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About This Item
Empirical Formula (Hill Notation):
C22H21NO5S2
CAS Number:
Molecular Weight:
443.54
MDL number:
NACRES:
NA.21
SMILES string
[S](=O)(=O)(\N=C2\c3c(cccc3)C(=O)C(=C\2)SCC(=O)O)c1ccc(cc1)C(C)(C)C
InChI
1S/C22H21NO5S2/c1-22(2,3)14-8-10-15(11-9-14)30(27,28)23-18-12-19(29-13-20(24)25)21(26)17-7-5-4-6-16(17)18/h4-12H,13H2,1-3H3,(H,24,25)/b23-18+
InChI key
BXWWOKYIKNEEHJ-PTGBLXJZSA-N
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: 2 mg/mL, clear
storage temp.
-10 to -25°C
Quality Level
Related Categories
Biochem/physiol Actions
Potent and selective peptidyl-prolyl cis-trans isomerase (PPIase) Pin1 covalent inhibitor with anti-cancer efficacy in cultures and in vivo.
KPT-6566 is a potent and selective peptidyl-prolyl cis-trans isomerase (PPIase) Pin1 inhibitor (IC50 = 640 nM) that targets Pin1 catalytic site for covalent modification, resulting in Pin1 degradation and the release of ROS-generating and DNA-damaging quinone-mimicking KPT-6566-B. KPT-6566 inhibits the proliferation of wild-type, but not Pin1-/-, MEFs (1-5 µM for 48h) with concomitant reduction of cellular pRB and Cyclin D1 hyperphosphorylation. KPT-6566 induces cancer cell death in cultures (1-10 µM for 48h) and reduces MDA-MB-231 lung metastasis in mice in vivo (5 mg/kg/d i.p.). KPT-6566 is more potent than juglone and does not affect the PPIase activity of GST-FKBP4 or GST-PPIA.
KPT-6566 is a potent and selective peptidyl-prolyl cis-trans isomerase (PPIase) Pin1 inhibitor (IC50 = 640 nM) that targets Pin1 catalytic site for covalent modification, resulting in Pin1 degradation and the release of ROS-generating and DNA-damaging quinone-mimicking KPT-6566-B. KPT-6566 inhibits the proliferation of wild-type, but not Pin1-/-, MEFs (1-5 µM for 48h) with concomitant reduction of cellular pRB and Cyclin D1 hyperphosphorylation. KPT-6566 induces cancer cell death in cultures (1-10 µM for 48h) and reduces MDA-MB-231 lung metastasis in mice in vivo (5 mg/kg/d i.p.). KPT-6566 is more potent than juglone and does not affect the PPIase activity of GST-FKBP4 or GST-PPIA.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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