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Generation of singlet oxygen by the oxidation of formylhydrazines found in fungi

Grant number: 19/11458-4
Support type:Scholarships in Brazil - Scientific Initiation
Effective date (Start): June 01, 2019
Effective date (End): May 31, 2021
Field of knowledge:Physical Sciences and Mathematics - Chemistry - Organic Chemistry
Principal Investigator:Etelvino José Henriques Bechara
Grantee:Fabricio dos Santos Senario
Home Institution: Instituto de Química (IQ). Universidade de São Paulo (USP). São Paulo , SP, Brazil
Associated research grant:17/22501-2 - Electronic chemiexcitation in biological systems: bioluminescence and photochemistry in the dark, AP.TEM

Abstract

Molecular oxygen excited to its singlet state (O21Dg) stands as one of the most reactive oxygen species involved in cell damage and signal transduction. Hence the interest in unveil its biological sources, targets, and responses. This project aims to study the generation of singlet oxygen by the aerobic oxidation of formylhydrazine (formohydrazide, IUPAC) and its ±N-methyl derivative, a poisoning fungus, notably Gyromitra spp., by H2O2/HRP (horseradish peroxidase) as an enzymatic model for endogenous oxidants like the superoxide anion radical and H2O2/hemeproteins. Likewise the glyoxal/peroxynitrite system, we hypothesize that formylhydrazine oxidation yields formyldiazene, and possibly nitrogen and formyl radical, whose Russell annihilation leads to singlet oxygen, CO2 and formic acid. We intend to shed more light on the mechanisms of Gyromitra spp. toxicity possibly via singlet oxygen generation.