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SM-164

Product Specifications

UNSPSC Description

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.

Target Antigen

Apoptosis; IAP

Type

Reference compound

Related Pathways

Apoptosis

Applications

Cancer-programmed cell death

Field of Research

Cancer

Assay Protocol

https://www.medchemexpress.com/SM-164.html

Solubility

DMSO : 25 mg/mL (ultrasonic)

Smiles

C[C@H](NC)C(N[C@H]1CCCC[C@](CC[C@H]2C(N[C@@H](C3=CC=CC=C3)C4=CN(CCCCC5=CC=C(CCCCN6N=NC([C@@H](NC([C@@H]7CC[C@@](CCCC[C@@H]8NC([C@@H](NC)C)=O)([H])N7C8=O)=O)C9=CC=CC=C9)=C6)C=C5)N=N4)=O)([H])N2C1=O)=O

Molecular Weight

1121.42

References & Citations

[1]Sun H, et al. 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. 2007 Dec 12;129(49):15279-94.|[2]Lu J, et al. 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. 2008 Nov 15;68(22):9384-93.Biomed Res Int. 2019 Apr 7;2019:2121357.|Bioorg Chem. 2022: 106339.|Bioorg Chem. 2023 Jun 1;137:106647.|Bioorg Chem. 2024 Jan, 142, 106964.|Bioorg Med Chem. 2023 Aug 15, 91, 117385.|Bioorg Med Chem. 2024 Feb 15:100:117611.|Bioorg Med Chem. 2024 Mar 1:102:117659.|bioRxiv. 2023 Apr 25.|bioRxiv. 2023 Aug 24.|Cell Death Dis. 2024 Oct 18;15(10):759.|Cell Death Dis. 2018 Nov 15;9(12):1140. |Cell Death Discov. 2024 Mar 23;10(1):152.|Cell Res. 2023 Sep 19.|Curr Protoc. 2021 Jun;1(6):e156.|Eur J Med Chem. 2021 Apr 27;220:113484.|Eur J Med Chem. 2022 Jun 5;236:114345.|Eur J Med Chem. 2024 Mar 9, 116304.|Georg Thieme Verlag KG|Int J Biol Macromol. 2023 Jun 13;125373.|J Cell Mol Med. 2023 Aug 29.|J Med Chem. 2022 Oct 26.|J Med Chem. 2023 Feb 23;66(4):3073-3087.|J Med Chem. 2023 Mar 12.|Mater Sci Eng C Mater Biol Appl. 29 December 2021, 112615.|Mol Neurobiol. 2023 Jan 5.|Nature. 2024 Apr;628(8009):835-843.|Patent. US20230192662A1.|Patent. US20240217963A1.|Patent. US20240294508A1.|PLoS Pathog. 2024 Aug 30;20(8):e1012387.|Proc Natl Acad Sci U S A. 2022 Sep 6;119(36):e2117396119.|Research Square Print. 2022 May.|Rheumatology. 2022 Oct 29;keac621.|Sci Immunol. 2024 Jul 12;9(97):eadn0178.|Signal Transduct Target Ther. 2020 Oct 9;5(1):235.|J Ethnopharmacol. 2023 Nov 1:117373.

Shipping Conditions

Room Temperature

Product Datasheet

http://file.medchemexpress.com/batch_PDF/HY-15989/SM-164-DataSheet-MedChemExpress.pdf

Product MSDS

http://file.medchemexpress.com/batch_PDF/HY-15989/SM-164-SDS-MedChemExpress.pdf

Clinical Information

No Development Reported

CAS Number

957135-43-2

Available Sizes

Curated Selection

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