On the Mechanism of Action of Fullerene Derivatives in Superoxide Dismutation
Identifieur interne : 000613 ( Main/Exploration ); précédent : 000612; suivant : 000614On the Mechanism of Action of Fullerene Derivatives in Superoxide Dismutation
Auteurs : Sílvia Osuna ; Marcel Swart [États-Unis, Espagne] ; Miquel SolàSource :
- Chemistry – A European Journal [ 0947-6539 ] ; 2010-03-08.
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Abstract
We have studied the mechanism of the antioxidant activity of C60 derivatives at the BP86/TZP level with inclusion of solvent effects (DMSO) by using the COSMO approach. The reaction studied here involves degradation of the biologically relevant superoxide radical (O2.−), which is linked to tissue damage in several human disorders. Several fullerene derivatives have experimentally been shown to be protective in cell culture and animal models of injury, but precisely how these compounds protect biological systems is still unknown. We have investigated the activity of tris‐malonyl C60 (also called C3), which efficiently removes the superoxide anion with an activity in the range of several biologically effective, metal‐containing superoxide dismutase mimetics. The antioxidant properties of C3 are attributed to the high affinity of C60 to accept electrons. Our results show that once the superoxide radical is in contact with the surface of C3, its unpaired electron is transferred to the fullerene. This process, which converts the damaging O2.− to neutral oxygen O2, is the rate‐determining step of the reaction. Afterwards, another superoxide radical reacts with C3.− to form hydrogen peroxide and in the process takes up the additional electron that was transferred in the first step. The overall process is clearly exothermic and, in general, involves reaction steps with relatively low activation barriers. The capability of C3 to degrade a highly reactive oxygen species that is linked to several human diseases is of immediate interest for future applications in the field of biology and medicine.
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DOI: 10.1002/chem.200902728
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The reaction studied here involves degradation of the biologically relevant superoxide radical (O2.−), which is linked to tissue damage in several human disorders. Several fullerene derivatives have experimentally been shown to be protective in cell culture and animal models of injury, but precisely how these compounds protect biological systems is still unknown. We have investigated the activity of tris‐malonyl C60 (also called C3), which efficiently removes the superoxide anion with an activity in the range of several biologically effective, metal‐containing superoxide dismutase mimetics. The antioxidant properties of C3 are attributed to the high affinity of C60 to accept electrons. Our results show that once the superoxide radical is in contact with the surface of C3, its unpaired electron is transferred to the fullerene. This process, which converts the damaging O2.− to neutral oxygen O2, is the rate‐determining step of the reaction. Afterwards, another superoxide radical reacts with C3.− to form hydrogen peroxide and in the process takes up the additional electron that was transferred in the first step. The overall process is clearly exothermic and, in general, involves reaction steps with relatively low activation barriers. The capability of C3 to degrade a highly reactive oxygen species that is linked to several human diseases is of immediate interest for future applications in the field of biology and medicine.</div></front></TEI><affiliations><list><country><li>Espagne</li><li>États-Unis</li></country></list><tree><noCountry><name sortKey="Osuna, Silvia" sort="Osuna, Silvia" uniqKey="Osuna S" first="Sílvia" last="Osuna">Sílvia Osuna</name><name sortKey="Sola, Miquel" sort="Sola, Miquel" uniqKey="Sola M" first="Miquel" last="Solà">Miquel Solà</name></noCountry><country name="États-Unis"><noRegion><name sortKey="Swart, Marcel" sort="Swart, Marcel" uniqKey="Swart M" first="Marcel" last="Swart">Marcel Swart</name></noRegion></country><country name="Espagne"><noRegion><name sortKey="Swart, Marcel" sort="Swart, Marcel" uniqKey="Swart M" first="Marcel" last="Swart">Marcel Swart</name></noRegion></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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