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DAPT

CAT: 0804-HY-13027-06Size: 200 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-13027-06Size:200 mg
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Description
DAPT (GSI-IX) is a potent and orally active γ-secretase inhibitor with IC50s of 115 nM and 200 nM for total amyloid-β (Aβ) and Aβ42, respectively. DAPT inhibits the activation of Notch 1 signaling and induces cell differentiation. DAPT also induces autophagy and apoptosis. DAPT has neuroprotection activity and has the potential for autoimmune and lymphoproliferative diseases, degenerative disease and cancers treatment[1][2].
CAS Number
208255-80-5
Product Name Alternative
GSI-IX
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Amyloid-β; Apoptosis; Autophagy; Notch; Organoid; γ-secretase
Type
Reference compound
Related Pathways
Apoptosis; Autophagy; Neuronal Signaling; Stem Cell/Wnt
Applications
Cancer-programmed cell death
Field of Research
Cancer; Inflammation/Immunology; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/DAPT.html
Concentration
10mM
Purity
99.97
Solubility
DMSO : 62.5 mg/mL (ultrasonic)
Smiles
FC1=CC(F)=CC(CC(N[C@H](C(N[C@H](C(OC(C)(C)C)=O)C2=CC=CC=C2)=O)C)=O)=C1
Molecular Formula
C23H26F2N2O4
Molecular Weight
432.46
Precautions
H302, H315, H319, H335
References & Citations
[1]Dovey HF, et al. Functional gamma-secretase inhibitors reduce beta-amyloid peptide levels in brain. J Neurochem. 2001 Jan;76 (1) :173-81.|[2]Zhou JX, et al. γ-secretase inhibition combined with NSC 119875 enhances apoptosis of nasopharyngeal carcinoma cells.Exp Ther Med. 2012 Feb;3 (2) :357-361.|[3]Li S, et al. DAPT protects brain against cerebral ischemia by down-regulating the expression of Notch 1 and nuclear factor κB in rats. Neurol Sci. 2012 Dec;33 (6) :1257-64.|[4]Tanimizu N, et al. Intrahepatic bile ducts are developed through formation of homogeneous continuous luminal network and its dynamic rearrangement in mice. Hepatology. 2016 Jul;64 (1) :175-88.|[5]Michael T. Chang, et al. Notch Drives Proliferation And Radiation Resistance Of Cancer Stem Cells In Adenoid Cystic Carcinoma. Yale University. January 2016.|[6]Majumder S, et al. Shifts in podocyte histone H3K27me3 regulate mouse and human glomerular disease. J Clin Invest. 2018 Jan 2;128 (1) :483-499.|[7]Yixin Tao, et al. β-catenin activation in hair follicle dermal stem cells induces ectopic hair outgrowth and skin fibrosis. J Mol Cell Biol. 2018 May 16.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Dapt

DAPT is a dipeptide consisting of alanylphenylglycine derivatised as a 3,5-difluorophenylacetamide at the amino terminal and a tert-butyl ester at the carboxy terminal. It is a gamma-secretase inhibitor. It has a role as an EC 3.4.23.46 (memapsin 2) inhibitor. It is a tert-butyl ester, a carboxylic ester, a difluorobenzene and a dipeptide.

CAS Number208255-80-5
PubChem CID5311272
IUPAC Nametert-butyl (2S)-2-[[(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoyl]amino]-2-phenylacetate
Molecular FormulaC23H26F2N2O4
Molecular Weight432.5
XLogP3.7
Topological Polar Surface Area84.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Heavy Atom Count31
Formal Charge0
Complexity622
SMILES
C[C@@H](C(=O)N[C@@H](C1=CC=CC=C1)C(=O)OC(C)(C)C)NC(=O)CC2=CC(=CC(=C2)F)F
InChI
InChI=1S/C23H26F2N2O4/c1-14(26-19(28)12-15-10-17(24)13-18(25)11-15)21(29)27-20(16-8-6-5-7-9-16)22(30)31-23(2,3)4/h5-11,13-14,20H,12H2,1-4H3,(H,26,28)(H,27,29)/t14-,20-/m0/s1
InChIKey
DWJXYEABWRJFSP-XOBRGWDASA-N
Chemical Structure
2D Structure
2D structure of Dapt
CAS: 208255-80-5
CID: 5311272
Formula: C23H26F2N2O4
MW: 432.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight432.5
XLogP33.7
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count9
Exact Mass432.18606364
Monoisotopic Mass432.18606364
Topological Polar Surface Area84.5 Ų
Heavy Atom Count31
Formal Charge0
Complexity622
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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