| Field | Specification |
|---|---|
| Target | |
| CAS no. | |
| Applications | |
| Molecular weight | |
| Molecular formula | C62H84N14O6 |
| Purity | |
| SMILES | |
| Form | Solid |
| Storage | |
| Shipping | |
| Catalog no. (Mfr.) | |
| Main SKU |
Compound Overview
SM-164 is a cell-permeable Smac mimetic compound that binds the XIAP protein containing both the BIR2 and BIR3 domains, with an IC50 of 1.39 nM, functioning as an extremely potent antagonist of XIAP. It is supplied as a white to light yellow solid (C62H84N14O6, MW 1121.42) at 99.53% purity.
Physical & Chemical Properties
| CAS Number | 957135-43-2 |
|---|---|
| Molecular Formula | C62H84N14O6 |
| Molecular Weight | 1121.42 g/mol |
| Purity | 99.53% |
| Appearance | Solid |
| Color | White to light yellow |
| SMILES | C[C@H](NC)C(N[C@H]1CCCC[C@](CC[C@H]2C(N[C@@H](C3=CC=CC=C3)C4=CN(CCCCC5=CC=C(CCCCN6N=NC([C@@H](NC([C@@H]7CC[C@@](CCCC[C@@H]8NC([C@@H](NC)C)=O)([H])N7C8=O)=O)C9=CC=CC=C9)=C6)C=C5)N=N4)=O)([H])N2C1=O)=O |
| Target | cIAP-1, cIAP-2, cIAP |
| Signaling Pathway | Apoptosis |
| Solubility | In Vitro: DMSO: 25 mg/mL (22.29 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. |
Biological Activity
Activity & Target
[1][2]
|
cIAP-1 0.31 nM (Ki) |
cIAP-2 1.1 nM (Ki) |
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 | 25 mg/mL (22.29 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 | 0.83 mg/mL (0.74 mM); clear solution; requires sonication |
| How to prepare | Gives a clear solution at 0.83 mg/mL. For 1 mL of working solution: add 100 μL DMSO stock (8.3 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. |
Data provided by the manufacturer.
In Vitro
SM-164 is a non-peptide, cell-permeable, bivalent small molecule that mimics the Smac protein to target XIAP. SM-164 binds XIAP that contains both BIR domains, with an IC50 value of 1.39 nM, making it 300 times more potent than its monovalent counterparts and 7000 times more potent than the natural Smac AVPI peptide. SM-164 interacts concurrently with both BIR domains in XIAP and acts as an ultra-potent XIAP antagonist in cell-free functional assays as well as cell-based assays. SM-164 targets cellular XIAP and effectively induces apoptosis in leukemia cancer cells at concentrations as low as 1 nM, while showing minimal toxicity to normal human primary cells at 10,000 nM[1]. Binding affinities of SM-164 for XIAP, cIAP-1, and cIAP-2 proteins are determined by fluorescence-polarization based assays. SM-164 has a Ki value of 0.56 nM for XIAP protein containing both BIR2 and BIR3 domains, and a Ki value of 0.31 nM for cIAP-1 protein containing both BIR2 and BIR3 domains. The Ki value of SM-164 for cIAP-2 BIR3 protein is 1.1 nM. Exogenous TNFα can significantly boost the activity of these Smac mimetics, particularly SM-164, in resistant cancer cell lines such as HCT116 and MDA-MB-453[2].
In Vivo
The tumor growth-inhibiting ability of SM-164 is evaluated. In the MDA-MB-231 xenograft model, SM-164 is highly effective at inhibiting tumor growth and can achieve tumor regression. SM-164 at 1 mg/kg completely inhibits tumor growth during treatment. At 5 mg/kg, SM-164 reduces tumor volume from 147±54 mm3 at the start of treatment (day 25) to 54±32 mm3 at the end of treatment (day 36), a reduction of 65%. The strong antitumor activity of SM-164 is long lasting rather than transient. At the end of treatment (P<0.01), or once control group tumors reached a size of 750 mm3 (P<0.02), SM-164 at 5 mg/kg is statistically more effective than Taxotere[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
Cell Assay[2]
Treat HCT116 colon cancer cells for 48 h with SM-164 (1, 10, and 100 nM) alone, with TNFα alone, or with the combination. Determine cell growth inhibition by WST assay[2].
Animal Administration[2]
Mice[2] Treat SCID mice (8-10 per group) bearing MDA-MB-231 xenograft tumors i.v. with 1 and 5 mg/kg of SM-164, 7.5 mg/kg of Taxotere, or vehicle control, daily, 5 d/wk for 2 wk. Measure tumor sizes and animal weights thrice a week[2].
Data provided by the manufacturer. Numbered citations refer to the Literature Cited list in the product description.
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