G1887
Gly-His-Lys acetate salt
≥97% (TLC)
Synonym(s):
Liver cell growth factor
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About This Item
Linear Formula:
C14H24N6O4C2H4O2
CAS Number:
Molecular Weight:
400.43
MDL number:
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.32
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Quality Level
Assay
≥97% (TLC)
composition
Peptide content, ~70%
storage temp.
−20°C
SMILES string
CC(O)=O.NCCCC[C@H](NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)CN)C(O)=O
InChI
1S/C14H24N6O4.C2H4O2/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;1-2(3)4/h7-8,10-11H,1-6,15-16H2,(H,17,18)(H,19,21)(H,20,22)(H,23,24);1H3,(H,3,4)/t10-,11-;/m0./s1
InChI key
MGNUTAFMLGJBGV-ACMTZBLWSA-N
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Amino Acid Sequence
Gly-His-Lys
General description
Gly-His-Lys is a tripeptide present at ∼200ng/ml in association with α-globulin and albumin, in human blood plasma.
Application
Gly-His-Lys (GHK) has been used for the preparation of post-operative intra-articular injection of GHK-Cu (copper).
Gly-His-Lys acetate salt has been used:
- individually or as a complex with copper to test its effect on cytokines production in the human normal fibroblasts cell lines
- as a model peptide in N,N-dimethyl-N-methacryloxyethyl-N-(3-sulfopropyl)ammonium betaine based capillary electrophoresis separation studies
- as a component of Coon′s modified Ham′s F-12 medium for culturing Fischer rat thyroid follicular cell line, FRTL-5
Biochem/physiol Actions
Gly-His-Lys (GHK) acetate salt displays affinity towards copper(II) ions. This property enables GHK to modulate the copper intake into cells. GHK is also involved in quenching toxic by-products generated by lipid peroxidation.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
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Wen Jiang et al.
Analytical chemistry, 75(11), 2768-2774 (2003-09-02)
A novel capillary with covalently bonded zwitterionic surface modification was prepared by photograft polymerization of the zwitterionic monomer N,N-dimethyl-N-methacryloxyethyl-N-(3-sulfopropyl)ammonium betaine, onto the inner surface of a UV-transparent fused-silica capillary. Although the zwitterionic moieties in the resulting polymeric "tentacles" comprise both
L Pickart et al.
Journal of chromatography, 175(1), 65-73 (1979-07-11)
Isolation and purification of growth-modulating peptides from biological sources is often accompanied by excessive losses of bioactive material. During the isolation of a growth-modulating tripeptide glycylhistidyllysine (GHL) from human plasma, copper and iron were found to co-isolate with the peptide.
Growth-modulating human plasma tripeptide: relationship between molecular structure and DNA synthesis in hepatoma cells.
L Pickart et al.
FEBS letters, 104(1), 119-122 (1979-08-01)
Y Zheng et al.
Organic letters, 3(21), 3277-3280 (2001-10-12)
[structure: see text]. A new fluorescent chemosensor for Cu2+ ions was synthesized by modifying the tripeptide glycyl-histidyl-lysine (GHK) with 9-carbonylanthracene via the standard Fmoc solid-phase peptide synthesis method. While significant fluorescence quenching was observed from the molecule upon binding with
A Siméon et al.
Life sciences, 67(18), 2257-2265 (2000-10-25)
Glycyl-histidyl-lysine-Cu2+ (GHK-Cu) is a tripeptide-copper complex known to be a potent wound healing agent. We previously showed its ability to stimulate in vitro and in vivo the synthesis of extracellular matrix components. The aim of this study was to determine
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