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Related Concept Videos

Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

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 property is crucial in...
Electron Transport Chain: Complex I and II01:46

Electron Transport Chain: Complex I and II

The mitochondrial electron transport chain (ETC) is the main energy generation system in the eukaryotic cells. However, mitochondria also produce cytotoxic reactive oxygen species (ROS) due to the large electron flow during oxidative phosphorylation. While Complex I is one of the primary sources of superoxide radicals, ROS production by Complex II is uncommon and may only be observed in cancer cells with mutated complexes.
ROS generation is regulated and maintained at moderate levels necessary...
Electron Transport Chain: Complex III and IV01:43

Electron Transport Chain: Complex III and IV

During the electron transport chain, electrons from NADH and FADH2 are first transferred to complexes I and II, respectively. These two complexes then transfer the electrons to ubiquinol, which carries them further to complex III. Complex III passes the electrons across the intermembrane space to Cyt c, which carries them further to complex IV. Complex IV donates electrons to oxygen and reduces it to water. As electrons pass through complexes I, III, and IV, the energy released aids the pumping...
The Electron Transport Chain01:30

The Electron Transport Chain

The electron transport chain or oxidative phosphorylation is an exothermic process in which free energy released during electron transfer reactions is coupled to ATP synthesis. This process is a significant source of energy in aerobic cells, and therefore inhibitors of the electron transport chain can be detrimental to the cell's metabolic processes.
Inhibitors of the electron transport chain
Rotenone, a widely used pesticide, prevents electron transfer from Fe-S cluster to ubiquinone or Q in...
Redox Titration: Other Oxidizing and Reducing Agents01:26

Redox Titration: Other Oxidizing and Reducing Agents

Besides iodine, other oxidizing or reducing agents can serve as titrants in redox titrations. Common oxidizing titrants include KMnO4, cerium(IV), and K2Cr2O7. The choice of oxidizing titrants depends on factors like stability, cost, analyte strength, and reaction rate between the analyte and titrant. KMnO4 is a strong oxidizing titrant that reduces from Mn(VII) to Mn(II) in a highly acidic solution, simultaneously oxidizing the analyte to a higher oxidation state. In this case, KMnO4 acts as a...
Phase I Oxidative Reactions: Overview01:19

Phase I Oxidative Reactions: Overview

Phase I biotransformation, or functionalization, is a crucial chemical process that converts drugs and other xenobiotics into more water-soluble forms, facilitating expulsion from the body. It involves oxidative, reductive, and hydrolytic reactions that add or unveil polar functional groups on lipophilic substrates. Key players in phase I reactions are the mixed-function oxidases. Situated in liver cell microsomes, these enzymes predominantly carry out drug metabolism. They require molecular...

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Retraction notice to "In vivo inhibition of tumor progression by 5 hydroxy-1,4-naphthoquinone (juglone) and 2-(4-hydroxyanilino)-1,4-naphthoquinone (Q7) in combination with ascorbate" [Biochem. Biophys. Res. Commun. 477 (2016) 640-646].

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A Rapid and Specific Microplate Assay for the Determination of Intra- and Extracellular Ascorbate in Cultured Cells
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Ascorbate-driven quinone redox cycling as a pro-oxidant anticancer strategy.

Christophe Glorieux1, Cinthya Enriquez-Lara2, Jaime A Valderrama3

  • 1Laboratory of Clinical and Molecular Gastroenterology, Institute for Digestive Research, Lithuanian University of Health Sciences, Kaunas, Lithuania.

Redox Biology
|June 24, 2026
PubMed
Summary

Quinones and ascorbate (vitamin C) can generate reactive oxygen species (ROS), offering a promising strategy to target cancer cells by exploiting their redox imbalance. This approach enhances ROS production, selectively harming tumors.

Keywords:
AscorbateCancerQuinonesROSRedox cyclingVitamin C

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Area of Science:

  • Biochemistry
  • Cell Biology
  • Oncology

Background:

  • Quinones are vital natural compounds in cellular energy metabolism across organisms.
  • Ascorbate (vitamin C) exhibits dual antioxidant/pro-oxidant roles influenced by concentration and cellular environment.
  • Quinone-ascorbate interactions can amplify reactive oxygen species (ROS) generation.

Purpose of the Study:

  • To review the mechanisms and biological effects of quinoid compounds.
  • To explore the synergistic interaction between quinones and ascorbate in cancer cells.
  • To highlight the potential of this combination as a cancer therapy.

Main Methods:

  • Literature review of natural and synthetic quinoid compounds.
  • Analysis of redox cycling mechanisms involving quinones and ascorbate.
  • Examination of ROS generation and its impact on cancer cell biology.

Main Results:

  • Quinones, especially with ascorbate, induce significant ROS production.
  • Cancer cells exhibit heightened susceptibility to ROS due to existing redox imbalance.
  • The combination therapy shows promise for selective cancer cell targeting.

Conclusions:

  • The interplay between quinones and ascorbate presents a viable strategy for cancer treatment.
  • Exploiting tumor-specific redox imbalance via ROS generation is a key therapeutic mechanism.
  • Further research into quinoid compounds and ascorbate interactions is warranted for clinical application.