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¹ Department of Medical Physics, ² Organic Synthesis Core Facility, Departments of ³ Medicine and ⁴ Radiology, Memorial Sloan-Kettering Cancer Center, New York, NY

Requests for Reprints:Jason A. Koutcher, Department of Medical Physics/MRI, Memorial Sloan-Kettering Cancer Center, 1275 York Avenue, New York, NY 10021. Fax: (212) 717-3676. E-mail: koutchej{at}mskcc.org

The synthesis and characterization of 3'-fluoromethotrexate (FMTX), a novel fluorine-labeled analogue of methotrexate, are presented. Molecular modeling studies indicate that the fluorine atom causes only minimal changes in the structure/binding in the complex of the antifolate with thymidine synthetase and dihydrofolate reductase (DHFR). The in vitro cytotoxicity of this compound is shown to be equivalent to that of the parent antifolate compound. While the focus of this report is the synthetic technique of FMTX, it is also demonstrated that tumor accumulation of the labeled compound in vivo can be observed via ¹⁹F magnetic resonance spectroscopy (MRS) in a human tumor xenograft model.

Grant support:NIH (R24CA83084, P50CA86438).

Received 3/14/03; revised 6/11/03; accepted 7/ 8/03.

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