N-(1-Oxohexyl)-L-tyrosyl-N-(6-amino-6-oxohexyl)-L-isoleucinamide
[CAS# 1401708-83-5]

Identification

• Classification: Organic raw materials >> Amino compound >> Amide compound
• Name: N-(1-Oxohexyl)-L-tyrosyl-N-(6-amino-6-oxohexyl)-L-isoleucinamide
• Synonyms: Dihexa; N-Hexanoic-Tyr-Ile-(6)aminohexanoic amide
• Protein Sequence: YI
• Molecular Formula: C₂₇H₄₄N₄O₅
• Molecular Weight: 504.66
• CAS Registry Number: 1401708-83-5
• SMILES: CCCCCC(=O)N[C@@H](CC1=CC=C(C=C1)O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)NCCCCCC(=O)N

Properties

• Solubility: Practically insoluble (0.027 g/L) (25 ºC), Calc.^*
• Density: 1.111±0.06 g/cm³ (20 ºC 760 Torr), Calc.^*
• Index of Refraction: 1.529, Calc.^*
• Boiling Point: 866.2±65.0 ºC (760 mmHg), Calc.^*
• Flash Point: 477.6±34.3 ºC, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2019 ACD/Labs)

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P305+P351+P351-P302+P352

Discovory and Applicatios

N-(1-Oxohexyl)-L-tyrosyl-N-(6-amino-6-oxohexyl)-L-isoleucinamide is a synthetic peptide-like compound that has garnered attention for its applications in biochemical research and pharmaceutical development. The molecule combines functional groups from amino acids with additional structural modifications, making it a versatile candidate for various biomedical applications.

The discovery of this compound can be attributed to the exploration of peptide derivatives that incorporate non-natural amino acid modifications. Researchers synthesized this molecule to study the influence of structural flexibility and functional diversity on peptide stability and activity. The inclusion of long alkyl chains and amide functionalities provides enhanced interactions with lipid membranes and proteins, expanding its application in drug delivery and receptor modulation.

One of the key areas of application for N-(1-oxohexyl)-L-tyrosyl-N-(6-amino-6-oxohexyl)-L-isoleucinamide lies in its potential as a substrate mimic for proteases. Due to its tailored structure, it serves as a model compound for studying enzyme-substrate interactions, particularly in the context of peptide-bond hydrolysis. Such studies are critical for understanding the activity of proteases implicated in diseases like cancer, neurodegeneration, and infectious diseases.

The compound has also been investigated as a building block in the design of targeted therapeutics. The presence of the tyrosyl residue enhances its compatibility with aromatic interactions, allowing it to serve as a ligand or carrier in receptor-targeted drug delivery systems. Furthermore, its hydrophobic hexyl chains make it suitable for interactions with cellular membranes, potentially aiding in the delivery of hydrophobic drugs or therapeutic peptides.

Another promising area of application is in the field of biomaterials. Due to its hybrid peptide-like structure, the compound has been studied for its potential to self-assemble into nanostructures. These nanostructures can be used in creating scaffolds for tissue engineering or as carriers for controlled drug release.

Despite its potential, the practical applications of N-(1-oxohexyl)-L-tyrosyl-N-(6-amino-6-oxohexyl)-L-isoleucinamide are still in the early stages of exploration. Studies to assess its biocompatibility, pharmacokinetics, and toxicity are ongoing, and these factors will determine its suitability for clinical applications. Advances in synthetic chemistry and peptide engineering may further expand its utility in diverse biomedical fields.

References

2015. Small-Molecule-Driven Hepatocyte Differentiation of Human Pluripotent Stem Cells. Stem Cell Reports. Richard Siller, Sebastian Greenhough, Elena Naumovska, Gareth J. Sullivan.
DOI: 10.1016/j.stemcr.2015.04.001

2014. RETRACTED: The Procognitive and Synaptogenic Effects of Angiotensin IV-Derived Peptides Are Dependent on Activation of the Hepatocyte Growth Factor/c-Met System. The Journal of Pharmacology and Experimental Therapeutics. Caroline C. Benoist, Leen H. Kawas, Mingyan Zhu, Katherine A. Tyson, Lori Stillmaker, Suzanne M. Appleyard, John W. Wright, Gary A. Wayman, Joseph W. Harding.
DOI: 10.1124/jpet.114.218735

2013. Evaluation of Metabolically Stabilized Angiotensin IV Analogs as Procognitive/Antidementia Agents. The Journal of Pharmacology and Experimental Therapeutics. Alene T. McCoy, Caroline C. Benoist, John W. Wright, Leen H. Kawas, Jyote M. Bule-Ghogare, Mingyan Zhu, Suzanne M. Appleyard, Gary A. Wayman, Joseph W. Harding.
DOI: 10.1124/jpet.112.199497