Journal
NANOMEDICINE-NANOTECHNOLOGY BIOLOGY AND MEDICINE
Volume 4, Issue 4, Pages 283-294Publisher
ELSEVIER SCIENCE BV
DOI: 10.1016/j.nano.2008.05.003
Keywords
Superoxide; Neuroprotection; Carboxyfullerenes; SOD mimetics
Funding
- NIA NIH HHS [R01 AG033679] Funding Source: Medline
- NINDS NIH HHS [NS47966, R01 NS037688-04, R01 NS037688-02, R01 NS037688-03] Funding Source: Medline
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Superoxide radical anion is a biologically important oxidant that has been linked to tissue injury and inflammation in several diseases. Here we carried out a structure-activity study on six different carboxyfullerene superoxide dismutase (SOD) mimetics with distinct electronic and biophysical characteristics. Neurotoxicity via N-methyl-D-aspartate receptors, which involves intracellular superoxide, was used as a model to evaluate structure-activity relationships between reactivity toward superoxide and neuronal rescue by these drugs. A significant correlation between neuroprotection by carboxyfullerenes and their k(i) toward superoxide radical was observed. Computer-assisted molecular modeling demonstrated that the reactivity toward superoxide is sensitive to changes in dipole moment, which are dictated not only by the number of carboxyl groups but also by their distribution on the fullerene ball. These results indicate that the SOD activity of these cell-permeable compounds predicts neuroprotection, and establishes a structure-activity relationship to aid in future studies on the biology of superoxide across disciplines. (c) 2008 Elsevier Inc. All rights reserved.
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