- Embelin
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| SM-164Anticancer agent |
Sample solution is provided at 25 µL, 10mM.
- 1. Alexander F. G. Wintges. "Tumor immunosurveiliance:Innate immune activation as a mechanistic prerequisite for efficient immune checkpoint blockade in cancer immunotherapy." d-nb.info. 2018.
- 2. Saleh D, Degterev A. "Chemical Library Screens to Identify Pharmacological Modulators of Necroptosis." Methods Mol Biol. 2018;1857:19-33.PMID:30136227
- 3. Hao Q, Tang H. "Interferon-γ and Smac mimetics synergize to induce apoptosis of lung cancer cells in a TNFα-independent manner." Cancer Cell Int. 2018 Jun 14;18:84.PMID:29946223
- 4. Gavin C. Sampey, David M. Irlbeck, et al. "The SMAC Mimetic AZD5582 is a Potent HIV Latency Reversing Agent" bioRxiv.2018.May 2.
- 5. Sarhan J, Liu BC, et al. "Constitutive interferon signaling maintains critical threshold of MLKL expression to license necroptosis." Cell Death Differ. 2018 May 21.PMID:29786074
- 6. Yang Z, Wang Y, et al. "RIP3 targets pyruvate dehydrogenase complex to increase aerobic respiration in TNF-induced necroptosis." Nat Cell Biol. 2018 Feb;20(2):186-197.PMID:29358703
- 7. Chen X, He WT, et al."Pyroptosis is driven by non-selective gasdermin-D pore and its morphology is different from MLKL channel-mediated necroptosis." Cell Res. 2016 Sep;26(9):1007-20.PMID:27573174
- 8. Shekhar TM, Miles MA, et al."IAP antagonists sensitize murine osteosarcoma cells to killing by TNFα."Oncotarget. 2016 Jun 7;7(23):33866-86.PMID:27129149
Quality Control & MSDS
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- Purity = 98.64%
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Chemical structure
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| Targets | IAP | |||||
| IC50 | 0.56 nM/0.31 nM/1.1 nM |
| Kinase experiment [1]: | |
Fluorescence-polarization-based binding assays for XIAP, cIAP-1 and cIAP-2 proteins | To determine the binding affinities of SM-164 to XIAP containing both BIR2 andBIR3 domains, an FP-based competitive binding assay was established using a bivalent fluorescently tagged tracer, named Smac-1F. The Kd value of the bivalent tagged tracer to XIAP containing BIR2 and BIR3 domains was determined to be 2.3 nM. In competitive binding experiments, a tested compound was incubated with 3 nM of XIAP protein containing both BIR2 and BIR3 domain (residues 120-356) and 1 nM of in the same assay buffer. |
| Cell experiment [1]: | |
Cell lines | MDA-MB-231 breast cancer cell |
Preparation method | Limited solubility. General tips for obtaining a higher concentration: Please warm the tube at 37 ℃ for 10 minutes and/or shake it in the ultrasonic bath for a while. Stock solution can be stored below -20℃ for several months. |
Reaction Conditions | 12 h-48 h |
Applications | 12 h 1 nmol/L SM-164 treatment induces 32%, 33%, and 37% of the MDA-MB-231, SK-OV-3 and MALME-3M cells to undergo apoptosis. SM-164 also leads to cIAP-1 degradation in resistant cancer cell line and effectively antagonizes cellular XIAP. Moreover, 3 to 10 nmol/L SM-164 induces cell death with or without TNFα in all these sensitive cancer cell lines. |
| Animal experiment [1]: | |
Animal models | MDA-MB-231 xenograft tumor mice model |
Dosage form | A single i.v. dose of SM-164 at 5 mg/kg. |
Applications | At the 3-hour time point, SM-164 induces prominent apoptosis in tumor tissues, and more than 50% of tumor cells were TUNEL positive at the 6-hour time point. SM-164 reduces the tumor volume from 147 ± 54 mm3 (day 25-start of the treatment) to 54 ± 32 mm3 (day 36-end of treatment), a 65% reduction. SM-164 treatment also shows no significant weight loss or sign of toxicity. |
Other notes | Please test the solubility of all compounds indoor, and the actual solubility may slightly differ with the theoretical value. This is caused by an experimental system error and it is normal. |
References: 1. Lu J, Bai L, Sun H, Nikolovska-Coleska Z et al.SM-164: a novel, bivalent Smac mimetic that induces apoptosis and tumor regression by concurrent removal of the blockade of cIAP-1/2 and XIAP. Cancer Res. 2008 Nov 15;68(22):9384-93. | |
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| Cas No. | 957135-43-2 | SDF | Download SDF |
| Synonyms | N/A | ||
| Chemical Name | (3S,6R,10aR)-6-((S)-2-(methylamino)propanamido)-N-((R)-(1-(4-(4-(4-(4-((S)-((3S,6S,10aS)-6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamido)(phenyl)methyl)-1H-1,2,3-triazol-1-yl)butyl)phenyl)butyl)-1H-1,2,3-triazol-4-yl)( | ||
| Canonical SMILES | O=C([C@H]1N(C([C@@H](NC([C@H](C)NC)=O)CCCC2)=O)[C@]2([H])CC1)N[C@H](C3=CN(CCCCC4=CC=C(CCCCN5C=C([C@H](NC([C@@H]6CC[C@](CCCC[C@@H]7NC([C@@H](NC)C)=O)([H])N6C7=O)=O)C8=CC=CC=C8)N=N5)C=C4)N=N3)C9=CC=CC=C9 | ||
| Formula | C62H84N14O6 | M.Wt | 1121.42 |
| Solubility | ≥56.071mg/mL in DMSO | Storage | Store at -20°C |
| Shipping Condition | Evaluation sample solution : ship with blue ice.All other available size:ship with RT , or blue ice upon request | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. | ||
SM-164 is a bivalent mimetic of Smac with Ki values of 0.31 nM, 1.1 nM and 0.56 nM for cIAP-1, cIAP-2 and XIAP, respectively 1.
SM-164 is developed as an anticancer agent. It plays its antitumor roles through inducing degradation of cellular inhibitor of apoptosis protein (cIAP)-1/2, antagonizing X-linked inhibitor of apoptosis protein (XIAP) and inducing TNFα–dependent apoptosis in tumor cells. SM-164 is a bivalent mimetic containing two SM-122 analogues. It binds to cIAP-1 protein containing bothBIR2 and BIR3 domains, cIAP-2 BIR3 protein and XIAP protein containing both BIR2 and BIR3 domains with Ki values of 0.31 nM, 1.1 nM and 0.56 nM, respectively. In tumor cells, treatment of SM-164 significantly reduced cIAP-1 level to undetectable levels (1nM, 60min), effectively antagonized cellular XIAP and enhanced TNFα secretion. In the MDA-MB-231 xenograft model, administration of SM-164 at dose of 5mg/kg markedly decreased cIAP-1 level within 1 hour and activated caspase-8, caspase-9 and caspase-3 at 3 hour 1.
References:1. Lu J, Bai L, Sun H, et al. SM-164: a novel, bivalent Smac mimetic that induces apoptosis and tumor regression by concurrent removal of the blockade of cIAP-1/2 and XIAP. Cancer research, 2008, 68(22): 9384-9393.
