Glycyl-L-histidyl-L-arginine
[CAS# 82224-83-7]

Identification

• Name: Glycyl-L-histidyl-L-arginine
• Synonyms: (2S)-2-[[(2S)-2-[(2-aminoacetyl)amino]-3-(1H-imidazol-5-yl)propanoyl]amino]-5-(diaminomethylideneamino)pentanoic acid
• Molecular Formula: C₁₄H₂₄N₈O₄
• Molecular Weight: 368.39
• Protein Sequence: GHR
• CAS Registry Number: 82224-83-7
• SMILES: C1=C(NC=N1)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)O)NC(=O)CN

Properties

• Solubility: Sparingly soluble (25 g/L) (25 °C), Calc.^*
• Density: 1.58±0.1 g/cm³ (20 °C 760 Torr), Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2016 ACD/Labs)

Discovery and Applications

Glycyl-L-histidine-L-arginine (GHK) is a naturally occurring tripeptide composed of glycine, histidine, and arginine. It was first discovered and characterized in the 1970s by biochemist Dr. Loren Pickart while studying the role of peptides in biological processes. Dr. Pickart discovered GHK as a component of human plasma and elucidated its diverse biological activities and therapeutic potential.

One of GHK's most well-known applications is in skin care and cosmetic formulations due to its remarkable ability to promote skin regeneration and wound healing. GHK has been shown to stimulate the synthesis of collagen, elastin, and other extracellular matrix proteins. It also enhances the migration and proliferation of fibroblasts and keratinocytes. GHK has powerful anti-inflammatory effects and can be used to treat various inflammatory skin diseases, such as eczema, dermatitis, and psoriasis. GHK regulates the expression of pro-inflammatory cytokines and mediators, inhibits oxidative stress, and inhibits the activation of inflammatory pathways, thereby reducing skin inflammation and irritation. GHK has a high affinity for copper ions and acts as a natural chelator to promote the absorption, transport and utilization of copper in the body. Copper-GHK complexes play important roles in various physiological processes, including angiogenesis, wound healing, and antioxidant defense. GHK promotes hair growth and prevents hair loss by stimulating the proliferation and differentiation of hair follicle cells. GHK enhances the expression of growth factors involved in hair follicle development, prolongs the anagen (anagen) phase of the hair cycle, and inhibits apoptosis of hair follicle cells. GHK has antioxidant properties and protects cells from oxidative damage by scavenging free radicals, inhibiting lipid peroxidation, and enhancing the activity of endogenous antioxidant enzymes. Emerging research suggests that GHK may have neuroprotective properties and have potential applications in the treatment of neurodegenerative diseases such as Alzheimer's disease and Parkinson's disease.

References

1983. Inhibition of fibrin polymerization by fragment D is affected by calcium, Gly-Pro-Arg and Gly-His-Arg. Biochimica et Biophysica Acta (BBA) - Protein Structure and Molecular Enzymology, 742(1).
DOI: 10.1016/0167-4838(83)90354-0

1982. Effect of Calcium and Synthetic Peptides on Fibrin Polymerization. Thrombosis and Haemostasis, 47(3).
DOI: 10.1055/s-0038-1657143