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G1269

Sigma-Aldrich

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

biological source

human

Quality Level

200

assay

≥97% (HPLC)

form

powder

technique(s)

blocking: suitable
ligand binding assay: suitable

storage temp.

−20°C

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

Gene Information

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

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Amino Acid Sequence

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

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.

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Arg-Gly-Glu-Ser acetate salt ≥95% (HPLC)

Sigma-Aldrich

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Yang Kyung Cho et al.
Investigative ophthalmology & visual science, 53(4), 2328-2336 (2012-03-20)
To determine if nanoparticles delivering plasmids expressing Flt23k (an anti-VEGF intraceptor) can enhance murine cornea transplant survival and whether their effect is synergistic with steroid therapy. Biodegradable PLGA Flt23k loaded or blank nanoparticles were prepared using the emulsion solvent evaporation
Kazuyuki Onodera et al.
European journal of cell biology, 84(1), 45-58 (2005-02-24)
Biomechanical forces are major epigenetic factors that determine the form and differentiation of skeletal tissues, and may be transduced through cell adhesion to the intracellular biochemical signaling pathway. To test the hypothesis that stepwise stretching is translated to molecular signals
Lily Y Koo et al.
Journal of cell science, 115(Pt 7), 1423-1433 (2002-03-16)
Integrin-mediated cell adhesion is central to cell survival, differentiation and motility. Many cell responses induced by integrins require both receptor occupancy and receptor aggregation, and appear to be regulated by both biochemical and biophysical means. Multidomain extracellular matrix molecules may
G A Gronowicz et al.
Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research, 9(2), 193-201 (1994-02-01)
The role of integrins, cell surface receptors involved in cell adhesion to the matrix, was studied in a mineralizing organ culture system. Integrin-mediated cell attachment to matrix proteins has been shown to depend partially on the amino acid sequence Arg-Gly-Asp
J Holland et al.
Biomaterials, 17(22), 2147-2156 (1996-11-01)
A synthetic peptide, Gly-Arg-Gly-Asp-Ser-Pro-Lys (GRGDSPK), which includes the cell-adhesive region of fibronectin, Arg-Gly-Asp (RGD), was covalently bound to a dialdehyde starch (DAS) coating on a polymer surface by reductive amination. The GRGDSPK/DAS-coated surface was characterized by atomic force microscopy (AFM)
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