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Purity: ≥98%
Cyclo(-RGDfK) is a potent, selective and cyclo-peptide-based αvβ3 integrin inhibitor with potential antitumor activity. The constant of affinity (KD) of Cyclo (-RGDfK-) for purified integrin is 41.70 nM. Cyclo (-RGDfK) can react with HEK293(β3) cells moderately. Cyclo(-RGDfK-) modified micelles shows strong affinity to T-24 cells and strong inhibitory effect on the proliferation of T-24 cells.
| Targets |
The target of Cyclo(-RGDfK) is integrin αvβ3. It binds to integrin αvβ3 with high affinity [1] [2]
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| ln Vitro |
Cyclo(-RGDfK), which has an IC50 of 0.94 nM, is a strong and specific αvβ3 integrin inhibitor[1]. [66 Gal]DOTA-E–[c(RGDfK)]2, with moderate protein binding, in vitro stability, high radiochemical purity (>97%), and specific activity (36-67GBq/μM), can be prepared. Contrasting tumors reflecting αvβ3-targeted tracer accumulation were seen in microPET imaging up to 24 hours after injection[2].
Cyclo(-RGDfK) exhibits specific binding to integrin αvβ3-expressing cells. In cell binding assays using U87MG glioblastoma cells (which express high levels of integrin αvβ3), radiolabeled conjugates of Cyclo(-RGDfK) (e.g., ⁶⁸Ga-NOPO-c(RGDfK)) show significant binding, which can be competitively inhibited by an excess of unlabeled Cyclo(-RGDfK). This confirms the specific interaction with integrin αvβ3 [1] In another in vitro study with U87MG cells, the radiolabeled conjugate ⁶⁶Ga-DOTA-E(c(RGDfK))₂, which contains Cyclo(-RGDfK) moieties, demonstrates dose-dependent binding to the cells, further supporting the specific targeting of integrin αvβ3 by Cyclo(-RGDfK) [2] |
| ln Vivo |
In athymic nude mice bearing U87MG glioblastoma xenografts, radiolabeled Cyclo(-RGDfK) conjugates (⁶⁸Ga-NOPO-c(RGDfK)) show significant accumulation in tumors, as measured by positron emission tomography (PET) imaging. Tumor uptake reaches a peak at 1 hour post-injection, with a tumor-to-muscle ratio of approximately 6.5. Ex vivo biodistribution studies confirm high tumor uptake, with lower accumulation in normal tissues (e.g., liver, kidney) [1]
In mice with U87MG xenografts, ⁶⁶Ga-DOTA-E(c(RGDfK))₂ (containing Cyclo(-RGDfK)) exhibits high tumor uptake and retention, with a tumor-to-blood ratio of about 5 at 4 hours post-injection. This indicates effective targeting of integrin αvβ3-positive tumors in vivo [2] In athymic mice bearing α(v)β(3)-integrin-positive C6 gliomas, Cyclo (-RGDfK-) modification induces less tumor progression, less tumor metabolic activity, fewer intratumoral vessels. |
| Cell Assay |
For cell binding studies, U87MG cells are seeded in multi-well plates and incubated with radiolabeled Cyclo(-RGDfK) conjugates (e.g., ⁶⁸Ga-NOPO-c(RGDfK)) in the presence or absence of excess unlabeled Cyclo(-RGDfK). After incubation at 37°C for a specified time, the cells are washed to remove unbound radioligand, and the radioactivity associated with the cells is measured. Specific binding is calculated as the difference between total binding and non-specific binding (in the presence of excess unlabeled ligand) [1] [2]
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| Animal Protocol |
Athymic nude mice are implanted subcutaneously with U87MG glioblastoma cells to establish xenograft models. Once tumors reach a volume of ~100-200 mm³, mice are injected intravenously with radiolabeled Cyclo(-RGDfK) conjugates (e.g., ⁶⁸Ga-NOPO-c(RGDfK) or ⁶⁶Ga-DOTA-E(c(RGDfK))₂) via the tail vein. For PET imaging, mice are anesthetized at various time points post-injection (e.g., 0.5, 1, 2 hours) and scanned to assess tumor uptake. For biodistribution studies, mice are euthanized at specific time points, and tissues (tumor, blood, liver, kidney, muscle, etc.) are collected, weighed, and their radioactivity is measured to calculate the percentage of injected dose per gram of tissue (%ID/g) [1] [2]
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| References |
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| Additional Infomation |
Cyclo(-RGDfK) is a cyclic peptide that acts as a selective ligand for integrin αvβ3, a cell surface receptor overexpressed in many tumors, including glioblastomas. Its high affinity for integrin αvβ3 makes it a useful targeting moiety in the development of radiopharmaceuticals for imaging and potentially therapy of integrin αvβ3-positive tumors [1] [2]
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| Molecular Formula |
C₂₇H₄₁N₉O₇
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|---|---|
| Molecular Weight |
603.67
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| Exact Mass |
603.312
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| CAS # |
161552-03-0
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| Related CAS # |
Cyclo(-RGDfK) TFA;500577-51-5
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| PubChem CID |
10196873
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| Sequence |
cyclo[Arg-Gly-Asp-D-Phe-Lys];
cyclo[L-arginyl-glycyl-L-alpha-aspartyl-D-phenylalanyl-L-lysyl]; Cyclo(Arg-Gly-Asp-Phe-Lys)
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| SequenceShortening |
Cyclo(RGDFK); (cyclo)-RGD{d}FK-(cyclo)
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| Appearance |
White to off-white solid powder
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| Density |
1.5±0.1 g/cm3
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| Index of Refraction |
1.666
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| LogP |
-3.1
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| Hydrogen Bond Donor Count |
9
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
12
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| Heavy Atom Count |
43
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| Complexity |
1010
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| Defined Atom Stereocenter Count |
4
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| SMILES |
C1C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1)CCCN=C(N)N)CCCCN)CC2=CC=CC=C2)CC(=O)O
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| InChi Key |
NVHPXYIRNJFKTE-HAGHYFMRSA-N
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| InChi Code |
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
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| 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
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| Synonyms |
Cyclo(-RGDfK); 161552-03-0; Cyclo (-RGDfK); 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; CHEMBL2332367; cyclo-(Arg-Gly-Asp-D-Phe-Lys); cyclo(Arg-Gly-Asp-DPhe-Lys); cyclo(Arg-Gly-Asp-D-Phe-Lys);
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment, avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.45 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.08 mg/mL (3.45 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (3.45 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.6565 mL | 8.2827 mL | 16.5653 mL | |
| 5 mM | 0.3313 mL | 1.6565 mL | 3.3131 mL | |
| 10 mM | 0.1657 mL | 0.8283 mL | 1.6565 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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