10219. GHK

Nomenclature

CAS number: 49557-75-7
Glycyl-l-histidyl-l-lysine; liver cell growth factor; GHL.
C14H24N6O4; mol wt 340.38.
C 49.40%, H 7.11%, N 24.69%, O 18.80%.

Description and references

Naturally occuring tripeptide found in plasma. Spontaneously forms complexes with copper and other transition metals; involved in the physiological transport and uptake of copper ions. Stimulates synthesis of collagen, glycosaminoglycans, and extracellular matrix proteins; has growth promoting and wound healing properties. Isoln from human serum: L. Pickart, M. M. Thaler, Nature New Biol. 243, 85 (1973) PubMed. Confirmation of peptide structure: D. H. Schlesinger et al., Experientia 33, 324 (1977) DOI PubMed. Characterization of copper complexes: S. Lau, B. Sarkar, Biochem. J. 199, 649 (1981) PubMed; J. H. Freedman et al., Biochemistry 21, 4540 (1982) DOI PubMed; C. Conato et al., Biochim. Biophys. Acta 1526, 199 (2001) PubMed. HPLC determn in plasma: T. Endo et al., J. Chromatogr. B 692, 37 (1997) DOI. Overview of use in cell culture systems: L. Pickart, S. Lovejoy, Methods Enzymol. 147B, 314-328 (1987) DOI. Effect of copper complex on wound healing: F.-X. Maquart et al., J. Clin. Invest. 92, 2368 (1993) DOI PubMed; A. Siméon et al., J. Invest. Dermatol. 115, 962 (2000) DOI PubMed. Veterinary trial in rabbits: I. T. Cangul et al., Vet. Dermatol. 17, 417 (2006) DOI PubMed. Membrane permeability study: L. Mazurowska, M. Mojski, Talanta 72, 650 (2007) DOI.

Chemical structure

Properties

Hygroscopic. pKa 2.91, 6.53, 7.93, 10.44.

Derivative

Acetate.

Nomenclature

CAS number: 72957-37-0
C14H24N6O4.C2H4O2; mol wt 400.43.
C 47.99%, H 7.05%, N 20.99%, O 23.97%.

Properties

Crystals from methanol + acetic acid, mp 146-148°.

Derivative

Complex with copper.

Nomenclature

CAS number: 89030-95-5
[Glycyl-κN-l-histidyl-κN,κN3-l-lysinato(2)] copper; GHK-Cu.
C14H22CuN6O4; mol wt 401.91.
C 41.84%, H 5.52%, Cu 15.81%, N 20.91%, O 15.92%.

Properties

Dark purple-blue, octahedral crystals from water + ethanol.

Derivative

Bis complex with copper.

Nomenclature

CAS number: 130120-56-8
Hydrogen [N2-(glycyl-l-histidyl-κN3)-l-lysinato][N2-(glycyl-κN-l-histidyl-κN3)-l-lysinato(2)]cuprate(1); PC-1020.
C28H46CuN12O8; mol wt 742.29.
C 45.31%, H 6.25%, Cu 8.56%, N 22.64%, O 17.24%.

Derivative

Bis complex with copper diacetate.

Nomenclature

CAS number: 130120-57-9
Hydrogen (glycyl-l-histidyl-κN1-l-lysinato)[glycyl-κN-l-histidyl-κN,κN3-l-lysinato(2)]cuprate(1) diacetate; prezatide copper acetate; Iamin (Procyte).
C28H46CuN12O8.2C2H4O2; mol wt 862.39.
C 44.57%, H 6.31%, Cu 7.37%, N 19.49%, O 22.26%.

Description and references

Clinical trial for diabetic ulcers: G. D. Mulder et al., Wound Repair Regen. 2, 259 (1994) DOI PubMed.

Use

Growth factor in cell culture systems. In cosmetics as anti-aging ingredient.

Therapeutic Category

Vulnerary.

Therapeutic Category (Veterinary)

Vulnerary.

Keywords

Prezatide Copper Acetate: Vulnerary