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Synthesis of 2‐[(2‐chloro‐2′‐[ 18 F]fluoroethyl)amino]‐2H‐1,3,2‐oxazaphosphorinane‐2‐oxide ( 18 F‐fluorocyclophosphamide), a potential tracer for breast tumor prognostic imaging with PET
Author(s) -
Lacan Goran,
Kesner Amanda L.,
Gangloff Anne,
Zheng Lei,
Czernin Johannes,
Melega William P.,
Silverman Daniel H. S.
Publication year - 2005
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.954
Subject(s) - chemistry , in vivo , radiochemistry , positron emission tomography , ex vivo , imaging agent , cyclophosphamide , nuclear medicine , nuclear chemistry , chemotherapy , in vitro , biochemistry , medicine , microbiology and biotechnology , biology
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.