A peptide from the cell attachment site of fibronectin
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RGDS Peptide (trifluoroacetate salt)

Item No. 15359

Technical Information
Formal Name
L-arginylglycyl-L-α-aspartyl-L-serine, trifluoroacetate salt
Synonyms
  • Fibronectin Inhibitor
  • H-Arg-Gly-Asp-Ser-OH
Molecular Formula
C15H27N7O8 • XCF3COOH
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 50 mg/mlDMSO: 25 mg/mlEthanol: 30 mg/mlPBS (pH 7.2): 10 mg/ml
SMILES
O=C(N[C@@H](CC(O)=O)C(N[C@@H](CO)C(O)=O)=O)CNC([C@@H](N)CCCNC(N)=N)=O.OC(C(F)(F)F)=O
InChi Code
InChI=1S/C15H27N7O8.C2HF3O2/c16-7(2-1-3-19-15(17)18)12(27)20-5-10(24)21-8(4-11(25)26)13(28)22-9(6-23)14(29)30;3-2(4,5)1(6)7/h7-9,23H,1-6,16H2,(H,20,27)(H,21,24)(H,22,28)(H,25,26)(H,29,30)(H4,17,18,19);(H,6,7)/t7-,8-,9-;/m0./s1
InChi Key
UMHUNRXMVGQLTE-YWUTZLAHSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    RGDS peptide is a tetrapeptide found on fibronectin, fibrinogen α, and von Willebrand factor, but not vitronectin or collagen.1,2 RGDS interacts with α5β1 and αVβ3 integrins.3 This tetrapeptide interferes with the attachment of cells to fibronectin-coated surfaces (Ki = 0.6 mM).1,2 It also blocks the attachment of certain pathogens to cells.4,5 RGDS peptide inhibits thrombin-induced binding of platelets to fibronectin, fibrinogen α, and von Willebrand factor (IC50 = ~10 μM).1,6,7 The interaction of RGDS peptide with cell surface integrins alters intracellular signaling in ways that are cell- and stimulus-specific.8,9

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Haverstick, D.M., Cowan, J.F., Yamada, K.M., et alInhibition of platelet adhesion to fibronectin, fibrinogen, and von Willebrand factor substrates by a synthetic tetrapeptide derived from the cell-binding domain of fibronectin. Blood 66(4), 946-952 (1985).

    2. Pierschbacher, M.D., and Ruoslahti, E. Cell attachment activity of fibronectin can be duplicated by small synthetic fragments of the molecule. Nature 309(5963), 30-33 (1984).

    3. Basani, R.B., D'Andrea, G., Mitra, N., et alRGD-containing peptides inhibit fibrinogen binding to platelet αIIbβ3 by inducing an allosteric change in the amino-terminal portion of αIIb. The Journal of Biological Chemisty 276(17), 13975-13981 (2014).

    4. Pottratz, S.T., and Martin, W.J., II Mechanism of Pneumocystis carinii attachment to cultured rat alveolar macrophages. J. Clin. Invest. 86(5), 1678-1683 (1990).

    5. Thomas, D.D., Baseman, J.B., and Alderete, J.F. Fibronectin tetrapeptide is target for syphilis spirochete cytadherence. J. Exp. Med. 162(5), 1715-1719 (1985).

    6. Gartner, T.K., and Bennett, J.S. The tetrapeptide analogue of the cell attachment site of fibronectin inhibits platelet aggregation and fibrinogen binding to activated platelets. The Journal of Biological Chemisty 260(22), 11891-11894 (1985).

    7. Ginsberg, M., Pierschbacher, M.D., Ruoslahti, E., et alInhibition of fibronectin binding to platelets by proteolytic fragments and synthetic peptides which support fibroblast adhesion. The Journal of Biological Chemisty 260(7), 3931-3936 (1985).

    8. Dekkers, B.G.J., Bos, I.S.T., Gosens, R., et alThe integrin-blocking peptide RGDS inhibits airway smooth muscle remodeling in a guinea pig model of allergic asthma. Am. J. Respir. Crit. Care Med. 181(6), 556-565 (2010).

    9. Moon, C., Han, J.R., Park, H.J., et alSynthetic RGDS peptide attenuates lipopolysaccharide-induced pulmonary inflammation by inhibiting integrin signaled MAP kinase pathways. Respir. Res. 10(1), 18 (2009).