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Radical Autoxidation01:20

Radical Autoxidation

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The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
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Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox...
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Oxidations of Aldehydes and Ketones to Carboxylic Acids01:15

Oxidations of Aldehydes and Ketones to Carboxylic Acids

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Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
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Electron Paramagnetic Resonance (EPR) Spectroscopy: Organic Radicals01:17

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Ideally, an unpaired electron shows a single peak in the EPR spectrum due to the transition between the two spin energy states. However, coupling interactions can occur between the spins of the unpaired electron and any neighboring spin-active nuclei. This hyperfine coupling results in hyperfine splitting, where the EPR signal is split into multiplets. The signals split into 2nI + 1 peaks, where n is the number of equivalent nuclei and I is the nuclear spin. These splitting patterns provide...
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Autoxidation of Ethers to Peroxides and Hydroperoxides02:23

Autoxidation of Ethers to Peroxides and Hydroperoxides

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Ethers represent a class of chemical compounds that become more dangerous with prolonged storage because they tend to form explosive peroxides when standing in the air. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly oxidize to form hydroperoxides and dialkyl peroxides.
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Oxidation of Alcohols02:37

Oxidation of Alcohols

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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
The process of oxidation in a chemical reaction is observed in any of the three forms:
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Antioxidant Effects of Tryptanthrin Oxime.

M B Plotnikov1, G A Chernysheva2, V I Smol'yakova2

  • 1Goldberg Research Institute of Pharmacology and Regenerative Medicine, Tomsk National Research Medical Center, Russian Academy of Sciences, Tomsk, Russia. mbp2001@mail.ru.

Bulletin of Experimental Biology and Medicine
|October 23, 2024
PubMed
Summary

Tryptanthrin oxime (TR-Ox) demonstrates antioxidant and cytoprotective effects, reducing oxidative stress in cell cultures. While TR-Ox shows some radical-binding ability, it lacks iron-chelating activity.

Keywords:
antioxidant activitycytoprotective activityradical binding activitytryptanthrintryptanthrin oxime

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Area of Science:

  • Medicinal Chemistry
  • Neuroscience
  • Biochemistry

Background:

  • Oxidative stress is implicated in neurodegenerative diseases.
  • Alkaloids and their derivatives are explored for therapeutic potential.
  • Tryptanthrin (TR) and its derivatives are novel compounds for study.

Purpose of the Study:

  • To evaluate the radical-binding and antioxidant activities of tryptanthrin (TR) and tryptanthrin oxime (TR-Ox).
  • To assess the cytoprotective effects of TR-Ox against oxidative stress in a neuroblastoma cell line.
  • To investigate the iron-chelating properties of TR-Ox.

Main Methods:

  • Antioxidant activity assessed using DPPH radical binding and superoxide radical generation assays.
  • Iron-chelating activity evaluated via the o-phenanthroline complex method.
  • Cytoprotective effects studied in SH-SY5Y neuroblastoma cells exposed to hydrogen peroxide (H₂O₂).
  • Chemiluminescence in brain homogenate measured to assess oxidative stress reduction.

Main Results:

  • TR-Ox exhibited antiradical activity in DPPH and superoxide radical tests, though less potent than ionol and dihydroquercetin.
  • TR showed no significant antiradical activity in the tested assays.
  • TR-Ox did not display iron-chelating activity.
  • TR-Ox significantly reduced spontaneous chemiluminescence in brain homogenate.
  • TR-Ox demonstrated significant cytoprotective activity in H₂O₂-induced oxidative stress in SH-SY5Y cells, increasing cell viability.

Conclusions:

  • Tryptanthrin oxime possesses notable antioxidant and cytoprotective properties.
  • TR-Ox may serve as a potential therapeutic agent for conditions involving oxidative stress.
  • Further research into TR-Ox's mechanism of action and in vivo efficacy is warranted.