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A Carborane‐Derivative “Click” Reaction under Heterogeneous Conditions for the Synthesis of a Promising Lipophilic MRI/GdBNCT Agent
Author(s) -
Toppino Antonio,
Bova Maria Elena,
Geninatti Crich Simonetta,
Alberti Diego,
Diana Eliano,
Barge Alessandro,
Aime Silvio,
Venturello Paolo,
Deagostino Annamaria
Publication year - 2013
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.201201634
Subject(s) - moiety , click chemistry , boron , chemistry , ligand (biochemistry) , gadolinium , carborane , neutron capture , adduct , homogeneous , combinatorial chemistry , nanocarriers , drug delivery , organic chemistry , biochemistry , physics , receptor , thermodynamics
In this study, the Huisgen reaction has been used to functionalise a carborane cage with a lipophilic moiety and a 1,4,7,10‐tetraazacyclododecane‐1,4,7,10‐tetraacetic acid (DOTA) ligand to obtain a new Gd boron neutron‐capture therapy (BNCT)/magnetic resonance imaging (MRI) agent. The introduction of the triazole units has been accomplished under both heterogeneous conditions, by the use of a Cu‐supported ionic‐liquid catalyst, and homogeneous conditions. The ability of the Gd complex of the synthesised ligand to form stable adducts with low‐density lipoproteins (LDLs) has been evaluated and then MRI has been performed on tumour melanoma cells incubated in the presence of a Gd‐complex/LDL imaging probe. It has been concluded that the high amount of intracellular boron necessary to perform BNCT can be reached even in the presence of a relatively low‐boron‐containing LDL concentration.