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Cyclo (-RGDfK)

Inhibitor of αvβ3 integrin CAS# 161552-03-0

Cyclo (-RGDfK)

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Quality Control of Cyclo (-RGDfK)

Number of papers citing our products

Chemical structure

Cyclo (-RGDfK)

3D structure

Chemical Properties of Cyclo (-RGDfK)

Cas No. 161552-03-0 SDF Download SDF
PubChem ID 10196873 Appearance Powder
Formula C27H41N9O7 M.Wt 603.7
Type of Compound N/A Storage Desiccate at -20°C
Solubility DMSO : 125 mg/mL (207.07 mM; Need ultrasonic)
H2O : 50 mg/mL (82.83 mM; Need ultrasonic)
Sequence Cyclo(-Arg-Gly-Asp-D-Phe-Lys)
Chemical Name 2-[(2S,5R,8S,11S)-8-(4-aminobutyl)-5-benzyl-11-[3-(diaminomethylideneamino)propyl]-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]acetic acid
SMILES C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CCCN=C(N)N)CCCCN)CC2=CC=CC=C2)CC(=O)O
Standard InChIKey NVHPXYIRNJFKTE-HAGHYFMRSA-N
Standard InChI InChI=1S/C27H41N9O7/c28-11-5-4-9-18-24(41)34-17(10-6-12-31-27(29)30)23(40)32-15-21(37)33-20(14-22(38)39)26(43)36-19(25(42)35-18)13-16-7-2-1-3-8-16/h1-3,7-8,17-20H,4-6,9-15,28H2,(H,32,40)(H,33,37)(H,34,41)(H,35,42)(H,36,43)(H,38,39)(H4,29,30,31)/t17-,18-,19+,20-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Cyclo (-RGDfK)

DescriptionCyclo (-RGDfK) is a potent and selective inhibitor of the αvβ3 integrin.
TargetsIntegrin    

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Background on Cyclo (-RGDfK)

In one study where this peptide was labeled with 125I, it was found to bind specifically and with high affinity to αvβ3 receptors on neovascular blood vessel sections of different major human cancers. The integrin alpha(IIb)beta(3)-specific cyclic hexapeptide contains an Arg-Gly-Asp (RGD) sequence.

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References on Cyclo (-RGDfK)

(18)F-Fluoroglucosylation of peptides, exemplified on cyclo(RGDfK).[Pubmed:19350236]

Eur J Nucl Med Mol Imaging. 2009 Sep;36(9):1469-74.

PURPOSE: Oxime formation between an aminooxy-functionalized peptide and an (18)F-labelled aldehyde has recently been introduced as a powerful method for the rapid one-step chemoselective synthesis of radiofluorinated peptides. MATERIALS AND METHODS: Here, the potential of using routinely produced and thus readily available [(18)F]fluorodeoxyglucose ([(18)F]FDG) as the aldehydic prosthetic group was investigated using an aminooxyacetyl-conjugated cyclic RGD peptide (cyclo(RGDfK(Aoa-(Boc)) as a model peptide. RESULTS: The use of [(18)F]FDG from routine production ([(18)F]FDGTUM) containing an excess of D: -glucose did not allow the radiosynthesis of [(18)F]FDG-RGD in activities >37 MBq in reasonable yield, rendering the direct use of clinical grade [(18)F]FDG for the routine clinical synthesis of (18)F-labelled peptides impossible. Using no-carrier-added (n.c.a.) [(18)F]FDG obtained via HPLC separation of [(18)F]FDGTUM from excess glucose, however, afforded [(18)F]FDG-RGD in yields of 56-93% (decay corrected) and activities up to 37 MBq. Suitable reaction conditions were 20 min at 120 degrees C and pH 2.5, and a peptide concentration of 5 mM. In a preliminary in vivo biodistribution study in M21 melanoma-bearing nude mice, [(18)F]FDG-RGD showed increased tumour accumulation compared to the "gold standard" [(18)F]galacto-RGD (2.18 vs 1.49 %iD/g, respectively, at 120 min after injection), but also slightly increased uptake in non-target organs, leading to comparable tumour/organ ratios for both compounds. CONCLUSION: These data demonstrate that chemoselective (18)F-labelling of aminooxy-functionalized peptides using n.c.a. [(18)F]FDG represents a radiofluorination/glycosylation strategy that allows preparation of (18)F-labelled peptides in high yield with suitable pharmacokinetics. As soon as the necessary n.c.a. preparation of [(18)F]FDG prior to reaction with the Aoa-peptide can be implemented in a fully automated [(18)F]FDG-synthesis, [(18)F]fluoroglucosylation of peptides may represent a promising alternative to currently used chemoselective one-step (18)F-labelling protocols.

Molecular targeting radiotherapy with cyclo-RGDFK(C) peptides conjugated to 177Lu-labeled gold nanoparticles in tumor-bearing mice.[Pubmed:24730235]

J Biomed Nanotechnol. 2014 Mar;10(3):393-404.

Peptides based on the cyclic Arg-Gly-Asp (RGD) sequence have been designed to antagonize the function of alpha(v)beta(3) integrin, thereby inhibiting angiogenesis. The conjugation of RGD peptides to radiolabeled gold nanoparticles (AuNP) produces biocompatible and stable multimeric systems with target-specific molecular recognition. The aim of this research was to evaluate the therapeutic response of 177Lu-AuNP-RGD in athymic mice bearing alpha(v)beta(3)-integrin-positive C6 gliomas and compare it with that of 177Lu-AuNP or 177Lu-RGD. The radiation absorbed dose, metabolic activity (SUV, [18F]fluor-deoxy-glucose-microPET/CT), histological characteristics and VEGF gene expression (by real-time polymerase chain reaction) in tumor tissues following treatment with 177Lu-AuNP-RGD, 177Lu-AuNP or 177Lu-RGD were assessed. Of the radiopharmaceuticals evaluated, 1177Lu-AuNP-RGD delivered the highest tumor radiation absorbed dose (63.8 +/- 7.9 Gy). These results correlated with the observed therapeutic response, in which 177Lu-AuNP-RGD significantly (p < 0.05) induced less tumor progression, less tumor metabolic activity, fewer intratumoral vessels and less VEGF gene expression than the other radiopharmaceuticals, a consequence of high tumor retention and a combination of molecular targeting therapy (multimeric RGD system) and radiotherapy (177Lu). There was a low uptake in non-target organs and no induction of renal toxicity. 177Lu-labeled gold nanoparticles conjugated to cyclo-RGDfK(C) demonstrate properties suitable for use as an agent for molecular targeting radiotherapy.

Description

Cyclo(-RGDfK) is a potent and selective inhibitor of the αvβ3 integrin, with an IC50 of 0.94 nM.

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