<i>In vitro</i> antifungal evaluation and structure–activity relationship of diphenyl diselenide and synthetic analogues

Loreto, Érico S.; Mario, Débora Alves Nunes; Santúrio, Jânio Morais; Alves, Sydney Hartz; Nogueira, Cristina W.; Zeni, Gilson

doi:10.1111/j.1439-0507.2010.01994.x

Cited by 36 publications

(25 citation statements)

References 12 publications

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“…Ebselen and diselenides have demonstrated activity against Fusarium sp. when administrated alone or in combination with other antifungal drugs showing good synergistic effects ,. It was shown that a piperidine isoselenocyanate derivative is the most active among its isosters against selected fungi, including Fusarium culmorum .…”

Section: Introductionmentioning

confidence: 99%

Allylic Selenocyanates as New Agents to Combat Fusarium Species Involved with Human Infections

et al. 2017

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Fusarium is an emerging opportunistic fungal pathogen that causes local or systemic infections. The successful use of a therapeutic drug or combination antifungal therapies against Fusarium spp. are compromised because reports of multidrug resistance are currently frequent. Thus, the development of new antifungal capable of combating multidrug‐resistant Fusarium strains becomes necessary. This study presents the synthesis of seven new allylic selenocyanates and their screening against Fusarium spp. Minimum inhibitory concentrations (MICs) of these compounds ranged from 4 to 64 μg mL−1, with the mechanism of action being related to fungal cell membrane disruption. Specific structural changes, such as widespread thinning along the hyphae, were observed by scanning electron microscopy. The effect of selenocyanates on cell viability and genotoxicity are concentration dependent, however they did not cause mutagenicity in human cells. Five selenocyanates were identified as nonirritant by the ex‐vivo HET‐CAM (Hen′s Egg Test‐Chorioallantoic Membrane) method. Allylic selenocyanates represents a promising alternative in the treatment and prevention of fusariosis.

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Section: Introductionmentioning

confidence: 99%

Allylic Selenocyanates as New Agents to Combat Fusarium Species Involved with Human Infections

et al. 2017

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“…In particular, organoselenium coating on cellulose was able to inhibit P. aeruginosa and S. aureus biofilm formation [ 38 , 39 ]. The antifungal property of biphelyl diselenide (PhSe) 2 against different species of Candida has been reported by Loreto ES et al [ 16 ]. The values for C. albicans reported in their study are similar to those obtained in our experimental conditions.…”

Section: Discussionmentioning

confidence: 99%

“…Many studies have demonstrated the antimicrobial activity of different organoselenium compounds [ 14 ]. Diselenides have been studied for their antimicrobial activity; diphenyl diselenide and 2,2’-dithienyl diselenide have shown antibacterial and antifungal acivities [ 15 , 16 ], moreover, selenocyanate and diselenides have been considered as a new class of antileishmanial compounds [ 17 ]. Finally, alkyl and aryl diselenides have shown microbial and antiviral activities [ 18 ].…”

Section: Introductionmentioning

confidence: 99%

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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“…Biological studies demonstrated its potential use as antimicrobial agent. In particular, it was reported its antifun-gal effects against some mycetes [4]. Compound 1b was tested in vitro and in vivo models, alone and in combination with antifungal drugs proving its inhibitory effect on the growth of Candida glabrata [5].…”

Section: Diselenides and Selenocyanatesmentioning

confidence: 99%

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Leo

Messina²,

Nascimento

et al. 2019

MROC

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In the recent years, an increasing attention has been given to the biological activities exerted by organoselenium compounds. In 1984, Sies reported for the first time the ability of ebselen to mimic the activity of glutathione peroxidase. From this milestone, several studies reported the pharmacological properties of selenium-containing compounds including their exploitation as antimicrobials. In this context, this minireview presents the most recent examples of seleno derivatives endowed with antimicrobial activities while discussing the most interesting and recent synthetic procedures used to obtain these compounds.

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In vitro antifungal evaluation and structure–activity relationship of diphenyl diselenide and synthetic analogues

Cited by 36 publications

References 12 publications

Allylic Selenocyanates as New Agents to Combat Fusarium Species Involved with Human Infections

Allylic Selenocyanates as New Agents to Combat Fusarium Species Involved with Human Infections

Diphenyl diselenide derivatives inhibit microbial biofilm formation involved in wound infection

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

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