Palmitoyl pentapeptide-4

Last updated

Palmitoyl pentapeptide-4
Palmitoyl pentapeptide-4.svg
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.126.177 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 606-757-9
PubChem CID
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).

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. ↑ Choi YL, Park EJ, Kim E, Na DH, Shin YH (July 2014). "Dermal Stability and In Vitro Skin Permeation of Collagen Pentapeptides (KTTKS and palmitoyl-KTTKS)". Biomolecules & Therapeutics. 22 (4): 321–327. doi:10.4062/biomolther.2014.053. PMC   4131521 . PMID   25143811.
  3. ↑ Park H, An E, Cho Lee AR (February 2017). "Effect of Palmitoyl-Pentapeptide (Pal-KTTKS) on Wound Contractile Process in Relation with Connective Tissue Growth Factor and α-Smooth Muscle Actin Expression". Tissue Engineering and Regenerative Medicine. 14 (1): 73–80. doi:10.1007/s13770-016-0017-y. PMC   6171572 . PMID   30603464.
  4. ↑ Mortazavi SM, Kobarfard F, Maibach HI, Moghimi HR (2019). "Effect of Palmitic Acid Conjugation on Physicochemical Properties of Peptide KTTKS: A Preformulation Study". Journal of Cosmetic Science. 70 (6): 299–312. PMID   31829923.
  5. ↑ Paccola AG, Santos TM, Minelo MC, Garbieri TF, Sanches ML, Dionísio TJ, et al. (August 2025). "Synergistic Effects of Injectable Platelet-Rich Fibrin and Bioactive Peptides on Dermal Fibroblast Viability and Extracellular Matrix Gene Expression: An In Vitro Study". Molecules. 30 (16): 3415. doi: 10.3390/molecules30163415 . PMC   12388378 . PMID   40871567.
  6. ↑ Maquart FX, Siméon A, Pasco S, Monboisse JC (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 RR, Castelletto V, Connon CJ, Hamley IW (March 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 K, Peschard O (June 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 LR, Fitzgerald NC, Doughty DG, Dawes NC, Berge CA, Bissett DL (June 2005). "Topical palmitoyl pentapeptide provides improvement in photoaged human facial skin". International Journal of Cosmetic Science. 27 (3): 155–160. doi:10.1111/j.1467-2494.2005.00261.x. PMID   18492182.
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