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Revision as of 14:27, 14 June 2012 editAnypodetos (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers39,350 editsm Wikilink← Previous edit Revision as of 12:34, 17 July 2012 edit undoPlasmic Physics (talk | contribs)Extended confirmed users, Rollbackers19,174 editsNo edit summaryNext edit →
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{{condense|date=July 2012}}
{{Chembox

{{chembox
| verifiedrevid = 399369270 | verifiedrevid = 399369270
| ImageFile = Argireline.png | ImageFile = Argireline.png
| ImageFile_Ref
| ImageSize = 200px
| ImageName = Stereo, skeletal formula of acetyl hexapeptide-3 ((4S)-4-{carbamoyl}butyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-4-acetamido)
| ImageAlt = Argireline
| IUPACName = (6''S'',9''S'',12''S'',15''S'',18''S'',21''S'')-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 | PIN = 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{{citation needed|reason=Is this the prefered IUPAC name? If not, move to OtherNames|date=July 2012}}
| IUPACName_hidden = yes | PIN_hidden = yes
| OtherNames = Argireline | OtherNames = Argireline{{citation needed|reason=Is this a genuine, non-proprietary name?|date=July 2012}}
| Section1 = {{Chembox Identifiers | Section1 = {{chembox Identifiers
| CASNo = 616204-22-9
| CASNo_Ref = {{cascite|changed|??}}
| PubChem = 53396027
| PubChem_Ref = {{pubchemcite|correct|pubchem}}
| PubChem1 = 11228338
| PubChem1_Ref = {{pubchemcite|correct|pubchem}}
| PubChem1_Comment = <small>(4''S'')-4-{carbamoyl}butyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-4-acetamido</small>
⚫ | ChemSpiderID = 9403386
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID_Comment = <small>(4''S'')-4-{carbamoyl}butyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-4-acetamido</small>
⚫ | ChemSpiderID = 9403386
| InChI = 1/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 | SMILES = CSCCC(NC(=O)C(CCC(O)=O)NC(=O)C(CCC(O)=O)NC(C)=O)C(=O)NC(CCC(N)=O)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(N)=O
| StdInChI = 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)
⚫ | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| InChIKey = RJZNPROJTJSYLC-LLINQDLYBN | StdInChIKey = RJZNPROJTJSYLC-UHFFFAOYSA-N
| SMILES1 = O=C(N(C(=O)N(C(=O)N(C(=O)N(C(=O)N)CCC/N=C(\N)N)CCC/N=C(\N)N)CCC(=O)N)CCSC)(NC(=O)(NC(=O)C)CCC(=O)O)CCC(=O)O
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
}}
| StdInChI = 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
⚫ | Section2 = {{chembox Properties
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| C = 34
| StdInChIKey = RJZNPROJTJSYLC-LLINQDLYSA-N
| CASNo = 616204-22-9 | H = 60
| PubChem = | N = 14
| O = 12
| SMILES = NC((CCCNC(N)=N)NC((CCCNC(N)=N)NC((CCC(N)=O)NC((CCSC)NC((CCC(O)=O)NC((CCC(O)=O)NC(C)=O)=O)=O)=O)=O)=O)=O}}
⚫ | S = 1
⚫ | Section2 = {{Chembox Properties
}}
| C=34 |H=60 |N=14 |O=12 |S=1
⚫ | Section3 = {{chembox Related
| Appearance =
| OtherCpds = {{unbulleted list|]|]}}
⚫ | Density =
}}
| MeltingPt =
| BoilingPt =
| Solubility = }}
⚫ | Section3 = {{Chembox Hazards
| MainHazards =
| FlashPt =
| Autoignition = }}
}} }}


'''Acetyl hexapeptide-3''' is a synthetic ] cosmetics ingredient. It is a ] which is a fragment of ], a substrate of ] (Botox). Acetyl hexapeptide-3 is marketed as '''Argireline''' by the Barcelona-based research laboratory Lipotec.<ref name="Blanes-Mira" /> '''Acetyl hexapeptide-3''' is a synthetic ] cosmetics ingredient. It is a ] which is a fragment of ], a substrate of ] (Botox). Acetyl hexapeptide-3 is marketed as '''Argireline''' by the Barcelona-based research laboratory Lipotec.<ref name="Blanes-Mira" />


== Overview and common uses == ==Overview and common uses==
Argireline 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.<ref name="Blanes-Mira">{{Cite journal|doi=10.1046/j.1467-2494.2002.00153.x|title=A synthetic hexapeptide (Argireline) with antiwrinkle activity|last=Blanes-Mira|first=C|coauthors=et al.|journal=Int J Cosmet Sci|date=October 2002|volume=24|issue=5|pages=303–10|pmid=18498523|postscript=}}</ref><ref>{{Cite journal | last1 = Ruiz | first1 = MA | last2 = Clares | first2 = B | last3 = Morales | first3 = ME | last4 = Cazalla | first4 = S | last5 = Gallardo | first5 = V | title = Preparation and stability of cosmetic formulations with an anti-aging peptide. | journal = Journal of cosmetic science | volume = 58 | issue = 2 | pages = 157–71 | year = 2007 | pmid = 17520155}}</ref> Argireline 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.<ref name="Blanes-Mira">{{Cite journal|doi=10.1046/j.1467-2494.2002.00153.x|title=A synthetic hexapeptide (Argireline) with antiwrinkle activity|last=Blanes-Mira|first=C|coauthors=et al.|journal=Int J Cosmet Sci|date=October 2002|volume=24|issue=5|pages=303–10|pmid=18498523|postscript=}}</ref><ref>{{Cite journal | last1 = Ruiz | first1 = MA | last2 = Clares | first2 = B | last3 = Morales | first3 = ME | last4 = Cazalla | first4 = S | last5 = Gallardo | first5 = V | title = Preparation and stability of cosmetic formulations with an anti-aging peptide. | journal = Journal of cosmetic science | volume = 58 | issue = 2 | pages = 157–71 | year = 2007 | pmid = 17520155}}</ref>


Chemically, when applied as a solution to specific areas of the face, Argireline inhibits the reactions that cause muscles to move or contract<ref name="Blanes-Mira"/> – for example when forming facial expressions such as smiling or frowning. Chemically, when applied as a solution to specific areas of the face, Argireline inhibits the reactions that cause muscles to move or contract<ref name="Blanes-Mira"/> – for example when forming facial expressions such as smiling or frowning.


== Cosmetic studies == ==Cosmetic studies==
Both '']'' (outside a living organism) and '']'' (using a living organism) tests have been carried out on Argireline, but ] ]s results have not been published. Both '']'' (outside a living organism) and '']'' (using a living organism) tests have been carried out on Argireline, but ] ]s results have not been published.


== Safety research == ==Safety research==
Argireline has been developed relatively recently and therefore reports on its long-term use have not yet been produced. Argireline has been developed relatively recently and therefore reports on its long-term use have not yet been produced.


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Argireline is the hexapeptide with the sequence ]-]-Glu-]-]-]-Arg-NH<sub>2</sub>.<ref name="Blanes-Mira"/> Argireline is the hexapeptide with the sequence ]-]-Glu-]-]-]-Arg-NH<sub>2</sub>.<ref name="Blanes-Mira"/>


== References == ==References==
{{Reflist}} {{reflist}}


{{DEFAULTSORT:Acetyl Hexapeptide-3}} {{DEFAULTSORT:Acetyl Hexapeptide-3}}

Revision as of 12:34, 17 July 2012

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{{chembox | verifiedrevid = 399369270 | ImageFile = Argireline.png | ImageFile_Ref | ImageName = Stereo, skeletal formula of acetyl hexapeptide-3 ((4S)-4-{carbamoyl}butyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-4-acetamido) | PIN = 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 | PIN_hidden = yes | OtherNames = Argireline | Section1 = {{chembox Identifiers | CASNo = 616204-22-9 | CASNo_Ref = | PubChem = 53396027 | PubChem_Ref = Template:Pubchemcite | PubChem1 = 11228338 | PubChem1_Ref = Template:Pubchemcite | PubChem1_Comment = (4S)-4-{carbamoyl}butyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-4-acetamido | ChemSpiderID = 9403386 | ChemSpiderID_Ref = | ChemSpiderID_Comment = (4S)-4-{carbamoyl}butyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}propyl]carbamoyl}-4-acetamido | SMILES = CSCCC(NC(=O)C(CCC(O)=O)NC(=O)C(CCC(O)=O)NC(C)=O)C(=O)NC(CCC(N)=O)C(=O)NC(CCCNC(N)=N)C(=O)NC(CCCNC(N)=N)C(N)=O | StdInChI = 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) | StdInChI_Ref = | StdInChIKey = RJZNPROJTJSYLC-UHFFFAOYSA-N | StdInChIKey_Ref = }} | Section2 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Properties

|-

|

Chemical formula

| C34H60N14O12S

|- | Molar mass

| 889.00 g·mol

|- | Section3 = ! colspan=2 style="background: #f8eaba; text-align: center;" |Related compounds

|- }}

Acetyl hexapeptide-3 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-3 is marketed as Argireline by the Barcelona-based research laboratory Lipotec.

Overview and common uses

Argireline 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.

Chemically, when applied as a solution to specific areas of the face, Argireline inhibits the reactions that cause muscles to move or contract – for example when forming facial expressions such as smiling or frowning.

Cosmetic studies

Both in vitro (outside a living organism) and in vivo (using a living organism) tests have been carried out on Argireline, but double-blind clinical trials results have not been published.

Safety research

Argireline has been developed relatively recently and therefore reports on its long-term use have not yet been produced.

Chemistry

Argireline is the hexapeptide with the sequence Ac-Glu-Glu-Met-Gln-Arg-Arg-NH2.

References

  1. ^ Blanes-Mira, C (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. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  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.
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