Flexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity
| Title | Flexible, polymer-supported synthesis of sphingosine derivatives provides ceramides with enhanced biological activity |
| Publication Type | Journal Article |
| Year of Publication | 2014 |
| Authors | El-Dahshan, A, Al-Gharabli, SI, Radetzki, S, Al-Tel, TH, Kumar, P, Rademann, J |
| Journal | Bioorganic & Medicinal Chemistry |
| Volume | 22 |
| Issue | 19 |
| Pagination | 5506-5512 |
| Date Published | OCT |
| ISSN | 0968-0896 |
| Keywords | Apoptosis, Ceramide, Lipid rafts, Lipids, Sphingosine |
| Abstract | A polymer-supported route for the synthesis of sphingosine derivatives is presented based on the C-acylation of polymeric phosphoranylidene acetates with an Fmoc-protected amino acid. The approach enables the flexible variation of the sphingosine tail through a deprotection-decarboxylation sequence followed by E-selective Wittig olefination cleavage. D-Erythro-sphingosine analogs have been synthesized by diastereoselective reduction of the keto group employing LiAlH(O-tBu)(3) as reducing agent. The effect of ceramides and keto-ceramides on the proliferation of three cancer cell lines HEP G-2, PC-12 and HL-60 was investigated and a ceramide containing an aromatic sphingosine tail was identified as being most active. (C) 2014 Elsevier Ltd. All rights reserved. |
| DOI | 10.1016/j.bmc.2014.07.024 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 1.57 |