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==Chemistry==

==Chemistry==

Palmitoyl pentapeptide-4 (Pal-Lys-Thr-Thr-Lys-Ser = Pal-KTTKS) contains 5 [[amino acid]]s linked to a 16-carbon [[aliphatic]] chain for improving the penetration of the molecule through the lipid structures of the skin. It is a matrikine.<ref>{{Cite web |title=Matrixyl™ {{!}} Palmitoyl pentapeptide-4; former Palmitoyl pentapeptide-3 {{!}} Ingredient {{!}} INCI Guide |url=https://inci.guide/peptides/matrixyltm |access-date=2023-07-03 |website=inci.guide}}</ref> A number of similar molecules are known.<ref>Choi YL, Park EJ, Kim E, Na DH, Shin YH. Dermal Stability and In Vitro Skin Permeation of Collagen Pentapeptides (KTTKS and palmitoyl-KTTKS). ”Biomol Ther (Seoul)”. 2014 Jul;22(4):321-7. {{doi|10.4062/biomolther.2014.053}} {{pmid|25143811}}</ref><ref>Park H, An E, Cho Lee AR. Effect of Palmitoyl-Pentapeptide (Pal-KTTKS) on Wound Contractile Process in Relation with Connective Tissue Growth Factor and α-Smooth Muscle Actin Expression. ”Tissue Eng Regen Med”. 2017 Jan 19;14(1):73-80. {{doi|10.1007/s13770-016-0017-y}} {{pmid|30603464}}</ref><ref>Mortazavi SM, Kobarfard F, Maibach HI, Moghimi HR. Effect of Palmitic Acid Conjugation on Physicochemical Properties of Peptide KTTKS: A Preformulation Study. ”J Cosmet Sci”. 2019 Nov/Dec;70(6):299-312. {{pmid|31829923}}</ref><ref>Paccola AGL, Santos TMCD, Minelo MC, Garbieri TF, Sanches MLR, Dionísio TJ, Oliveira RC, Santos CF, Buzalaf MAR. Synergistic Effects of Injectable Platelet-Rich Fibrin and Bioactive Peptides on Dermal Fibroblast Viability and Extracellular Matrix Gene Expression: An In Vitro Study. ”Molecules”. 2025 Aug 19;30(16):3415. {{doi|10.3390/molecules30163415}} {{pmid|40871567}}</ref>

Palmitoyl pentapeptide-4 (Pal-Lys-Thr-Thr-Lys-Ser = Pal-KTTKS) contains 5 [[amino acid]]s linked to a 16-carbon [[aliphatic]] chain for improving the penetration of the molecule through the lipid structures of the skin. It is a matrikine.<ref>{{Cite web |title=Matrixyl™ {{!}} Palmitoyl pentapeptide-4; former Palmitoyl pentapeptide-3 {{!}} Ingredient {{!}} INCI Guide |url=https://inci.guide/peptides/matrixyltm |access-date=2023-07-03 |website=inci.guide}}</ref> A number of similar molecules are known.<ref>{{doi|10.4062/biomolther.2014.053}}</ref><ref>{{doi|10.1007/s13770-016-0017-y}}</ref><ref>{{pmid|31829923}}</ref><ref>{{doi|10.3390/molecules30163415}}</ref>

Matrikines are messenger [[peptides]] capable of regulating cell activities by interacting with their specific receptors. They activate certain genes involved in the process of extracellular matrix renewal and cell proliferation.<ref>{{Cite journal | doi = 10.1051/jbio/1999193040423 | title = Régulation de l’activité cellulaire par la matrice extracelulaire : Le concept de matrikines | journal = Journal de la Société de Biologie | volume = 193 | issue = 4–5 | pages = 423–428 | year = 1999 | last1 = Maquart | first1 = François-Xavier | last2 = Siméon | first2 = Alain | last3 = Pasco | first3 = Sylvie | last4 = Monboisse | first4 = Jean-Claude }}</ref> By activating the neosynthesis of extracellular matrix macromolecules, palmitoyl pentapeptide-4 provides an anti-wrinkle effect.{{medcn|date=January 2015}} Studies (”[[in vitro]]” and ”[[in vivo]]”) demonstrating the anti-wrinkle efficacy of this [[peptide]] have been conducted and published by Sederma and by independent organisations.<ref>{{Cite journal | doi = 10.1021/mp300549d | pmid = 23320752 | title = Collagen Stimulating Effect of Peptide Amphiphile C16–KTTKS on Human Fibroblasts | journal = Molecular Pharmaceutics | volume = 10 | issue = 3 | pages = 1063–1069 | year = 2013 | last1 = Jones | first1 = Roanne R. | last2 = Castelletto | first2 = Valeria | last3 = Connon | first3 = Che J. | last4 = Hamley | first4 = Ian W. }}</ref><ref>{{Cite journal | doi = 10.1046/j.1467-2494.2000.00010.x| pmid = 18503476| title = Biologically active peptides: From a laboratory bench curiosity to a functional skin care product| journal = International Journal of Cosmetic Science| volume = 22| issue = 3| pages = 207–218| year = 2000| last1 = Lintner| last2 = Peschard}}</ref><ref>{{Cite journal | doi = 10.1111/j.1467-2494.2005.00261.x| pmid = 18492182| title = Topical palmitoyl pentapeptide provides improvement in photoaged human facial skin1| journal = International Journal of Cosmetic Science| volume = 27| issue = 3| pages = 155–160| year = 2005| last1 = Robinson| first1 = L. R.| last2 = Fitzgerald| first2 = N. C.| last3 = Doughty| first3 = D. G.| last4 = Dawes| first4 = N. C.| last5 = Berge| first5 = C. A.| last6 = Bissett| first6 = D. L.}}</ref>

Matrikines are messenger [[peptides]] capable of regulating cell activities by interacting with their specific receptors. They activate certain genes involved in the process of extracellular matrix renewal and cell proliferation.<ref>{{Cite journal | doi = 10.1051/jbio/1999193040423 | title = Régulation de l’activité cellulaire par la matrice extracelulaire : Le concept de matrikines | journal = Journal de la Société de Biologie | volume = 193 | issue = 4–5 | pages = 423–428 | year = 1999 | last1 = Maquart | first1 = François-Xavier | last2 = Siméon | first2 = Alain | last3 = Pasco | first3 = Sylvie | last4 = Monboisse | first4 = Jean-Claude }}</ref> By activating the neosynthesis of extracellular matrix macromolecules, palmitoyl pentapeptide-4 provides an anti-wrinkle effect.{{medcn|date=January 2015}} Studies (”[[in vitro]]” and ”[[in vivo]]”) demonstrating the anti-wrinkle efficacy of this [[peptide]] have been conducted and published by Sederma and by independent organisations.<ref>{{Cite journal | doi = 10.1021/mp300549d | pmid = 23320752 | title = Collagen Stimulating Effect of Peptide Amphiphile C16–KTTKS on Human Fibroblasts | journal = Molecular Pharmaceutics | volume = 10 | issue = 3 | pages = 1063–1069 | year = 2013 | last1 = Jones | first1 = Roanne R. | last2 = Castelletto | first2 = Valeria | last3 = Connon | first3 = Che J. | last4 = Hamley | first4 = Ian W. }}</ref><ref>{{Cite journal | doi = 10.1046/j.1467-2494.2000.00010.x| pmid = 18503476| title = Biologically active peptides: From a laboratory bench curiosity to a functional skin care product| journal = International Journal of Cosmetic Science| volume = 22| issue = 3| pages = 207–218| year = 2000| last1 = Lintner| last2 = Peschard}}</ref><ref>{{Cite journal | doi = 10.1111/j.1467-2494.2005.00261.x| pmid = 18492182| title = Topical palmitoyl pentapeptide provides improvement in photoaged human facial skin1| journal = International Journal of Cosmetic Science| volume = 27| issue = 3| pages = 155–160| year = 2005| last1 = Robinson| first1 = L. R.| last2 = Fitzgerald| first2 = N. C.| last3 = Doughty| first3 = D. G.| last4 = Dawes| first4 = N. C.| last5 = Berge| first5 = C. A.| last6 = Bissett| first6 = D. L.}}</ref>

Revision as of 03:11, 10 November 2025

Palmitoyl pentapeptide-4
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard 100.126.177 Edit this at Wikidata
EC Number
UNII

  • InChI=1S/C39H75N7O10/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-23-32(50)42-29(21-17-19-24-40)36(52)45-34(28(3)49)38(54)46-33(27(2)48)37(53)43-30(22-18-20-25-41)35(51)44-31(26-47)39(55)56/h27-31,33-34,47-49H,4-26,40-41H2,1-3H3,(H,42,50)(H,43,53)(H,44,51)(H,45,52)(H,46,54)(H,55,56)/t27-,28-,29+,30+,31+,33+,34+/m1/s1

    Key: WSGCRSMLXFHGRM-DEVHWETNSA-N

  • CCCCCCCCCCCCCCCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CO)C(=O)O
Properties
C39H75N7O10
Molar mass 802.068 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Chemical compound

Palmitoyl pentapeptide-4 (palmitoyl pentapeptide-3 before 2006) is a matrikine used in anti-wrinkle cosmetics. It was launched in 2000 as an active ingredient for the personal care industry under the trade name Matrixyl by the Spanish cosmetic active ingredient manufacturer Sederma SAS.

Chemistry

Palmitoyl pentapeptide-4 (Pal-Lys-Thr-Thr-Lys-Ser = Pal-KTTKS) contains 5 amino acids linked to a 16-carbon aliphatic chain for improving the penetration of the molecule through the lipid structures of the skin. It is a matrikine.[1] A number of similar molecules are known.[2][3][4][5]

Matrikines are messenger peptides capable of regulating cell activities by interacting with their specific receptors. They activate certain genes involved in the process of extracellular matrix renewal and cell proliferation.[6] By activating the neosynthesis of extracellular matrix macromolecules, palmitoyl pentapeptide-4 provides an anti-wrinkle effect.[medical citation needed] Studies (in vitro and in vivo) demonstrating the anti-wrinkle efficacy of this peptide have been conducted and published by Sederma and by independent organisations.[7][8][9]

References

  1. ^ “Matrixyl™ | Palmitoyl pentapeptide-4; former Palmitoyl pentapeptide-3 | Ingredient | INCI Guide”. inci.guide. Retrieved 2023-07-03.
  2. ^ doi:10.4062/biomolther.2014.053
  3. ^ doi:10.1007/s13770-016-0017-y
  4. ^ PMID 31829923
  5. ^ doi:10.3390/molecules30163415 {{doi}}: unflagged free DOI (link)
  6. ^ Maquart, François-Xavier; Siméon, Alain; Pasco, Sylvie; Monboisse, Jean-Claude (1999). “Régulation de l’activité cellulaire par la matrice extracelulaire : Le concept de matrikines”. Journal de la Société de Biologie. 193 (4–5): 423–428. doi:10.1051/jbio/1999193040423.
  7. ^ Jones, Roanne R.; Castelletto, Valeria; Connon, Che J.; Hamley, Ian W. (2013). “Collagen Stimulating Effect of Peptide Amphiphile C16–KTTKS on Human Fibroblasts”. Molecular Pharmaceutics. 10 (3): 1063–1069. doi:10.1021/mp300549d. PMID 23320752.
  8. ^ Lintner; Peschard (2000). “Biologically active peptides: From a laboratory bench curiosity to a functional skin care product”. International Journal of Cosmetic Science. 22 (3): 207–218. doi:10.1046/j.1467-2494.2000.00010.x. PMID 18503476.
  9. ^ Robinson, L. R.; Fitzgerald, N. C.; Doughty, D. G.; Dawes, N. C.; Berge, C. A.; Bissett, D. L. (2005). “Topical palmitoyl pentapeptide provides improvement in photoaged human facial skin1”. International Journal of Cosmetic Science. 27 (3): 155–160. doi:10.1111/j.1467-2494.2005.00261.x. PMID 18492182.

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