ORGN 541 |
Photoactivatable analogues of sphingosine-1-phosphate: synthesis and binding to protein targets
| Xuequan Lu1, Sandor Cseh2, Daniel L Baker2, Hoe-Sup Byun1, Gabor Tigyi2, and Robert Bittman1. (1) Department of Chemistry and Biochemistry, Queens College and The Graduate Center of CUNY, Flushing, NY 11367-1597, (2) Department of Physiology, University of Tennessee Health Science Center Memphis, Memphis, TN 38163 |
Sphingosine-1-phosphate (S1P) is a member of the lysophospholipid growth factor family. As an extracellular mediator, S1P acts on five G protein-coupled plasma membrane receptors present in many cell types. S1P is generated intracellularly from sphingosine, and acts on targets that have not yet been fully characterized. We report the synthesis of two [32P]-labeled photoactivatable probes of S1P in which a benzophenone or a phenoxydiazirine moiety is incorporated into the long-chain base (compounds 1 and 2, respectively). The S1P1 receptor in rat hepatoma cell membranes interacted in a specific manner with compound 1 (Kd=84 nM). Both probes labeled plasma proteins and a 25-kDa protein in rat plasma.  |
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Bioorganic, Molecular Recognition, Asymmetric Reactions and Syntheses
11:00 AM-1:00 PM, Wednesday, September 10, 2003 Javits Convention Center -- Hall 1B/1C, Poster
Division of Organic Chemistry
The 226th ACS National Meeting, New York, NY, September 7-11, 2003
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