|
|
| Product Name: | SM-164 | | Synonyms: | SM-164;(3S,3'S,6S,6'S,10aS,10'aS)-N,N'-[1,4-Phenylenebis[4,1-butanediyl-1H-1,2,3-triazole-1,4-diyl[(S)-phenylmethylene]]]bis[decahydro-6-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-5-oxo-pyrrolo[1,2-a]azocine-3-carboxamide;SM 164 (pharmaceutical);SM-164;SM 164;SM164;(S,3S,3'S,6S,6'S,10aS,10a'S)-N,N'-((1S,1'S)-(1,1'-(4,4'-(1,4-phenylene)bis(butane-4,1-diyl))bis(1H-1,2,3-triazole-4,1-diyl))bis(phenylmethylene))bis(6-((S)-2-(2-methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide);SM 164; SM164;Pyrrolo[1,2-a]azocine-3-carboxamide, N,N'-[1,4-phenylenebis[4,1-butanediyl-1H-1,2,3-triazole-1,4-diyl[(S)-phenylmethylene]]]bis[decahydro-6-[[(2S)-2-(methylamino)-1-oxopropyl]amino]-5-oxo-, (3S,3'S,6S,6'S,10aS,10'aS)-;Apoptosis,inhibit,SM164,IAP,Inhibitor,SM-164,SM 164 | | CAS: | 957135-43-2 | | MF: | C62H84N14O6 | | MW: | 1121.45 | | EINECS: | | | Product Categories: | | | Mol File: | 957135-43-2.mol |  |
| | SM-164 Chemical Properties |
| density | 1.33±0.1 g/cm3(Predicted) | | storage temp. | -20°C | | solubility | Soluble in DMSO (50 mg/ml) | | form | solid | | pka | 12.62±0.40(Predicted) | | color | White to pale-yellow | | Stability: | Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months. |
| | SM-164 Usage And Synthesis |
| Description | SM-164 (957135-43-2) is a cell-permeable Smac (DIABLO) mimetic that inhibits caspase blockers XIAP, cIAP1, and cIAP2 (Ki = 36, <1, and <1.9 nM), thus inducing apoptosis.1-3 SM-164 sensitizes cancer cells to DNA damaging agents.4 It also prevents binding of Hsp70 to XIAP.5 At high concentrations, it causes lytic cell death that is neither apoptosis nor necroptosis.6 | | Definition | ChEBI: SM-164 is a potent cell-permeable and bivalent Smac mimetic which binds to XIAP, cIAP-1 and cIAP-2 proteins (Ki = 0.56 nM, 0.31 nM and 1.1 nM, respectively). It induces apoptosis and tumor regression in cancer xenograft models. It has a role as a radiosensitizing agent, an antineoplastic agent and an apoptosis inducer. It is a member of triazoles, a member of benzenes, a secondary carboxamide and an organic heterobicyclic compound. | | target | IAP | | References | Sun et al. (2007) Design, synthesis, and characterization of a potent, nonpeptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP; J. Am.Chem.Soc.?129 15279
Sun et al. (2010) Nonpeptidic and potent small-molecule inhibitors of cIAP-1/2 and XIAP proteins; Med. Chem.?53 6361
Lu et al. (2008) 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.?68 9384
Chen et al. (2019) SM-164 enhances the antitumor activity of adriamycin in human U2-OS cells via downregulation of X-linked inhibitor of apoptosis protein; Med. Rep.?19 5079
Cesa et al. (2018) X-linked inhibitor of apoptosis protein (XIAP) is a client of heat shock protein 70 (Hsp70) and a biomarker of its inhibition; Biol. Chem.?293 2370
Miles et al. (2020) Smac mimetic can provoke lytic cell death that is neither apoptotic nor necroptotic; Apoptosis?25 500 |
| | SM-164 Preparation Products And Raw materials |
|