Involvement of free radicals in the oxidative degradation of indole-3-acetic acid

1969 ◽  
Vol 47 (2) ◽  
pp. 220-224 ◽  
Author(s):  
E. V. Parups

The enzymic or nonenzymic oxidation of indole-3-acetic acid (IAA) was promoted in the presence of the stable free radical 2,2-diphenyl-1-picrylhydrazyl (DPPH). The involvement of DPPH with the IAA free-radicals in the nonenzymic and the peroxidase-catalyzed oxidations was discussed. Methylene-oxindole was identified as a breakdown product of IAA, indicating a pathway operative with this radical.

1993 ◽  
Vol 305 ◽  
Author(s):  
Myong K. Ahn ◽  
Thomas C. Stringfellow ◽  
Jianming Lei ◽  
Kenneth J. Bowles ◽  
Michael Meador

AbstractPolyimide resins are used as matrix materials in fiber reinforced composites. Such composites are lightweight, have relatively high strength, and can be used at temperatures above 300°C. Postcured PMR-15 produces room temperature electron paramagnetic resonance (epr) spectra from stable free radical species formed during the postcuring stages. The variable temperature EPR spectral intensities indicate the presence of at least two free radical species. The thermo-oxidative degradation involves free radicals generated during the postcuring process in the presence of oxygen gas. These and other recent results including ENDOR and HYSCORE work are discussed.


2020 ◽  
Vol 21 (5) ◽  
pp. 1579 ◽  
Author(s):  
Yun Ji ◽  
Wenzhen Yin ◽  
Yuan Liang ◽  
Lijun Sun ◽  
Yue Yin ◽  
...  

The cellular and molecular mechanisms by which indole-3-acetic acid (IAA), a tryptophan-derived metabolite from gut microbiota, attenuates inflammation and oxidative stress has not been fully elucidated. The present study was to unearth the protective effect and underlying mechanism of IAA against lipopolysaccharide (LPS)-induced inflammatory response and free radical generation in RAW264.7 macrophages. IAA significantly ameliorated LPS-induced expression of interleukin-1β (IL-1β), interleukin-6 (IL-6), and monocyte chemoattractant protein-1 (MCP-1) as well as generation of reactive oxidative species (ROS) and nitric oxide (NO). LPS-triggered nuclear translocation of nuclear factor kappa B (NF-κB) p65 was mitigated by IAA treatment. Further, an up-regulation of heme oxygenase-1 (HO-1) was observed in IAA-treated cells in dose-dependent manner under both normal and LPS-stimulated condition. Interference of HO-1 activity by tin protoporphyrin IX (SnPP) impeded the alleviative effects of IAA on expression of IL-1β and IL-6 induced by LPS, whereas demonstrated no effect on its suppression of ROS and NO production. This result suggests a HO-1-dependent anti-inflammatory effect of IAA and its direct scavenging action on free radicals. Treatment with CH-223191, a specific antagonist of aryl hydrocarbon receptor (AhR), showed no significant effects on the beneficial role of IAA against inflammation and free radical generation. In summary, our findings indicate that IAA alleviates LPS-elicited inflammatory response and free radical generation in RAW264.7 macrophages by induction of HO-1 and direct neutralization of free radicals, a mechanism independent of AhR.


1971 ◽  
Vol 44 (8) ◽  
pp. 2207-2210 ◽  
Author(s):  
Takao Yoshioka ◽  
Susumu Higashida ◽  
Syoji Morimura ◽  
Keisuke Murayama

Author(s):  
A. A. Safonov ◽  
I. S. Nosulenko

The process of studying free radicals began in the middle of the last century (the free radical theory of aging in 1956). Multiple studies have revealed the effect of free radicals on the cells of the body and the development of various diseases, such as diabetes, autoimmune diseases, diseases of the nervous system, and others. As a result, the term antioxidant has emerged, compounds that reduce and prevent the effects of free radicals. Most of the newly synthesized substances are studied for their antiradical properties. 1,2,4-Triazole derivatives are no exception, which has already proven themselves as biologically active compounds. The aim of this work was the investigation antiradical activity among 4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol derivatives. Materials and methods. Previously synthesized 4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol derivatives were used as test compounds. The research of antiradical activity was based on the interaction between 4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol derivatives and 2,2-diphenyl-1-picrylhydrazyl (DPPH) in vitro. DPPH is a stable free radical. The color of its alcoholic solutions were intense purple (λmax = 517 nm). When DPPH interacted with compounds that were capable of scavenging free radicals, it produced products. These products are yellow in color and do not absorb light of the aforementioned wavelength. The study was carried out according to the method. Results. The antiradical activity of 10 new 4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol derivatives was studied. Most of the test compounds show antiradical activity against DPPH. Compound 1 was the most active at a concentration of 1 × 10-3 M and the antiradical effect was close to ascorbic acid. Conclusions. The most active compound is 4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol, which in a concentration of 1 × 10-3 M has an antiradical effect in 88.89 %. When reducing the concentration to 1 × 10-4 M, also reduces the antiradical activity to 53.78 %. Some conclusions are drawn regarding the “structure – effect” dependence between 4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol derivatives: – the introduction of 4-fluorobenzylidene radical (compound 2) into the 4-amino-5-(thiophen-2-ylmethyl)-4H-1,2,4-triazole-3-thiol molecule results in a slight decrease in activity; – the introduction of 2-hydroxybenzylidene radical (compound 3) into initial molecule results a high antiradical effect, which hardly changes with decreasing concentration; – transformation to 2-((5-(thiophen-2-ylmethyl)-4-((R)amino)-4H-1,2,4-triazol-3-yl)thio)acetic acid has almost no effect on antiradical activity, except for compound 9 (the antiradical effect is reduse).


1983 ◽  
Vol 38 (2) ◽  
pp. 265-268 ◽  
Author(s):  
Astrid Dorfer ◽  
Karl E. Schwarzhans

Abstract The stable free radical 4,4,5,5-tetramethyl-imidazoline-1-oxyl-2-p-pyridyl-3-oxide (L1) has been prepared and used as a ligand in copper (I), silver(I) and rhodium(III) complexes, the meta isomer (L2) as a ligand in a rhodium(III) complex, too. The magnetic moments and the EPR spectra of the free radicals and the complexes have been investigated. A solvent and temperature dependent intramolecular interaction between the radicalic ligands was found in the silver(I) complex, but in none of the complexes any intramolecular interaction between the metal ions and the unpaired electrons of the ligands could be observed.


1994 ◽  
Vol 98 (40) ◽  
pp. 10131-10137 ◽  
Author(s):  
Luis P. Candeias ◽  
Lisa K. Folkes ◽  
Madeleine F. Dennis ◽  
Kantilal B. Patel ◽  
Steven A. Everett ◽  
...  

2016 ◽  
Vol 42 (2) ◽  
Author(s):  
Nyoun Soo Kwon ◽  
Yun-Mi Jeong ◽  
Hyo-Soon Jeong ◽  
Myo-Kyoung Kim ◽  
Young Sil Min ◽  
...  

AbstractObjective:Indole-3-acetic acid (IAA) activation has been suggested as a new strategy for cancer therapy. It has been reported that ultraviolet B (UVB) radiation can activate IAA. In the present study, we investigated whether UVB-irradiated IAA (IAAMethods:DNA fragmentation was measured to examine apoptosis. IAAResults:Our results show that IAAConclusions:These results suggest that free radicals generated from IAA by UV irradiation may cause apoptosis, and IAA


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