Liquid chromatographic/electrospray ionization mass spectrometric identification of the oxidation end-products of metformin in aqueous solutions

Journal of Mass Spectrometry : JMS
Fabrice CollinMonique Gardès-Albert

Abstract

Metformin is an antihyperglycemic drug that exhibits some antioxidant properties. HO*-induced oxidation of metformin was studied in aqueous solution, in both aerated and deaerated conditions. Gamma radiolysis of water was used to generate HO* free radicals, capable of initiating one-electron oxidation of metformin. Oxidation end-products were identified by direct infusion mass spectrometry (MS) and high-performance liquid chromatography/mass spectrometry (HPLC/MSn): for every product, structure elucidation was based on its mass (simple mass spectra confirmed by HPLC/MS). In addition, fragmentation spectra (MS2, MS3 and MS4) and the determination of deuterium-hydrogen exchange sites provided valuable information allowing the complete identification of some of the end-products. At low radiation dose, four products were identified as primary ones, since they result from the direct attack of HO* radicals on metformin. These primary oxidation end-products were identified respectively as hydroperoxide of metformin, covalent dimer of metformin, methylbiguanide and 2-amino-4-imino-5-methyl-1,3,5-triazine. At high radiation dose, seven other products were identified as secondary ones, resulting from the HO*-induced oxidation of the prim...Continue Reading

Citations

Oct 3, 2015·Free Radical Research·László SzabóLászló Wojnárovits
Apr 1, 2011·Journal of Pharmaceutical Sciences·Changkang PanMichael Motto
Dec 21, 2004·European Journal of Biochemistry·H KhouriM Gardès-Albert
Sep 12, 2017·Critical Reviews in Analytical Chemistry·Mariana Teixeira da TrindadeHérida Regina Nunes Salgado
May 16, 2013·Physical Chemistry Chemical Physics : PCCP·P TrouillasF Collin
Dec 3, 2009·Physical Chemistry Chemical Physics : PCCP·E AnouarP Trouillas
Apr 7, 2020·Journal of Environmental Management·Caroline F CarbuloniAna M Ferrari
Jul 20, 2021·The Science of the Total Environment·Xiaobin LiaoChao Chen

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