| 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
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)
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by scientists at CIBA-Geigy Limited as a potential anti tumor compound, although certain early in vivo studies have been retracted.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
PubMed
Patents
Sample Use Guides
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
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.
SUBSTANCE RECORD
