99896-85-2

Basic information

• Product Name: ARG-GLY-ASP
• Synonyms: H2N-RGD-OH;H-ARG-GLY-ASP-OH;L-ARG-GLY-ASP;ARGINYL-GLYCYL-ASPARTIC ACID;ARG-GLY-ASP;ARG-GLY-ASP PEPTIDE;Arg-Gly-Asp acetate;Arginyl-glycyl-asparagilin
• CAS NO: 99896-85-2
• Molecular Formula: C₁₂H₂₂N₆O₆
• Molecular Weight: 346.34
• Product Categories: Peptide;Cell Signaling Enzymes;ECM ProteinsCytoskeleton and Extracellular Matrix;Extracellular Matrix;Extracellular Matrix Peptides (ECM);Extracellular Matrix Peptides and ProteinsPeptides for Cell Biology;Fibronectin Fragments and Analogs;Matrix Metalloproteinases Products;Various Peptides
• Mol File: 99896-85-2.mol

Chemical Properties

• Melting Point: 153-155℃ (ethyl ether )
• Boiling Point: 597.205°C at 760 mmHg
• Flash Point: 314.979°C
• Appearance: /
• Density: 1.61 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: −20°C
• Solubility: Soluble in 0.1N acetic acid at 20mg/ml
• PKA: 2.85±0.10(Predicted)
• CAS DataBase Reference: ARG-GLY-ASP(CAS DataBase Reference)
• NIST Chemistry Reference: ARG-GLY-ASP(99896-85-2)
• EPA Substance Registry System: ARG-GLY-ASP(99896-85-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 99896-85-2(Hazardous Substances Data)

Usage

Uses

Used in Tissue Engineering:
ARG-GLY-ASP is used as a functional component in peptide-modified hydrogels for promoting cell adhesion and migration. The RGD peptide sequence helps to enhance the interaction between the hydrogel and cells, leading to improved tissue integration and regeneration.
Used in Adhesion Assays:
In cell biology research, ARG-GLY-ASP is used as a saturating agent to block cell surface RGD receptors, inhibiting marrow stromal cell (MSC) attachment to peptide-modified hydrogels. This application aids in understanding the role of specific cell adhesion molecules in cell behavior.
Used in Inhibition Assays:
ARG-GLY-ASP is employed in inhibition assays to confirm the β1-integrin-dependency of cell adhesion. By using the RGD peptide, researchers can investigate the specific interactions between cells and their extracellular matrix, providing insights into cell signaling and adhesion mechanisms.
Used in Textile Fabrication:
In the textile industry, ARG-GLY-ASP is used for RGD textile functionalization, which allows for the engineering of textiles with specific cell adhesive properties. This can lead to the development of innovative materials for medical applications, such as wound dressings or implants.
Used in Cell Culture:
ARG-GLY-ASP is used in the cell culture of human mammary epithelial cells, human dermal fibroblasts, and human bone marrow mesenchymal stem cells (hBM-MSCs) to modify their behavior and enhance their attachment, migration, and proliferation on various substrates.
Overall, ARG-GLY-ASP is a versatile molecule with applications in various industries, including biomedical research, tissue engineering, and textile manufacturing, due to its ability to modulate cell adhesion and migration.

Biological Activity

synthetic peptides containing the arginine-glycine-aspartate (rgd) were extensively used as inhibitors of integrin-ligand interactions in studies of cell adhesion, migration, growth and differentiation, since the rgd motif is an integrin-recognition motif found in many ligands.

Biochem/physiol Actions

Primary sequence involved with the binding of proteins to cell surfaces

in vitro

rgd peptide can induce apoptosis in the absence of signals and integrin-mediated cell clustering. previous study demonstrates that rgd peptides promote apoptosis through activation of conformation changes enhancing pro-caspase-3 activation and autoprocessing [1].

in vivo

anima study suggested that the rgd-4c-fitc-peptide bound to both endothelial and tumor cells in vivo and that peptide targeting should allow the delivery of therapeutic drugs to both endothelial and tumor cells [2].

references

[1] nature. 1999 feb 11;397(6719):534-9.rgd peptides induce apoptosis by direct caspase-3 activation. buckley cd1, pilling d, henriquez nv, parsonage g, threlfall k, scheel-toellner d, simmons dl, akbar an, lord jm, salmon m. [2] cancer res. 2002 sep 15;62(18):5139-43. arginine-glycine-aspartic acid (rgd)-peptide binds to both tumor and tumor-endothelial cells in vivo. zitzmann s1, ehemann v, schwab m.

InChI:InChI=1/C12H22N6O6/c13-4-6(19)12(17,10(23)24)7(9(21)22)8(20)5(14)2-1-3-18-11(15)16/h5,7H,1-4,13-14,17H2,(H,21,22)(H,23,24)(H4,15,16,18)

Synthetic route

Arg(Pbf)-Gly-Asp(OtBu) → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
With methanol; triethylsilane; water; trifluoroacetic acid at 20℃; for 2h;	72%

glycyl-L-aspartic acid (4685-12-5) + Nα,NG,NG'-tri-Boc-L-arginine N-hydroxysuccinimide ester (108787-79-7) → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
Stage #1: glycyl-L-aspartic acid; Nα,NG,NG'-tri-Boc-L-arginine N-hydroxysuccinimide ester With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 24h; Addition; Stage #2: With trifluoroacetic acid In chloroform Hydrolysis; deprotection;	54%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-(tBu)Asp-OH (71989-14-5) + N-α-Fmoc-N-γ-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-L-arginine → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
Multistep reaction;

Z-Gly-Asp(OBu)-OH (131668-52-5) → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 4-toluenesulfonic acid; H2 / Pd/C / dimethylformamide / 48 h 2.1: N-methylmorpholine / dimethylformamide / 24 h / 20 °C 2.2: 54 percent / TFA, 50 percent / CHCl3 View Scheme

p-cresol (106-44-5) + thiophenol (108-98-5) → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
In hydrogen fluoride

N-Fmoc-β-alanine (35737-10-1) + Arg-Gly-Asp (99896-85-2) + β-Alanine pNb ester hydrochloride + N-α-Fmoc-N-β-alloc-L-diaminopropionic acid (188970-92-5) → c[L-Dapa(RGD)-βAla-L-Dapa(RGD)-βAla]

Conditions	Yield
Multistep reaction;	100%

α-acryloyl-ω-N-succinimidyl-acetate-PEG + Arg-Gly-Asp (99896-85-2) → Ac-PEG-RGD

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 17h; Product distribution / selectivity; Sonographic reaction;	59%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Product distribution / selectivity;

1,2-dioleyol-sn-glycero-3-phosphoethanolamine-n-[poly(ethyleneglycol)]-N-benzotriazole carbonate, PEG MW = 3400 + Arg-Gly-Asp (99896-85-2) → 1,2-dioleyol-sn-glycero-3-phosphoethanolamine-n-[poly(ethyleneglycol)]-N-benzotriazole carbonate : Arg-Gly-Asp conjugate, 2:1 molar ratio, PEG MW = 3400

Conditions	Yield
In various solvent(s) at 4℃; for 4h; pH=7.5;

α-hydroxy-ω-N-succinimidyl-acetate-PEG + Arg-Gly-Asp (99896-85-2) → HO-PEG-RGD

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 19h;

Arg(Pbf)-Gly-Asp(OtBu) → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
With methanol; triethylsilane; water; trifluoroacetic acid at 20℃; for 2h;	72%

glycyl-L-aspartic acid (4685-12-5) + Nα,NG,NG'-tri-Boc-L-arginine N-hydroxysuccinimide ester (108787-79-7) → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
Stage #1: glycyl-L-aspartic acid; Nα,NG,NG'-tri-Boc-L-arginine N-hydroxysuccinimide ester With 4-methyl-morpholine In N,N-dimethyl-formamide at 20℃; for 24h; Addition; Stage #2: With trifluoroacetic acid In chloroform Hydrolysis; deprotection;	54%

N-(fluoren-9-ylmethoxycarbonyl)glycine (29022-11-5) + Fmoc-(tBu)Asp-OH (71989-14-5) + N-α-Fmoc-N-γ-(2,2,5,7,8-pentamethylchroman-6-sulfonyl)-L-arginine → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
Multistep reaction;

Z-Gly-Asp(OBu)-OH (131668-52-5) → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: 4-toluenesulfonic acid; H2 / Pd/C / dimethylformamide / 48 h 2.1: N-methylmorpholine / dimethylformamide / 24 h / 20 °C 2.2: 54 percent / TFA, 50 percent / CHCl3 View Scheme

p-cresol (106-44-5) + thiophenol (108-98-5) → Arg-Gly-Asp (99896-85-2)

Conditions	Yield
In hydrogen fluoride

N-Fmoc-β-alanine (35737-10-1) + Arg-Gly-Asp (99896-85-2) + β-Alanine pNb ester hydrochloride + N-α-Fmoc-N-β-alloc-L-diaminopropionic acid (188970-92-5) → c[L-Dapa(RGD)-βAla-L-Dapa(RGD)-βAla]

Conditions	Yield
Multistep reaction;	100%

α-acryloyl-ω-N-succinimidyl-acetate-PEG + Arg-Gly-Asp (99896-85-2) → Ac-PEG-RGD

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 17h; Product distribution / selectivity; Sonographic reaction;	59%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 1h; Product distribution / selectivity;

1-(vinylsulfonyl)-4-fluorobenzene (28122-14-7) + Arg-Gly-Asp (99896-85-2) → C20H29FN6O8S

Conditions	Yield
In methanol at 50℃; pH=8.5;	55%

1,2-dioleyol-sn-glycero-3-phosphoethanolamine-n-[poly(ethyleneglycol)]-N-benzotriazole carbonate, PEG MW = 3400 + Arg-Gly-Asp (99896-85-2) → 1,2-dioleyol-sn-glycero-3-phosphoethanolamine-n-[poly(ethyleneglycol)]-N-benzotriazole carbonate : Arg-Gly-Asp conjugate, 2:1 molar ratio, PEG MW = 3400

Conditions	Yield
In various solvent(s) at 4℃; for 4h; pH=7.5;

α-hydroxy-ω-N-succinimidyl-acetate-PEG + Arg-Gly-Asp (99896-85-2) → HO-PEG-RGD

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 19h;

Arg-Gly-Asp (99896-85-2) + collagen → arginine-glycine-aspartic acid peptide modified 3D collagen matrix

Conditions	Yield
With 1,2-dichloro-ethane In water at 37℃; for 18h;

isoleucinyllysinylvalylalanylvaline + Arg-Gly-Asp (99896-85-2) + collagen → arginine-glycine-aspartic acid-isoleucine-lysine-valine-alanine-valine peptides modified 3D collagen matrix

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; 1,2-dichloro-ethane In water at 37℃; for 18h;

Arg-Gly-Asp (99896-85-2) → L-malic acid (2174-58-5) + L-arginine (74-79-3) + glycine (56-40-6)

Conditions	Yield
With hydrogenchloride In water for 24h; Reflux;

Arg-Gly-Asp (99896-85-2) → α-D-L-arginine (127290-62-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 24 h / Reflux 2: deuterium / water-d2 / 36 h / 55 °C / 1500.15 Torr / Inert atmosphere View Scheme

Arg-Gly-Asp (99896-85-2) → Arg-Gly-Asp

Conditions	Yield
With deuterium In water-d2 at 55℃; under 1500.15 Torr; for 36h; Inert atmosphere; enantiospecific reaction;

C8H13N3O4S + Arg-Gly-Asp (99896-85-2) → C20H33N9O10

Conditions	Yield
With hydrogenchloride; sodium hydroxide; potassium hexacyanoferrate(III) In water; water-d2 at 20℃; for 0.333333h; pH=9;	76 %Spectr.

[18F]-1-fluoro-4-(vinylsulfonyl)benzene + Arg-Gly-Asp (99896-85-2) → C20H29(18)FN6O8S

Conditions	Yield
In methanol at 35℃; for 0.5h;

Upstream product

• 4685-12-5 glycyl-L-aspartic acid 
• 108787-79-7 N^α,N^G,N^G'-tri-Boc-L-arginine N-hydroxysuccinimide ester 
• 29022-11-5 N-(fluoren-9-ylmethoxycarbonyl)glycine 
• 71989-14-5 Fmoc-(tBu)Asp-OH 
• 131668-52-5 Z-Gly-Asp(OBu)-OH 
• 106-44-5 p-cresol 
• 108-98-5 thiophenol 

Downstream Products

• 2174-58-5 L-malic acid 
• 74-79-3 L-arginine 
• 56-40-6 glycine 

Relevant articles and documents

Synthesis of Modified RGD-Based Peptides and Their in vitro Activity

Arg-Gly-Asp (RGD) peptides represent the most outstanding recognition motif involved in cell adhesion that binds to the αvβ3 integrin, which has been targeted for cancer therapy. Various RGD-containing peptides and peptidomimetics have been designed and synthesized to selectively inhibit this integrin. In this study, the synthesis of RGD-based peptides through the incorporation of the short bioactive peptide Phe-Ala-Lys-Leu-Phe (FAKLF) at the C and N termini of RGD has been achieved by using a solid-phase peptide synthesis approach. The peptides were purified by means of preparative RP-HPLC and their structures were confirmed through HRMS (ESI). The MTT assay revealed that the RGD and FAKLF peptides inhibited the proliferation of human umbilical vein endothelial cells (HUVECs) in a dose-dependent manner, with IC50 values of 3000 and 500 ng mL?1, respectively. Interestingly, a drastic improvement was observed in the antiproliferative activity of the combined structures of the FAKLFRGD and RGDFAKLF peptides, leading to IC50 values of 200 and 136.7 ng mL?1, respectively. Meanwhile, based on apoptosis results, the potential of peptides to induce apoptosis, in accordance with their antiproliferative activity, indicated that the RGD and FAKLF peptides, and the peptides synthesized based on their combinations induced cell apoptosis in a dose-dependent manner followed by inhibition of the proliferation of endothelial cells. Moreover, the incorporation of d-leucine increased the induction of apoptosis by these peptides.

Arg-Gly-Asp (RGD) Sequence Containing Cyclic Peptide and Its Active Targeting Liposomes

The present invention relates to the field of pharmaceutics and clinical pharmacy, involving the preparation method and application of a cyclic peptide containing Argnine-Glycine-Aspartate sequence and its active targeting liposomes. The cyclic peptide described here meets the requirement for ligand in that it forms ring by amide linkage with stable sterical structure, it shows low propensity to degrade, and it carries an active hydrosulfide group which is easy to modify carriers. The artificially synthesized peptide, which has a small molecular weight and low propensity to cause immune response, can be used as the ligand to bind with the integrin on the surface of HSC. The active targeting liposome established with the cyclic peptide realized cell-targeted therapy of experimental hepatic fibrosis via receptor-mediated pathway. The invention can target RGD cyclic peptide-labeled interferon-loaded liposomes to the fibrotic liver and its good efficacy in the treatment of hepatic fibrosis has been proven by experiments in rats in vitro and in vivo.

Preparation and biological activities of a bivalent poly(ethylene glycol) hybrid containing an active site and its synergistic site of fibronectin.

A bivalent poly(ethylene glycol) or PEG hybrid of fibronectin-related peptides was prepared. An active site peptide (RGD) and its synergistic site peptide (PHSRN) of fibronectin were conjugated with an amino acid-type PEG (aaPEG) to form PHSRN-aaPEG-RGD.

Tripeptides useful as immunostimulants as well as in the prevention of metastases

The present invention is referred to tripeptides having the following general formula: where X=L-Arg or D-Arg and Y=L-Asp or D-Asp. These tripeptides, endowed with both immunostimulant and antimetastatic properties, are active not only after parenteral administration, but also after oral treatment. The invention is also related to the procedure for the preparation of said compounds.