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Chemical Compound Review

Iamin     (2S)-6-amino-2-[[(2S)-2-(2...

Synonyms: Gly-his-lys, SureCN259085, CHEMBL1814493, Copper(II)ghk, CHEBI:75430, ...
 
 
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Disease relevance of Gly-his-lys

 

High impact information on Gly-his-lys

  • It is found that the aminoacyl-tRNA synthetases (EC 6.1.1.-) with specificity for Arg, Asn, Ile, Leu, Met, Phe, Thr, Trp, and Val attach the amino acid to the 2'-position; those with specificity for Gly, His, Lys, and Ser attach the amino acid to the 3'-position; and that Tyr and Cys can be enzymatically attached to both the 2'- and 3'-positions [4].
  • Two tripeptides, glycylhistidyllysine and N-formylmethionylleucylphenylalanine, were also found to be potent chemoattractants for mast cells [5].
  • FRTL-5 rat thyroid cells grown in culture medium supplemented with serum and 6H (TSH, insulin, hydrocortisone, transferrin, glycylhistidyllysine, and somatostatin) showed a significant increase in TSH-dependent cAMP accumulation and I- efflux after prolonged incubation (5 to 10 days) of the cells in culture medium containing 5H (6H - TSH) or serum [6].
  • The 72-h influence of serum and six supplements (thyrotropin, insulin, somatostatin, transferrin, hydrocortisone, glycyl-histidyl-lysine acetate) on growth and function in presence of 3-isobutyl-L-methyl-xanthine (IBMX) was investigated [7].
  • Binding competition experiments using the radioligand [125I][Sar1-Ile8]angiotensin II clearly indicated that Gly-His-Lys interacts with AT1 receptors [8].
 

Biological context of Gly-his-lys

  • Other hormones used to enhance differentiation and growth in thyroid cells in culture i.e. transferrin, somatostatin, cortisol and glycyl-histidyl-lysine acetate had no marked effects on IGFBP secretion nor on TSH-dependent, insulin-mediated iodide uptake and organification and cell growth [9].
  • It forms a complex with vanadate (association constant K approximately 145 +/- 30 M-1; delta (51V) = -514 ppm) with spectral features similar to the less stable complexes obtained with di- and tripeptides (Gly-His, Pros-His-Ala, Gly-His-Lys, Val-Glu) containing amino acids that are constituents at the active site of the enzyme [10].
  • Reactions of QMs with the tripeptide Gly-His-Lys confirmed the results with amino acids as N alpha-glycine alkylation predominated, but side chain adducts also formed with BHTOH-QM and BDMP-QM [11].
 

Anatomical context of Gly-his-lys

  • Gly-His-Lys, a tripeptide isolated from human plasma that increases the growth rate of many cells, stimulated in dose-dependent fashion the activity of phosphorylase a in isolated rat hepatocytes [8].
  • Biologically active tripeptides such as Met-Leu-Tyr (chemotactic factor), Gly-His-Lys (liver growth factor) and Thr-Val-leu central nervous system tripeptide) were hydrolyzed at rates 0.05-0.15-times that of Leu-Gly-Gly [12].
  • Dissociated cells from 7-day-old chick embryo cerebral hemispheres were cultivated on collagen in Falcon Petri dishes in the presence of various concentrations of fetal calf serum and of a chemically synthesized tripeptide Gly-His-Lys [13].
 

Associations of Gly-his-lys with other chemical compounds

 

Gene context of Gly-his-lys

References

  1. Growth-modulating tripeptide (glycylhistidyllysine): association with copper and iron in plasma, and stimulation of adhesiveness and growth of hepatoma cells in culture by tripeptide-metal ion complexes. Pickart, L., Thaler, M.M. J. Cell. Physiol. (1980) [Pubmed]
  2. Effects of glycyl-histidyl-lysine on Morris hepatoma 7777 cells. Barra, R. Cytobios (1987) [Pubmed]
  3. Tripeptide Gly-His-Lys is a hepatotropic immunosuppressor. Smakhtin, M.Y., Sever'yanova, L.A., Konoplya, A.I., Shveinov, I.A. Bull. Exp. Biol. Med. (2002) [Pubmed]
  4. Site of aminoacylation of tRNAs from Escherichia coli with respect to the 2'- or 3'-hydroxyl group of the terminal adenosine. Sprinzl, M., Cramer, F. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  5. Stimulation of rat peritoneal mast cell migration by tumor-derived peptides. Poole, T.J., Zetter, B.R. Cancer Res. (1983) [Pubmed]
  6. Requirement of insulin growth factor I plus hydrocortisone for the regeneration of thyrotropin (TSH)-dependent mechanism of I-efflux and Ca2+ mobilization in FRTL-5 cells during TSH depletion. Sho, K., Okajima, F., Akiyama, H., Shoda, Y., Kobayashi, I., Kondo, Y. Endocrinology (1989) [Pubmed]
  7. Human thyroid epithelial cells cultured in monolayers. II. Influence of serum on thyroglobulin and cAMP production. Rasmussen, A.K., Kayser, L., Perrild, H., Brandt, M., Bech, K., Feldt-Rasmussen, U. Mol. Cell. Endocrinol. (1996) [Pubmed]
  8. Glycyl-histidyl-lysine interacts with the angiotensin II AT1 receptor. García-Sáinz, J.A., Olivares-Reyes, J.A. Peptides (1995) [Pubmed]
  9. Thyrotropin inhibits while insulin, epidermal growth factor and tetradecanoyl phorbol acetate stimulate insulin-like growth factor binding protein secretion from sheep thyroid cells. Eggo, M.C., Bachrach, L.K., Brown, A.L., Burrow, G.N. Growth Factors (1991) [Pubmed]
  10. Binding of vanadate (V) to ribonuclease-T1 and inosine, investigated by 51V NMR spectroscopy. Rehder, D., Holst, H., Quaas, R., Hinrichs, W., Hahn, U., Saenger, W. J. Inorg. Biochem. (1989) [Pubmed]
  11. Influence of quinone methide reactivity on the alkylation of thiol and amino groups in proteins: studies utilizing amino acid and peptide models. Bolton, J.L., Turnipseed, S.B., Thompson, J.A. Chem. Biol. Interact. (1997) [Pubmed]
  12. A highly specific aminotripeptidase of rat brain cytosol. Substrate specificity and effects of inhibitors. Sachs, L., Marks, N. Biochim. Biophys. Acta (1982) [Pubmed]
  13. Effects of synthetic tripeptide on the differentiation of dissociated cerebral hemisphere nerve cells in culture. Sensenbrenner, M., Jaros, G.G., Moonen, G., Mandel, P. Neurobiology. (1975) [Pubmed]
  14. ESR studies of the interaction of copper(II)GHK, histidine, and Ehrlich cells. Antholine, W.E., Petering, D.H., Pickart, L. J. Inorg. Biochem. (1989) [Pubmed]
  15. Mobilization of copper(II) from plasma components and mechanisms of hepatic copper transport. Darwish, H.M., Cheney, J.C., Schmitt, R.C., Ettinger, M.J. Am. J. Physiol. (1984) [Pubmed]
  16. A morphologic and immunofluorescent analysis of primary guinea pig glomerular cell types grown in chemically defined media. Evidence for clonal growth and cell differentiation. Oberley, T.D., Murphy, P.J., Steinert, B.W., Albrecht, R.M. Virchows Arch., B, Cell Pathol. (1982) [Pubmed]
  17. Effect of glucocorticoids, insulin and a growth promoting tripeptide on the biosynthesis of plasma proteins in serum-free hepatocyte cultures. Fouad, F.M., Abd-El-Fattah, M., Scherer, R., Ruthenstroth-Bauer, G. Z. Naturforsch., C, Biosci. (1981) [Pubmed]
 
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