbial membranes or interfering with important cellular processes. Cyclo [aspartyl-glutamyl-tyrosyl-valyl-ornityl-leucyl-D-phenylalanyl-prolyl-phenylalanyl-DL-phenylalanyl] can be incorporated into drug delivery systems to enhance targeted delivery of therapeutic agents. Its cyclic structure provides stability and resistance to enzymatic degradation, ensuring sustained release and improved bioavailability of encapsulated drugs. In biochemical studies, Cyclo [aspartyl-glutamyl-tyrosyl-valyl-ornityl-leucyl-D-phenylalanyl-prolyl-phenylalanyl-DL-phenylalanyl] is a valuable tool for studying protein-protein interactions, cell signaling pathways, and enzyme dynamics. Its selective binding affinity for specific molecular targets enables researchers to elucidate complex biological processes and identify potential drug targets.

References

Kopp Florian. Macrocyclization strategies in polyketide and nonribosomal peptide biosynthesis, Natural Product Reports, 2007