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Merck
CN

G1269

Gly-Arg-Gly-Asp-Ser-Pro-Lys

≥97% (HPLC)

Synonym(s):

GRGDSPK

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About This Item

Empirical Formula (Hill Notation):
C28H49N11O11
CAS Number:
111119-28-9
Molecular Weight:
715.76
MDL number:
MFCD00076462
UNSPSC Code:
12352209
PubChem Substance ID:
24895055
NACRES:
NA.32
Form:
powder
Assay:
≥97% (HPLC)
Biological source:
human

Key Documents

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Product Name

Gly-Arg-Gly-Asp-Ser-Pro-Lys, ≥97% (HPLC)

SMILES string

NCCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](CO)NC(=O)[C@H](CC(O)=O)NC(=O)CNC(=O)[C@H](CCCNC(N)=N)NC(=O)CN)C(O)=O

InChI

1S/C28H49N11O11/c29-8-2-1-5-16(27(49)50)37-25(47)19-7-4-10-39(19)26(48)18(14-40)38-24(46)17(11-22(43)44)36-21(42)13-34-23(45)15(35-20(41)12-30)6-3-9-33-28(31)32/h15-19,40H,1-14,29-30H2,(H,34,45)(H,35,41)(H,36,42)(H,37,47)(H,38,46)(H,43,44)(H,49,50)(H4,31,32,33)/t15-,16-,17-,18-,19-/m0/s1

InChI key

ZRVZOBGMZWVJOS-VMXHOPILSA-N

biological source

human

assay

≥97% (HPLC)

form

powder

technique(s)

blocking: suitable
ligand binding assay: suitable

storage temp.

−20°C

Quality Level

200

Gene Information

human ... ITGA2B(3674), ITGAV(3685)

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Application

Gly-Arg-Gly-Asp-Ser-Pro-Lys (RGD peptide) has been used-
  • as a blocking peptide to inhibit integrin-fibronectin binding
  • in adhesion assay performed on porcine trophectoderm to study the influence of TGFβ (transforming growth factor) on cell adhesion
  • for incubation of MC3T3-E1 osteoblast cells to determine its effect on cell adhesion measured by AFM (atomic force microscopy)
  • for the preparation of RGD.Flt23k.NR nanoparticles
  • to determine the involvement of RGD-integrin bonding in cell adhesion process

Biochem/physiol Actions

Fibronectin analog that binds to integrins.

General description

Gly-Arg-Gly-Asp-Ser-Pro-Lys is a RGD peptide. Naturally occurring RGD peptides, present in the ECM (extracellalar matrix) proteins, are involved in facilitating integrin-mediated cell adhesion to matrix proteins. RGD peptide is present as repeats in cell-adhesion protein, such as fibronectin and vitronectin. This tripeptide is recognized by cells by specific integrins (e.g. β1 , β3 , and β5 subunits), present on the cell surface and associated with the actin filament via the FA (focal adhesion)-complex.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

常规特殊物品
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Certificates of Analysis (COA)

Lot/Batch Number
0000477487
0000477487
0000471363
0000471363
0000323122

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E J Filardo et al.
The Journal of cell biology, 130(2), 441-450 (1995-07-01)
The NPXY sequence is highly conserved among integrin beta subunit cytoplasmic tails, suggesting that it plays a fundamental role in regulating integrin-mediated function. Evidence is provided that the NPXY structural motif within the beta 3 subunit, comprising residues 744-747, is
E A Cowles et al.
Journal of biomedical materials research, 52(4), 725-737 (2000-10-18)
Since osteoblast proliferation is critical for bone development, the effect of bone extracellular matrix (ECM) proteins on osteoblast signaling and proliferation in serum-free medium was investigated. Proliferation was highest in primary rat calvarial osteoblasts cells grown on fibronectin but less
A M Moursi et al.
Journal of cell science, 109 ( Pt 6), 1369-1380 (1996-06-01)
The secretion of fibronectin by differentiating osteoblasts and its accumulation at sites of osteogenesis suggest that fibronectin participates in bone formation. To test this directly, we determined whether fibronectin-cell interactions regulate progressive differentiation of cultured fetal rat calvarial osteoblasts. Spatial
M R Custodio et al.
The Journal of eukaryotic microbiology, 42(6), 721-724 (1995-11-01)
Developmental processes in multicellular organisms require structural elements, such as adhesion molecules, to stabilize cells at functional positions. In vertebrates, a series of extracellular matrix proteins, e.g. fibronectin and laminin, are involved in cell adhesion. These proteins contain Arg-Gly-Asp [RGD]
Che-Yi Chang et al.
International journal of nanomedicine, 12, 279-294 (2017-01-25)
Neovascularization (NV) of the cornea can disrupt visual function, causing ocular diseases, including blindness. Therefore, treatment of corneal NV has a high public health impact. Epigalloccatechin-3-gallate (EGCG), presenting antiangiogenesis effects, was chosen as an inhibitor to treat human vascular endothelial
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