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About This Item
Empirical Formula (Hill Notation):
C24H28N2O3
CAS Number:
Molecular Weight:
392.49
MDL number:
UNSPSC Code:
51111800
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
Storage condition:
OK to freeze, protect from light
assay
≥98% (HPLC)
Quality Level
form
powder
manufacturer/tradename
Calbiochem®
storage condition
OK to freeze, protect from light
color
off-white
solubility
DMSO: 100 mg/mL
storage temp.
2-8°C
SMILES string
[nH]1c2c([c](c(c1)C(=O)Nc3c(cc(c(c3)O)C(C)(C)C)C(C)(C)C)=O)cccc2
InChI
1S/C24H28N2O3/c1-23(2,3)16-11-17(24(4,5)6)20(27)12-19(16)26-22(29)15-13-25-18-10-8-7-9-14(18)21(15)28/h7-13,27H,1-6H3,(H,25,28)(H,26,29)
InChI key
PURKAOJPTOLRMP-UHFFFAOYSA-N
General description
A cell-permeable, orally bioavailable dihydroquinoline-carboxamide compound that acts as a potentiator of Cystic Fibrosis Transmembrane Conductance Regulator (CFTR) by directly binding to WT and G551D mutant forms in an allosteric and reversible manner (~ 10 µM) and increases the open probability to restore lung function. Enhances cAMP/PKA-signaling mediated gating activity of both WT and G551D mutants and its potentiation activity is dependent upon the phosphorylated status of CFTR. Does not compete for binding to the canonical ATP-binding catalytic site; but the rate of flux through CFTR increase by 1.5 to 2 fold when ATP concentrations are increased. Shown to increase Cl- secretion by about 10 fold in cultured human CF bronchial epethelia (HBE) carrying G551D/F508del mutations and increases forskolin-stimulated transepethial current (IT; EC50 = 236 nM) far more effectively than genistein (EC50 = 16 µM). Displays favorable pharmacokinetic properties with t1/2= 12 h.
Please note that the molecular weight for this compound is batch-specific due to variable water content.
Please note that the molecular weight for this compound is batch-specific due to variable water content.
Biochem/physiol Actions
Cell permeable: yes
Primary Target
WT and G551D mutant forms of cell surface CFTR
WT and G551D mutant forms of cell surface CFTR
Reversible: yes
Packaging
Packaged under inert gas
Preparation Note
Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 6 months at -20°C.
Other Notes
Namkung, W., et al. 2013. Mol. Pharmacol.84, 384.
Eckford, P.D.W., et al. 2012. J. Biol. Chem.287, 36639.
Van Goor, F., et al 2009. Proc. Natl. Acad. Sci. USA106, 18825.
Eckford, P.D.W., et al. 2012. J. Biol. Chem.287, 36639.
Van Goor, F., et al 2009. Proc. Natl. Acad. Sci. USA106, 18825.
Legal Information
CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany
Disclaimer
Toxicity: Standard Handling (A)
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
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