1-(2-(2-(2-(1-Aminoethyl)phenyl)diselanyl)phenyl)ethanamine: An amino organoselenium compound with interesting antioxidant profile

Ibrahim, Mohammad; Hassan, Waseem; Anwar, Javed; Deobald, Anna M.; Kamdem, Jean Paul; Souza, Diogo O.; Rocha, João Batista Teixeira da

doi:10.1016/j.tiv.2013.12.010

Cited by 18 publications

(13 citation statements)

References 33 publications

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“…These agents do not change the redox balance themselves, but their activities depend on the cellular redox state in which they are placed. Mounting evidence suggests that regular uptake of antioxidants is required to scavenge ROS (Radical Oxygen Species) and RNS (Radical Nitrogen Species) [ 36 , 37 ].…”

Section: Resultsmentioning

confidence: 99%

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Diphenyl diselenide derivatives inhibit microbial biofilm formation involved in wound infection

et al. 2016

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BackgroundOrganoselenium compounds have antimicrobial activity against some bacteria and fungi; furthermore, the antioxidant activity of diselenides has been demonstrated. The aim of the present work was to examine the in vitro minimal inhibitory concentration of a panel of differently substituted diselenides and their effectiveness in inhibiting biofilm formation and dispersing preformed microbial biofilm of Staphylococcus epidermidis, Staphylococcus aureus, Streptococcus pyogenes and Pseudomonas aeruginosa and the yeast Candida albicans, all involved in wound infections. Moreover, the cytotoxicity of the compounds was determined in human dermal fibroblast and keratinocytes. In closing, we tested their direct antioxidant activity.ResultsDiselenides showed different antimicrobial activity, depending on the microorganism. All diselenides demonstrated a good antibiofilm activity against S. aureus and S. epidermidis, the compounds camphor diselenide, bis[ethyl-N-(2’-selenobenzoyl) glycinate] and bis[2’-seleno-N-(1-methyl-2-phenylethyl) benzamide] were active against S. pyogenes and C. albicans biofilm while only diselenides 2,2’-diselenidyldibenzoic acid and bis[ethyl-N-(2’-selenobenzoyl) glycinate] were effective against P. aeruginosa. Moreover, the compounds bis[ethyl-N-(2’-selenobenzoyl) glycinate] and bis[2’-seleno-N-(1-methyl-2-phenylethyl) benzamide] showed an antioxidant activity at concentrations lower than the 50 % of cytotoxic concentration.ConclusionsBecause microbial biofilms are implicated in chronic infection of wounds and treatment failure, the combination of antimicrobial activity and potential radical scavenging effects may contribute to the improvement of wound healing. Therefore, this study suggests that bis[ethylN-(2’-selenobenzoyl) glycinate] and bis[2’-seleno-N-(1-methyl-2-phenylethyl) benzamide] are promising compounds to be used in preventing and treating microbial wound infections.

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Section: Resultsmentioning

confidence: 99%

“…The antibiofilm activity of other organoselenium compounds against P. aeruginosa [ 36 ] and S. aureus has been tested in in vivo and in vitro studies [ 36 , 37 ]. We tested six diselenides for their activity against preformed biofilms as well during biofilm formation.…”

Section: Discussionmentioning

confidence: 99%

Diphenyl diselenide derivatives inhibit microbial biofilm formation involved in wound infection

et al. 2016

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“…Studies on the antioxidant effect of (PhSe) 2 toward tert-butyl hydroperoxide are available in the literature. In fact, Ibrahim and colleagues [54] , [55] , [56] reported the antioxidant effects of some organoselenium compounds, including (PhSe) 2 (used as a prototypal compound). The authors showed that although (PhSe) 2 did not present DPPH radical scavenger activity, the organoselenium compounds were efficient in reducing in vitro oxidative stress markers in brain homogenates and attributed this effect to their GPx-like activity.…”

Section: Discussionmentioning

confidence: 99%

Diphenyl diselenide protects neuronal cells against oxidative stress and mitochondrial dysfunction: Involvement of the glutathione-dependent antioxidant system

et al. 2019

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Oxidative stress and mitochondrial dysfunction are critical events in neurodegenerative diseases; therefore, molecules that increase cellular antioxidant defenses represent a future pharmacologic strategy to counteract such conditions. The aim of this study was to investigate the potential protective effect of (PhSe)2 on mouse hippocampal cell line (HT22) exposed to tert-BuOOH (in vitro model of oxidative stress), as well as to elucidate potential mechanisms underlying this protection. Our results showed that tert-BuOOH caused time- and concentration-dependent cytotoxicity, which was preceded by increased oxidants production and mitochondrial dysfunction. (PhSe)2 pre-incubation significantly prevented these cytotoxic events and the observed protective effects were paralleled by the upregulation of the cellular glutathione-dependent antioxidant system: (PhSe)2 increased GSH levels (> 60%), GPx activity (6.9-fold) and the mRNA expression of antioxidant enzymes Gpx1 (3.9-fold) and Gclc (2.3-fold). Of note, the cytoprotective effect of (PhSe)2 was significantly decreased when cells were treated with mercaptosuccinic acid, an inhibitor of GPx, indicating the involvement of GPx modulation in the observed protective effect. In summary, the present findings bring out a new action mechanism concerning the antioxidant properties of (PhSe)2. The observed upregulation of the glutathione-dependent antioxidant system represents a future pharmacologic possibility that goes beyond the well-known thiol-peroxidase activity of this compound.

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“…Since selenium anticancer activity has been related with its ability to interact with the redox status of the cell 20,51 and it has been reported that some selenium-containing organic molecules are stronger antioxidants than ''classical'' ones, 52 we decided to test the newly synthesised compounds to determine their radical scavenging activity. With this purpose we measured the ability of the compounds to scavenge both DPPH Å and ABTS +Å .…”

Section: Radical Scavenging Activitymentioning

confidence: 99%

In vitro radical scavenging and cytotoxic activities of novel hybrid selenocarbamates

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et al. 2015

Bioorganic & Medicinal Chemistry

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1-(2-(2-(2-(1-Aminoethyl)phenyl)diselanyl)phenyl)ethanamine: An amino organoselenium compound with interesting antioxidant profile

Cited by 18 publications

References 33 publications

Diphenyl diselenide derivatives inhibit microbial biofilm formation involved in wound infection

Diphenyl diselenide derivatives inhibit microbial biofilm formation involved in wound infection

Diphenyl diselenide protects neuronal cells against oxidative stress and mitochondrial dysfunction: Involvement of the glutathione-dependent antioxidant system

In vitro radical scavenging and cytotoxic activities of novel hybrid selenocarbamates

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