Arginyl-glycine

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Arginyl-glycine
Category Others
Catalog number BBF-05088
CAS 2418-67-9
Molecular Weight 231.25
Molecular Formula C8H17N5O3

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Specification

Synonyms Arg-Gly; L-Arginyl glycine
Sequence H-Arg-Gly-OH
IUPAC Name 2-[[(2S)-2-amino-5-(diaminomethylideneamino)pentanoyl]amino]acetic acid
Canonical SMILES C(CC(C(=O)NCC(=O)O)N)CN=C(N)N
InChI InChI=1S/C8H17N5O3/c9-5(2-1-3-12-8(10)11)7(16)13-4-6(14)15/h5H,1-4,9H2,(H,13,16)(H,14,15)(H4,10,11,12)/t5-/m0/s1
InChI Key XUUXCWCKKCZEAW-YFKPBYRVSA-N

Reference Reading

1. Constrained refinement based on NOE and chemical shift information: the monomer form of arginine-vasopressin-like insect factor
B Busetta, P Picard J Pept Sci. 1997 Mar-Apr;3(2):133-40. doi: 10.1002/(SICI)1099-1387(199703)3:2%3C133::AID-PSC91%3E3.0.CO;2-H.
Via the refinement process of the monomer form of an arginine-vasopressin-like insect factor, the paper analyses the most relevant NMR information to define the solution structure of a flexible peptide. The relative importance of the different NOE constraints is discussed.
2. (99m)Tc-labeled monomeric and dimeric NGR peptides for SPECT imaging of CD13 receptor in tumor-bearing mice
Wenhui Ma, Fei Kang, Zhe Wang, Weidong Yang, Guiyu Li, Xiaowei Ma, Guoquan Li, Kai Chen, Yingqi Zhang, Jing Wang Amino Acids. 2013 May;44(5):1337-45. doi: 10.1007/s00726-013-1469-1. Epub 2013 Mar 1.
CD13 receptor plays a critical role in tumor angiogenesis and metastasis. We therefore aimed to develop (99m)Tc-labeled monomeric and dimeric NGR-containing peptides, namely, NGR1 and NGR2, for SPECT imaging of CD13 expression in HepG2 hepatoma xenografts. Both NGR-containing monomer and dimer were synthesized and labeled with (99m)Tc. In vivo receptor specificity was demonstrated by successful blocking of tumor uptake of (99m)Tc-NGR dimer in the presence of 20 mg/kg NGR2 peptide. Western blot and immunofluorescence staining confirmed the CD13 expression in HepG2 cells. The NGR dimer showed higher binding affinity and cell uptake in vitro than the NGR-containing monomer, presumably due to a multivalency effect. (99m)Tc-Labeled monomeric and dimeric NGR-containing peptides were subjected to SPECT imaging and biodistribution studies. SPECT scans were performed in HepG2 tumor-bearing mice at 1, 4, 12, and 24 h post-injection of ~7.4 MBq tracers. The metabolism of tracers was determined in major organs at different time points after injection which demonstrated rapid, significant tumor uptake and slow tumor washout for both traces. Predominant clearance from renal and hepatic system was also observed in (99m)Tc-NGR1 and (99m)Tc-NGR2. In conclusion, monomeric and dimeric NGR peptide were developed and labeled with (99m)Tc successfully, while the high integrin avidity and long retention in tumor make (99m)Tc-NGR dimer a promising agent for tumor angiogenesis imaging.
3. Entamoeba histolytica: tyrosine kinase activity induced by fibronectin through the beta1-integrin-like molecule
V I Hernández-Ramírez, M Anaya-Ruiz, A Rios, P Talamás-Rohana Exp Parasitol. 2000 Jun;95(2):85-95. doi: 10.1006/expr.2000.4522.
Previously, we characterized a 140-kDa protein from Entamoeba histolytica as a beta1-integrin-like molecule that binds fibronectin. In this work we present data showing that the amoebic receptor is associated with another surface molecule, the 220-kDa lectin, and with protein tyrosine kinase activity. By immunoprecipitation with the alphabeta1Eh antibody, we demonstrated by immune complex assays for tyrosine protein kinases that the amoebic fibronectin receptor was associated with two phosphorylated proteins of 50 and 70 kDa when internal membranes were used as the source of antigen. When cells were stimulated with fibronectin, two proteins of 55 and 90 kDa were tyrosine phosphorylated, as shown by Western blot with alphaPY20, its phosphorylation being time dependent after fibronectin stimulation. However, when the actin cytoskeleton of fibronectin-stimulated trophozoites was stabilized with phalloidin, the level and the pattern of phosphorylated proteins were different. In this case, a high-molecular-weight component, heavily phosphorylated, was present, which may include the 220-kDa lectin. We also present data confirming that the signaling pathway that is activated by fibronectin is specific. This was demonstrated by comparing the pattern of phosphoproteins obtained in immune complexes prepared with alphabeta1Eh, alphaL220, and alphaPY20 from total extracts obtained in the presence of phalloidin, from cells that had been exposed to fibronectin, soluble concanavalin A, or concanavalin-A-coated substrate. The presence of tyrosine kinases associated with the beta1-integrin-like amoebic molecule was confirmed by immunoprecipitation assays along with the combined use of a tyrosine kinase-specific substrate, the peptide RR-SRC, and a tyrosine kinase inhibitor, genistein.

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