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Synthesis of 2-[(2-chloro-2′-[18F]fluoroethyl)amino]-2H-1,3,2-oxazaphosphorinane-2-oxide (18F-fluorocyclophosphamide), a potential tracer for breast tumor prognostic imaging with PET

✍ Scribed by Goran Lacan; Amanda L. Kesner; Anne Gangloff; Lei Zheng; Johannes Czernin; William P. Melega; Daniel H. S. Silverman


Publisher
John Wiley and Sons
Year
2005
Tongue
French
Weight
116 KB
Volume
48
Category
Article
ISSN
0022-2135

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✦ Synopsis


Abstract

A fluorine‐18 labeled analog of the widely used chemotherapeutic agent cyclophosphamide was synthesized as a tracer for prognostic imaging with positron emission tomography. 2‐[(2‐Chloro‐2′‐[^18^F]fluoroethyl)amino]‐2H‐1,3,2‐oxazaphosphorinane‐2‐oxide (^18^F‐fluorocyclophosphamide), was prepared by direct halogen exchange reaction from the parent cyclophosphamide. In small‐scale syntheses, radiochemical yields of up to 4.9% and specific activities of 960 Ci/mmol were achieved in a total synthesis time of 60–75 min. The [^18^F]‐labeled cyclophosphamide analog with radioactive purity >99% and chemical purity >96% was suitable for in vivo (microPET imaging) and ex vivo studies of a murine model of human breast tumors. Copyright © 2005 John Wiley & Sons, Ltd.


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