Fenretinide

Fenretinide is a synthetic derivative of retinoic acid (Cay-11017) and an inhibitor of dihydroceramide desaturase (IC50 = 2.32 µM). It promotes the generation of reactive oxygen species (ROS), the degradation of anti-apoptotic MCL-1, and the cleavage of pro-apoptotic PKCdelta. At 5-20 µM, fenretinide selectively activates retinoic acid receptor gamma (RARgamma) and is reported to inhibit the growth of Caov-3, OVCAR-3, and SKOV3 ovarian cancer cells with IC50 values of 3.7, 6.9, and 8.2 µM, respectively. It also increases activity of serine palmitoyl transferase (SPT) by 1.75-fold and induces caspase-dependent apoptosis in BMEC cells (IC50 = 2.4 µM). Fenretinide prevents lipid-induced reductions in insulin-stimulated glucose uptake in isolated rat soleus muscle. In vivo, fenretinide (10 mg/ml in drinking water) reduces liver and soleus muscle neutral lipid content and inhibits high-fat diet-induced increases in dihydroceramide desaturase transcription.Formal Name: N-(4-hydroxyphenyl)-retinamide. CAS Number: 65646-68-6. Synonyms: 4-HPR, 4-Hydroxy(phenyl)retinamide, MK-4016, Retinoic Acid p-hydroxyphenylamide, Ro 22-4667. Molecular Formula: C26H33NO2. Formula Weight: 391.6. Purity: >98%. Formulation: (Request formulation change), A crystalline solid. Solubility: DMF: 10 mg/ml, DMSO: 10 mg/ml, Ethanol: 10 mg/ml, Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/ml. lambdamax: 363 nm. SMILES: CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C(NC2=CC=C(O)C=C2)=O)C(C)(C)CCC1. InChi Code: InChI=1S/C26H33NO2/c1-19(11-16-24-21(3)10-7-17-26(24,4)5)8-6-9-20(2)18-25(29)27-22-12-14-23(28)15-13-22/h6,8-9,11-16,18,28H,7,10,17H2,1-5H3,(H,27,29)/b9-6+,16-11+,19-8+,20-18+. InChi Key: AKJHMTWEGVYYSE-FXILSDISSA-N.