Copper tripeptide Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

solubility 

Soluble in DMSO

Sequence

(Cu2+ )H-Glu-His-Lys-OH

InChI

InChI=1/C14H23N6O4.Cu/c15-4-2-1-3-10(14(23)24)20-13(22)11(19-12(21)6-16)5-9-7-17-8-18-9;/h7-8,10-11,16H,1-6,15H2,(H4,17,18,19,20,21,22,23,24);/q-1;+3/p-2/t10-,11-;/s3

InChIKey

DDNUEECOCUBKBT-MIIMWFGWNA-L

SMILES

C([C@@H]1CC2=CNC=N2[Cu+2]2NCC(=O)[N-]12)(=O)N[C@H](C(=O)[O-])CCCCN |&1:1,16,r|

Copper tripeptide Usage And Synthesis

Description

Copper tripeptide, also known as [N2-(N-Glycyl-L-histidyl)-L-lysinato(2-)]copper or GHK-Cu, is a naturally occurring tripeptide. It was first isolated from human plasma but can be found in saliva and urine. During wound healing, it may be freed from existing extracellular proteins via proteolysis. Studies have shown that GHK-Cu has a maximal biological effect at 10^-9 mol/L and Its concentration in the body decreases with age[1].

Uses

Copper tripeptide (GHK-Cu) can be used as a skin antiaging agent. It could lead to the extracellular matrix accumulation increases in the rat wound model. Copper Peptide preparations were able to promote wound healing rates in diabetic ulcers and patients undergoing Mohs surgery. It could induce angiogenesis in rabbit models at 10?12 mol/L by acting as a chemoattractant for capillary cells. It may also improve the autocrine growth factor milieu in keloid fibroblasts[1-2]. It can also be doped into It can also be doped into binary binary PBDB-T: ITIC to tune the crystallinity and phase separation of the active layer, improving the performance of polymer solar cells[3].

Mechanism of action

At this concentration (10^-9 mol/L), GHK-Cu has been shown to increase messenger RNA production for collagen, elastin, proteoglycans, and glycosaminoglycans in fibroblasts. It has been demonstrated that GHK-Cu stimulates cultured normal fibroblasts to synthesize collagen and induces a dose-dependent increase in the synthesis of glycosaminoglycans. It could stimulate the regeneration of skin, nervous tissue, bones, lungs, and liver, protect the liver from oxidative damage, restore the activity of irradiated fibroblasts, reduce inflammation, and increase levels of antioxidant enzymes[1].

Side effects

Copper tripeptide (GHK-Cu) is considered to be very safe but there are always a few side effects related to any substance that is taken for health. When using creams, you might have mild skin irritation if you are one of the very few people with sensitivity. When the substance has been injected, people have reported that they experience cramping and burning at the injection site.
Other reported side effects are: Headache; Dizziness; Fatigue; Nausea; Elevated blood pressure; Lowered blood pressure; Increase in appetite; Redness and pain at the injection site; Cramping at the injection site.

References

[1] Jeffrey D, et al. Effects of Copper Tripeptide on the Growth and Expression of Growth Factors by Normal and Irradiated Fibroblasts. Archives of Facial Plastic Surgery, 2005; 7.
[2] Huang J, et al. Efficient Ternary Polymer Solar Cells with Tunable Crystallinity and Phase Separation of Active Layers via Incorporating GHK-Cu. ACS Applied Materials Interfaces, 2021; 13: 46927–46937.
[3] Pickart L, et al.Modulation of Gene Expression in Human Breast Cancer MCF7 and Prostate Cancer PC3 Cells by the Human Copper-Binding Peptide GHK-Cu, 2021; 5.

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