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SML2384

Sigma-Aldrich

BAY 87-2243

≥98% (HPLC)

Synonyme(s) :

1-Cyclopropyl-4-[4-[[5-methyl-3-[3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl]-1H-pyrazol-1-yl]methyl]-2-pyridinyl]piperazine, 1-Cyclopropyl-4-{4-[(5-methyl-3-{3-[4-(trifluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}-1H-pyrazol-1-yl)methyl]pyridin-2-yl}piperazine

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About This Item

Formule empirique (notation de Hill):
C26H26F3N7O2
Numéro CAS:
1227158-85-1
Poids moléculaire :
525.53
Numéro MDL:
MFCD28143915
Code UNSPSC :
12352200
Nomenclature NACRES :
NA.77

Essai

≥98% (HPLC)

Forme

powder

Couleur

white to beige

Solubilité

DMSO: 2 mg/mL, clear

Température de stockage

2-8°C

Chaîne SMILES 

CC1=CC(C2=NC(C3=CC=C(OC(F)(F)F)C=C3)=NO2)=NN1CC4=CC(N5CCN(C6CC6)CC5)=NC=C4

InChI

1S/C26H26F3N7O2/c1-17-14-22(25-31-24(33-38-25)19-2-6-21(7-3-19)37-26(27,28)29)32-36(17)16-18-8-9-30-23(15-18)35-12-10-34(11-13-35)20-4-5-20/h2-3,6-9,14-15,20H,4-5,10-13,16H2,1H3

Clé InChI

CDJNNOJINJAXPV-UHFFFAOYSA-N

Actions biochimiques/physiologiques

BAY 87-2243 has a therapeutic effect on ferroptosis‐based cancer, hypoxic pancreatic cancer cells.
BAY 87-2243 is an orally active oxidative phosphorylation (OxPhos) inhibitor that potently suppresses hypoxia-induced HIF-1 activation (IC50 = 0.7 nM by HCT-116-based reporter assay; 24 h 1% O2) by selectively targeting mitochondrial complex I (IC50 = 10 nM using mitochondria from PC3; no inhibition of complex III), exhibiting antiproliferation activity in cancer cultures only in the absence of glucose (IC50 ∼3 nM in H460 cultures with 10 mM galactose or lactate, >10 μM with 10 mM glucose). BAY 87-2243 selectively inhibits hypoxia-induced, but not hypoxia-independent, HIF-1α & HIF-2α upregulation and HIF-1 target genes expression in cultures (IC50 ≤10 nM/ADM, ANGPTL4, CA9 mRNA in H460 cells; IC50 = 2 nM/carbonic anhydrase 9 (CA9) protein in HCT116 cells) and effectively suppresses H460 xenograft tumor growth in mice via daily oral admiminstration in vivo (ED50 ∼2 mg/kg).
Highly potent and selective mitochondrial complex I inhibitor that prevents hypoxia-induced HIF-1 activation both in vitro and in vivo.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000165039
0000165039
0000165038
0000112218
0000112219

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Retrouvez la documentation relative aux produits que vous avez récemment achetés dans la Bibliothèque de documents.

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Matthew J Martin et al.
Oncotarget, 7(52), 86313-86325 (2016-11-20)
Metabolic plasticity is an emerging hallmark of cancer, and increased glycolysis is often observed in transformed cells. Small molecule inhibitors that target driver oncogenes can potentially inhibit the glycolytic pathway. Osimertinib (AZD9291) is a novel EGFR tyrosine kinase inhibitor (TKI)
Richard A Noble et al.
Haematologica, 102(7), 1247-1257 (2017-04-08)
Inhibition of monocarboxylate transporter 1 has been proposed as a therapeutic approach to perturb lactate shuttling in tumor cells that lack monocarboxylate transporter 4. We examined the monocarboxylate transporter 1 inhibitor AZD3965, currently in phase I clinical studies, as a
Gina-Eva Görtz et al.
The Journal of clinical endocrinology and metabolism, 101(12), 4834-4842 (2016-09-10)
In Graves' ophthalmopathy (GO), inflammation with tissue expansion in a closed compartment like the bony orbit and smoking may cause tissue hypoxia. In this study, we investigated whether hypoxia-inducible factor-1 (HIF-1) action impacts on tissue remodeling in GO with the
Linda Helbig et al.
Radiation oncology (London, England), 9, 207-207 (2014-09-23)
The transcription factor hypoxia-inducible factor-1 (HIF-1) pathway plays an important role in tumor response to cytotoxic treatments. We investigated the effects of a novel small molecule inhibitor of mitochondrial complex I and hypoxia-induced HIF-1 activity BAY-87-2243, on tumor microenvironment and
Emerging strategies of cancer therapy based on ferroptosis
Shen z, et al.
Advanced Materials, 30(12), 1704007-1704007 (2018)
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