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Revision as of 19:56, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,084 edits Saving copy of the {{chembox}} taken from revid 470567508 of page Acetyl_hexapeptide-3 for the Chem/Drugbox validation project (updated: 'CASNo').		Latest revision as of 03:49, 17 October 2024 edit Graeme Bartlett (talk | contribs)Administrators250,259 edits added Category:Acetamides using HotCat
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			{{chembox
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			| ImageFile = Oligopetide_P11-4.png
	{{Chembox
			| ImageSize = 200px
	| verifiedrevid = 399369270
			| Verifiedfields = changed
	| ImageFile = Argireline.png
			| Watchedfields = changed
	| ImageSize = 200px
			| verifiedrevid = 477239973
	| ImageAlt = Argireline
			| IUPACName = (4''S'')-4-amino]-1,5-dihydroxy-5-iminopentylidene]amino]-1-hydroxypentylidene]amino]-1-hydroxy-3-phenylpropylidene]amino]-4-carboxy-1-hydroxybutylidene]amino]-1-hydroxy-3-(1H-indol-3-yl)propylidene]amino]-4-carboxy-1-hydroxybutylidene]amino]-1-hydroxy-3-phenylpropylidene]amino]-5-imino-1,5-dihydroxy-5-iminopentan-2-yl]imino-5-hydroxypentanoic acid
	| 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
			| OtherNames = {{unbulleted list|oligopeptide 104
	| IUPACName_hidden = yes
			Ac-Gln-Gln-Arg-Phe-Glu-Trp-Glu-Phe-Glu-Gln-Gln-NH2
	| OtherNames = Argireline
			Ace-QQRFEWEFEQQ-NH2}}
	| Section1 = {{Chembox Identifiers
			|Section1={{Chembox Identifiers
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 9403386		| ChemSpiderID = 52082515
			| PubChem = 101261581
	| 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 = CC(=O)N(CCC(=O)N)C(=O)N(CCC(=O)N)C(=O)N(CCCNC(=N)N)C(=O)N(Cc1ccccc1)C(=O)N(CCC(=O)O)C(=O)N(Cc2cc3c2cccc3)C(=O)N(CCC(=O)O)C(=O)N(Cc4ccccc4)C(=O)N(CCC(=O)O)C(=O)N(CCC(=O)N)C(=O)N(CCC(=O)N)C(=O)N
	| InChIKey = RJZNPROJTJSYLC-LLINQDLYBN
			| InChI = 1/C72H98N20O22/c1-37(93)82-45(19-26-55(74)95)63(106)85-47(21-28-57(76)97)65(108)84-44(17-10-32-80-72(78)79)62(105)90-51(33-38-11-4-2-5-12-38)69(112)88-50(24-31-60(102)103)68(111)92-53(35-40-36-81-42-16-9-8-15-41(40)42)71(114)89-49(23-30-59(100)101)67(110)91-52(34-39-13-6-3-7-14-39)70(113)87-48(22-29-58(98)99)66(109)86-46(20-27-56(75)96)64(107)83-43(61(77)104)18-25-54(73)94/h2-9,11-16,36,43-53,81H,10,17-35H2,1H3,(H2,73,94)(H2,74,95)(H2,75,96)(H2,76,97)(H2,77,104)(H,82,93)(H,83,107)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,112)(H,89,114)(H,90,105)(H,91,110)(H,92,111)(H,98,99)(H,100,101)(H,102,103)(H4,78,79,80)/t43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-/m0/s1
	| 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
			| InChIKey = SMSPMXWRKWKZBG-ZOOWYRFPBV
	| StdInChI_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		| StdInChI = 1S/C72H98N20O22/c1-37(93)82-45(19-26-55(74)95)63(106)85-47(21-28-57(76)97)65(108)84-44(17-10-32-80-72(78)79)62(105)90-51(33-38-11-4-2-5-12-38)69(112)88-50(24-31-60(102)103)68(111)92-53(35-40-36-81-42-16-9-8-15-41(40)42)71(114)89-49(23-30-59(100)101)67(110)91-52(34-39-13-6-3-7-14-39)70(113)87-48(22-29-58(98)99)66(109)86-46(20-27-56(75)96)64(107)83-43(61(77)104)18-25-54(73)94/h2-9,11-16,36,43-53,81H,10,17-35H2,1H3,(H2,73,94)(H2,74,95)(H2,75,96)(H2,76,97)(H2,77,104)(H,82,93)(H,83,107)(H,84,108)(H,85,106)(H,86,109)(H,87,113)(H,88,112)(H,89,114)(H,90,105)(H,91,110)(H,92,111)(H,98,99)(H,100,101)(H,102,103)(H4,78,79,80)/t43-,44-,45-,46-,47-,48-,49-,50-,51-,52-,53-/m0/s1
			| StdInChIKey = SMSPMXWRKWKZBG-ZOOWYRFPSA-N
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = RJZNPROJTJSYLC-LLINQDLYSA-N
	| CASNo = <!-- blanked - oldvalue: 616204-22-9 -->
	| PubChem =
	| 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}}
	| Section2 = {{Chembox Properties
	| C=34 |H=60 |N=14 |O=12 |S=1
	| Appearance =
	| Density =
	| MeltingPt =
	| BoilingPt =
	| Solubility = }}
	| Section3 = {{Chembox Hazards
	| MainHazards =
	| FlashPt =
	| Autoignition = }}
	}}		}}
			|Section2={{Chembox Properties
			| C=72 | H=98 | N=20 | O=22
			}}
			|Section3={{Chembox Related
			| OtherCompounds = {{unbulleted list|}}
			}}
			}}
			'''Oligopeptide P11-4''' is a synthetic, pH controlled ] used for ] e.g. for ]<ref>{{cite journal|last1=Brunton|first1=P.A.|last2=Davies|first2=R.P.W.|title=Treatment of early caries lesions using biomimetic self-assembling-peptides – a clinical safety trial|journal=Br Dent J|date=2 July 2013|volume=215|issue=E6|pages=E6|doi=10.1038/sj.bdj.2013.741|pmid=23969679|pmc=3813405}}</ref> or as an oral care agent. P11-4 (INCI name Oligopeptide 104) consists of the natural occurring amino acids ], ], ], ] and ].<ref>{{cite web|title=European Commission database with information on cosmetic substances and ingredients|url=http://ec.europa.eu/consumers/cosmetics/cosing/index.cfm?fuseaction=search.details_v2&id=90913|website=Oligopeptide 104|access-date=1 July 2015}}</ref> The resulting higher molecular structure has a high affinity to tooth mineral.<ref>{{cite journal|last1=Kirkham|first1=J|title=Self-assembling Peptide Scaffolds Promote Enamel Remineralization|journal=J Dent Res|date=May 2007|volume=86|issue=5|pages=426–430|doi=10.1177/154405910708600507|pmid=17452562|s2cid=21582771|display-authors=etal}}</ref>
			P11-4 has been developed and patented by The ] (UK). The Swiss company ] has licensed the peptide technology and markets it under the trade names including '''CUROLOX''', '''REGENAMEL''', and '''EMOFLUOR'''. They offer three products with this technology.<ref>{{cite web|title=credentis webpage|url=http://www.credentis.com|access-date=1 July 2015}}</ref> As of June 2016 in Switzerland products are available with new Brand names from Dr. Wild & Co AG.<ref>{{Cite web|url=http://www.credentis.com/en/news/credentis-ag-und-dr-wild-co-ag-staerken-ihre-erfolgreiche-partnerschaft/2b20c33de662c559b3a5d4fefc23f393/|title=Credentis: credentis ag and Dr. Wild & Co. AG strengthen their successful partnership|last=AG|first=Touch Design|website=www.credentis.com|access-date=2016-06-29}}</ref>
			==Mechanism of action==
			P11-4 is an α-peptide that self-assembles into β-sheet ]s with a hydrogel appearance at low pH.<ref>{{cite journal|last1=Aggeli|first1=A|last2=Bell|first2=M|title=Responsive gels formed by the spontaneous self-assembly of peptides into polymeric β-sheet tapes|journal=Nature|date=20 March 1997|volume=386|issue=6622|pages=259–262|doi=10.1038/386259a0|display-authors=etal|pmid=9069283|bibcode=1997Natur.386..259A|s2cid=4343341}}</ref> It builds a 3-D bio-matrix with binding sites for calcium ions serving as nucleation point for hydroxyapatite (tooth mineral) formation. The high affinity to tooth mineral is based on matching distances of Ca-ion binding sites on P11-4 and Ca spacing in the crystal lattice of hydroxyapatite. The matrix formation is pH controlled and thus allows control matrix activity and place of formation.
			==P11-4 in dental applications==
			Self assembling properties of P11-4 are used to regenerate early caries lesions. By application of P11-4 on the tooth surface, the peptide diffuse through the intact hypomineralized plate into the early caries lesion body and start, due to the low pH in such a lesion, to self-assemble generating a peptide scaffold mimicking the enamel matrix.
			Around the newly formed matrix de-novo enamel-crystals are formed from calcium phosphate present in saliva. Through the remineralization caries activity is significantly reduced in comparison with a fluoride treatment alone.<ref>{{cite journal|last1=Alkilzy|first1=M|title=Efficacy, Clinical Applicability and Safety, of CurodontTM Repair in Children with Early Occlusal Caries|journal=Caries Res|date=May 15, 2015|volume=49|page=311|doi=10.1159/000381323|s2cid=79016534|url=http://www.karger.com/Article/Pdf/381323|display-authors=etal}}</ref>
			In aqueous oral care gels the peptide is present as matrix. It binds directly as matrix to the tooth mineral and forms a stable layer on the teeth.<ref>{{cite journal|last1=Chen|first1=X|title=Dentine Tubule Occlusion of a Novel Self-n Vitro Evaluation of Dentine Remineralisation by a Self-Assembling Peptide Using Scanning Electron Microscopy|journal=Caries Res|date=Sep 2014|volume=48|page=402|doi=10.1159/000360836|url=http://www.karger.com/Article/Pdf/360836|access-date=1 July 2015|display-authors=etal|doi-access=free}}</ref> This layer does protect the teeth from acid attacks. It also occludes open dentin tubules and thus reduces the dental sensitivity.
			==Uses==
			* Treatment of initial caries lesions
			* Regenerating enamel
			* ]
			* Acid protection
			==Availability==
			Availability of products containing P11-4 vary by country, with some products available only to dentists, and others available to the retail public.
			Medical device for caries treatment and enamel regeneration:
			* CURODONT REPAIR (EU)
			* REGENAMEL (CH)
			Cosmetic products for acid protection and dentin desensitization:
			* CURODONT PROTECT (EU)
			* EMOFLUOR PROTECT GEL PROFESSIONAL (CH)
			* CURODONT D'SENZ (EU & CH)
			* EMOFLUOR DESENS GEL PROFESSIONAL (CH)
			* Candida Protect Professional<ref>{{cite web|title=Candida Zahnpasta Protect Professional|url=https://produkte.migros.ch/candida-zahnpasta-protect-professional|access-date=1 July 2015}}</ref> (CH)
			==See also==
			{{Portal|Medicine}}
			*] (Recaldent)
			*]
			*]
			*]
			*]
			==References==
			{{Reflist}}
			==External links==
			*
			*
			*
			]
			]
			]
			]