SM-164
- Product Name
- SM-164
- CAS No.
- 957135-43-2
- Chemical Name
- SM-164
- Synonyms
- SM-164;SM 164; SM164;SM-164;SM 164;SM164;SM 164 (pharmaceutical);Apoptosis,inhibit,SM164,IAP,Inhibitor,SM-164,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;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)-;(3S,3'S,6S,6'S,10aS,10a'S)-N,N'-((1S,1'S)-((1,4-Phenylenebis(butane-4,1-diyl))bis(1H-1,2,3-triazole-1,4-diyl))bis(phenylmethylene))bis(6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide);(S,3S,3'S,6S,6'S,10aS,10a'S)-N,N'-((1S,1'S)-(1,1'-(1,4-phenylenebis(butane-4,1-diyl))bis(1H-1,2,3-triazole-4,1-diyl))bis(phenylmethylene))bis(6-((S)-2-(methylamino)propanamido)-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxamide);(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)
- CBNumber
- CB92705096
- Molecular Formula
- C62H84N14O6
- Formula Weight
- 1121.45
- MOL File
- 957135-43-2.mol
SM-164 Property
- 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 and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- 28632
- Product name
- SM-164
- Packaging
- 500μg
- Price
- $99
- Updated
- 2024/03/01
- Product number
- 28632
- Product name
- SM-164
- Packaging
- 1mg
- Price
- $188
- Updated
- 2024/03/01
- Product number
- A8815
- Product name
- SM-164
- Packaging
- 10mg
- Price
- $500
- Updated
- 2021/12/16
- Product number
- A8815
- Product name
- SM-164
- Packaging
- 10mM(in 1mL DMSO)
- Price
- $630
- Updated
- 2021/12/16
- Product number
- A8815
- Product name
- SM-164
- Packaging
- 5mg
- Price
- $350
- Updated
- 2021/12/16
SM-164 Chemical Properties,Usage,Production
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