SNIPER(ER)-110 - CAS 2241690-03-7

SNIPER(ER)-110 consists of a cIAP1 ligand and an estrogen ligand, connected by a linker. SNIPER(ER)-51 induces estrogen receptor (ER) protein degradation with DC50s of <3 nM and 7.7 nM after 4 h and 48 h, respectively[1].

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Molecular Formula
Molecular Weight


    • Specification
      • Storage
        Please store the product under the recommended conditions in the Certificate of Analysis.
        Room temperature in continental US; may vary elsewhere
        IUPAC Name
        (2S,4S)-1-((S)-2-cyclohexyl-2-((S)-2-(methylamino)propanamido)acetyl)-4-(3-((1-(4-((Z)-1-(4-hydroxyphenyl)-2-phenylbut-1-en-1-yl)phenoxy)-3-methyl-4-oxo-6,9,12-trioxa-3-azatetradecan-14-yl)oxy)phenoxy)-N-((R)-1,2,3,4-tetrahydronaphthalen-1-yl)pyrrolidine-2-carboxamide; SNIPER(ER) 110
    • Properties
      • Boiling Point
        1171.3±65.0°C at 760 Torr
        1.25±0.1 g/cm3
        InChI Key
        Canonical SMILES
    • Reference Reading
      • 1. Derivatization of inhibitor of apoptosis protein (IAP) ligands yields improved inducers of estrogen receptor α degradation.
        Ohoka, N., Morita, Y., Nagai, K., Shimokawa, K., Ujikawa, O., Fujimori, I., Ito, M., Hayase, Y., Okuhira, K., Shibata, N. and Hattori, T., 2018. Journal of Biological Chemistry, 293(18), pp.6776-6790.
        Aberrant expression of proteins often underlies many diseases, including cancer. A recently developed approach in drug development is small molecule-mediated, selective degradation of dysregulated proteins. We have devised a protein-knockdown system that utilizes chimeric molecules termed specific and nongenetic IAP-dependent protein erasers (SNIPERs) to induce ubiquitylation and proteasomal degradation of various target proteins. SNIPER(ER)-87 consists of an inhibitor of apoptosis protein (IAP) ligand LCL161 derivative that is conjugated to the estrogen receptor α (ERα) ligand 4-hydroxytamoxifen by a PEG linker, and we have previously reported that this SNIPER efficiently degrades the ERα protein. Here, we report that derivatization of the IAP ligand module yields SNIPER(ER)s with superior protein-knockdown activity. These improved SNIPER(ER)s exhibited higher binding affinities to IAPs and induced more potent degradation of ERα than does SNIPER(ER)-87. Further, they induced simultaneous degradation of cellular inhibitor of apoptosis protein 1 (cIAP1) and delayed degradation of X-linked IAP (XIAP). Notably, these reengineered SNIPER(ER)s efficiently induced apoptosis in MCF-7 human breast cancer cells that require IAPs for continued cellular survival. We found that one of these molecules, SNIPER(ER)-110, inhibits the growth of MCF-7 tumor xenografts in mice more potently than the previously characterized SNIPER(ER)-87. Mechanistic analysis revealed that our novel SNIPER(ER)s preferentially recruit XIAP, rather than cIAP1, to degrade ERα. Our results suggest that derivatized IAP ligands could facilitate further development of SNIPERs with potent protein-knockdown and cytocidal activities against cancer cells requiring IAPs for survival.
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