N2-(1-Oxohexadecyl)-L-lysyl-L-threonyl-L-threonyl-L-lysyl-L-serine
[CAS# 214047-00-4]

Identification

• Classification: Biochemical >> Peptide
• Name: N2-(1-Oxohexadecyl)-L-lysyl-L-threonyl-L-threonyl-L-lysyl-L-serine
• Molecular Formula: C₃₉H₇₅N₇O₁₀
• Molecular Weight: 802.05
• Protein Sequence: KTTKS
• CAS Registry Number: 214047-00-4
• EC Number: 606-757-9
• SMILES: CCCCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)O

Properties

• Density: 1.147

Discovery and Applications

N2-(1-Oxohexadecyl)-L-lysyl-L-threonyl-L-threonyl-L-lysyl-L-serine, often referred to as a lipidated tetrapeptide, was discovered as part of research into lipid-peptide conjugates for biomedical applications. The compound was synthesized through chemical modification of amino acids, specifically lysine, threonine, and serine, with a hexadecanoyl group. This modification enhances the compound's lipophilicity and bioavailability, making it suitable for various biomedical applications. The discovery of lipidated tetrapeptides represents a significant advancement in peptide chemistry.

Lipidated tetrapeptides, including N2-(1-Oxohexadecyl)-L-lysyl-L-threonyl-L-threonyl-L-lysyl-L-serine, are utilized in drug delivery systems to enhance the pharmacokinetic properties and target-specific delivery of therapeutic agents. The lipid modification enables these peptides to interact with cell membranes and facilitate cellular uptake, thereby improving the delivery of drugs to target tissues or organs. Lipid-peptide conjugates have been explored for the delivery of anticancer drugs, antimicrobial agents, and therapeutic peptides.

Lipidated tetrapeptides are employed as vaccine adjuvants to enhance immune responses and improve the efficacy of vaccines. By conjugating peptides with lipid moieties, researchers can enhance their immunogenicity and promote antigen presentation to immune cells, leading to a stronger and longer-lasting immune response. Lipid-peptide conjugates have been investigated as adjuvants for various vaccines, including those against infectious diseases, cancer, and autoimmune disorders.

Lipidated tetrapeptides exhibit antimicrobial properties and are explored as novel antimicrobial agents for the treatment of bacterial infections. The lipid modification enhances the peptides' ability to interact with bacterial cell membranes, disrupting membrane integrity and leading to microbial cell death. Lipidated peptides have shown promising activity against a wide range of pathogenic bacteria, including multidrug-resistant strains, making them potential candidates for the development of new antibiotics and antimicrobial therapies.

In biomedical imaging and diagnostic applications, lipidated tetrapeptides are used as targeting ligands for specific biomarkers or receptors associated with diseases such as cancer and inflammation. The lipid modification allows these peptides to efficiently penetrate biological barriers and accumulate at target sites, enabling the visualization and detection of diseased tissues or cells. Lipid-peptide conjugates have been employed in various imaging modalities, including magnetic resonance imaging (MRI), positron emission tomography (PET), and fluorescence imaging, for early disease detection, monitoring treatment response, and guiding surgical interventions.

References

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DOI: 10.1016/j.aca.2009.03.015

2019. The Effects of a Novel Series of KTTKS Analogues on Cytotoxicity and Proteolytic Activity. Molecules (Basel, Switzerland), 24(20).
DOI: 10.3390/molecules24203698

2014. Microneedle Enhanced Delivery of Cosmeceutically Relevant Peptides in Human Skin. PLoS ONE, 9(7).
DOI: 10.1371/journal.pone.0101956