Literature DB >> 23932646

Synthesis and preclinical characterization of [64Cu]NODAGA-MAL-exendin-4 with a Nε-maleoyl-L-lysyl-glycine linkage.

Cheng-Bin Yim1, Kirsi Mikkola, Veronica Fagerholm, Viki-Veikko Elomaa, Tamiko Ishizu, Johan Rajander, Joern Schlesinger, Anne Roivainen, Pirjo Nuutila, Olof Solin.   

Abstract

INTRODUCTION: Renal localization of high radioactivity levels during targeted imaging compromises tissue visualization in the kidney region and limits diagnostic accuracy. Radioiodinated antibody fragments with a renal enzyme-cleavable N(ε)-maleoyl-L-lysyl-glycine (MAL) linkage demonstrated low renal radioactivity levels in mice, from early postinjection times. This study tested the hypothesis whether a (64)Cu-labeled NODAGA-exendin-4 peptide with a MAL linkage ([(64)Cu]NODAGA-MAL-exendin-4) could decrease kidney radioactivity levels in rats, compared to a [(64)Cu]NODAGA-exendin-4 reference, without impairing the radioactivity levels in the target tissue.
METHODS: NODAGA-MAL-exendin-4 was synthesized in a two-phase approach using solid support to prepare maleoyl-derivatized NODAGA followed by Michael addition to cysteine-derivatized exendin-4 in solution. Radiolabeling was performed in buffered aqua with [(64)Cu]CuCl2, which was produced via the (64)Ni(p,n)(64)Cu nuclear reaction. The in vitro and in vivo stability, lipophilicity, and distribution kinetics in major rat organs for [(64)Cu]NODAGA-MAL-exendin-4 were studied and compared to [(64)Cu]NODAGA-exendin-4. Labeling of pancreatic islets was assessed using autoradiography.
RESULTS: NODAGA-MAL-exendin-4 was synthesized, with an overall yield of 9%, and radiolabeled with (64)Cu with high specific radioactivity. Serum incubation studies showed high stability for [(64)Cu]NODAGA-MAL-exendin-4. Similar tissue distribution kinetics was observed for [(64)Cu]NODAGA-MAL-exendin-4 and [(64)Cu]NODAGA-exendin-4, with high kidney radioactivity levels.
CONCLUSIONS: The incorporated MAL linkage in [(64)Cu]NODAGA-MAL-exendin-4 was unable to reduce kidney radioactivity levels, compared to [(64)Cu]NODAGA-exendin-4. The applicability of metabolizable linkages in the design of kidney-saving exendin-4 analogs requires further investigation.
© 2013.

Entities:  

Keywords:  Copper-64; Exendin; GLP-1 receptor; NODAGA; Renal brush border membrane

Mesh:

Substances:

Year:  2013        PMID: 23932646     DOI: 10.1016/j.nucmedbio.2013.06.012

Source DB:  PubMed          Journal:  Nucl Med Biol        ISSN: 0969-8051            Impact factor:   2.408


  10 in total

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Authors:  Ganesan Vaidyanathan; Choong Mo Kang; Darryl McDougald; Il Minn; Mary Brummet; Martin G Pomper; Michael R Zalutsky
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4.  Evaluation of ¹¹¹in-labelled exendin-4 derivatives containing different meprin β-specific cleavable linkers.

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8.  Low kidney uptake of GLP-1R-targeting, beta cell-specific PET tracer, 18F-labeled [Nle14,Lys40]exendin-4 analog, shows promise for clinical imaging.

Authors:  Kirsi Mikkola; Cheng-Bin Yim; Paula Lehtiniemi; Saila Kauhanen; Miikka Tarkia; Tuula Tolvanen; Pirjo Nuutila; Olof Solin
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  10 in total

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