| Field | Specification |
|---|---|
| Alternative names | CHR-2797 |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C21H30N2O6 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
Tosedostat, also known as CHR-2797, is an orally active aminopeptidase inhibitor that exerts antiproliferative effects against a range of tumor cell lines[1]. It is supplied as a white to off-white solid (C21H30N2O6, MW 406.47) at 99.68% purity.
Physical & Chemical Properties
| CAS Number | 238750-77-1 |
|---|---|
| Molecular Formula | C21H30N2O6 |
| Molecular Weight | 406.47 g/mol |
| Purity | 99.68% |
| Appearance | Solid |
| Color | White to off-white |
| SMILES | O=C(OC1CCCC1)[C@@H](NC([C@@H]([C@H](O)C(NO)=O)CC(C)C)=O)C2=CC=CC=C2 |
| Signaling Pathway | Metabolic Enzyme/Protease |
| Solubility | In Vitro: DMSO: 100 mg/mL (246.02 mM; Requires sonication; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO) |
| Storage | Powder: -20°C, 3 years; 4°C, 2 years. In solvent: -80°C, 2 years; -20°C, 1 year. |
| Shipping | Room temperature in continental US; may vary elsewhere. |
Literature Cited
Sources cited in this description and in the In Vitro & In Vivo Data tab. Peer-reviewed publications that used this product are listed under References.
Safety
For Research Use Only. Not for use in diagnostic or therapeutic procedures, and not for human or veterinary use. Handle in accordance with the Safety Data Sheet and your institution's chemical hygiene plan.
In Vitro
| Solvent | Solubility | Notes |
|---|---|---|
| DMSO | 100 mg/mL (246.02 mM) | requires sonication; use freshly opened DMSO (absorbed moisture lowers solubility) |
Aliquot the stock solution and store it at -80°C (up to 2 years) or -20°C (up to 1 year); avoid repeated freeze-thaw cycles.
In Vivo
Choose the formulation that suits the animal model and route of administration; percentages are volume ratios of the final working solution. Start from a clear DMSO stock (see In Vitro above), add the co-solvents one at a time in the order listed, mixing after each addition, and prepare the working solution fresh on the day of dosing. If precipitation or phase separation occurs, gentle warming or sonication can help.
Protocol 1
| Composition | 10% DMSO + 40% PEG300 + 5% Tween-80 + 45% saline |
|---|---|
| Result | ≥ 2.5 mg/mL (6.15 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 400 μL PEG300; then 50 μL Tween-80; then 450 μL saline to bring the volume to 1 mL. Saline: dissolve 0.9 g sodium chloride in ddH2O and make up to 100 mL. |
Protocol 2
| Composition | 10% DMSO + 90% (20% SBE-β-CD in saline) |
|---|---|
| Result | ≥ 2.5 mg/mL (6.15 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 900 μL 20% SBE-β-CD in saline. 20% SBE-β-CD in saline: dissolve 2 g SBE-β-CD powder in 10 mL saline until clear (4°C, store up to one week). |
Protocol 3
| Composition | 10% DMSO + 90% Corn Oil |
|---|---|
| Result | ≥ 2.5 mg/mL (6.15 mM); clear solution |
| How to prepare | Gives a clear solution at ≥ 2.5 mg/mL (saturation not determined). Use with caution if continuous dosing will exceed two weeks. For 1 mL of working solution: add 100 μL DMSO stock (25.0 mg/mL) to 900 μL corn oil. |
Data provided by the manufacturer.
In Vitro
Treating HL-60 cells with Tosedostat (CHR-2797) increases secretion of Stanniocalcin 2 (STC2) protein into the growth medium. Higher SLC7A11 expression can be detected as early as 2 h posttreatment, at 60 nM Tosedostat. Tosedostat inhibits proliferation in U-937 and HuT 78 cell lines, with IC50s of 10 nM and >10 μM, respectively. In U-937 cells but not in HuT 78 cells, Tosedostat treatment raises expression of amino acid deprivation response (AADR) genes[1]. At 24 h, 0.01 μM Tosedostat reduces mean MCA production to 77.8% of that in untreated control cells; MCA production is likewise reduced to 51.3% at 1 μM, 38.5% at 5 μM, and 35.3% at 10 μM Tosedostat[2].
In Vivo
Tosedostat (CHR-2797) is active in vivo as an anticancer agent in rodent cancer models; a dose-response relationship has been shown in two models. When tumor burden is higher before treatment, the effect of Tosedostat is less apparent[1].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
Kinase Assay[1]
Seed cells at a density of 4×104/mL, culture for 24 h, and then treat with Tosedostat (CHR-2797) at 0.06 to 6 μM for 24 h. After treatment, wash 5×104 cells with PBS and seed in 100 μL Cys/Met-free RPMI 1640 containing Tosedostat and supplemented with 10% dialyzed FBS. Add 1.5 μCi [35S]Cys/Met (>1,000 Ci/mmol) and continue incubation for 1 h at 37°C. Capture cells onto 96-well GF/B filter plates and wash twice with PBS, then precipitate with 10% ice-cold trichloroacetic acid (TCA) for 1 h at 4°C. Wash the precipitated proteins four times with ice-cold 10% TCA and air-dry for 1 h. Add UltimaGold scintillation cocktail, allow to mix for 1 h, and count with a scintillation counter[1].
Cell Assay[2]
Wash leukemic cells and suspend in phosphate buffered saline (PBS). Mix 100 μL of cell suspension (1×105 cells/mL) with 100 μL of Tosedostat (CHR-2797) at 0.01 to 10 μM and 200 μM L-alanine 4-methyl-coumaryl-7-amide (ala-MCA); use a 96 well plate and run in duplicate. Measure aminopeptidase activity by detecting the fluorescent 7-amino-4-methylcoumarin (MCA) released as cellular aminopeptidases cleave ala-MCA (excitation 355 nm, emission 460 nm)[2].
Animal Administration[3]
Use a breeding colony of NOD/SCID IL2R gammanull mice in this study. Inoculate H929 myeloma cells (2×106) in 50 μL RPMI-1640 mixed with 50 μL MatrigelTM Basement Membrane Matrix Growth Factor Reduced into the right flank of the mice subcutaneously. Assign the mice to the following four groups of 10 animals each: no treatment, Tosedostat 75 mg/kg, CHR-3996 30 mg/kg, or Tosedostat 75 mg/kg together with concomitant CHR-3996 30 mg/kg. Administer Tosedostat daily by intra-peritoneal injection beginning four days after tumor cell inoculation. Perform caliper measurements of the longest perpendicular tumor diameters (length) and width every other day to estimate tumor volume[3].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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