1. Synthesis of 3′-fluoro-3′-deoxythymidine and studies of its 18F-radiolabeling, as a tracer for the noninvasive monitoring of the biodistribution of drugs against AIDS
- Author
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S. Chatterjee, I.K. Wilson, and W. Wolf
- Subjects
Biodistribution ,Stereochemistry ,Organic Chemistry ,Radiochemistry ,Human immunodeficiency virus (HIV) ,chemistry.chemical_element ,Ether ,medicine.disease_cause ,Biochemistry ,3'-fluoro-3'-deoxythymidine ,Potassium fluoride ,Inorganic Chemistry ,chemistry.chemical_compound ,chemistry ,Sufficient time ,Fluorine ,medicine ,Environmental Chemistry ,Physical and Theoretical Chemistry ,Derivative (chemistry) - Abstract
3′-Fluoro-3′-deoxy-thymidine (FDT), a fluorinated analog of 3′-azido-thymidine (AZT), is both more active against the HIV virus but also more toxic than AZT. Because of its fluorine atom, it can be labeled with 18 F to be used to monitor this drug's biodistribution and targeting. A new synthesis for FDT, suited for 18 F labeling, has been developed. After protecting the 5′-hydroxy group with a trityl group, the 3′-hydroxy group was subtituted with a mesyl group in the lyxo configuration. Treatment with 18 F potassium fluoride and crown-18 ether yielded the 18 F-labeled fluoro derivative which on detritylation afforded 18 F FDT with 7% labeling efficiency. This is the first reported synthesis of 3′- fluoro-5′-O-trityl deoxythymidine using potassium fluoride and preparing its 18 F labeled analog. The time required to incorporate 18 F in the intermediate compound and isolate the end-product is reasonably short (approximately 2 h) which will allow sufficient time to conduct biological studies with this short-lived radionuclide.
- Published
- 1991
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