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| 5mg |
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| 10mg |
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| 25mg |
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Purity: ≥98%
iRGD peptide (sequence: CRGDKGPDC) is a 9-amino acid cyclic peptide, and a molecular mimicry agent that was originally identified in an in vivo screening of phage display libraries in tumor-bearing mice. It triggers tissue penetration of drugs by first binding to av integrins, then proteolytically cleaved in the tumor to produce CRGDK/R to interact with neuropilin-1, and has tumor-targeting and tumor-penetrating properties. The peptide was able to home to tumor tissues, but in contrast to standard RGD (Arginylglycylaspartic acid) peptides, also spread much more extensively into extravascular tumor tissue. It was later identified that this extravasation and transport through extravascular tumor tissue was due to the bifunctional action of the molecule: after the initial RGD-mediated tumor homing, another pharmacological motif is able to manipulate tumor microenvironment, making it temporarily accessible to circulating drugs. This second step is mediated through specific secondary binding to neuropilin-1 receptor, and subsequent activation of a trans-tissue pathway, dubbed the C-end Rule (CendR) pathway.
| ln Vitro |
Three processes are involved in iRGD peptide-mediated tumor penetration: first, it binds to αv-integrins on tumor vasculature or tumor cells; second, it exposes a C-terminal motif that binds to neuropilin-1 (NRP-1); and third, it internalizes the cell. The insertion of an iRGD peptide into the C terminus of the ICOVIR15K fiber only improves binding and internalization in MCF7 cells that express integrins and NRP-1. Viral infection and replication are unaffected by iRGD insertion[1]. When coupled with 5-FU, iRGD peptide (0.3 μmol/mL) increases the chemotherapeutic efficacy of 5-FU on gastric cancer cells through NRP1[2]. However, iRGD peptide alone has no discernible effect on gastric cancer cells.
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| ln Vivo |
When iRGD is introduced into the oncolytic adenovirus ICOVIR15K, the result is an increased anticancer effect in mice as well as improved early viral diffusion into the tumor mass[1]. When 5-FU is combined with iRGD (4 mmol/kg, iv), it considerably slows down the formation of tumors in nude mice that are harboring human stomach cancer cells[2].
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| References |
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| Additional Infomation |
Internalized-arginylglycylaspartic Acid Cyclic Peptide is a 9 amino acid-based cyclic, tumor specific homing, arginine-glycine-aspartic acid (RGD)-based peptide (CRGDKRGPDC), with tumor penetrating activity. The iRGD contains the RGD motif as well as the C-terminal end binding (CendR) motif that increases internalization. Upon administration, the RGD motif of the iRGD peptide is able to specifically target tumors by binding to alphavbeta3/alphavbeta5 integrins on tumor endothelium. In turn, iRGD is cleaved by specific tumor proteases, which exposes the positively charged CendR motif. This motif binds to neuropilin-1 (NRP-1), a receptor overexpressed on certain tumor cells. This increases vascular permeability of tumor blood vessels and promotes tumor penetration. Compared to other RGD peptides, this agent is able to both improve delivery and increase the accumulation of co-administered or conjugated chemotherapeutic agents in the tumor.
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| Molecular Formula |
C35H57N13O14S2
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|---|---|
| Molecular Weight |
948.035784482956
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| Exact Mass |
947.358
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| CAS # |
1392278-76-0
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| PubChem CID |
134611625
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| Appearance |
White to off-white solid powder
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| LogP |
-11.3
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| Hydrogen Bond Donor Count |
14
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| Hydrogen Bond Acceptor Count |
19
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
64
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| Complexity |
1750
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| Defined Atom Stereocenter Count |
7
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| SMILES |
S1CC(C(=O)O)NC(C(CC(=O)O)NC(C2CCCN2C(CNC(C(CCCCN)NC(C(CC(=O)O)NC(CNC(C(CCC/N=C(\N)/N)NC(C(CS1)N)=O)=O)=O)=O)=O)=O)=O)=O
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| InChi Key |
YHTTWXCDIRTOQX-FQJIPJFPSA-N
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| InChi Code |
InChI=1S/C35H57N13O14S2/c36-8-2-1-5-18-30(57)42-14-25(50)48-10-4-7-23(48)33(60)46-21(12-27(53)54)32(59)47-22(34(61)62)16-64-63-15-17(37)28(55)44-19(6-3-9-40-35(38)39)29(56)41-13-24(49)43-20(11-26(51)52)31(58)45-18/h17-23H,1-16,36-37H2,(H,41,56)(H,42,57)(H,43,49)(H,44,55)(H,45,58)(H,46,60)(H,47,59)(H,51,52)(H,53,54)(H,61,62)(H4,38,39,40)/t17-,18-,19-,20-,21-,22-,23-/m0/s1
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| Chemical Name |
(6S,9S,15S,18R,23R,26S,29S)-18-amino-6-(4-aminobutyl)-9,26-bis(carboxymethyl)-15-[3-(diaminomethylideneamino)propyl]-2,5,8,11,14,17,25,28-octaoxo-20,21-dithia-1,4,7,10,13,16,24,27-octazabicyclo[27.3.0]dotriacontane-23-carboxylic acid
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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 (e.g. under nitrogen), avoid exposure to moisture and light. |
| 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) |
H2O : ≥ 50 mg/mL (~52.74 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 100 mg/mL (105.48 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.
(Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 1.0548 mL | 5.2740 mL | 10.5481 mL | |
| 5 mM | 0.2110 mL | 1.0548 mL | 2.1096 mL | |
| 10 mM | 0.1055 mL | 0.5274 mL | 1.0548 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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