Presentation Title

Theoretical Study of the Secondary Antioxidant Activity of Aminoguanidine

Format of Presentation

Poster to be presented the Friday of the conference

Presenter Information

Guillermo García DíezFollow

Abstract

Glycation (or nonenzymatic glycosylation) is a natural process in which sugars in the bloodstream attach to nucleophilic groups present in proteins, lipids or DNA, forming harmful new molecules that are related to various diseases. The main mechanisms to inhibit glycation are believed to be the scavenging of carbonyl and radical species and the chelation of metal ions such as Cu(II) and Fe(III). Aminoguanidine is known to be a glycation inhibitor. Its free radical activity has been recently studied.

The thermodynamic stability of the various complexes aminoguanidine can form with Cu(II) and Fe(III) under physiological pH conditions in a polar environment is explored. Calculations are performed at the M05/6-31++G(d,p) level of theory combined with the SMD continuum solvation model. We aim to identify the most thermodynamically stable complexes and to explore the secondary antioxidant capacity of aminoguanidine.

Aminoguanidine is said to have secondary antioxidant capacity if, by forming a complex with Cu(II) or Fe(III), it can slow down the initial step (the copper- or iron-catalyzed Haber-Weiss reaction) of the reaction sequence shown below and reduce the potential damage caused by •OH radical formation in the second step (the Fenton reaction).

Cu(H2O)42+ or Fe(H2O)63+ + O2•− → Cu(H2O)4+ or Fe(H2O)62+ + O2

Cu(H2O)4+ or Fe(H2O)62+ + H2O2 → Cu(H2O)42+ or Fe(H2O)63+ + OH- + •OH

Department

Chemistry

Faculty Advisor

Nelaine Mora-Díez

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Theoretical Study of the Secondary Antioxidant Activity of Aminoguanidine

Glycation (or nonenzymatic glycosylation) is a natural process in which sugars in the bloodstream attach to nucleophilic groups present in proteins, lipids or DNA, forming harmful new molecules that are related to various diseases. The main mechanisms to inhibit glycation are believed to be the scavenging of carbonyl and radical species and the chelation of metal ions such as Cu(II) and Fe(III). Aminoguanidine is known to be a glycation inhibitor. Its free radical activity has been recently studied.

The thermodynamic stability of the various complexes aminoguanidine can form with Cu(II) and Fe(III) under physiological pH conditions in a polar environment is explored. Calculations are performed at the M05/6-31++G(d,p) level of theory combined with the SMD continuum solvation model. We aim to identify the most thermodynamically stable complexes and to explore the secondary antioxidant capacity of aminoguanidine.

Aminoguanidine is said to have secondary antioxidant capacity if, by forming a complex with Cu(II) or Fe(III), it can slow down the initial step (the copper- or iron-catalyzed Haber-Weiss reaction) of the reaction sequence shown below and reduce the potential damage caused by •OH radical formation in the second step (the Fenton reaction).

Cu(H2O)42+ or Fe(H2O)63+ + O2•− → Cu(H2O)4+ or Fe(H2O)62+ + O2

Cu(H2O)4+ or Fe(H2O)62+ + H2O2 → Cu(H2O)42+ or Fe(H2O)63+ + OH- + •OH