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Melanoma Uptake of 99mTc Complexes Containing the N-(2-Diethylaminoethyl)benzamide Structural Element

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German Cancer Research Center and Department of Nuclear Medicine, University of Heidelberg, Heidelberg, Germany, and Department of Radiology, Harvard Medical School and Brigham and Women's Hospital, Harvard University, Boston, Massachusetts 02115
Cite this: J. Med. Chem. 2002, 45, 26, 5802–5805
Publication Date (Web):November 23, 2002
https://doi.org/10.1021/jm021026z
Copyright © 2002 American Chemical Society

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    Abstract

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    On the basis of the avid uptake of radioiodinated benzamides by melanoma cells, 99mTc complexes containing the structural elements of N-(dialkylaminoalkyl)benzamide pharmacophores have been synthesized and evaluated in vitro and in vivo for melanoma uptake. One of the complexes Tc-12 containing the ligand 4-(S-benzoyl-2-thioacetyl-glycyl-glycylamido)-N-(2-diethylaminoethyl)benzamide (11) displayed the highest melanoma uptake. The 1-h melanoma uptake values and the corresponding blood counts indicate an interdependence of tumor uptake and bioavailability of the 99mTc complexes.

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     This article is dedicated to Harald zur Hausen on the occasion of his retirement as head of the Deutsches Krebsforschungszentrum Heidelberg.

    *

     Author for correspondence:  Michael Eisenhut, Ph.D., Deutsches Krebsforschungszentrum Heidelberg, Abt. Radiochemie und Radiopharmakologie (E0300), Im Neuenheimer Feld 280, 69120 Heidelberg, Germany. Fax:  06221-422421. E-mail:  [email protected].

     German Cancer Research Center, University of Heidelberg.

    §

     Department of Nuclear Medicine, University of Heidelberg.

     Harvard Medical School and Brigham and Women's Hospital.

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    Experimental Section including syntheses, electrophoresis, determination of octanol−buffer partition coefficients, and biological investigations. This material is available free of charge via the Internet at http://pubs.acs.org.

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