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Tuning Glutamine Binding Modes in Gd‐DOTA‐Based Probes for an Improved MRI Visualization of Tumor Cells
Author(s) -
Stefania Rachele,
Tei Lorenzo,
Barge Alessandro,
Geninatti Crich Simonetta,
Szabo Ibolya,
Cabella Claudia,
Cravotto Giancarlo,
Aime Silvio
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801567
Subject(s) - glutamine , moiety , dota , chemistry , transporter , stereochemistry , magnetic resonance imaging , amino acid , biochemistry , nuclear magnetic resonance , chelation , gene , medicine , organic chemistry , physics , radiology
Abstract Three new magnetic resonance imaging probes that target glutamine transporters have been synthesized. They consist of a Gd‐DOTA‐monoamide moiety (DOTA=1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid) linked through a six carbon atom chain to a vector represented by a glutamine residue bound through α‐carboxylic, γ‐carboxamidic, or α‐amino functionalities. Their uptake by HTC (rat hepatocarcinoma) and healthy rat hepatocytes has shown that the system containing the glutamine vector bound through the α‐carboxylic group displays a markedly higher affinity for tumor cells. The observed behavior is rationalized in terms of the exploitation of an additional glutamine transporter active in hepatic tumor cells.