NDLI: Target Visualization by MRI Using the Avidin/Biotin Amplification Route: Synthesis and Testing of a Biotin–Gd-DOTA Monoamide $Trimer^{†}$

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Target Visualization by MRI Using the Avidin/Biotin Amplification Route: Synthesis and Testing of a Biotin–Gd-DOTA Monoamide $Trimer^{†}$

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Target Visualization by MRI Using the Avidin/Biotin Amplification Route: Synthesis and Testing of a Biotin–Gd-DOTA Monoamide $Trimer^{†}$

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Negri, Viviana Cravotto, Giancarlo Tei, Lorenzo Geninatti Crich, Simonetta Ramella, Daniela Barge, Alessandro Pagliarin, Roberto Aime, Silvio
Description	Author Affiliation: Tei L ( Dipartimento di Scienze dell'Ambiente e della Vita, Università del Piemonte Orientale Amedeo Avogadro, Viale T. Michel 11, 15121 Alessandria, Italy.)
Abstract	To design efficient targeting strategies in magnetic resonance (MR) molecular imaging applications, the formation of supramolecular adducts between (strept)avidin ((S)Av) and tribiotinylated Gd-DOTA-monoamide complexes (DOTA=1,4,7,10-tetraazacyclododecane-N,N′,N′′,N′′′-tetraacetic acid) was explored. Two compounds based on the trivalent core of tris(2-aminoethyl)amine each containing three biotin molecules and one (L1) or three (L2) DOTA-monoamide (DOTAMA) ligands were synthesized. In these tribiotinylated derivatives the biotins are spaced far enough apart to allow the formation of the supramolecular adduct with the protein and to host the chelating units in between the (S)Av layers. Size exclusion HPLC analyses indicated complete formation of very high molecular weight polymers (>2 MDa) with (S)Av in solution. A $^{1}H NMR$ spectroscopy relaxometric study on the obtained polymeric adducts showed a marked increase of the relaxivity at 35–40 MHz as a consequence of the lengthening of the tumbling time due to the formation of Gd-chelates/(S)Av polymers. The most efficient $Gd_{3}L2/(S)Av$ polymeric system was used for a test in cell cultures. The target is represented by a neural cell adhesion molecule (NCAM), which is overexpressed in Kaposi’s sarcoma cells and tumor endothelial cells (TEC) and that is efficiently recognized by a biotinylated tetrameric peptide (C3d-Bio). In vitro experiments showed that only cells incubated with both C3d-Bio and $Gd_{3}L2/SAv$ polymer were hyperintense with respect to the control. Relaxation rates of cell pellets incubated with $Gd_{3}L2/SAv$ alone were not significantly different from the untreated cells demonstrating the absence of a specific binding.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	27
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-07-19
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Avidin Chemistry Biotin Analogs & Derivatives Gadolinium Magnetic Resonance Imaging Organometallic Compounds Chemical Synthesis Chelating Agents Ligands Molecular Structure Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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