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| Targets |
RR-11a analog targets asparaginyl endopeptidases (AEs), which are cysteine proteases also known as legumain. It is a potent and irreversible inhibitor of these enzymes. By binding covalently to the active site cysteine residue, it permanently inactivates the enzyme. This makes it a valuable tool for studying the function of legumain in various biological processes, including parasite biology and cancer.
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| ln Vitro |
In vitro, RR-11a analog is a potent inhibitor of legumain, with IC₅₀ values of 4.5 nM, 4.5 nM, and 31 nM against AEs from T. vaginalis, I. ricinus, and S. mansoni, respectively. Its activity is demonstrated in enzyme assays using purified recombinant legumain or in cell-based assays using parasite lysates. It is a highly specific and potent tool compound.
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| ln Vivo |
Analogs of RR-11a have a half-life of three to ten minutes [2].
In vivo, RR-11a analog has been shown to have a half-life of 3-10 minutes. This suggests that it is rapidly cleared, which may limit its utility for in vivo studies. However, it is primarily used as a research tool in vitro to study the role of legumain in parasite biology and other diseases. |
| Enzyme Assay |
In vitro non-cell enzyme assays for RR-11a analog involve measuring the inhibition of legumain activity using a fluorogenic substrate. The compound is incubated with the enzyme and substrate, and the decrease in fluorescence is measured to determine the IC₅₀. As an irreversible inhibitor, the assay conditions, such as pre-incubation time, are important for accurately determining its potency.
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| Cell Assay |
In vitro cell-based assays for RR-11a analog use parasite cultures (e.g., S. mansoni, T. vaginalis) or mammalian cell lines. Cells are treated with the compound, and its effects on parasite viability, growth, or specific legumain-dependent processes are assessed. Its effects on mammalian legumain can also be studied in relevant cell lines.
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| Animal Protocol |
In vivo animal studies for RR-11a analog are limited, given its short half-life of 3-10 minutes. It could be used in animal models of schistosomiasis or other parasitic infections to study the role of legumain, but its rapid clearance may necessitate continuous infusion or frequent dosing.
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| ADME/Pharmacokinetics |
RR-11a analog has a molecular weight of 491.49 g/mol and a molecular formula of C₂₂H₂₉N₅O₈. It is an aza-peptide Michael acceptor. It is soluble in DMSO. It should be stored at -20°C or 4°C. Its short half-life (3-10 minutes) indicates rapid clearance.
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| Toxicity/Toxicokinetics |
The toxicity profile of RR-11a analog is not extensively detailed in the provided search results. As a potent, irreversible inhibitor of legumain, it could have significant off-target effects. It is a research compound and is not intended for human therapeutic use.
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| References |
[1]. Götz MG, et al. Aza-peptidyl Michael acceptors. A new class of potent and selective inhibitors of asparaginyl endopeptidases (legumains) from evolutionarily diverse pathogens. J Med Chem. 2008 May 8;51(9):2816-32.
[2]. Ekici OD, et al. Aza-peptide Michael acceptors: a new class of inhibitors specific for caspases and other clan CD cysteine proteases. J Med Chem. 2004 Apr 8;47(8):1889-92. |
| Additional Infomation |
RR-11a analog is a potent and irreversible inhibitor of asparaginyl endopeptidases (legumain). It is an aza-Asn derivative and aza-peptide Michael acceptor. It is used as a research tool to study legumain biology in parasites and other organisms. It is not approved for clinical use and is intended for research purposes only.
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| Molecular Formula |
C22H29N5O8
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|---|---|
| Molecular Weight |
491.49436545372
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| Exact Mass |
491.201
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| CAS # |
685543-66-2
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| Related CAS # |
RR-11a;1361390-56-8
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| PubChem CID |
11294791
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| Appearance |
White to off-white solid powder
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| LogP |
0
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| Hydrogen Bond Donor Count |
4
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| Hydrogen Bond Acceptor Count |
8
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| Rotatable Bond Count |
13
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| Heavy Atom Count |
35
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| Complexity |
810
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| Defined Atom Stereocenter Count |
2
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| SMILES |
CCOC(=O)/C=C/C(=O)N(CC(=O)N)NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OCC1=CC=CC=C1
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| InChi Key |
YGVKPQSVBJEMMQ-BWLFODOESA-N
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| InChi Code |
InChI=1S/C22H29N5O8/c1-4-34-19(30)11-10-18(29)27(12-17(23)28)26-21(32)15(3)24-20(31)14(2)25-22(33)35-13-16-8-6-5-7-9-16/h5-11,14-15H,4,12-13H2,1-3H3,(H2,23,28)(H,24,31)(H,25,33)(H,26,32)/b11-10+/t14-,15-/m0/s1
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| Chemical Name |
ethyl (E)-4-[(2-amino-2-oxoethyl)-[[(2S)-2-[[(2S)-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoyl]amino]amino]-4-oxobut-2-enoate
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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 |
| 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) |
DMSO : ~125 mg/mL (~254.33 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.23 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 (4.23 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 (4.23 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 | 2.0346 mL | 10.1731 mL | 20.3463 mL | |
| 5 mM | 0.4069 mL | 2.0346 mL | 4.0693 mL | |
| 10 mM | 0.2035 mL | 1.0173 mL | 2.0346 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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