Wikipedia

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
Systematic IUPAC name
tert-Butyl (S)-{(2S)-2-[2-(3,5-difluorophenyl)acetamido]propanamido}phenylacetate
Other names
gamma-Secretase Inhibitor IX; GSI-IX; LY-374973; N-[N-(3,5-Difluorophenacetyl)-L-alanyl]-S-phenylglycine t-butyl ester
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
  • 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
  • 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
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).

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

References

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  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 12101103.688-694&rft.date=2002&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1084181#id-name=PMC&rft_id=info:pmid/12101103&rft_id=info:doi/10.1093/embo-reports/kvf124&rft.aulast=Geling&rft.aufirst=A.&rft.au=Steiner, H.&rft.au=Willem, M.&rft.au=Bally-Cuif, L.&rft.au=Haass, C.&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1084181&rfr_id=info:sid/en.wikipedia.org:DAPT (chemical)" class="Z3988">
  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 11145990.173-81&rft.date=2001&rft_id=info:doi/10.1046/j.1471-4159.2001.00012.x&rft_id=info:pmid/11145990&rft.aulast=Dovey&rft.aufirst=H. F.&rft.au=John, V.&rft.au=Anderson, J. P.&rft.au=Chen, L. Z.&rft.au=De Saint Andrieu, P.&rft.au=Fang, L. Y.&rft.au=Freedman, S. B.&rft.au=Folmer, B.&rft.au=Goldbach, E.&rft.au=Holsztynska, E. J.&rft.au=Hu, K. L.&rft.au=Johnson-Wood, K. L.&rft.au=Kennedy, S. L.&rft.au=Kholodenko, D.&rft.au=Knops, J. E.&rft.au=Latimer, L. H.&rft.au=Lee, M.&rft.au=Liao, Z.&rft.au=Lieberburg, I. M.&rft.au=Motter, R. N.&rft.au=Mutter, L. C.&rft.au=Nietz, J.&rft.au=Quinn, K. P.&rft.au=Sacchi, K. L.&rft.au=Seubert, P. A.&rft.au=Shopp, G. M.&rft.au=Thorsett, E. D.&rft.au=Tung, J. S.&rft.au=Wu, J.&rft.au=Yang, S.&rft_id=https://doi.org/10.1046%2Fj.1471-4159.2001.00012.x&rfr_id=info:sid/en.wikipedia.org:DAPT (chemical)" class="Z3988">
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