Acetyl hexapeptide-3

Acetyl hexapeptide-3 or acetyl hexapeptide-8 (sources differ) is a synthetic anti-wrinkle cosmetics ingredient. It is a peptide which is a fragment of SNAP-25, a substrate of botulinum toxin (Botox). Acetyl hexapeptide-8 is marketed as Argireline by the Barcelona-based research laboratory Lipotec.[1]

Acetyl hexapeptide-3
Stereo, skeletal formula of acetyl hexapeptide-8
Names
Other names
  • (6S,9S,12S,15S,18S,21S)-21-Acetamido-1-amino-12-(3-amino-3-oxopropyl)-6-carbamoyl-18-(2-carboxyethyl)-9-(3-guanidinopropyl)-1-imino-15-(2-(methylthio)ethyl)-8,11,14,17,20-pentaoxo-2,7,10,13,16,19-hexaazatetracosan-24-oic acid
  • Argireline
  • Ac-EEMQRR-NH2
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C34H60N14O12S/c1-17(49)43-20(8-11-25(51)52)29(57)47-22(9-12-26(53)54)31(59)48-23(13-16-61-2)32(60)46-21(7-10-24(35)50)30(58)45-19(6-4-15-42-34(39)40)28(56)44-18(27(36)55)5-3-14-41-33(37)38/h18-23H,3-16H2,1-2H3,(H2,35,50)(H2,36,55)(H,43,49)(H,44,56)(H,45,58)(H,46,60)(H,47,57)(H,48,59)(H,51,52)(H,53,54)(H4,37,38,41)(H4,39,40,42)/t18-,19-,20-,21-,22-,23-/m0/s1 checkY
    Key: RJZNPROJTJSYLC-LLINQDLYSA-N checkY
  • CSCC[C@H](NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(C)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(N)=O
Properties
C34H60N14O12S
Molar mass 889.00 g·mol−1
Related compounds
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Overview and common uses

Acetyl hexapeptide-3 is used in attempts to decrease the visible effects of aging by reducing the deep wrinkles and lines that occur around the forehead and eyes.[1][2]

Chemically, when applied as a solution to specific areas of the face, acetyl hexapeptide-3 inhibits the reactions that cause muscles to move or contract[1] – for example when forming facial expressions such as smiling or frowning.

Studies

Both in vitro (outside a living organism) and in vivo (using a living organism) tests have been carried out, but no double-blind anti-wrinkle studies are available.

In a 2012 double-blind, placebo-controlled trial investigating treatment of blepharospasm (abnormal contraction or twitch of the eyelid), botulinum toxin injections with subsequent acetyl hexapeptide-3 treatment were compared to botulinum toxin injections with placebo cream treatment. Of the 12 patients in the acetyl hexapeptide-3 group, four experienced an extension of symptom control by 3.3 to 7.1 months.[3]

Safety research

The 2012 study concluded there were no significant adverse effects. Patients receiving botulinum toxin injections exhibited longer times until return to baseline symptoms when supported with daily application of acetyl hexapeptide-8.[3]

Chemistry

Acetyl hexapeptide-3 is the hexapeptide with the sequence Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2.[1]

References
  1. Blanes-Mira, C; et al. (October 2002). "A synthetic hexapeptide (Argireline) with antiwrinkle activity". Int J Cosmet Sci. 24 (5): 303–10. doi:10.1046/j.1467-2494.2002.00153.x. PMID 18498523.
  2. Ruiz, MA; Clares, B; Morales, ME; Cazalla, S; Gallardo, V (2007). "Preparation and stability of cosmetic formulations with an anti-aging peptide". Journal of Cosmetic Science. 58 (2): 157–71. PMID 17520155.
  3. Lungu, MD, Codrin; Considine, RN, Elaine; Zahir, MS, Sana; Ponsati, PhD, Berta; Arrastia, MS, Silvia; Hallet, MD, Mark (November 12, 2012). "Pilot Study of Topical Acetyl Hexapeptide-8 in Treatment of Blepharospasm in Patients Receiving Botulinum Neurotoxin Therapy". Eur J Neurol. 20 (3): 515–8. doi:10.1111/ene.12009. PMC 4747634. PMID 23146065.
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