ORGN 542 |
Synthesis and antiproliferative properties of novel unnatural ceramide analogues
| Robert Bittman1, Jiong Chun1, Hoe-Sup Byun1, and Gilbert Arthur2. (1) Department of Chemistry and Biochemistry, Queens College and The Graduate Center of CUNY, Flushing, NY 11367-1597, (2) Biochemistry, University of Manitoba, Winnipeg, MB R3E 0W3, Canada |
The sphingolipid ceramide is a lipid second messenger that regulates a myriad of cell functions. This poster will describe the syntheses of N-palmitoylceramide analogues 1-4 and compare their antiproliferative activities against MCF-7 breast cancer cells in vitro. Under the conditions used, D-erythro-C16-ceramide (naturally occurring) was ineffective, as was allenyl-ceramide analogue 4. However, D-ribo-Phytoceramide (1) and (3S,4S)-2-[(1'E)-1'-tetradecenyl]-3-hydroxy-4-palmitoylamidotetrahydrofuran (2) were the most potent in this series (IC50 9.5 micromolar), followed by phenyl derivative 3 (IC50 16-20 micromolar).  |
| |
|
Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Sci-Mix
8:00 PM-10:00 PM, Monday, September 8, 2003 Javits Convention Center -- North Pavillion, Sci-Mix
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
|