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D5942

Sigma-Aldrich

DAPT

≥98% (HPLC), solid, γ-secretase inhibitor

Synonym(s):

GSI-IX, LY-374973, N-[N-(3,5-Difluorophenacetyl)-L-alanyl]-S-phenylglycine t-butyl ester

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About This Item

Empirical Formula (Hill Notation):
C23H26F2N2O4
CAS Number:
208255-80-5
Molecular Weight:
432.46
MDL number:
MFCD04974585
UNSPSC Code:
12352200
PubChem Substance ID:
24893987
NACRES:
NA.77

Product Name

DAPT, ≥98% (HPLC), solid

biological source

synthetic (organic)

Quality Level

100

Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: ~18 mg/mL

originator

Eli Lilly

storage temp.

2-8°C

SMILES string

C[C@H](NC(=O)Cc1cc(F)cc(F)c1)C(=O)N[C@@H](C(=O)OC(C)(C)C)c2ccccc2

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

InChI key

DWJXYEABWRJFSP-VBKZILBWSA-N

Gene Information

human ... APH1A(51107) , APH1B(83464) , NCSTN(23385) , NOTCH1(4851) , NOTCH2(4853) , NOTCH3(4854) , NOTCH4(4855) , PSEN1(5663) , PSEN2(5664) , PSENEN(55851)
mouse ... Aph1a(226548) , Aph1b(208117) , Ncstn(59287) , Notch1(18128) , Notch2(18129) , Notch3(18131) , Notch4(18132) , Psen1(19164) , Psen2(19165) , Psenen(66340)
rat ... Aph1a(365872) , Aph1b(300802) , Ncstn(289231) , Notch1(25496) , Notch2(29492) , Notch3(56761) , Notch4(406162) , Psen1(29192) , Psen2(81751) , Psenen(292788)

Application

DAPT has been used: as acomponent in neuronal differentiation medium (NDM) to initiate cortical neuronpatterning, as a Notch signaling inhibitor to study its effects on hair cellregeneration in zebrafish, as a γ-secretase inhibitor to block the Notchpathway to evaluate its effects on rat pulmonary artery smooth muscle cells(PASMC) proliferation

Biochem/physiol Actions

DAPT is a γ-secretase inhibitor and indirectly an inhibitor of Notch, a γ-secretase substrate. Other γ-secretase substrates include LDL receptor-related protein, E-cadherin and ErbB-4. As an inhibitor of γ-secretase, DAPT may be useful in the study of β-amyloid (Aβ) formation. DAPT has been shown to inhibit Notch signaling in studies of autoimmune and lymphoproliferative diseases, such as ALPS and lupus erythematosus (SLE), as well as in cancer cell growth, angiogenesis, and differentiation of human induced pluripotent stem cells (hIPSC).

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Eli Lilly. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000406279
0000406279
0000406278
0000406278
0000223795

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is Product D5942, DAPT soluble in?

    DAPT is soluble in DMSO at approximately 18 mg/ml.

  4. Are solutions of Product D5942, DAPT stable?

    Sigma has not evaluated the solution stability of DAPT. However, in a study of cultured insect cells, DAPT inhibited γ-secretase activity for 12 hours, which is indicative of its stability in solution at a presumed 37 °C temperature. Pitsi, D., and Octave, J.N., Presenilin 1 stabilizes the C-terminal fragment of the amyloid precursor protein independently of γ-secretase activity. J. Biol. Chem., 279(24), 25333-25338 (2004).

  5. Is Product D5942, DAPT, a reversible or irreversible inhibitor of beta secretase?

    The literature indicates that in a treatment of PDAPP neuronal cultures with DAPT, removal of DAPT from the protocol restores amyloid precursor protein β production. This implies that DAPT may be a reversible inhibitor. Dovey, H.F., et al. Functional gamma-secretase inhibitors reduce beta-amyloid peptide levels in brain. J. Neurochem., 76(1), 173-181 (2001).

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  7. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

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    Ask a Scientist here.

Yu-Chen Ye et al.
Cancer research, 79(16), 4160-4172 (2019-07-04)
Tumor-associated macrophages (TAM) play pivotal roles in tumor progression and metastasis, but the contribution and regulation of different macrophage populations remain unclear. Here we show that Notch signaling plays distinct roles in regulating different TAM subsets in hepatocellular carcinoma (HCC).
Antonia Sambola et al.
Cardiovascular drugs and therapy, 33(4), 425-433 (2019-07-25)
The impact of short or prolonged use of triple therapy (TT) on outcomes in patients with atrial fibrillation (AF) and high risk of bleeding undergoing percutaneous coronary intervention (PCI) is unclear. We compared clinical outcomes according to the duration of
Jonathan E Wosen et al.
Frontiers in immunology, 10, 1970-1970 (2019-09-05)
The role of intestinal epithelial cells (IECs) in mucosal tolerance and immunity remains poorly understood. We present a method for inducing MHC class II (MHC-II) in human enteroids, "mini-guts" derived from small intestinal crypt stem cells, and show that the
Y Wang et al.
Nutrition, metabolism, and cardiovascular diseases : NMCD, 29(6), 639-651 (2019-04-08)
Early postnatal life is a critical developmental period that affects health of the whole life. Extrauterine growth restriction (EUGR) causes cardiovascular development problems and diseases, including pulmonary arterial hypertension (PAH). PAH is characterized by proliferation, migration, and anti-apoptosis of pulmonary
Masahiro Yoshioka et al.
Journal of experimental & clinical cancer research : CR, 36(1), 101-101 (2017-08-03)
Epidermal growth factor receptor (EGFR) plays a pivotal role in the pathophysiology of esophageal squamous cell carcinoma (ESCC). However, the clinical effects of EGFR inhibitors on ESCC are controversial. This study sought to identify the factors determining the therapeutic efficacy
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