Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C15H27N7O8 |
| Molecular Weight | 433.417 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
N[C@@H](CCCNC(N)=N)C(=O)NCC(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CO)C(O)=O
InChI
InChIKey=NNRFRJQMBSBXGO-CIUDSAMLSA-N
InChI=1S/C15H27N7O8/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/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)/t7-,8-,9-/m0/s1
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11262082 | https://www.ncbi.nlm.nih.gov/pubmed/11844677 | https://www.ncbi.nlm.nih.gov/pubmed/17571867
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/11262082 | https://www.ncbi.nlm.nih.gov/pubmed/11844677 | https://www.ncbi.nlm.nih.gov/pubmed/17571867
Fibronectin tetrapeptide (RGDS peptide) is a key component of the cell attachment domain of fibronectin fibrinogen α, and von Willebrand factor, that interacts with αVβ1 and αVβ3 integrins. The Fibronectin tetrapeptide sequence was found initially to promote the attachment of rat kidney fibroblasts (NRK cells) to fibronectin and synthetic fibronectin peptides coupled to protein-coated plastic. Further investigation indicated that the free Fibronectin tetrapeptide peptide inhibited the attachment of NRK cells to fibronectin-coated substrates. The RGDS sequence has been shown to occur in several other proteins, such as the λ receptor on E. coli and the Sindbis coat protein. RGDS is also a target sequence for spirochete adherence of the syphilis bacterium Treponema pallidum. RGDS has been shown to block fibrinogen-induced aggregation of intact erythrocytes and specific binding of fibrinogen to erythrocyte membranes. The effect of RGDS on transforming growth factor ß1 (TGFß1) mRNA expression and secretion in cultured human mesangial cells have been investigated. RGDS has been utilized in a study of integrin-mediated signal transduction in cultured cells from the sponge Suberites domuncula. RGDS has been demonstrated to mitigate the binding of Mycobacterium tuberculosis to murine alveolar macrophages
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Experimental study of the preparation of targeted microbubble contrast agents carrying urokinase and RGDS. | 2009-12 |
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| Insulin-induced laminin expression promotes a hypercontractile airway smooth muscle phenotype. | 2009-10 |
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| Binding of plasma factor XIII to thrombin-receptor activated human platelets. | 2009-07 |
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| Controlled capture and release of cardiac fibroblasts using peptide-functionalized alginate gels in microfluidic channels. | 2009-06-07 |
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| The role of RGD-tagged helical rosette nanotubes in the induction of inflammation and apoptosis in human lung adenocarcinoma cells through the P38 MAPK pathway. | 2009-06 |
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| Photodegradable hydrogels for dynamic tuning of physical and chemical properties. | 2009-04-03 |
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| Synthetic RGDS peptide attenuates lipopolysaccharide-induced pulmonary inflammation by inhibiting integrin signaled MAP kinase pathways. | 2009-03-09 |
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| Inhibition of integrin alphavbeta3 prevents urokinase plasminogen activator-mediated impairment of cerebrovasodilation after cerebral hypoxia/ischemia. | 2009-03 |
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| Integrin alpha(v)beta(3) on human endothelial cells binds von Willebrand factor strings under fluid shear stress. | 2009-02-12 |
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| A simple electrochemical cytosensor array for dynamic analysis of carcinoma cell surface glycans. | 2009 |
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| Development of a RGDS-peptide modified polyurethane for tissue regeneration. | 2009 |
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| Cellular procoagulant activity dictates clot structure and stability as a function of distance from the cell surface. | 2008-12 |
|
| Titanium foam-bioactive nanofiber hybrids for bone regeneration. | 2008-12 |
|
| Alcalase-catalysed synthesis of the precursor tetrapeptide N-benzoylarginylglycylaspartylserinamide (Bz-RGDS-NH2) of the cell-adhesion peptide arginylglycylaspartylserine (RGDS). | 2008-11 |
|
| Three-dimensional micropatterning of bioactive hydrogels via two-photon laser scanning photolithography for guided 3D cell migration. | 2008-07 |
|
| Influence of integrin-blocking peptide on gadolinium- and hypertonic shrinking-induced neurotransmitter release in rat brain synaptosomes. | 2008-07 |
|
| Peptide array-based screening of human mesenchymal stem cell-adhesive peptides derived from fibronectin type III domain. | 2008-06-20 |
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| Expression of podocalyxin enhances the adherence, migration, and intercellular communication of cells. | 2008-06-10 |
|
| Phospholipase D in human platelets: presence of isoenzymes and participation of autocrine stimulation during thrombin activation. | 2008-05 |
|
| Adhesion to fibronectin induces megakaryocytic differentiation of JAS-REN cells. | 2008-04-04 |
|
| Covalent functionalization of NiTi surfaces with bioactive peptide amphiphile nanofibers. | 2008-03 |
|
| Physico-chemical and thermodynamic aspects of fibroblastic attachment on RGDS-modified chitosan membranes. | 2008-02-15 |
|
| TGF beta-induced contraction is not promoted by fibronectin-fibronectin receptor interaction, or alpha SMA expression. | 2008-02 |
|
| A vascular targeted pan phosphoinositide 3-kinase inhibitor prodrug, SF1126, with antitumor and antiangiogenic activity. | 2008-01-01 |
|
| RGDS peptides immobilized on titanium alloy stimulate bone cell attachment, differentiation and confer resistance to apoptosis. | 2007-12-01 |
|
| The use of biotin-avidin binding to facilitate biomodification of thermoresponsive culture surfaces. | 2007-12 |
|
| EGFR plays a pivotal role in the regulation of polyamine-dependent apoptosis in intestinal epithelial cells. | 2007-12 |
|
| Src tyrosine kinases mediate activations of NF-kappaB and integrin signal during lipopolysaccharide-induced acute lung injury. | 2007-11-15 |
|
| [The degrading mechanism of collagen promoted by RGDS in hepatic stellate cell]. | 2007-09 |
|
| Patterned biofunctional designs of thermoresponsive surfaces for spatiotemporally controlled cell adhesion, growth, and thermally induced detachment. | 2007-09 |
|
| Evaluation of L929 fibroblast attachment and proliferation on Arg-Gly-Asp-Ser (RGDS)-immobilized chitosan in serum-containing/serum-free cultures. | 2007-07 |
|
| Glucose modulates handling of apoptotic cells by mesangial cells: involvement of TGF-beta1. | 2007-07 |
|
| Chondrogenic differentiation potential of human mesenchymal stem cells photoencapsulated within poly(ethylene glycol)-arginine-glycine-aspartic acid-serine thiol-methacrylate mixed-mode networks. | 2007-05 |
|
| Efficient modification on PLLA by ozone treatment for biomedical applications. | 2007-04-10 |
|
| Transendothelial migration enhances integrin-dependent human neutrophil chemokinesis. | 2007-03 |
|
| The effect of heparin-functionalized PEG hydrogels on three-dimensional human mesenchymal stem cell osteogenic differentiation. | 2007-01 |
|
| Staphylococcus aureus adhesion via Spa, ClfA, and SdrCDE to immobilized platelets demonstrates shear-dependent behavior. | 2006-10 |
|
| Bio-functionalized thermoresponsive interfaces facilitating cell adhesion and proliferation. | 2006-10 |
|
| Synthesis of tetrapeptide Bz-RGDS-NH2 by a combination of chemical and enzymatic methods. | 2006-09-18 |
|
| [Inhibitory effect of RGDS peptide on experimental choroidal neovascularization in a rat model]. | 2006-09 |
|
| Integrin engagement modulates the phosphorylation of focal adhesion kinase, phagocytosis, and cell spreading in molluscan defence cells. | 2006-08 |
|
| Biomimetic modification of titanium dental implant model surfaces using the RGDSP-peptide sequence: a cell morphology study. | 2006-07 |
|
| Effects of CD44 antibody-- or RGDS peptide--immobilized magnetic beads on cell proliferation and chondrogenesis of mesenchymal stem cells. | 2006-06-15 |
|
| Presentation of RGDS epitopes on self-assembled nanofibers of branched peptide amphiphiles. | 2006-06 |
|
| Synthesis of a precursor dipeptide of RGDS (Arg-Gly-Asp-Ser) catalysed by the industrial protease alcalase. | 2006-05 |
|
| Photolithographic patterning of polyethylene glycol hydrogels. | 2006-04 |
|
| RGD-containing molecules induce macropinocytosis in ascidian hyaline amoebocytes. | 2006-02 |
|
| Generic bioaffinity silicone surfaces. | 2006-01-19 |
|
| CHO cells expressing the high affinity alpha(IIb)beta3 T562N integrin demonstrate enhanced adhesion under shear. | 2006-01 |
|
| Alcalase-catalyzed, kinetically controlled synthesis of a precursor dipeptide of RGDS in organic solvents. | 2006 |
Patents
Sample Use Guides
Ovariectomized mice have been treated with Fibronectin tetrapeptide at 0.1103 mmol/kg, i.p. once daily for 4 weeks
Route of Administration:
Intraperitoneal
Effects of compound 6 (Fibronectin tetrapeptide) were evaluated on the adhesion of highly pulmonary metastatic SACC cell line SACC-LM and platelets. Cells (5 x 10^4) were incubated with the fluorescent dye (2 mkg/ml) in HBSS for 30 min at 37C. Following incubation, cells were washed once in PBS and finally resuspended in serum-free DMEM/HF12K containing 0.5% of the medium supplement ITS +. Plates were coated overnight at 4C with 50 mkl of fibronectin (30mkg/ml), vitronectin (15 mkg/ml), laminin (15 mkg/ml) and collagen type I and type IV (80 mkg/ml) in PBS. Cells were treated with rhodostomin or Fibronectin tetrapeptide (15 min at 25C) before adhesion assay. Control or treated cells (2.5 x 10^4) were added to each well and incubated for 24 h at 37C. The non-adherent cells were removed by aspiration and the plates read with a CytoFluor 2300 fluorescence plate reader
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DTXSID50920002
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91037-65-9
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107775
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AC6UDA2MFC
Created by
admin on Mon Mar 31 19:44:06 GMT 2025 , Edited by admin on Mon Mar 31 19:44:06 GMT 2025
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ACTIVE MOIETY
