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MedKoo Cat#: 330197 | Name: Matrixyl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Matrixyl
Matrixyl
CAS#214047-00-4

Theoretical Analysis

MedKoo Cat#: 330197

Name: Matrixyl

CAS#: 214047-00-4

Chemical Formula: C39H75N7O10

Exact Mass: 801.5575

Molecular Weight: 802.07

Elemental Analysis: C, 58.40; H, 9.43; N, 12.22; O, 19.95

Price and Availability

Size Price Availability Quantity
200mg USD 750.00 2 Weeks
500mg USD 1,450.00 2 Weeks
1g USD 1,950.00 2 Weeks
2g USD 3,450.00 2 Weeks
5g USD 4,950.00 2 Weeks
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Related CAS #
214047-00-4
Synonym
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
IUPAC/Chemical Name
N2-(1-Oxohexadecyl)-L-lysyl-L-threonyl-L-threonyl-L-lysyl-L-serine
InChi Key
WSGCRSMLXFHGRM-DEVHWETNSA-N
InChi Code
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
SMILES Code
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
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
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.[citation needed] 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. By activating the neosynthesis of extracellular matrix macromolecules, palmitoyl pentapeptide-4 provides an anti-wrinkle effect. 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.
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Matrixyl, also known as Palmitoyl pentapeptide-4 (palmitoyl pentapeptide-3 before 2006) is a matrikine used in anti-wrinkle cosmetics.
In vitro activity:
Pal-KTTKS (Palmitoyl-pentapeptide) (0-0.5 µM) induced CTGF and α-SMA protein levels were determined by western blot analysis and fibroblast contractility was assessed in three-dimensional collagen lattice contraction assay. Without Pal-KTTKS treatment, three quarters of the fibroblasts differentiates into the myofibroblast; α-SMA-positive stress fibers per field decreased twofold with 0.1 µM Pal-KTTKS treatment (75 ± 7.1 vs 38.6 ± 16.1%, n = 3, p < 0.05). The inhibitory effect was not significant in 0.5 µM Pal-KTTKS treatment. In conclusion, Pal-KTTKS (0.1 µM) reduces α-SMA expression and trans-differentiation of fibroblasts to myofibroblast. Reference: Tissue Eng Regen Med. 2017 Jan 19;14(1):73-80. https://pubmed.ncbi.nlm.nih.gov/30603464/
In vivo activity:
In this study, animals were randomly divided into seven groups and studied for 21 days: patches containing two different concentrations of MTI (Matrixyl) (P-MTI-0.1 mg and P-MTI-1 mg), a cream containing MTI (C-MTI-1 mg), a patch (P-MTI-0), a cream with no MTI (C-MTI-0), a positive control (Comfeel), and a negative control (sham) group. In addition, C-MTI-1 and P-MTI-1 had a larger impact on wound healing compared to that in the positive control group (Comfeel, P < 0.05). In hematoxylin and eosin (H&E) staining analysis, the rejuvenation of skin appendage was visible in both groups of cream and patches with MTI. Reference: ACS Omega. 2022 Jul 11;7(28):24695-24704. https://pubmed.ncbi.nlm.nih.gov/35874243/

Preparing Stock Solutions

The following data is based on the product molecular weight 802.07 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. 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; PMCID: PMC6171572. 2. 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; PMCID: PMC4131521. 3. Kachooeian M, Mousivand Z, Sharifikolouei E, Shirangi M, Firoozpour L, Raoufi M, Sharifzadeh M. Matrixyl Patch vs Matrixyl Cream: A Comparative In Vivo Investigation of Matrixyl (MTI) Effect on Wound Healing. ACS Omega. 2022 Jul 11;7(28):24695-24704. doi: 10.1021/acsomega.2c02592. PMID: 35874243; PMCID: PMC9301720.
In vitro protocol:
1. 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; PMCID: PMC6171572. 2. 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; PMCID: PMC4131521.
In vivo protocol:
1. Kachooeian M, Mousivand Z, Sharifikolouei E, Shirangi M, Firoozpour L, Raoufi M, Sharifzadeh M. Matrixyl Patch vs Matrixyl Cream: A Comparative In Vivo Investigation of Matrixyl (MTI) Effect on Wound Healing. ACS Omega. 2022 Jul 11;7(28):24695-24704. doi: 10.1021/acsomega.2c02592. PMID: 35874243; PMCID: PMC9301720.
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.