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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
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
assay
≥97% (TLC)
composition
Peptide content, ~70%
storage temp.
−20°C
Quality Level
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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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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Jingyuan Xiong et al.
Drug and chemical toxicology, 41(4), 501-508 (2017-11-17)
Thyroid hormones are involved in many important physiological activities including regulation of energy metabolism, development of nervous system, maintenance of cerebral functions, and so on. Endocrine-disrupting chemicals (EDCs) that interfere with thyroid functions raise serious concerns due to their frequent
Sai-Chuen Fu et al.
Journal of orthopaedic research : official publication of the Orthopaedic Research Society, 33(7), 1024-1033 (2015-03-04)
After anterior cruciate ligament reconstruction (ACLR), the biological healing of the graft is a rate-limiting step which can contribute to graft failure. The tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu(II) (GHK-Cu) is a well-known activator of tissue remodeling. We investigated whether GHK-Cu can improve
C Conato et al.
Biochimica et biophysica acta, 1526(2), 199-210 (2001-04-28)
Copper complex formation equilibria of glycyl-L-histidyl-L-lysine (Gly-His-Lys, GHK) and of two synthetic analogues, where the histidine residue was replaced with a synthetic amino acid (L-spinacine or L-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid), have been carefully investigated using different experimental techniques: potentiometry, solution calorimetry, UV-VIS
Sherman O Canapp et al.
Veterinary surgery : VS, 32(6), 515-523 (2003-12-03)
To evaluate the effects of topical glycyl-L-histidyl-L-lysine tripeptide-copper complex (TCC; Iamin 2% Gel; Procyte Corporation, Redmond, WA) on healing in ischemic open wounds. Experimental study. Twenty-four adult male Sprague-Dawley rats. Rats were divided into 3 groups: topical TCC, topical TCC
I Taci Cangul et al.
Veterinary dermatology, 17(6), 417-423 (2006-11-07)
In this study the clinical and histopathological effects of topically applied tripeptide-copper complex (TCC) and zinc oxide on open-wound healing in rabbits was evaluated. Eighteen New Zealand rabbits were divided into three groups: TCC, zinc oxide and no treatment. One
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