Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi

Brackman, Gilles; Quntar, Abed Al Aziz Al; Enk, Claes D.; Karalić, Izet; Nelis, Hans; Calenbergh, Serge Van; Srebnik, Morris; Coenye, Tom

doi:10.1016/j.bmc.2012.11.055

Cited by 51 publications

(36 citation statements)

References 32 publications

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“…In addition, thiazolidinediones (TZDs) have been proposed as potential QS inhibitors for the bacterium Vibrio harveyi (13). Given all of the findings described above, we propose that one of the possible modes of the antibiofilm action of S-8 toward fungi could be interference in the fungal QS cascade, as it may directly or indirectly interact with the synthesis and/or activity of C. albicans QS molecules.…”

Section: Discussionmentioning

confidence: 93%

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Sustained Release of a Novel Anti-Quorum-Sensing Agent against Oral Fungal Biofilms

Feldman

Shenderovich

Al-Quntar

et al. 2015

Antimicrob Agents Chemother

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b Thiazolidinedione-8 (S-8) has recently been identified as a potential anti-quorum-sensing/antibiofilm agent against bacteria and fungi. Based on these results, we investigated the possibility of incorporating S-8 in a sustained-release membrane (SRM) to increase its pharmaceutical potential against Candida albicans biofilm. We demonstrated that SRM containing S-8 inhibits fungal biofilm formation in a time-dependent manner for 72 h, due to prolonged release of S-8. Moreover, the SRM effectively delivered the agent in its active form to locations outside the membrane reservoir. In addition, eradication of mature biofilm by the SRM containing S-8 was also significant. Of note, S-8-containing SRM affected the characteristics of mature C. albicans biofilm, such as thickness, exopolysaccharide (EPS) production, and morphogenesis of fungal cells. The concept of using an antibiofilm agent with no antifungal activity incorporated into a sustained-release delivery system is new in medicine and dentistry. This concept of an SRM containing a quorum-sensing quencher with an antibiofilm effect could pave the way for combating oral fungal infectious diseases.

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Section: Discussionmentioning

confidence: 93%

“…QS is associated with biofilm formation and the increased pathogenicity of fungi in biofilms (12). Thiazolidinediones (TZDs) have been proposed as potential QS inhibitors in Vibrio harveyi (13). Several TZD derivatives have also been tested for their ability to affect C. albicans pathogenicity (9).…”

mentioning

confidence: 99%

Sustained Release of a Novel Anti-Quorum-Sensing Agent against Oral Fungal Biofilms

Feldman

Shenderovich

Al-Quntar

et al. 2015

Antimicrob Agents Chemother

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“…6) was prepared according to a previously described method [16], [21] with some modifications. Briefly, 0.085 g (1 mmol) piperidine was added to 0.170 g (1 mmol) thiazolidine-2,4-dione in 8 ml ethanol, followed by addition of 0.098 g (1 mmol) decanal.…”

Section: Methodsmentioning

confidence: 99%

“…Farnesol regulates C. albicans morphology and inhibits biofilm formation [18], [19], whereas tyrosol is associated with increased biomass of C. albicans biofilms, probably by stimulating hyphal growth [20]. Thiazolidinediones (TZDs) have been proposed as potential QS inhibitors in Vibrio harveyi [21]. Several TZD derivatives have also been tested for their ability to affect C. albicans pathogenicity [16].…”

Section: Introductionmentioning

confidence: 99%

Therapeutic Potential of Thiazolidinedione-8 as an Antibiofilm Agent against Candida albicans

et al. 2014

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Candida albicans is known as a commensal microorganism but it is also the most common fungal pathogen in humans, causing both mucosal and systemic infections. Biofilm-associated C. albicans infections present clinically important features due to their high levels of resistance to traditional antifungal agents. Quorum sensing is closely associated with biofilm formation and increasing fungal pathogenicity. We investigated the ability of the novel bacterial quorum sensing quencher thiazolidinedione-8 (S-8) to inhibit the formation of, and eradication of mature C. albicans biofilms. In addition, the capability of S-8 to alter fungal adhesion to mammalian cells was checked. S-8 exhibited specific antibiofilm and antiadhesion activities against C. albicans, at four- to eightfold lower concentrations than the minimum inhibitory concentration (MIC). Using fluorescence microscopy, we observed that S-8 dose-dependently reduces C. albicans–GFP binding to RAW macrophages. S-8 at sub-MICs also interfered with fungal morphogenesis by inhibiting the yeast-to-hyphal form transition. In addition, the tested agent strongly affected fungal cell wall characteristics by modulating its hydrophobicity. We evaluated the molecular mode of S-8 antibiofilm and antiadhesion activities using real-time RT-PCR. The expression levels of genes associated with biofilm formation, adhesion and filamentation, HWP1, ALS3 and EAP1, respectively, were dose-dependently downregulated by S-8. Transcript levels of UME6, responsible for long-term hyphal maintenance, were also significantly decreased by the tested agent. Both signaling pathways of hyphal formation-cAMP-PKA and MAPK-were interrupted by S-8. Their upstream general regulator RAS1 was markedly suppressed by S-8. In addition, the expression levels of MAPK cascade components CST20, HST7 and CPH1 were downregulated by S-8. Finally, transcriptional repressors of filament formation, TUP1 and NRG1, were dramatically upregulated by our compound. Our results indicate that S-8 holds a novel antibiofilm therapeutic mean in the treatment and prevention of biofilm-associated C. albicans infections.

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“…For instance, the thiazolidinediones (resemble the QSIs such as N-acylaminofuranones and/or acyl-homoserine lactone signalling molecules), dioxazaborocanes (structurally resemble the oxazaborolidine derivatives) and brominated thiophenones were shown to block the AI-2 QS in V. harveyi (Brackman et al 2013).…”

Section: Targeting Ai-2 Receptorsmentioning

confidence: 99%

Strategies for Silencing Bacterial Communication

Ivanova

Fernandes

Tzanov

2014

Quorum Sensing vs Quorum Quenching: A Battle With No End in Sight

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Synthesis and evaluation of thiazolidinedione and dioxazaborocane analogues as inhibitors of AI-2 quorum sensing in Vibrio harveyi

Cited by 51 publications

References 32 publications

Sustained Release of a Novel Anti-Quorum-Sensing Agent against Oral Fungal Biofilms

Sustained Release of a Novel Anti-Quorum-Sensing Agent against Oral Fungal Biofilms

Therapeutic Potential of Thiazolidinedione-8 as an Antibiofilm Agent against Candida albicans

Strategies for Silencing Bacterial Communication

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