Free radicals produced during the oxidation of hydrazines by hypochlorous acid

Chemical Research in Toxicology
D C GoodwinT A Grover

Abstract

Hypochlorous acid (HOCl) derived from activated neutrophils and monocytes has been implicated in the activation of hydrazine-containing drugs to toxic intermediates. However, reactive intermediates formed during the reaction between HOCl and these drugs have not been identified. We investigated the oxidation of the hydrazine derivatives isoniazid, iproniazid, and hydralazine by HOCl. The reaction between HOCl and all three hydrazines resulted in O2 consumption, indicating that free radicals were produced, but the rate and extent of O2 consumption were different for each hydrazine. Moreover, reduction of nitroblue tetrazolium (NBT) was observed only during the reaction between HOCl and isoniazid, suggesting that different radical species may be produced from HOCl reaction with each hydrazine. The oxidation of iproniazid by HOCl in the presence of the radical trap 5,5-dimethyl-1-pyrroline N-oxide (DMPO) resulted in the formation of a carbon-centered radical adduct. In contrast, the reaction between HOCl and hydralazine resulted in the formation of a nitrogen-centered DMPO radical adduct. The oxidation of isoniazid by HOCl resulted in the formation of two oxygen-centered radical adducts, DMPO-OOH and DMPO-OH. Myeloperoxidase-catal...Continue Reading

Citations

Jul 8, 2000·Microbes and Infection·R A Slayden, C E Barry
Jun 8, 2002·Pharmacogenomics·Peter Meisel
Jan 18, 2017·Journal of Chemical Neuroanatomy·Meha Fatima AftabRizwana S Waraich
Jul 2, 2005·Critical Reviews in Toxicology·Jennie L WalgrenDavid C Thompson
Jun 18, 2017·Dalton Transactions : an International Journal of Inorganic Chemistry·Jingran DongLars I Elding
Apr 2, 1999·Antimicrobial Agents and Chemotherapy·I WiidP van Helden
Jun 28, 2008·The Journal of Physical Chemistry. B·AbdulAziz AnasVasudevanpillai Biju

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