Iodophenyl tagged sphingosine derivatives: synthesis and preliminary biological evaluation.
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.
Qu
Wenchao
W
Department of Radiology, University of Pennsylvania, 3700 Market Street, Room 305, Philadelphia, PA 19104, United States. wenchao.qu@sunmac.spect.upenn.edu
Ploessl
Karl
K
Truong
Hong
H
Kung
Mei-Ping
MP
Kung
Hank F
HF
D006801:Humans; D007456:Iodine Isotopes / Q000737:chemistry*; D017853:Phosphotransferases (Alcohol Group Acceptor) / Q000037:antagonists & inhibitors* / Q000378:metabolism; D019275:Radiopharmaceuticals / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000099157:Sphingosine Kinase
D007456:Iodine Isotopes; D017853:Phosphotransferases (Alcohol Group Acceptor); D019275:Radiopharmaceuticals; D013110:Sphingosine; D000099157:Sphingosine Kinase; C061800:N,N-dimethylsphingosine