| Identification | Back Directory | [Name]
SM-164 | [CAS]
957135-43-2 | [Synonyms]
SM-164
SM 164; SM164
SM-164;SM 164;SM164
SM 164 (pharmaceutical)
(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
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)-
(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) | [Molecular Formula]
C62H84N14O6 | [MDL Number]
MFCD28167763 | [MOL File]
957135-43-2.mol | [Molecular Weight]
1121.45 |
| Chemical Properties | Back Directory | [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. |
| Hazard Information | Back Directory | [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 | [Uses]
SM-164 is a cell-permeable Smac mimetic compound. SM-164 binds to XIAP protein containing both the BIR2 and BIR3 domains with an IC50 value of 1.39 nM and functions as an extremely potent antagonist of XIAP. | [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. | [in vivo]
SM-164 is evaluated for its ability to inhibit tumor growth. SM-164 is highly effective in inhibition of tumor growth and capable of achieving tumor regression in the MDA-MB-231 xenograft model. Treatment with SM-164 at 1 mg/kg completely inhibits tumor growth during the treatment. Treatment with SM-164 at 5 mg/kg reduces the tumor volume from 147±54 mm3 at the beginning of the treatment (day 25) to 54±32 mm3 at the end of the treatment (day 36), a reduction of 65%. The strong antitumor activity by SM-164 is long lasting and not transient. SM-164 at 5 mg/kg is statistically more effective than Taxotere at the end of the treatment (P<0.01) or when the tumor size in the control group reached 750 mm3 (P<0.02)[2]. | [target]
IAP | [IC 50]
cIAP-1: 0.31 nM (Ki); cIAP-2: 1.1 nM (Ki); cIAP | [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 |
|
| Company Name: |
ChemCell Biomedicine Co.,Ltd.
|
| Tel: |
020-13556033878 2965585218 13556033878 |
| Website: |
www.chemicalbook.com/ShowSupplierProductsList15061/0_EN.htm |
|