DAPT (chemical)

DAPT is a chemical compound used in the study of the Notch signaling pathway.[1] DAPT is a γ-secretase inhibitor. It indirectly inhibits Notch, which is a substrate for γ-secretase.[2]

DAPT

Names
IUPAC name tert-Butyl (2S)-2-[[(2S)-2-[[2-(3,5-difluorophenyl)acetyl]amino]propanoyl]amino]-2-phenylacetate
Other names gamma-Secretase Inhibitor IX; GSI-IX; LY-374973; N-[N-(3,5-Difluorophenacetyl)-L-alanyl]-S-phenylglycine t-butyl ester
Identifiers
CAS Number	208255-80-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:86193
ChEMBL	ChEMBL255682
ChemSpider	4470783
PubChem CID	5311272
CompTox Dashboard (EPA)	DTXSID00415519
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 Key: DWJXYEABWRJFSP-XOBRGWDASA-N
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
Properties
Chemical formula	C23H26F2N2O4
Molar mass	432.468 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

In a mouse model of Alzheimer's disease, DAPT reduces the levels of beta-amyloid.[3]

References

1. Geling, A.; Steiner, H.; Willem, M.; Bally-Cuif, L.; Haass, C. (2002). "A gamma-secretase inhibitor blocks Notch signaling in vivo and causes a severe neurogenic phenotype in zebrafish". EMBO Reports. 3 (7): 688–694. doi:10.1093/embo-reports/kvf124. PMC 1084181. PMID 12101103.
2. "DAPT". Sigma-Aldrich.
3. Dovey, H. F.; John, V.; Anderson, J. P.; Chen, L. Z.; De Saint Andrieu, P.; Fang, L. Y.; Freedman, S. B.; Folmer, B.; Goldbach, E.; Holsztynska, E. J.; Hu, K. L.; Johnson-Wood, K. L.; Kennedy, S. L.; Kholodenko, D.; Knops, J. E.; Latimer, L. H.; Lee, M.; Liao, Z.; Lieberburg, I. M.; Motter, R. N.; Mutter, L. C.; Nietz, J.; Quinn, K. P.; Sacchi, K. L.; Seubert, P. A.; Shopp, G. M.; Thorsett, E. D.; Tung, J. S.; Wu, J.; et al. (2001). "Functional gamma-secretase inhibitors reduce beta-amyloid peptide levels in brain". Journal of Neurochemistry. 76 (1): 173–81. doi:10.1046/j.1471-4159.2001.00012.x. PMID 11145990.