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G1269

Sigma-Aldrich

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

≥97% (HPLC)

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Synonym(s):
GRGDSPK
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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Information

常规特殊物品

Certificates of Analysis (COA)

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Pierre-Henri Puech et al.
Journal of cell science, 118(Pt 18), 4199-4206 (2005-09-13)
During vertebrate gastrulation, progenitor cells of different germ layers acquire specific adhesive properties that contribute to germ layer formation and separation. Wnt signals have been suggested to function in this process by modulating the different levels of adhesion between the
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)
Christine Selhuber-Unkel et al.
Biophysical journal, 95(11), 5424-5431 (2008-08-12)
We have studied the initial phase of cell adhesion as a function of the lateral organization of individual integrin molecules with single-cell force microscopy. Nanostructures, consisting of hexagonally ordered gold dots, were prepared with diblock-copolymer micelle lithography and functionalized with
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
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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