article · Current Organic Synthesis
This research aimed to investigate the antioxidant activity of a newly synthesised series of isoniazid-hydrazide hydrazones (2a-e). The compounds were characterised using spectroscopic and mass spectrometry techniques. Their antioxidant properties were then evaluated through 2,2-diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and Fe2+ chelating tests, complemented by computational studies. Results showed that compound 2d exhibited the highest DPPH scavenging activity, while compound 2a, with an ortho-hydroxyl group, demonstrated the strongest Fe2+ chelating ability. Computational analysis indicated varying mechanisms for radical scavenging among the compounds. Overall, compound 2c proved highly effective in both DPPH radical scavenging and Fe2+ chelation, performing comparably to established antioxidants like ascorbic acid and ethylenediaminetetraacetic acid.
Reactive oxygen species contribute to various diseases through oxidative damage. Discovering new compounds with strong antioxidant properties is crucial for developing treatments or preventative measures. This research identifies novel compounds with promising antioxidant capabilities, potentially leading to new therapeutic agents.
This early-stage research identifies novel compounds with significant antioxidant and metal-chelating properties. These findings could be of interest to the pharmaceutical and nutraceutical industries for the development of new antioxidant agents or supplements. The compounds could potentially be used in formulations aimed at mitigating oxidative stress in biological systems, but further research and development are required to assess their safety and efficacy in real-world applications.
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INTRODUCTION/OBJECTIVE: Reactive oxygen species (ROS) are involved in diverse pathologies. To reduce their oxidative damage, antioxidants are used to trap them and form stable molecules. The present work aims to investigate the antioxidant activity of a synthesized series of isoniazid- hydrazide hydrazones (2a-e). METHODS: 2a-e are characterized by means of spectroscopic and mass spectrometry with electrospray ionization (MS-ESI) techniques. Their antioxidant activities are evaluated using the 2,2- diphenyl-1-picrylhydrazyl (DPPH) free radical scavenging and Fe2+ chelating property tests. In addition, the antioxidant properties of isoniazid-hydrazide hydrazones and their Fe2+ chelates were explored using computational tools. RESULTS: According to the DPPH test, 2d shows the highest antioxidant activity with an IC50 of 0.16 mM, whilst the chelating ferrous ions test reveals that 2a, with an OH group at the ortho position, has the highest antioxidant activity and the highest reducing capacity, with an IC50 of 11.24 μM. The calculated bond dissociation enthalpies (BDEs) of 2a-e reveal that scavenging of DPPH radicals may return to the occurrence of hydroxyl in 2a and 2b, while for 2c-e it may return to the transfer of electrons to the DPPH radical. DISCUSSION: The ability of 2a-e to chelate Fe2+ ions may return in part to the stability of the formed Fe2+ chelates and to the electron transfer from 2a-e isoniazid-hydrazide hydrazones to the vacant orbitals of Fe2+ ions. CONCLUSION: In conclusion, 2c proved highly effective in terms of DPPH radical scavenging and Fe2+ chelating properties with IC50 values of 40 and 5 μg/mL, respectively, compared to ascorbic acid and ethylenediaminetetraacetic acid (EDTA).
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DOI: 10.2174/0115701794478111260806041132
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