Matrixyl

• CAT Number: I031560
• CAS Number: 214047-00-4
• Molecular Formula: C39H75N7O10
• Molecular Weight: 802.068
• Purity: 98%
• Synonyms: Palmitoyl pentapeptide; Pal-Lys-Thr-Thr-Lys-Ser-OH; Matrixyl; PAL-Lys-Thr-Thr-Lys-Ser; Palmitoyl-KTTKS; palmitoyl-Lys-Thr-Thr-Lys-Ser; palmitoyl pentapeptide-3
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: N2-(1-Oxohexadecyl)-L-lysyl-L-threonyl-L-threonyl-L-lysyl-L-serine
• InChI: 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
• InChIKey: WSGCRSMLXFHGRM-DEVHWETNSA-N
• SMILES: OC[C@@H](C(O)=O)NC([C@H](CCCCN)NC([C@H]([C@H](O)C)NC([C@H]([C@H](O)C)NC([C@H](CCCCN)NC(CCCCCCCCCCCCCCC)=O)=O)=O)=O)=O

Matrixyl, also known as 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 French cosmetic active ingredient manufacturer Sederma SAS.

Reference

1: Giangreco F, Höfinger S, Bakalis E, Zerbetto F. Impact of the green tea ingredient epigallocatechin gallate and a short pentapeptide (Ile-Ile-Ala-Glu-Lys) on the structural organization of mixed micelles and the related uptake of cholesterol. Biochim Biophys Acta Gen Subj. 2018 Sep;1862(9):1956-1963. doi: 10.1016/j.bbagen.2018.06.005. Epub 2018 Jun 15. PubMed PMID: 29886279.
2: 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. eCollection 2017 Feb. PubMed PMID: 30603464; PubMed Central PMCID: PMC6171572.
3: 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. PubMed PMID: 25143811; PubMed Central PMCID: PMC4131521.
4: Rubinchik E, Schneider T, Elliott M, Scott WR, Pan J, Anklin C, Yang H, Dugourd D, Müller A, Gries K, Straus SK, Sahl HG, Hancock RE. Mechanism of action and limited cross-resistance of new lipopeptide MX-2401. Antimicrob Agents Chemother. 2011 Jun;55(6):2743-54. doi: 10.1128/AAC.00170-11. Epub 2011 Apr 4. PubMed PMID: 21464247; PubMed Central PMCID: PMC3101398.
5: Kamiya M, Oyauchi K, Sato Y, Yokoyama T, Wang M, Aizawa T, Kumaki Y, Mizuguchi M, Imai K, Demura M, Suzuki K, Kawano K. Structure-activity relationship of a novel pentapeptide with cancer cell growth-inhibitory activity. J Pept Sci. 2010 May;16(5):242-8. doi: 10.1002/psc.1225. PubMed PMID: 20401925.
6: Sato Y, Yang P, An Y, Matsukawa K, Ito K, Imanishi S, Matsuda H, Uchiyama Y, Imai K, Ito S, Ishida Y, Suzuki K. A palmitoyl conjugate of insect pentapeptide Yamamarin arrests cell proliferation and respiration. Peptides. 2010 May;31(5):827-33. doi: 10.1016/j.peptides.2010.02.017. Epub 2010 Mar 3. PubMed PMID: 20206219.
7: Chirita RI, Chaimbault P, Archambault JC, Robert I, Elfakir C. Development of a LC-MS/MS method to monitor palmitoyl peptides content in anti-wrinkle cosmetics. Anal Chim Acta. 2009 May 8;641(1-2):95-100. doi: 10.1016/j.aca.2009.03.015. Epub 2009 Mar 20. PubMed PMID: 19393372.
8: Robinson LR, Fitzgerald NC, Doughty DG, Dawes NC, Berge CA, Bissett DL. Topical palmitoyl pentapeptide provides improvement in photoaged human facial skin. Int J Cosmet Sci. 2005 Jun;27(3):155-60. doi: 10.1111/j.1467-2494.2005.00261.x. PubMed PMID: 18492182.
9: Lopes SC, Fedorov A, Castanho MA. Lipidic membranes are potential "catalysts" in the ligand activity of the multifunctional pentapeptide neokyotorphin. Chembiochem. 2005 Apr;6(4):697-702. PubMed PMID: 15750999.
10: Clarke AL, Petrou S, Walsh JV Jr, Singer JJ. Site of action of fatty acids and other charged lipids on BKCa channels from arterial smooth muscle cells. Am J Physiol Cell Physiol. 2003 Mar;284(3):C607-19. Epub 2002 Oct 30. PubMed PMID: 12409285.
11: Romanowski M, Zhu X, Ramaswami V, Misicka A, Lipkowski AW, Hruby VJ, O’Brien DF. Interaction of a highly potent dimeric enkephalin analog, biphalin, with model membranes. Biochim Biophys Acta. 1997 Oct 23;1329(2):245-58. PubMed PMID: 9371416.
12: Delie F, Couvreur P, Nisato D, Michel JB, Puisieux F, Letourneux Y. Synthesis and in vitro study of a diglyceride prodrug of a peptide. Pharm Res. 1994 Aug;11(8):1082-7. PubMed PMID: 7971705.
13: Dmitriev BA, Ovchinnikov MV, Lapina EB, Pluzhnikova GN, Lopyrev IV, Chernyak AYa. Glycopeptidolipids–a new class of artificial antigens with carbohydrate determinants. Synthesis of artificial antigen with type-specific oligosaccharide hapten from Neisseria meningitidis group B. Glycoconj J. 1992 Aug;9(4):168-73. PubMed PMID: 1422136.
14: Brade L, Bessler WG, Brade H. Mitogenic activities of synthetic Escherichia coli lipid A and a synthetic partial structure (tripalmitoyl pentapeptide) of E. coli lipoprotein. Infect Immun. 1988 May;56(5):1382-4. PubMed PMID: 3281910; PubMed Central PMCID: PMC259838.
15: Kleine B, Sprenger R, Martinez-Alonso C, Bessler WG. Polyclonal B-cell activation by a synthetic analogue of bacterial lipoprotein is functionally different from activation by bacterial lipopolysaccharide. Immunology. 1987 May;61(1):29-34. PubMed PMID: 3495485; PubMed Central PMCID: PMC1453309.
16: Biesert L, Scheuer W, Bessler WG. Interaction of mitogenic bacterial lipoprotein and a synthetic analogue with mouse lymphocytes. Isolation and characterization of binding proteins. Eur J Biochem. 1987 Feb 2;162(3):651-7. PubMed PMID: 3549292.
17: Lex A, Wiesmüller KH, Jung G, Bessler WG. A synthetic analogue of Escherichia coli lipoprotein, tripalmitoyl pentapeptide, constitutes a potent immune adjuvant. J Immunol. 1986 Oct 15;137(8):2676-81. PubMed PMID: 3531339.
18: Scheuer WV, Biesert L, Bessler WG. Binding of a synthetic analogue of mitogenic bacterial lipoprotein to murine major histocompatibility complex (MHC) gene products. Biol Chem Hoppe Seyler. 1986 Oct;367(10):1085-94. PubMed PMID: 3491614.
19: Johnson RB, Köhl S, Wiesmüller K, Jung G, Bessler WG. Synthetic analogues of the N-terminal lipid part of bacterial lipoprotein are B-lymphocyte mitogens in vitro and in vivo. Immunobiology. 1983 Jul;165(1):27-35. PubMed PMID: 6350164.
20: Wiesmüller KH, Bessler W, Jung G. Synthesis of the mitogenic S-[2,3-bis(palmitoyloxy)propyl]-N-palmitoylpentapeptide from Escherichia coli lipoprotein. Hoppe Seylers Z Physiol Chem. 1983 May;364(5):593-606. PubMed PMID: 6347861.