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Argireline

Argireline is made up of chains of amino acids. Such chains can affect how our cells work, e.g. relaxing our face muscles. It is derived from the peptide Acetyl hexapeptide-3, a substrate of Botulinum toxin, or more commonly known as Botox.

CAS
616204-22-9
EINECS
Molecular Formula
C34H60N14O12S
Molecular Weight
888.992
PubChem CID
329825391
MDL Number
MFCD22666393
Beilstein
Merck Index
GHS

Chemical Properties

Density 1.5±0.1 g/cm3 Boiling point
Melting point Refractive index
Flash point Optical Activity
Water solubility Physical State
Purity Appearance
InChI 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
InChIKey RJZNPROJTJSYLC-LLINQDLYSA-N
Synonyms Ac-Glu-Glu-Met-Glu-Arg-Arg-NH2;N-Acetyl-L-alpha-glutamyl-L-alpha-glutamyl-L-methionyl-L-glutaminyl-L-arginyl-L-argininamide;Acetyl Hexapeptide-3/Acetyl Hexapeptide-8;Argireline,Acetyl hexapeptide-3, BR;Anti-Wrinkle Multi-Peptides;Reproage;Argireline;Argireline acetate Ac-Glu-Glu-Met-Arg-Arg-NH2
SMILES CC(=O)NC(CCC(=O)O)C(=O)NC(CCC(=O)O)C(=O)NC(CCSC)C(=O)NC(CCC(=O)N)C(=O)NC(CCCN=C(N)N)C(=O)NC(CCCN=C(N)N)C(=O)N
Solubility data

Biological Description

IC50
Ki Data
pK Values 4.43±0.10(Predicted) Storage

Sealed storage, away from moisture

Powder -80°C 2 years
  -20°C 1 year
Sequence
Sequence(single)
In Vitro TheincubationofArgirelinesolutionindifferentconcentrationswithhumanembryonickidneyHEK-293(IC50of34.862μM)andneuroblastomaIMR-32cells(IC50of68.458μM))for48hhavedosedependentantiproliferatChemicalbookiveeffect.ArgirelinesolutionincubatedindifferentconcentrationswithHSFhasadose-dependentantiproliferativeeffectonthosecells.CellularproliferationisnoteffectedinArgirelinelowconcentration.
In Vivo Argirelineisappliedtotheagedmicetwicedailyfor6weeks.Thereisanimprovementinthehistologicalstructureofskintissueintheagedmice;theamountoftypeIcollaChemicalbookgenfibersincreased,whilethatoftypeIIIcollagenfibersdecreased.Argirelinecouldimprovethehistologicalstructureofskintissueandrejuvenatetheagingskin.

Application

Application Botox is a common, anti-wrinkle treatment which is applied using a needle. You may achieve the same anti-aging results with products which contain Argireline. Argireline can help prevent the formation of wrinkles by inhibiting muscle movement in the face. Because of this, Argireline cream is sometimes known as “Botox in a jar.”

Security information

Hazard Symbols
Risk Codes
Safety Description

References

References 1.Iontophoretic skin permeation of peptides: an investigation into the influence of molecular properties, iontophoretic conditions and formulation parameters. Krishnan G1, Roberts MS, Grice J, Anissimov YG, Moghimi HR, Benson HA. Drug Deliv Transl Res. 2014 Jun;4(3):222-32. doi: 10.1007/s13346-013-0181-8. The transdermal route offers advantages for delivery of peptides and proteins. However, these polar and large molecules do not permeate the skin barrier well. Various enhancement methods have been employed to address this problem. Iontophoresis is one of the methods that shows promise but its application to peptide delivery has yet to be fully explored. This study investigates the effects of different molecular properties and iontophoretic conditions on the skin permeation of peptides. In this study, the permeation of alanine-tryptophan dipeptide (MW 276 Da), alanine-alanine-proline-valine tetrapeptide (MW 355 Da), Argireline® (Acetyl hexapeptide-3, MW 889 Da) and Triptorelin acetate (decapeptide, MW 1311 Da) through excised human skin under passive or iontophoretic current of 0.4 mA was investigated. The effects of pH change (3.0-7.4, to provide different net negative, neutral, and positive charges) to the peptide, donor concentration (1-10 mg/ml), background electrolyte (34-137 mM NaCl and/or 5-20 mM HEPES) and current direction (anodal vs cathodal) were also studied.
Uses   
   
Argireline is an anti-wrinkle peptide. Synthetically produced and considered to be highly effective, clinical studies indicate it can reduce the depth of existing wrinkles. May be incorporated into products marketed as having a topical-BoToX. or “wrinkle-erasing” effect.  

benefits      

Acetyl Hexapeptide-8 is effectivly reduce various kind of facial wrinkles;Replenish the collagen and polysaccharide, repairthe skin.Winkey patented productin China.It is recommended dosage is 3~10%.  

Clinical claims and research
     
Argireline is a synthetic oligopeptide that emulates the sequence of SNAP-25, a type of SNARE. It has significant skin permeation, interferes with the SNARE ternary complex, and has demonstrated interference with catecholamine release from chromaffin cells. Topical use of 10% argireline resulted in a reduced depth and roughness of periorbital wrinkles in 10 healthy women. One study on 14 volunteers showed that 5% argireline reduced periorbital wrinkles by 32% in 28 days. Most recently, argireline’s efficacy has been measured in 60 Chinese women from a randomized control trial. Its total efficacy was 48.9% compared to 0% in the placebo group, and resulted in significantly decreased wrinkle roughness.

Biochem/physiol Actions

Ac-EEMQRR-NH2 is a SNAP25 N-terminal-derived peptide that inhibits the SNARE complex and possibly blocks neuronal exocytosis. Ac-EEMQRR-NH2 exhibits anti-inflammatory and anti-wrinkle activity. It is used as anti-wrinkle cosmetics ingredient.
Ac-EEMQRR-NH2 trifluoroacetate salt is considered 4000 times less toxic than botulin toxin. It has restricted transdermal penetration and hence has limited application for topical usage.
 
 

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Peptide
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