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Antiadhesive Properties of Imidazolium Ionic Liquids Based on (-)-Menthol Against Candida spp.

ABSTRACT: Infections with Candida spp. are commonly found in long-time denture wearers, and when under immunosuppression can lead to stomatitis. Imidazolium ionic liquids with an alkyl or alkyloxymethyl chain and a natural (1R,2S,5R)-(-)-menthol substituent possess high antifungal and antiadhesive properties towards C. albicans, C. parapsilosis, C. glabrata and C. krusei. We tested three compounds and found they disturbed fungal plasma membranes, with no significant hemolytic properties. In the smallest hemolytic concentrations, all compounds inhibited C. albicans biofilm formation on acrylic, and partially on porcelain and alloy dentures. Biofilm eradication may result from hyphae inhibition (for alkyl derivatives) or cell wall lysis and reduction of adhesins level (for alkyloxymethyl derivative). Thus, we propose the compounds presented herein as potential anti-fungal denture cleaners or denture fixatives, especially due to their low toxicity towards mammalian erythrocytes after short-term exposure.

SUBMITTER: Suchodolski J

PROVIDER: S-EPMC8304783 | biostudies-literature | 2021 Jul

REPOSITORIES: biostudies-literature

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Antiadhesive Properties of Imidazolium Ionic Liquids Based on (-)-Menthol Against Candida spp.

Suchodolski Jakub J Feder-Kubis Joanna J Krasowska Anna A

International journal of molecular sciences 20210714 14

Infections with Candida spp. are commonly found in long-time denture wearers, and when under immunosuppression can lead to stomatitis. Imidazolium ionic liquids with an alkyl or alkyloxymethyl chain and a natural (1R,2S,5R)-(-)-menthol substituent possess high antifungal and antiadhesive properties towards C. albicans, C. parapsilosis, C. glabrata and C. krusei. We tested three compounds and found they disturbed fungal plasma membranes, wit ...[more]

PMID: 34299160

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Project description:We investigated the influence of anion type (salicylate, [(MOB)MIm][Sal], vs chloride, [(MOB)MIm][Cl]) of imidazolium-based ionic liquid (IL) and its content on the curing kinetics of bisphenol A diglicydyl ether (DGEBA of molecular weight M n = 340 g/mol). Further physicochemical properties (i.e., glass transition temperature, T g, and conductivity, σdc) of produced polymers were investigated. The polymerization of the studied systems was examined at various molar ratios (1:1, 10:1, and 20:1) at different reaction temperatures (T reaction = 353-383 K) by using differential scanning calorimetry (DSC). Interestingly, both DGEBA/IL compositions studied herein revealed significantly different reaction kinetics and yielded materials of completely distinct physical properties. Surprisingly, in contrast to [(MOB)MIm][Cl], for the low concentration of [(MOB)MIm][Sal] in the reaction mixture, an additional step in the kinetic curves, likely due to the combined enhanced initiation activity of anion (salicylate)-cation (imidazolium-based), was noted. To thoroughly analyze the kinetics of all studied systems, including the two-step kinetics of DGEBA/[(MOB)MIm][Sal], we applied a new approach that relies on the combination of the two phenomenological Avrami equations. Analysis of the determined constant rates revealed that the reaction occurring in the presence of the salicylate anion is characterized by higher activation energy with respect to those with the chloride. Moreover, DGEBA/[(MOB)MIm][Sal] cured materials have higher T g in comparison to DGEBA polymerized with [(MOB)MIm][Cl] independent of the IL concentration. This fact might indicate that, most likely, the products of hardening are highly cross-linked (high T g) or oligomeric linear polymers (low T g) in the former and latter cases, respectively. Such a change in the chemical structure of the polymer is also reflected in the dc conductivity measured at the glass transition temperature, which is much higher for DGEBA cured with [(MOB)MIm][Cl]. Herein, we have clearly demonstrated that the type of anion has a crucial impact on the polymerization mechanism, kinetics, and properties of produced materials.

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Antiadhesive Properties of Imidazolium Ionic Liquids Based on (-)-Menthol Against Candida spp.

Publications

Antiadhesive Properties of Imidazolium Ionic Liquids Based on (-)-Menthol Against <i>Candida</i> spp.

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