GHK-Cu (acetate)
(Synonyms: Gly-His-Lys-Cu(II)) 目录号 : GC45706
A tripeptide-copper(II) complex
Cas No.:300801-03-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
GHK-Cu is a complex of the tripeptide Gly-His-Lys and a copper(II) ion that has wound healing and anti-inflammatory activities.1,2,3 It increases proliferation and the levels of collagen and secreted pro-matrix metalloproteinase-2 (MMP-2) in isolated human fibroblasts when used at a concentration of 1 nM.2,4,1 GHK-Cu (2 mg) increases levels of collagen and glycosaminoglycans (GAGs) and the expression of decorin in the wound tissue of rats.5 It decreases LPS-induced increases in the levels of reactive oxygen species (ROS), IL-6, and TNF-α in RAW 264.7 cells when used at a concentration of 10 μM.3 GHK-Cu (10 μg/g) prevents LPS-induced decreases in lung superoxide dismutase (SOD) activity and glutathione (GSH) levels and reduces LPS-induced increases in the number of cells and the level of total protein in bronchoalveolar lavage fluid (BALF) in a mouse model of acute lung injury.
|1. SimÉon, A., Emonard, H., Hornebeck, W., et al. The tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+ stimulates matrix metalloproteinase-2 expression by fibroblast cultures. Life Sci. 67(18), 2257-2265 (2000).|2. Maquart, F.-X., Pickart, L., Laurent, M., et al. Stimulation of collagen synthesis in fibroblast cultures by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+. FEBS Lett. 238(2), 343-346 (1988).|3. Park, J.-R., Lee, H., Kim, S.-I., et al. The tri-peptide GHK-Cu complex ameliorates lipopolysaccharide-induced acute lung injury in mice. Oncotarget 7(36), 58405-58417 (2016).|4. Pollard, J.D., Quan, S., Kang, T., et al. Effects of copper tripeptide on the growth and expression of growth factors by normal and irradiated fibroblasts. Arch. Facial Plast. Surg. 7(1), 27-31 (2005).|5. SimÉon, A., Wegrowski, Y., Bontemps, Y., et al. Expression of glycosaminoglycans and small proteoglycans in wounds: Modulation by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+. J. Invest. Dermatol. 115(6), 962-968 (2000).
| Cas No. | 300801-03-0 | SDF | |
| 别名 | Gly-His-Lys-Cu(II) | ||
| Canonical SMILES | CC(O)=O.O=C([C@H]1[N-](C2=O)[Cu+2]([NH2]C2)[N]3=CNC=C3C1)N[C@H](C([O-])=O)CCCCN | ||
| 分子式 | C14H22CuN6O4.C2H4O2 | 分子量 | 462 |
| 溶解度 | PBS (pH 7.2): 5 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 2.1645 mL | 10.8225 mL | 21.645 mL |
| 5 mM | 0.4329 mL | 2.1645 mL | 4.329 mL |
| 10 mM | 0.2165 mL | 1.0823 mL | 2.1645 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Stimulation of sulfated glycosaminoglycan synthesis by the tripeptide-copper complex glycyl-L-histidyl-L-lysine-Cu2+
Life Sci 1992;51(13):1049-56.PMID:1522753DOI:10.1016/0024-3205(92)90504-i.
Glycyl-L-histidyl-L-lysine-copper (II) complex (GHK-Cu) is a naturally occurring tripeptide with potential healing properties. We studied the effect of GHK-Cu on the synthesis of glycosaminoglycans (GAGs) by normal human fibroblasts in culture. Cells were incubated with 3H glucosamine and 35S sulfate and the radioactivity of isolated GAGs was determined. GHK-Cu induced a dose-dependent increase of the synthesis of total GAGs secreted into the culture medium and those associated with the cell layer. The effect of GHK-Cu was biphasic with a maximal stimulation at 10(-9) to 10(-8) M. At higher concentrations, the rate of synthesis returned progressively to that of control cultures. Electrophoretic analysis of the different GAG populations showed that GHK-Cu preferentially stimulated the synthesis of extracellular dermatan sulfate and cell layer associated heparan sulfate. No influence of GHK-Cu on the synthesis of hyaluronic acid was observed. GHK-Cu stimulation of GAG synthesis may be one of the phenomenons implicated in the wound healing properties of the peptide.
Selected Biomarkers Revealed Potential Skin Toxicity Caused by Certain Copper Compounds
Sci Rep 2016 Nov 28;6:37664.PMID:27892491DOI:10.1038/srep37664.
Copper is an essential mineral and plays important roles in skin growth and activity. Copper delivery through skin can provide beneficial effects but its potential to induce skin irritation reactions is often overlooked. Data on dermal toxicity caused by copper compounds is scant. Some recognized in vitro skin toxicity methods are unsuitable for all metal compounds. Here, we employ a keratinocyte-based model and evaluated the skin irritation potential of copper compounds at cellular, genomic and proteomic levels. We determined cell viability and cytotoxicity by using tetrazolium reduction assay and Lactate Dehydrogenase (LDH) assay, performed real-time PCR and protein quantification to assess the expression of biomarkers after treating cells with copper peptide (GHK-Cu), copper chloride (CuCl2) and copper acetate (Cu(OAc)2). These copper compounds exhibited different irritancy potentials at the same treatment concentrations. GHK-Cu was not cytotoxic and did not induce any significant change in the expression levels of various skin irritation-related biomarkers. IL-1α and IL-8, HSPA1A and FOSL1 were significantly upregulated following 24-h treatment with CuCl2 and Cu(OAc)2 at 58 and 580 μM without concomitant inhibition in cell viability. GHK-Cu has a low potential of inducing skin irritation and therefore provides a safer alternative for the delivery of copper through skin.
Effect of tripeptide-copper complexes on the process of skin wound healing and on cultured fibroblasts
Arch Int Pharmacodyn Ther 1995 Nov-Dec;330(3):345-60.PMID:8836453doi
The effects of Gly-His-Lys-Cu and of three synthetic analogues (I, II and III) on wound healing of the guinea-pig dorsal skin, as well as on cultured fibroblasts, were examined. Gly-His-Lys-Cu and peptide I-Cu were tested in vivo. Hydroxyproline, proteins, DNA and semicarbazide-sensitive amine oxidase, with a high affinity for benzylamine, were measured, and the histology of the wounds was observed after staining with hematoxylin/eosin. Another set of wounds was treated in parallel with equivalent amounts of copper acetate. Gly-His-Lys-Cu and the analogues caused a decrease of the activity of semicarbazide-sensitive amine oxidase, with a high affinity for benzylamine, 4-8 days after surgery, followed by an increase on day 11 that was higher than in the control group. No significant difference was found between the two peptides. A slower reorganization of the skin and a delayed activation of fibroblasts are the main effects observed with these peptides-Cu complexes. Preliminary studies on cultured fibroblasts were monitored to see whether these peptides had a direct effect on fibroblasts. The products studied at a concentration of 10(-7) M, decreased cell reproduction and increased collagen expression.
An in vivo assay for chemoattractant activity
Lab Invest 1985 Sep;53(3):362-8.PMID:3162062doi
We have devised an implantable device for the study of leukocyte chemoattraction. The device consists of a 0.25-mm thick patch of Dacron fabric coupled to a disc of ethylene vinyl acetate copolymer. Such polymers can release biologically active molecules at a constant rate for at least 18 days. Attracted cells invade and are trapped within the Dacron fabric. Upon removal from the host, the fabric patches are sectioned and stained to reveal the distribution of attracted cells. Distinct patterns of cellular accumulation can be seen for different chemoattractant molecules. These include the attraction of eosinophils by histamine, monocytes by tuftsin, and mast cells by glycyl-histidyl-lysine. Maximal accumulation of specific cell types occurs at postimplantation days 1 to 2 for neutrophils, days 3 to 5 for monocytes, and days 5 to 6 for macrophages and eosinophils. Control polymers fail to cause significant leukocyte accumulation, indicating that neither the polymer nor the Dacron fabric provokes an inflammatory response.
Iron delivery during proliferation and differentiation of kidney tubules
J Biol Chem 1985 Dec 15;260(29):15580-4.PMID:4066687doi
Proliferation during kidney development can be stimulated with an iron chelator, ferric pyridoxal isonicotinoyl hydrazone (FePIH). Neither the starting products nor the intermediary in FePIH synthesis stimulated proliferation. Thus, the growth-promoting effects of FePIH are due to the iron ion. Some other low molecular weight, saturated iron chelators such as glycyl-histidyl-lysine acetate, nitrilotriacetic acid, ascorbate, citrate, and unchelated ferrous sulfate could not support as high a degree of proliferation as FePIH or transferrin. FePIH delivered just slightly less radioactive iron into the trichloroacetic acid-precipitable fraction than transferrin. The octanol/saline partition coefficients of radioactive iron in solution with transferrin, nitrilotriacetic acid, or chloride were all less than 0.06. Thus, these compounds cannot efficiently traverse the lipid membrane. On the other hand, Fe3+ carried by PIH had a partition coefficient of 0.96. Hence, FePIH can stimulate proliferation because it can carry iron through the lipid membrane. Transferrin is not lipophilic but it delivers iron by receptor-mediated endocytosis.