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Merck

G4391

Gly-Arg-Gly-Asp-Ser

≥97% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C17H30N8O9
CAS Number:
96426-21-0
Molecular Weight:
490.47
MDL number:
MFCD00076459
UNSPSC Code:
12352209
PubChem Substance ID:
24895169
NACRES:
NA.32

Product Name

Gly-Arg-Gly-Asp-Ser, ≥97% (HPLC)

SMILES string

NCC(=O)N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(O)=O

InChI

1S/C17H30N8O9/c18-5-11(27)23-8(2-1-3-21-17(19)20)14(31)22-6-12(28)24-9(4-13(29)30)15(32)25-10(7-26)16(33)34/h8-10,26H,1-7,18H2,(H,22,31)(H,23,27)(H,24,28)(H,25,32)(H,29,30)(H,33,34)(H4,19,20,21)/t8-,9-,10-/m0/s1

InChI key

RGNVSYKVCGAEHK-GUBZILKMSA-N

assay

≥97% (HPLC)

form

powder

composition

Peptide content, ≥60%

technique(s)

blocking: suitable
cell culture | mammalian: suitable

storage temp.

−20°C

Quality Level

200

Gene Information

human ... ITGB3(3690)

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Application

Gly-Arg-Gly-Asp-Ser has been used-
  • as an antigen to determine whether integrin α4 or α5 hinders the adhesion of day 3 postirradiation thymocytes to thymic epithelial cells, in mice
  • for the treatment of collagen IV-coated dishes to study the role of integrins α1, αv, β1, and β3 in Sca-1+ progenitor cell differentiation into SMCs (smooth muscle cells)
  • as a blocking peptide for the pre-incubation of Nisseria meningitides strains, to perform blocking experiments to study the interactions between these bacterial strains and fibronectin
  • for the pre-treatment of EL-4 cells infected by AdCMV-GFP (cytomegalovirus-green fluorescent protein), to study whether interaction with cellular integrins is essential for the transduction of adenovirus

Biochem/physiol Actions

Antagonist of integrin function
Gly-Arg-Gly-Asp-Ser inhibits metastasis in syngeneic mice or in mice lacking platelet function, when co-injected with B16-Fl0 melanoma cells.

General description

Gly-Arg-Gly-Asp-Ser peptide sequence is identical to the cell-binding region of fibronectin protein. Arg-Gly-Asp (RGD) region is found in various proteins, and is crucial for facilitating cell-adhesive activity.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000397532
0000387101
0000322880
0000324778
0000305034

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Yves Lecarpentier et al.
PloS one, 14(10), e0222683-e0222683 (2019-10-02)
Mesenchymal stem cells (MSCs) were obtained from human bone marrow and amplified in cultures supplemented with human platelet lysate in order to generate myofibroblasts. When MSCs were seeded in solid collagen scaffolds, they differentiated into myofibroblasts that were observed to
PCL-PEG-based nanoparticles grafted with GRGDS peptide: preparation and surface analysis by XPS.
Vincent Pourcelle et al.
Biomacromolecules, 8(12), 3977-3983 (2007-11-28)
T Eberhard et al.
Infection and immunity, 66(4), 1791-1794 (1998-04-07)
Adhesion of Neisseria meningitidis strains to extracellular matrix (ECM) and purified matrix components was examined. Most strains bound to subendothelial ECM as well as to immobilized fibronectin and types I, III, and V collagen. Strains from healthy carriers adhered significantly
Yukie Aizawa et al.
Biomaterials, 33(21), 5198-5205 (2012-05-09)
Cell-cell interactions are critical to understanding functional tissues. A number of stem cell populations have been shown to receive key regulatory information from endothelial cells (ECs); however, the role of ECs in the retinal stem and progenitor cell (RSPC) niche
Yves Lecarpentier et al.
Cells, 9(6) (2020-06-25)
Mesenchymal stromal cells (MSCs) were obtained from human bone marrow and amplified in cultures supplemented with human platelet lysate. Once semi-confluent, cells were seeded in solid collagen scaffolds that were rapidly colonized by the cells generating a 3D cell scaffold.
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