| Synonym: | Argireline |
| Sequence: | Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2 |
| CAS #: | 616204-22-9 |
| Molecular Formula: | C34H60N14O12S |
| Molecular Weight: | 889.0 |
| Acetyl Hexapeptide-8, commonly known as Argireline, is a synthetic peptide widely used in the cosmetic industry for its anti-aging properties, particularly its ability to reduce the appearance of wrinkles and fine lines. This six-amino-acid peptide (Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2) mimics a fragment of the SNAP-25 protein, a component of the SNARE complex involved in neurotransmitter release, thereby inhibiting muscle contraction with a non-invasive application. 1. Chemistry of Acetyl Hexapeptide-8 1.1 Structure Acetyl Hexapeptide-8 is a hexapeptide with the sequence Acetyl-Glu-Glu-Met-Gln-Arg-Arg-NH2. Key structural features include: • N-Terminal Acetylation: The acetyl group enhances stability against enzymatic degradation and improves skin penetration. • C-Terminal Amidation: The amide group increases resistance to carboxypeptidases, prolonging the peptide’s activity. • Amino Acid Composition: The sequence includes glutamic acid (Glu), methionine (Met), glutamine (Gln), and arginine (Arg), which contribute to its hydrophilic nature and interaction with biological targets. 1.2 Synthesis Acetyl Hexapeptide-8 is synthesized using solid-phase peptide synthesis (SPPS) with the Fmoc/tBu strategy: • Resin-Based Synthesis: The peptide is assembled on a solid support (e.g., Rink amide resin) to yield the C-terminal amide. • Fmoc Deprotection and Coupling: Iterative cycles of Fmoc removal and amino acid coupling (using reagents like HBTU or DIC/HOBt) build the sequence. • Acetylation: The N-terminus is acetylated using acetic anhydride post-synthesis. • Cleavage and Purification: The peptide is cleaved from the resin with trifluoroacetic acid (TFA) and purified via high-performance liquid chromatography (HPLC) to achieve >95% purity. 1.3 Chemical Properties • Molecular Weight: ~888.99 Da. • Solubility: Highly water-soluble due to its polar amino acid composition. • Stability: Stable under neutral pH and refrigerated conditions but susceptible to degradation in highly acidic or basic environments or at elevated temperatures. 2. Mechanism of Action Acetyl Hexapeptide-8 targets the SNARE (Soluble N-ethylmaleimide-sensitive factor Attachment protein REceptor) complex, which mediates vesicle fusion and neurotransmitter release at neuromuscular junctions. Its mechanism involves: • Mimicry of SNAP-25: The peptide mimics the N-terminal region of SNAP-25, a protein essential for forming the SNARE complex with syntaxin and VAMP (vesicle-associated membrane protein). • Competitive Inhibition: By competing with SNAP-25 for binding within the SNARE complex, Acetyl Hexapeptide-8 disrupts vesicle docking and acetylcholine release, reducing muscle contraction. • Reduction of Dynamic Wrinkles: Inhibited muscle contraction decreases repetitive facial movements, particularly in expression lines, smoothing the skin’s appearance. Acetyl Hexapeptide-8 is a groundbreaking peptide in the skincare industry, offering a non- invasive solution for wrinkle reduction and skin hydration. Its ability to relax facial muscles and promote collagen synthesis makes it a valuable addition to anti-aging routines, especially for early intervention. References: 1. Acetyl hexapeptide-8 2. In vitro skin penetration of acetyl hexapeptide-8 from a cosmetic formulation |
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