Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 125, Issue 18, Pages 5471-5478Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja0340984
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Funding
- NCI NIH HHS [5-R44-CA66383] Funding Source: Medline
- NIBIB NIH HHS [1-R01-EB000703] Funding Source: Medline
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M@C-60 and related endohedral metallofullerenes comprise a significant portion of the metallofullerene yield in the traditional arc synthesis, but their chemistry and potential applications have been largely overlooked because of their sparse solubility. In this work, procedures are described to solublize Gd@C-60 species for the first time by forming the derivative, Gd@C-60[C(COOCH2CH3)(2)](10), and its hydrolyzed water-soluble form, Gd@C-60[C(COOH)(2)](10). Imparting water solubility to Gd@C-60 permits its evaluation as a magnetic resonance imaging (MRI) contrast agent. Relaxometry measurements for Gd@C-60[C(COOH)(2)](10) reveal it to possess a relaxivity (4.6 mM(-1) s(-1) at 20 MHz and 40 degreesC) comparable to that of commercially available Gd(III) chelate-based MRI agents. An in vivo MRI biodistribution study in a rodent model reveals Gd@C-60[C(COOH)(2)](10) to possess the first non-reticuloendothelial system (RES) localizing behavior for a water-soluble endohedral metallofullerene species, consistent with its lack of intermolecular aggregation in solution as determined by light-scattering measurements. This first derivatization and use of a M@C-60 species suggests new potential for metallofullerene technologies by reducing reliance on the chromatographic purification procedures normally employed for the far less abundant M@C-82 and related endohedrals. The recognition that water-soluble fullerene derivatives can be designed to avoid high levels of RES uptake is an important step toward fullerene-based pharmaceutical development.
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