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N'Dongo, H W P; Raposinho, P D; Fernandes, C; Santos, I; Can, D; Schmutz, P; Spingler, B; Alberto, R (2010). Preparation and biological evaluation of cyclopentadienyl-based 99mTc-complexes [(Cp-R)99mTc(CO)3] mimicking benzamides for malignant melanoma targeting. Nuclear Medicine and Biology, 37(3):255-264.

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Abstract

The biological evaluation of half-sandwich (99m)Tc-complexes that surrogate iodobenzamide with a high affinity for melanin tumor tissue is described. We have synthesized via retro Diels-Alder reaction two models of (99m)Tc complexes which possess the piano stool [Cp(99m)Tc(CO)(3)] motif instead of a phenyl ring as in the original iodobenzamide (123)I-N-(N-benzylpiperidin-4-yl)-2-iodobenzamide (2-IBP) and N-(2-diethylaminoethyl)-4-iodobenzamide (BZA). Diels-Alder products 2a-b (HCp-CONHR)(2) (2a, R=2-diethylaminoethyl; 2b, R=benzylpiperidin-4-yl) were prepared and reacted with fac-[(99m)Tc(H(2)O)(3)(CO)(3))](+) 1 in water to produce the corresponding (99m)Tc complexes [(2a)(99m)Tc(CO)(3))] 4a and [(2b)(99m)Tc(CO)(3))] 4b. The structures of the (99m)Tc complexes on the no-carrier-added level have been confirmed by chromatographic comparison with the corresponding rhenium complexes 3a and 3b, macroscopically characterized by IR, NMR, ESI-MS and X-ray crystallography for 3a [triclinic, P-1, a=7.3518(1) A, b=8.0309(2) A, c=17.5536(3) A, alpha=99.1260(5) degrees, beta=90.4215(14) degree , gamma=117.0187(11) degrees]. The radioconjugate 4b showed good in vitro stability. In murine melanoma B16F1 cells, significant cellular uptake (43.9% of the total applied activity) was attained after 4 h at 37 degrees C with about 50% of the cell-associated radioactivity being internalized in the cells (22% of the applied activity). Furthermore, in melanoma-bearing C57BL6 mice, tumor uptake values of 3.39+/-0.50 %ID g(-1) and 3.21+/-0.26 %ID g(-1) at 1 and 4 h postinjection, respectively, were observed indicating a good retention of 4b in the tumor.
Copyright 2010 Elsevier Inc. All rights reserved.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
DDC:540 Chemistry
Uncontrolled Keywords:Bioorganometallic Chemistry; Melanoma; Tumor uptake; Technetium; Radiopharmaceuticals; Labelling; Retro Diels-Alder
Language:English
Date:2010
Deposited On:18 Feb 2011 16:06
Last Modified:28 Nov 2013 01:02
Publisher:Elsevier
ISSN:0969-8051
Funders:Swiss Federal Secretariat for Research and Education, University of Zurich
Publisher DOI:10.1016/j.nucmedbio.2009.11.006
PubMed ID:20346865

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