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Design and Synthesis of [111In]DTPA−Folate for Use as a Tumor-Targeted Radiopharmaceutical

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    Design and Synthesis of [111In]DTPA−Folate for Use as a Tumor-Targeted Radiopharmaceutical
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    Department of Chemistry, Department of Veterinary Clinical Sciences, and Department of Medicinal Chemistry and Molecular Pharmacology, Purdue University, West Lafayette, Indiana 47907
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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 1997, 8, 5, 673–679
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    https://doi.org/10.1021/bc9701297
    Published September 25, 1997
    Copyright © 1997 American Chemical Society
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    Abstract

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    Folate-conjugated metal chelates have been proposed as potential imaging agents for cancers that overexpress folate receptors. In a previous study, folic acid was linked through its γ-carboxyl group to deferoxamine (DF), and the 67Ga-labeled complex ([67Ga]DF−folate) was examined for in vivo tumor targeting efficiency in athymic mice with a human tumor cell implant. Although superb tumor-to-background contrast was obtained, slow hepatobiliary clearance would compromise imaging of abdominal tumors such as ovarian cancer. In the present study, folic acid was conjugated to an alternative chelator, diethylenetriaminepentaacetic acid (DTPA), via an ethylenediamine spacer. The desired DTPA−folate(γ) regioisomer was synthesized by two different approaches, purified by reversed phase column chromatography, and characterized mainly by analytical HPLC, mass spectroscopy, and NMR. In cultured tumor cells, uptake of [111In]DTPA−folate(γ) was found to be specific for folate receptor-bearing cells, and the kinetics of uptake were similar to those of free folate and other folate-conjugated molecules. In the normal rat, intravenously administered [111In]DTPA−folate(γ) was found to be rapidly excreted into the urine, giving intestinal levels of radiotracer 10-fold lower than those observed with [67Ga]DF−folate(γ) at 4 h. In a preliminary mouse imaging study, a folate receptor-positive KB cell tumor was readily visualized by γ scintigraphy 1 h following intravenous administration of [111In]DTPA−folate(γ).

    Copyright © 1997 American Chemical Society

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    †

     Department of Chemistry.

    ‡

     Department of Veterinary Clinical Sciences.

    §

     Department of Medicinal Chemistry and Molecular Pharmacology.

    *

     To whom correspondence should be addressed. Phone:  (317) 494-5273. Fax:  (317) 494-0239.

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     Abstract published in Advance ACS Abstracts, September 1, 1997.

    Supporting Information Available

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    1H and 13C NMR spectra of EDA−folate(γ), 1H and 13C NMR spectra of DTPA−folate(γ), analytical HPLC chromatograms of the two compounds with the conditions described in Experimental Procedures, and a table showing the biodistribution of [111In]DTPA−folate and [67Ga]DF−folate in rats calculated as a percentage of the injected dose per gram (%ID/g) of tissue wet weight (7 pages). Ordering information is given on any current masthead page.

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    Bioconjugate Chemistry

    Cite this: Bioconjugate Chem. 1997, 8, 5, 673–679
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    https://doi.org/10.1021/bc9701297
    Published September 25, 1997
    Copyright © 1997 American Chemical Society
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