Hexapeptide-12

Hexapeptide-12
Identifiers
  • 2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[2-[[(2S)-2-amino-3-methylbutanoyl]amino]acetyl]amino]-3-methylbutanoyl]amino]propanoyl]pyrrolidine-2-carbonyl]amino]acetic acid
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC22H38N6O7
Molar mass498.581 g·mol−1
3D model (JSmol)
  • C[C@@H](C(=O)N1CCC[C@H]1C(=O)NCC(=O)O)NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](C(C)C)N
  • InChI=1S/C22H38N6O7/c1-11(2)17(23)20(33)24-9-15(29)27-18(12(3)4)21(34)26-13(5)22(35)28-8-6-7-14(28)19(32)25-10-16(30)31/h11-14,17-18H,6-10,23H2,1-5H3,(H,24,33)(H,25,32)(H,26,34)(H,27,29)(H,30,31)/t13-,14-,17-,18-/m0/s1
  • Key:RLCSROTYKMPBDL-USJZOSNVSA-N

Hexapeptide-12 (Elastin hexapeptide) is a hexapeptide with the sequence VGVAPG, which is derived from a sequence found in the connective tissue protein elastin. At low concentrations it can stimulate biosynthesis of elastin and also inhibits production of the inflammatory signalling protein interleukin-6, which gives it an additional antiinflammatory effect.[1][2] However, at higher concentrations VGVAPG upregulates Sirtuin 2 expression which has a pro-aging and neurodegenerative effect, and progressive build-up of VGVAPG levels from degradation of elastin is thought to be an important contributor to the aging process,[3] so VGVAPG is mainly used in research applications into the pro-aging effects of some matrikine peptides, rather than being used as an ingredient in skincare products as with other related compounds.[4][5][6][7]

See also

References

  1. ^ Tajima S, Wachi H, Uemura Y, Okamoto K (July 1997). "Modulation by elastin peptide VGVAPG of cell proliferation and elastin expression in human skin fibroblasts". Archives of Dermatological Research. 289 (8): 489–492. doi:10.1007/s004030050227. PMID 9266029.
  2. ^ Blanchevoye C, Floquet N, Scandolera A, Baud S, Maurice P, Bocquet O, et al. (January 2013). "Interaction between the elastin peptide VGVAPG and human elastin binding protein". The Journal of Biological Chemistry. 288 (2): 1317–1328. doi:10.1074/jbc.M112.419929. PMC 3543015. PMID 23166321.
  3. ^ Szychowski KA, Skóra B, Wójtowicz AK (November 2022). "Elastin-Derived Peptides in the Central Nervous System: Friend or Foe". Cellular and Molecular Neurobiology. 42 (8): 2473–2487. doi:10.1007/s10571-021-01140-0. PMC 9560920. PMID 34374904.
  4. ^ Skóra B, Piechowiak T, Szychowski KA (January 2025). "Interaction Between Aging-Related Elastin-Derived Peptide (VGVAPG) and Sirtuin 2 and its Impact on Functions of Human Neuron Cells in an In Vitro Model". Molecular Neurobiology. 62 (1): 819–831. doi:10.1007/s12035-024-04298-y. PMC 11711152. PMID 38914873.
  5. ^ Skóra B, Szychowski KA (July 2025). "Proteostasis and autophagy disruption by the aging-related VGVAPG hexapeptide - preliminary insights into a potential novel elastin-induced neurodegeneration pathway in an in vitro human cellular neuron model". Neurochemistry International. 187 105992. doi:10.1016/j.neuint.2025.105992. PMID 40348194.
  6. ^ Yi J, Wang Y, Sui H, Chen Z, Ye T, Zhong Y, et al. (December 2025). "Elastin-derived extracellular matrix fragments drive aging through innate immune activation". Nature Aging. 5 (12): 2380–2398. doi:10.1038/s43587-025-00961-8. PMC 12705442. PMID 41023316.
  7. ^ Skóra B, Piechowiak T, Szychowski KA (February 2026). "Multi-kinase-mediated alterations in Tau phosphorylation, synaptic proteins, and choline metabolism in a human neuronal in vitro model exposed to the elastin-derived hexapeptide VGVAPG". Neuropharmacology. 284 110781. doi:10.1016/j.neuropharm.2025.110781. PMID 41297585.
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