SM-164 | Smac mimetic

CAS:
957135-43-2
Catalog Number:
10-5464
Activity:
Smac mimetic
Chemical Names:
(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
Molecular Weight:
1121.45
Molecular Formula:
C62H84N14O6
Solubility:
Soluble in DMSO (50 mg/ml)
Physical Properties:
White to pale-yellow solid
Purity:
>98% HPLC
NMR (Conforms)
Storage Temperature:
-20°C
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.
Shipping Code:
RT

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1 mg$190.00
5 mg$400.00
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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

References:

  1. 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
  2. Sun et al. (2010) Nonpeptidic and potent small-molecule inhibitors of cIAP-1/2 and XIAP proteins; Med. Chem. 53 6361
  3. 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
  4. 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
  5. 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
  6. Miles et al. (2020) Smac mimetic can provoke lytic cell death that is neither apoptotic nor necroptotic; Apoptosis 25 500
CAS:
957135-43-2
Catalog Number:
10-5464
Activity:
Smac mimetic
Chemical Names:
(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
Molecular Weight:
1121.45
Molecular Formula:
C62H84N14O6
Solubility:
Soluble in DMSO (50 mg/ml)
Physical Properties:
White to pale-yellow solid
Purity:
>98% HPLC
NMR (Conforms)
Storage Temperature:
-20°C
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.
Shipping Code:
RT

Safety Data Sheet:

N/A

Product Data Sheet:

Download Product Data Sheet

Materials provided by Focus Biomolecules are for laboratory research use only and are not intended for human or veterinary applications. Please note that we do not sell to individuals and that all orders placed by non-research organizations will incur a $20 restocking/refund fee

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

References:

  1. 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
  2. Sun et al. (2010) Nonpeptidic and potent small-molecule inhibitors of cIAP-1/2 and XIAP proteins; Med. Chem. 53 6361
  3. 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
  4. 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
  5. 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
  6. Miles et al. (2020) Smac mimetic can provoke lytic cell death that is neither apoptotic nor necroptotic; Apoptosis 25 500

Focus Biomolecules • Plymouth Meeting, PA USA • 1-855-FOCUS21

Focus Biomolecules
Plymouth Meeting, PA USA
1-855-FOCUS21

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