Abstract
A facile synthesis of six 4-iodophenyl tagged sphingosine (SP) derivatives bearing alkyl chain lengths from 6 to 13 is described. The key steps for the assembly of these molecules, 5a-f, are Suzuki-Miyaura cross-coupling and cross-metathesis reactions. The feasibility of radiolabeling was demonstrated by synthesizing two (125)I labeled compounds, [(125)I]5c and [(125)I]5e. In vitro enzyme assays indicated that the molecules, 5c-e, are potent inhibitors. Thus, they deserve further evaluation as potential radioactive probes for tumor imaging.
MeSH terms
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Humans
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Iodine Isotopes / chemistry*
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Phosphotransferases (Alcohol Group Acceptor) / antagonists & inhibitors*
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Phosphotransferases (Alcohol Group Acceptor) / metabolism
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Radiopharmaceuticals / chemical synthesis*
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Radiopharmaceuticals / chemistry
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Radiopharmaceuticals / pharmacology
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Sphingosine / analogs & derivatives*
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Sphingosine / chemical synthesis
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Sphingosine / chemistry
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Sphingosine / pharmacology
Substances
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Iodine Isotopes
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Radiopharmaceuticals
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Phosphotransferases (Alcohol Group Acceptor)
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sphingosine kinase
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N,N-dimethylsphingosine
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Sphingosine