Twice acting antioxidants: synthesis and antioxidant properties of selenium and sulfur-containing zingerone derivatives

Martinez, Débora M.; Barcellos, Angelita M.; Casaril, Angela Maria; Savegnago, Lucielli; Perin, Gelson; Schiesser, Carl H.; Callaghan, Kimberley L.; Lenardão, Eder J.

doi:10.1016/j.tetlet.2015.03.030

Cited by 23 publications

(8 citation statements)

References 65 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[21] Several chalcogen-containing antioxidants were found to be regenerable in the presence of N-acetylcysteine (NAC). Under our standard conditions (40 mm of antioxidant), both ebselenols 4 (R inh = 11 mm h À1 )a nd 6 (R inh = 16 mm h À1 )c ould outperform a-tocopherol (R inh = 28 mm h À1 )i nt he quenching of peroxyl radicals.A lthough the T inh values for 6 (105 min) and a-tocopherol (109 min) were very similar, compound 4 could inhibit peroxidation for ac onsiderably longer time (155 min).…”

Section: A-tocopherolmentioning

confidence: 99%

See 1 more Smart Citation

Multifunctional Antioxidants: Regenerable Radical‐Trapping and Hydroperoxide‐Decomposing Ebselenols

et al. 2016

View full text Add to dashboard Cite

Regenerable, multifunctional ebselenol antioxidants were prepared that could quench peroxyl radicals more efficiently than α-tocopherol. These compounds act as better mimics of the glutathione peroxidase enzymes than ebselen. Production of reactive oxygen species (ROS) and reactive nitrogen species (RNS) in human mononuclear cells was considerably decreased upon exposure to the organoselenium compounds. At a concentration of 25 μm, the ebselenol derivatives showed minimal toxicity in pre-osteoblast MC3T3 cells.

show abstract

Section: A-tocopherolmentioning

confidence: 99%

“…The long inhibition time of ebselenol 4 seems to indicate that it is quenching peroxyl radicals with a stoichiometric number of n =3. Increased n values in the quenching of 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) radicals were recently reported as a consequence of phenylseleno substitution in zingerones (vanillylacetones) …”

Section: Figurementioning

confidence: 99%

Multifunctional Antioxidants: Regenerable Radical‐Trapping and Hydroperoxide‐Decomposing Ebselenols

et al. 2016

View full text Add to dashboard Cite

show abstract

“…For example, α-(phenylselanyl) acetophenone possesses antioxidant and antidepressant-like activity (Gerzson et al, 2012) without genotoxic effects in mice leucocytes (Casaril et al, 2015). The 4-(4-hydroxy-3-methoxyphenyl)-4-(phenylseleno)-2-butanone (Martinez et al, 2015) and (R)-Se-aryl thiazolidine-4-carboselenoate (Victoria et al, 2013) have shown antioxidant activity via in vitro assays, while (octylseleno)-xylofuranoside has antidepressant-like effects through modulation of the monoaminergic system (Brod et al, 2016). The presence of selenium is relevant because this micronutrient is a constituent of several antioxidant proteins in humans (Kudva et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Antidepressant-like effect of a new selenium-containing compound is accompanied by a reduction of neuroinflammation and oxidative stress in lipopolysaccharide-challenged mice

et al. 2017

Self Cite

View full text Add to dashboard Cite

Organoselenium compounds and indoles have gained attention due to their wide range of pharmacological properties. Depression is a recurrent and disabling psychiatric illness and current evidences support that oxidative stress and neuroinflammation are mechanisms underlying the pathophysiology of this psychiatric condition. Here, we evaluated the effect of 3-((4-chlorophenyl)selanyl)-1-methyl-1H-indole (CMI) in lipopolysaccharide (LPS)-induced depressive-like behaviour, neuroinflammation and oxidative stress in male mice. CMI pre-treatment (20 and 50 mg/kg, intragastrically) significantly attenuated LPS (0.83 mg/kg, intraperitoneally)-induced depressive-like behaviour in mice by reducing the immobility time in the tail suspension test (TST) and forced swimming test (FST). CMI pre-treatment ameliorated LPS-induced neuroinflammation by reducing the levels of interleukin (IL)-1β, IL-4 and IL-6 in the hippocampus and prefrontal cortex, as well as markers of oxidative damage. Additionally, we investigated the toxicological effects of CMI (200 mg/kg, i.g.) in the liver, kidney and brain through determination of the activity of aspartate aminotransferase (AST), alanine aminotransferase (ALT), δ-aminolevulinate dehydratase (δ-ALA-D) and creatinine levels. These biomarkers were not modified, indicating the possible absence of neuro-, hepato- and nephrotoxic effects. Our results suggest that CMI could be a therapeutic approach for the treatment of depression and other neuropsychiatric disorders associated with inflammation and oxidative stress.

show abstract

“…The development of new preservatives is directly linked to the economic importance of the food’s spoilage. The chemical modification of natural products has attracted the attention of many research groups, which aims to improve their original biological activities [ 5 , 6 , 7 , 8 ]. Recent studies have shown that semi-synthetic compounds functionalized with organochalcogen groups (sulfur and selenium) and nitrones could be an alternative to the synthetic additives currently used in food and pharmaceutical industries [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal

et al. 2017

Self Cite

View full text Add to dashboard Cite

Background: The main constituents of Cymbopogonnardus (L) Rendle and C. citratus (DC) Stapfessential oils are (R)-citronellal and citral, respectively. Organochalcogen compounds can boost the biological activities of natural products. Methods: Several chalcogen-containing nitrones derived from (R)-citronellal and citral were prepared and evaluated for their antimicrobial and antioxidant activities. The antimicrobial activity was evaluated by the disc diffusion test and the antioxidant properties were evaluated in vitro by DPPH (1,1-diphenyl-2-picryl-hydrazyl), ABTS (2,2′-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid), and FRAP (ferric ion reducing antioxidant power) assays. Results: In the antimicrobial assay, (E)-N,3,7-trimethyl-3-(phenylthio)oct-6-en-1-imine oxide 5c exhibited halos between 21.5 mm (Escherichia coli O157:H7) and 26.0 mm (Listeria monocytogenes), while (E)-N,3,7-trimethyloct-6-en-1-imine oxide 5d presented halos between 22.5 mm (E. coli O157:H7) and 31.0 mm (L. monocytogenes). (E)-N,3,7-Trimethyl-2-(phenylthio)oct-6-en-1-imine oxide 5a showed the lowest minimal inhibitory concentration (MIC) value against Bacillus cereus (0.48 mM), and 5c was the most potent bactericide, with a minimal bactericidal concentration (MBC) of 0.52 mM for E. coli O157:H7. In the antioxidant assays, 5c, 5d, and 10 ((E)-3,7-dimethyl-2-(phenylselanyl)oct-6-enal oxime) were the most actives in the DPPH, ABTS, and FRAP assays, respectively. Conclusions: The presence of a phenylthio group in the nitrone increases its antimicrobial activity against Gram-positive and Gram-negative foodborne pathogens in the disk diffusion test and the antioxidant activity in vitro.

show abstract

Twice acting antioxidants: synthesis and antioxidant properties of selenium and sulfur-containing zingerone derivatives

Cited by 23 publications

References 65 publications

Multifunctional Antioxidants: Regenerable Radical‐Trapping and Hydroperoxide‐Decomposing Ebselenols

Multifunctional Antioxidants: Regenerable Radical‐Trapping and Hydroperoxide‐Decomposing Ebselenols

Antidepressant-like effect of a new selenium-containing compound is accompanied by a reduction of neuroinflammation and oxidative stress in lipopolysaccharide-challenged mice

Synthesis, Antimicrobial, and Antioxidant Activities of Chalcogen-Containing Nitrone Derivatives from (R)-citronellal

Contact Info

Product

Resources

About