N-(1-Oxohexadecyl)glycyl-L-histidyl-L-lysine
[CAS# 147732-56-7]

Identification

• Classification: Biochemical >> Peptide
• Name: N-(1-Oxohexadecyl)glycyl-L-histidyl-L-lysine
• Synonyms: Pal-GHK; Palmitoyl Tripeptide-1; N2-[N-[N-(1-oxohexadecyl)glycyl]-L-histidyl]-L-lysine
• Molecular Formula: C₃₀H₅₄N₆O₅
• Molecular Weight: 578.79
• Protein Sequence: GHK
• CAS Registry Number: 147732-56-7
• EC Number: 680-607-0
• SMILES: CCCCCCCCCCCCCCCC(=O)NCC(=O)N[C@@H](CC1=CN=CN1)C(=O)N[C@@H](CCCCN)C(=O)O

Properties

• Density: 1.105±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.524, Calc.^*
• Boiling Point: 913.0±65.0 °C (760 mmHg), Calc.^*
• Flash Point: 506.0±34.3 °C, Calc.^*

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

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

N-(1-Oxohexadecyl)glycyl-L-histidyl-L-lysine is a synthetic peptide-lipid conjugate designed for use in advanced drug delivery systems and cosmetic formulations. This molecule combines the bioactivity of a peptide with the hydrophobic properties of a lipid chain, enabling it to interact with biological membranes and deliver therapeutic or cosmetic agents effectively.

The discovery of this compound was driven by the need to develop biocompatible molecules capable of facilitating the transport of active substances through cellular barriers. Traditional drugs often struggle with issues such as poor solubility or rapid degradation in biological systems. By attaching a lipid chain to a peptide sequence, researchers sought to enhance the stability and membrane permeability of bioactive compounds, thereby improving their therapeutic efficacy.

The structure of N-(1-Oxohexadecyl)glycyl-L-histidyl-L-lysine features a hexadecyl lipid chain, which provides hydrophobicity, and a glycyl-L-histidyl-L-lysine tripeptide, which retains the biofunctional properties of the peptide sequence. This design enables the compound to self-assemble into micelles or vesicles in aqueous environments, making it suitable for encapsulating and transporting hydrophilic and hydrophobic drugs.

In pharmaceutical applications, N-(1-Oxohexadecyl)glycyl-L-histidyl-L-lysine has shown potential in delivering peptides, nucleotides, and small-molecule drugs. Its amphiphilic nature allows it to form stable nanoparticles or liposomes, protecting encapsulated drugs from enzymatic degradation and facilitating controlled release. These properties are particularly advantageous in cancer therapy, where targeted and sustained drug delivery is crucial for maximizing therapeutic outcomes while minimizing side effects.

Cosmetic applications of this compound leverage its ability to improve the delivery of active ingredients into the skin. The lipid-peptide conjugate enhances the penetration of anti-aging agents, antioxidants, and moisturizers, increasing their effectiveness. Moreover, the tripeptide component can stimulate collagen synthesis and promote skin repair, making it a valuable ingredient in skincare formulations.

The synthesis of N-(1-Oxohexadecyl)glycyl-L-histidyl-L-lysine involves multiple steps, starting with the solid-phase synthesis of the peptide chain. The lipid chain is introduced through coupling reactions, typically using hexadecanoic acid or its derivatives. Purification is achieved through techniques such as reverse-phase high-performance liquid chromatography (HPLC) to ensure the high purity of the final product.

Research continues to explore the potential of this compound in theranostics, where it can serve as a carrier for both therapeutic and imaging agents. By functionalizing the peptide sequence with targeting ligands, it is possible to achieve selective delivery to specific cells or tissues, such as tumors or inflamed sites. This targeted delivery not only enhances treatment efficacy but also reduces systemic toxicity.

N-(1-Oxohexadecyl)glycyl-L-histidyl-L-lysine is also being investigated for its environmental impact and biodegradability. Initial studies suggest that the compound can be broken down into non-toxic metabolites, supporting its use in environmentally conscious formulations. However, further studies are required to fully evaluate its long-term safety and degradation pathways.

The development of N-(1-Oxohexadecyl)glycyl-L-histidyl-L-lysine exemplifies the innovative integration of peptides and lipids to create multifunctional molecules for medical and cosmetic applications. Its ability to enhance drug delivery, improve skin health, and provide targeted therapeutic effects highlights its versatility and potential for future applications.

References

2015. Peptide-Mediated Transdermal Drug Delivery. Percutaneous Penetration Enhancers Chemical Methods in Penetration Enhancement, 1, 1.
DOI: 10.1007/978-3-662-47039-8_22

2009. Development of a LC-MS/MS method to monitor palmitoyl peptides content in anti-wrinkle cosmetics. Analytica Chimica Acta, 645, 1.
DOI: 10.1016/j.aca.2009.03.015