A cell-permeable Smac mimetic
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Product Categories

Product Type

Biochemicals

Research Area

Cancer
Cell Death
Apoptosis
Cell Biology

SM-164

Item No. 28632

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(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
CAS Number
957135-43-2
Molecular Formula
C62H84N14O6
Formula Weight
1121.4
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: 50 mg/ml
SMILES
O=C1N2[C@@](CC[C@H]2C(N[C@H](C3=CN(CCCCC4=CC=C(CCCCN5C=C([C@@H](NC([C@@H]6CC[C@@](CCCC[C@@H]7NC([C@H](C)NC)=O)([H])N6C7=O)=O)C8=CC=CC=C8)N=N5)C=C4)N=N3)C9=CC=CC=C9)=O)([H])CCCC[C@@H]1NC([C@@H](NC)C)=O
InChi Code
InChI=1S/C62H84N14O6/c1-41(63-3)57(77)65-49-27-13-11-25-47-33-35-53(75(47)61(49)81)59(79)67-55(45-21-7-5-8-22-45)51-39-73(71-69-51)37-17-15-19-43-29-31-44(32-30-43)20-16-18-38-74-40-52(70-72-74)56(46-23-9-6-10-24-46)68-60(80)54-36-34-48-26-12-14-28-50(62(82)76(48)54)66-58(78)42(2)64-4/h5-10,21-24,29-32,39-42,47-50,53-56,63-64H,11-20,25-28,33-38H2,1-4H3,(H,65,77)(H,66,78)(H,67,79)(H,68,80)/t41-,42-,47-,48-,49-,50-,53-,54-,55-,56-/m0/s1
InChi Key
LGYDZXNSSLRFJS-IOQQVAQYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $109

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    1 mg

    $207

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    Cayman Chemical
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    Product Description

    SM-164 is a cell-permeable bivalent mimetic of Smac and an inhibitor of X-linked inhibitor of apoptosis (XIAP).1 It binds to BIR2 and BIR3 domain-containing XIAP with an IC50 value of 1.39 nM and interacts with both domains. SM-164 inhibits growth (IC50 = 1 nM), as well as activates caspase-3 and caspase-9, and induces cleavage of the caspase-3 substrate poly(ADP-ribose)-polymerase (PARP), a marker of apoptosis, in HL-60 leukemia cells when used at a concentration of 10 nM. It also reduces tumor volume by 80% in a 2LMP breast cancer mouse xenograft model when administered at a dose of 5 mg/kg in combination with TNF-related apoptosis-inducing ligand (TRAIL).2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sun, H., Nikolovska-Coleska, Z., Lu, J., et al. Design, synthesis, and characterization of a potent, non-peptide, cell-permeable, bivalent Smac mimetic that concurrently targets both the BIR2 and BIR3 domains in XIAP. J. Am. Chem. Soc. 129(49), 15279-15294 (2007).

    2. Lu, J., McEachern, D., Sun, H., et al. Therapeutic potential and molecular mechanism of a novel, potent, nonpeptide, Smac mimetic SM-164 in combination with TRAIL for cancer treatment. Mol. Cancer Ther. 10(5), 902-914 (2011).