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Lanthanide( III ) Complexes of DOTA–Glycoconjugates: A Potential New Class of Lectin‐Mediated Medical Imaging Agents
Author(s) -
André João P.,
Geraldes Carlos F. G. C.,
Martins José A.,
Merbach André E.,
Prata Maria I. M.,
Santos Ana C.,
de Lima João J. P.,
Tóth Éva
Publication year - 2004
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.200400187
Subject(s) - glycoconjugate , dota , chemistry , lanthanide , moiety , lectin , chelation , amide , stereochemistry , nuclear magnetic resonance , biochemistry , ion , organic chemistry , physics
The synthesis and characterization of a new class of DOTA (1,4,7,10‐tetrakis(carboxymethyl)‐1,4,7,10‐tetraazacyclododecane) monoamide‐linked glycoconjugates (glucose, lactose and galactose) of different valencies (mono, di and tetra) and their Sm III , Eu III and Gd III complexes are reported. The 1 H NMR spectrum of Eu III –DOTALac 2 shows the predominance of a single structural isomer of square antiprismatic geometry of the DOTA chelating moiety and fast rotation about the amide bond connected to the targeting glycodendrimer. The in vitro relaxivity of the Gd III –glycoconjugates was studied by 1 H nuclear magnetic relaxation dispersion (NMRD), yielding parameters close to those reported for other DOTA monoamides. The known recognition of sugars by lectins makes these glycoconjugates good candidates for medical imaging agents (MRI and gamma scintigraphy).