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Details

Stereochemistry ACHIRAL
Molecular Formula C20H15N3O2
Molecular Weight 329.352
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 4,5-DIANILINOPHTHALIMIDE

SMILES

O=C1NC(=O)C2=C1C=C(NC3=CC=CC=C3)C(NC4=CC=CC=C4)=C2

InChI

InChIKey=AAALVYBICLMAMA-UHFFFAOYSA-N
InChI=1S/C20H15N3O2/c24-19-15-11-17(21-13-7-3-1-4-8-13)18(12-16(15)20(25)23-19)22-14-9-5-2-6-10-14/h1-12,21-22H,(H,23,24,25)

HIDE SMILES / InChI

Description

4,5-Dianilinophthalimide (DAPH-1) is an inhibitor of human Epithelial growth factor (IC50 0.3 microM). It was originally developed by scientists at CIBA-Geigy Limited as a potential anti tumor compound, although certain early in vivo studies have been retracted. DAPH-1 was found to be rapidly metabolized in the liver, however, a fluorinated analog (DAPH-2) was more stable in vivo. More recently DAPH-1 has found interest as an anti-amyloid compound. DAPH-1 shows specific efficacy against the yeast prion and may be a useful model for the development of other anti prion compounds.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.3 µM [IC50]
0.58 µM [IC50]
4.8 µM [IC50]
6.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Female nude mice were transfected in the left flank with human A431 epithelial carcinoma, v-sis transfected BALB/c 3T3 cells, or T24 bladder carcinoma cells. DAPH-1 was administered as a single oral dose of 100 mg/kg, unfortunately, DAPH-1 is readily metabolized by the liver and no physiological effect could be observed. Anti tumor activity was observed using fluorinated analog DAPH-2, which is not rapidly metabolized.
Route of Administration: Oral
In Vitro Use Guide
Prion expressing yeast cells ([PSI+] delta-PDR5) were treated with 0 - 100 microM DAPH-1 while growing in the mid-log phase. Cells were incubated in the treatment condition for 24 hours in liquid culture. The fraction of prion +/- cells was determined by plating on YPD media and by fluorescence microscopy. DAPH-1 demonstrated a dose dependent ability to cure prion positive yeast cells, which was 5 fold more effective than 1% DMSO.