N-(4-Hydroxyphenyl)retinamide
Fenretinide is a synthetic retinol/vitamin A analog that binds RBP4 and exhibits anti-diabetic, antihypertensive, an anticancer chemotherapeutic activities. Fenretinide increases ceramide levels in vivo. In obese mice, fenretinide increases fat oxidation and decreases levels of total cholesterol and triglycerides, preventing fatty liver disease. Fenretinide also inhibits Des1, improving insulin sensitivity and normalizing glucose homeostasis in other animal models. Additionally, this compound induces caspase 3-dependent apoptosis in cancer cells and decrease tumor volume in animal models of lung cancer.
References PubMed ID：:http://www.ncbi.nlm.nih.gov/pubmed/18946323
| Cas No. |
65646-68-6 |
|---|---|
| Purity |
≥98% |
| Formula |
C26H33NO2 |
| Formula Wt. |
391.55 |
| IUPAC Name |
(2E,4E,6E,8E)-N-(4-hydroxyphenyl)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenamide |
| Synonym |
Fenretinide; 4-HPR, Retinoic acid p-hydroxyanilide |
| Melting Point |
173-175°C |
| Solubility |
Soluble in DMSO (25mg/mL) or ethanol (25mg/mL). |
Durante S, Orienti I, Teti G, et al. Anti-tumor activity of fenretinide complexed with human serum albumin in lung cancer xenograft mouse model. Oncotarget. 2014 May 28. [Epub ahead of print]. PMID: 25015569.
Bikman BT, Guan Y, Shui G, et al. Fenretinide prevents lipid-induced insulin resistance by blocking ceramide biosynthesis. J Biol Chem. 2012 May 18;287(21):17426-37. PMID: 22474281.
Koh IU, Jun HS, Choi JS, et al. Fenretinide ameliorates insulin resistance and fatty liver in obese mice. Biol Pharm Bull. 2012;35(3):369-75. PMID: 22382323.
Guilbault C, De Sanctis JB, Wojewodka G, et al. Fenretinide corrects newly found ceramide deficiency in cystic fibrosis. Am J Respir Cell Mol Biol. 2008 Jan;38(1):47-56. PMID: 17656682.
Wu JM, DiPietrantonio AM, Hsieh TC. Mechanism of fenretinide (4-HPR)-induced cell death. Apoptosis. 2001 Oct;6(5):377-88. PMID: 11483862.
