Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H22N6O6 |
| Molecular Weight | 346.3397 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| 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)=O
InChI
InChIKey=IYMAXBFPHPZYIK-BQBZGAKWSA-N
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
| Molecular Formula | C12H22N6O6 |
| Molecular Weight | 346.3397 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28815721 | https://www.ncbi.nlm.nih.gov/pubmed/27768038 | https://www.ncbi.nlm.nih.gov/pubmed/26514175
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/28815721 | https://www.ncbi.nlm.nih.gov/pubmed/27768038 | https://www.ncbi.nlm.nih.gov/pubmed/26514175
Arginyl-Glycyl-Aspartic Acid is a tripeptide composed of L-arginine, glycine, and L-aspartic acid, used as a biochemical tool in the study of cellular recognition. Arginylglycylaspartic acid hows great affinity for the integrin receptors and Arg-Gly-Asp tripeptide motif can be used for Peptide-Based Target Drug Delivery of anticancer agents. The tripeptide Arg-Gly-Asp (RGD) is an important protein sequence in the binding of proteins to cell surfaces. The RGD motif was identified in fibronectin, vitronectin, osteopontin, collagens, thrombospondin, fibrinogen, and von Willebrand factor. Many adhesive extracellular matrix, blood, and cell surface proteins recognize the RGD sequence for cell attachment.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Processing of integrin alpha(v) subunit by membrane type 1 matrix metalloproteinase stimulates migration of breast carcinoma cells on vitronectin and enhances tyrosine phosphorylation of focal adhesion kinase. | 2002-03-22 |
|
| Identification of a contact domain between echistatin and the integrin alpha(v)beta(3) by photoaffinity cross-linking. | 2001-12-18 |
|
| In vivo characterization of a porous hydrogel material for use as a tissue bulking agent. | 2001-12-15 |
|
| Ketone-DNA: a versatile postsynthetic DNA decoration platform. | 2001-12-13 |
|
| Platelets modulate ischemia/reperfusion-induced leukocyte recruitment in the mesenteric circulation. | 2001-12 |
|
| Localization of an integrin binding site to the C terminus of talin. | 2001-11-30 |
|
| Stearylated arginine-rich peptides: a new class of transfection systems. | 2001-11-22 |
|
| Molecular cloning of POEM: a novel adhesion molecule that interacts with alpha8beta1 integrin. | 2001-11-09 |
|
| Efficient gene transfer by fiber-mutant adenoviral vectors containing RGD peptide. | 2001-11-07 |
|
| A novel synthetic Arg-Gly-Asp-containing peptide cyclo(-RGDf==V-) is the potent inhibitor of angiogenesis. | 2001-11-02 |
|
| Efficient antigen gene transduction using Arg-Gly-Asp fiber-mutant adenovirus vectors can potentiate antitumor vaccine efficacy and maturation of murine dendritic cells. | 2001-11-01 |
|
| Polarity, protrusion-retraction dynamics and their interplay during keratinocyte cell migration. | 2001-11-01 |
|
| Vasomotor effects of arg-gly-asp (RGD) peptides are limited and not related to endothelium-derived hyperpolarizing factor-mediated relaxation in rat mesenteric arteries. | 2001-11 |
|
| In vivo modulation of host response and macrophage behavior by polymer networks grafted with fibronectin-derived biomimetic oligopeptides: the role of RGD and PHSRN domains. | 2001-11 |
|
| Effect of RGD coating on osteocompatibility of PLGA-polymer disks in a rat tibial wound. | 2001-11 |
|
| Photochemical rearrangement of oxaziridines and nitrones in the hexahydroindole series: a convenient synthetic route to 1-azabicyclo[5.2.0]nonan-2-ones as novel RGD mimetics. | 2001-10-04 |
|
| Scaling the microrheology of living cells. | 2001-10-01 |
|
| Potential tumor-targeting peptide vector of histidylated oligolysine conjugated to a tumor-homing RGD motif. | 2001-10 |
|
| Induction of apoptosis of integrin-expressing human prostate cancer cells by cyclic Arg-Gly-Asp peptides. | 2001-10 |
|
| Radiation-mediated control of drug delivery. | 2001-10 |
|
| Osteoclast inhibitory peptide 2 inhibits osteoclast formation via its C-terminal fragment. | 2001-10 |
|
| Antibody neutralization epitopes and integrin binding sites on nonenveloped viruses. | 2001-09-30 |
|
| Intrinsic activating properties of GP IIb/IIIa blockers. | 2001-09-30 |
|
| In vivo gene transfer to cerebral white matter lesions with a recombinant adenovirus vector. | 2001-09-21 |
|
| Targeting of high-capacity adenoviral vectors. | 2001-09-20 |
|
| Highly efficient synthesis of peptide-oligonucleotide conjugates: chemoselective oxime and thiazolidine formation. | 2001-09-17 |
|
| Integrin-mediated activation of Cdc42 controls cell polarity in migrating astrocytes through PKCzeta. | 2001-08-24 |
|
| Recognition of fibronectin by the platelet integrin alpha IIb beta 3 involves an extended interface with multiple electrostatic interactions. | 2001-08-07 |
|
| [In vitro bovine and human lens epithelial cell culture studies on inhibition of posterior capsule opacification using a cyclic RGD peptide]. | 2001-08 |
|
| Structural studies of a neuropeptide precursor protein with an RGD proteolytic site. | 2001-07-31 |
|
| Enhanced gene transfer to rabbit jugular veins by an adenovirus containing a cyclic RGD motif in the HI loop of the fiber knob. | 2001-07-17 |
|
| Thy-1 binds to integrin beta(3) on astrocytes and triggers formation of focal contact sites. | 2001-07-10 |
|
| Incorporation of map kinases into the platelet cytoskeleton. | 2001-07-01 |
|
| Positional importance of Pro53 adjacent to the Arg49-Gly50-Asp51 sequence of rhodostomin in binding to integrin alphaIIbbeta3. | 2001-07-01 |
|
| Radiolabeled peptide ligands for imaging thrombi and emboli. | 2001-07 |
|
| Prevention of posterior capsule opacification by intraoperative single-dose pharmacologic agents. | 2001-07 |
|
| AlphaIIbbeta3 and its antagonism at the new millennium. | 2001-07 |
|
| Novel platelet products, substitutes and alternatives. | 2001-06 |
|
| Conjugation of Arg-Gly-Asp (RGD) sequence in copolymer bearing sugar moiety for insulinoma cell line (MIN6) culture. | 2001-06 |
|
| Gingival, dermal, and periodontal ligament fibroblasts express different extracellular matrix receptors. | 2001-06 |
|
| [RGD peptides and endothelialization of biomaterials]. | 2001-06 |
|
| Intravitreal injection of plasminogen kringle 5, an endogenous angiogenic inhibitor, arrests retinal neovascularization in rats. | 2001-06 |
|
| Insulin-like growth factor-binding protein 1 stimulates human trophoblast migration by signaling through alpha 5 beta 1 integrin via mitogen-activated protein Kinase pathway. | 2001-06 |
|
| Costimulation by extracellular matrix proteins determines the response to TCR ligation. | 2001-05-25 |
|
| Topical application of integrin antagonists inhibits proliferative retinopathy. | 2001-05 |
|
| Fibronectin modulates macrophage adhesion and FBGC formation: the role of RGD, PHSRN, and PRRARV domains. | 2001-04 |
|
| Platelet aggregation inhibition with glycoprotein IIb--IIIa inhibitors. | 2001-04 |
|
| Suppression of murine collagen-induced arthritis by targeted apoptosis of synovial neovasculature. | 2001 |
|
| Platelet-fibrinogen interactions. | 2001 |
|
| Immunosuppressory activity of the cyclodimeric peptide with RGD-sequences. | 2001 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:12:39 GMT 2025
by
admin
on
Mon Mar 31 22:12:39 GMT 2025
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| Record UNII |
78VO7F77PN
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| Record Status |
Validated (UNII)
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| Record Version |
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Preferred Name | English | ||
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Arginylglycylaspartic acid
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78VO7F77PN
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99896-85-2
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DTXSID30912420
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C047981
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104802
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