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The Design and Synthesis of Highly Branched and Spherically Symmetric Fluorinated Macrocyclic Chelators.


ABSTRACT: Two novel, highly fluorinated macrocyclic chelators with highly branched and spherically symmetric fluorocarbon moieties have been designed and efficiently synthesized. This is achieved by conjugating a spherically symmetric fluorocarbon moiety to the macrocyclic chelator DOTA, with or without a flexible oligo-oxyethylene linker between these two parts. As a result of the spherical symmetry, all 27 fluorine atoms in each fluorinated chelator give a sharp singlet (19)F NMR signal. The hydrophilicity and the (19)F relaxation behavior of fluorinated chelators can be modulated by the insertion of a flexible linker between the fluorocarbon moiety and the macrocyclic linker. These chelators serve as prototypes for (1)H-(19)F dual-nuclei magnetic resonance imaging agents.

SUBMITTER: Jiang ZX 

PROVIDER: S-EPMC2888522 | biostudies-literature | 2008 Jan

REPOSITORIES: biostudies-literature

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The Design and Synthesis of Highly Branched and Spherically Symmetric Fluorinated Macrocyclic Chelators.

Jiang Zhong-Xing ZX   Yu Y Bruce YB  

Synthesis 20080101 2


Two novel, highly fluorinated macrocyclic chelators with highly branched and spherically symmetric fluorocarbon moieties have been designed and efficiently synthesized. This is achieved by conjugating a spherically symmetric fluorocarbon moiety to the macrocyclic chelator DOTA, with or without a flexible oligo-oxyethylene linker between these two parts. As a result of the spherical symmetry, all 27 fluorine atoms in each fluorinated chelator give a sharp singlet (19)F NMR signal. The hydrophilic  ...[more]

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