Lanthanide(III) Complexes of DOTA-Glycoconjugates: A Potential New Class of Lectin-Mediated Medical Imaging Agents

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 SmIII, EuIII and GdIII complexes are reported. The 1H NM...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2004-11, Vol.10 (22), p.5804-5816
Main Authors: 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
Format: Article
Language:English
Subjects:
Carbohydrates - chemistry
Galactose - chemistry
Glucose - chemistry
glycoconjugates
Heterocyclic Compounds, 1-Ring - chemistry
Lactose - chemistry
lanthanides
Lanthanoid Series Elements - chemistry
lectins
Lectins - chemistry
Life Sciences
Ligands
macrocycles
magnetic resonance imaging
Magnetic Resonance Imaging - methods
Molecular Structure
Radionuclide Imaging - methods
Solutions
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary: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 SmIII, EuIII and GdIII complexes are reported. The 1H NMR spectrum of EuIII–DOTALac2 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 GdIII–glycoconjugates was studied by 1H 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). A suitable glycodendrimer architecture made it possible to obtain a new class of stable hydrophilic glycoconjugates. The synthesis of the glycodendrimers by using different carbohydrates (glucose, galactose and lactose) is reported, as well as their SmIII, EuIII and GdIII complexes. The in vitro relaxivity of the GdIII–glycoconjugates such as 1 was studied by 1H nuclear magnetic relaxation dispersion (NMRD).
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.200400187