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Reagents for Astatination of Biomolecules:  Comparison of the in Vivo Distribution and Stability of Some Radioiodinated/Astatinated Benzamidyl and nido-Carboranyl Compounds

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Departments of Radiation Oncology, and Urology, University of Washington, Seattle, Washington 98195, Department of Radiology, Duke University, Durham, North Carolina 27710, and Department of Chemistry and Biochemistry, University of California, Los Angeles, California
Cite this: Bioconjugate Chem. 2004, 15, 1, 203–223
Publication Date (Web):December 30, 2003
https://doi.org/10.1021/bc034175k
Copyright © 2004 American Chemical Society

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    Abstract

    An investigation has been conducted to assess the in vivo stability of a series of astatinated benzamides and astatinated nido-carborane compounds in mice. It was hypothesized that the higher bond strength of boron−astatine bonds in the nido-carboranes might provide increased stability toward in vivo deastatination. Four tri-n-butylstannylbenzamides were prepared for radiohalogenation and evaluation in vivo. Those compounds were N-propyl-4-(tri-n-butylstannyl)benzamide 1a, N-propyl-3-(tri-n-butylstannyl)benzamide 2a, ethyl 4-tri-n-butylstannylhippurate 3a, and 4-tri-n-butylstannyl-hippuric acid 4a. Seven mono-nido-carboranyl derivatives were prepared for radiohalogenation and in vivo evaluation. Four of the seven mono-carboranyl derivatives (5a, 6a, 7a, 13a) contained a 3-(nido-carboranyl)propionamide functionality, and the remaining compounds (8a, 8g, 10a) contained a 4-(nido-carboranyl)aniline functionality. Two additional derivatives (11a, 12a) were prepared that contained bis-(nido-carboranylmethyl)benzene moieties (also referred to as Venus flytrap complexes (VFCs). All benzamide and nido-carborane compounds underwent facile iodination and radiohalogenation, except a 4-(nido-carboranyl)aniline derivative, 8a. Iodination of 8a resulted in a mixture, of which the desired iodinated product was a minor component. Therefore, radiohalogenation was not attempted. It is believed that the mixture of products is due to the presence of a thiourea bond. Previous studies have shown that thiourea bonds can interfere with halogenation reactions. In vivo comparisons of the compounds were conducted by co-injection of dual labeled (125/131I and 211At) compounds. Tissue distribution data were obtained at 1 and 4 h postinjection of the radiolabeled compounds, as that was sufficient to determine if astatine was being released. Stability of the astatinated compound was assessed by the difference in concentration of radioiodine and astatine in lung and spleen. All of the benzamides were found to undergo rapid deastatination in vivo. The nido-carborane derivatives appeared to be slightly more stable to in vivo deastatination; however, they had long blood residence times. The surprising finding was that the VFC derivatives did not release 211At in vivo, even though they rapidly localized to liver. This finding provides encouragement that stable conjugates of 211At may be attained if appropriate modifications of the VFC can be made to redirect their excretion through the renal system.

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    *

     Address correspondence to D. Scott Wilbur, Ph.D., Department of Radiation Oncology, University of Washington, 2121 N. 35th Street, Seattle, WA 98103-9103. Phone:  206-685-3085. FAX:  206-685-9630. E-mail:  [email protected].

     Department of Radiation Oncology.

     Department of Urology, University of Washington.

    §

     Duke University.

    #

     University of California.

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    Complete tissue distribution data (Tables 1−13). HPLC chromatograms, 1H NMR spectra, and mass spectra for new compounds (1a, 1b, 2a, 2b, 2e, 2f, 3a, 3b, 4a, 4b, 5a, 5b, 5e5g, 6a, 6b, 7a, 7b, 7d7f, 8a, 8b, 9b, 10a, 10b, 10e, 12a, 12b, 13a, 13b, 13e) prepared in the research described in this paper. This material is available free of charge via the Internet at http://pubs.acs.org.

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