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Merck

A8052

Arg-Gly-Asp

≥97% (TLC)

Synonym(s):

L-arginyl-glycyl-L-aspartic acid

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About This Item

Empirical Formula (Hill Notation):
C12H22N6O6
CAS Number:
99896-85-2
Molecular Weight:
346.34
NACRES:
NA.32
PubChem Substance ID:
24891310
UNSPSC Code:
12352209
MDL number:
MFCD00057952

Product Name

Arg-Gly-Asp, ≥97% (TLC)

InChI

1S/C12H22N6O6/c13-6(2-1-3-16-12(14)15)10(22)17-5-8(19)18-7(11(23)24)4-9(20)21/h6-7H,1-5,13H2,(H,17,22)(H,18,19)(H,20,21)(H,23,24)(H4,14,15,16)/t6-,7-/m0/s1

SMILES string

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

InChI key

IYMAXBFPHPZYIK-BQBZGAKWSA-N

biological source

synthetic

assay

≥97% (TLC)

form

powder

technique(s)

cell culture | stem cell: suitable

UniProt accession no.

P02751

storage temp.

−20°C

Quality Level

200

Gene Information

human ... FN1(2335)

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Application

Arg-Gly-Asp has been used:
  • to saturate the cell surface Arg-Gly-Asp (RGD) receptors and inhibit marrow stromal cell (MSC) attachment to peptide modified hydrogel
  • in adhesion assay
  • in inhibition assay to confirm the β1-integrin-dependency of cell adhesion
  • in textile fabrication and RGD textile functionalization
  • to engineer a population of human dermal fibroblasts with impaired migration
  • to modify glass substrate and evaluate the behavior of human bone marrow mesenchymal stem cells (hBM-MSCs)
  • in the cell culture of human mammary epithelial cells

Biochem/physiol Actions

Primary sequence involved with the binding of proteins to cell surfaces

General description

Arg-Gly-Asp (RGD) is an integrin binding site, which belongs to the class of adhesive proteins. It functions as a brain tumor targeting ligand.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

Tripeptide from the cell-attachment domain of fibronectin

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
BCCN2027
BCCH7083
BCCF2800
BCCB4405
BCBV5526

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Cell attachment to thrombospondin: the role of ARG-GLY-ASP, calcium, and integrin receptors.
Lawler J, et al.
The Journal of cell biology, 107(6), 2351-2361 (1988)
Bio-active molecules modified surfaces enhanced mesenchymal stem cell adhesion and proliferation
Mobasseri R, et al.
Biochemical and biophysical research communications, 483(1), 312-317 (2017)
The effect of incorporating RGD adhesive peptide in polyethylene glycol diacrylate hydrogel on osteogenesis of bone marrow stromal cells
Yang F, et al.
Biomaterials, 26(30), 5991-5998 (2005)
Evaluation of the Osteoblast Behavior to PGA Textile Functionalized with RGD as a Scaffold for Bone Regeneration
Ortiz M, et al.
Journal of Nanomaterials, 2017 (2017)
CCN2 promotes keratinocyte adhesion and migration via integrin alpha5beta1
Kiwanuka E, et al.
Experimental Cell Research, 319(19), 2938-2946 (2013)
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