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Novel Alkylimidazolium Ionic Liquids as an Antibacterial Alternative to Pathogens of the Skin and Soft Tissue Infections.

ABSTRACT: Keeping in mind the concept of green chemistry, this research aims to synthesize and characterize new ionic liquids (ILs) derived from N-cinnamyl imidazole with different sizes of alkyl chains (1, 6, 8, and 10 carbon atoms), and evaluate their antibacterial activity against Skin and soft tissue infections (SSTIs) causative bacteria. The antibacterial screening was carried out by agar well diffusion and the Minimum Inhibitory Concentration (MIC) and Half Maximum Inhibitory Concentration (IC₅₀) of the different ILs were determined by microdilution in broth, also Molecular dynamics simulations were performed to study the interaction mechanism between ILs and membranes. The MIC value in Gram-positive bacteria showed that as the hydrocarbon chain increases, the MIC value decreases with a dose-dependent effect. Furthermore, Gram-negative bacteria showed high MIC values, which were also evidenced in the antibacterial screening. The molecular dynamics showed an incorporation of the ILs with the longer chain (10 C), corresponding to a passive diffusion towards the membrane surface, for its part, the ILs with the shorter chain due to its lack of hydrophobicity was not incorporated into the bilayer. Finally, the new ILs synthesized could be an alternative for the treatment of Gram-positive bacteria causative of SSTIs.

SUBMITTER: Forero Doria O

PROVIDER: S-EPMC6225289 | biostudies-literature | 2018 Sep

REPOSITORIES: biostudies-literature

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Novel Alkylimidazolium Ionic Liquids as an Antibacterial Alternative to Pathogens of the Skin and Soft Tissue Infections.

Forero Doria Oscar O Castro Ricardo R Gutierrez Margarita M Gonzalez Valenzuela Diego D Santos Leonardo L Ramirez David D Guzman Luis L

Molecules (Basel, Switzerland) 20180914 9

Keeping in mind the concept of green chemistry, this research aims to synthesize and characterize new ionic liquids (ILs) derived from <i>N</i>-cinnamyl imidazole with different sizes of alkyl chains (1, 6, 8, and 10 carbon atoms), and evaluate their antibacterial activity against Skin and soft tissue infections (SSTIs) causative bacteria. The antibacterial screening was carried out by agar well diffusion and the Minimum Inhibitory Concentration (MIC) and Half Maximum Inhibitory Concentration (I ...[more]

PMID: 30223457

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Project description:Candida albicans is an opportunistic pathogen causes fungal infections that range from common skin infections to persistent infections through biofilm formation on tissues, implants and life threatening systemic infections. New antifungal agents or therapeutic methods are desired due to high incidence of infections and emergence of drug-resistant strains. The present study aimed to evaluate (i) the antifungal and antibiofilm activity of 1-alklyl-3-methyl imidazolium ionic liquids ([CnMIM]+[X]-, n = 4, 12 and 16) against Candida albicans ATCC 10231 and two clinical C. albicans strains and (ii) the mechanism of action of promising antifungal ionic liquid on C. albicans. Two of the tested compounds were identified as more effective in preventing growth and biofilm formation. These ionic liquid compounds with -dodecyl and -hexadecyl alkyl groups effectively prevented biofilm formation by fluconazole resistant C. albicans 10231 and two other clinical C. albicans strains. Although both the compounds caused viability loss in mature C. albicans biofilms, an ionic liquid with -hexadecyl group ([C16MIM]+[Cl]-) was more effective in dispersing mature biofilms. This promising ionic liquid compound ([C16MIM]+[Cl]-) was chosen for determining the underlying mode of action on C. albicans cells. Light microscopy showed that ionic liquid treatment led to a significant reduction in cell volume and length. Increased cell membrane permeability in the ionic liquid treated C. albicans cells was evident in propidium iodide staining. Leakage of intracellular material was evident in terms of increased absorbance of supernatant and release of potassium and calcium ions into extracellular medium. A decrease in ergosterol content was evident when C. albicans cells were cultured in the presence of antifungal ionic liquid. 2',7'-Dichlorodihydrofluorescein acetate assay revealed reactive oxygen species generation and accumulation in C. albicans cells upon treatment with antifungal ionic liquid. The effect of antifungal ionic liquid on mitochondria was evident by decreased membrane potential (measured by Rhodamine 123 assay) and loss of metabolic activity (measured by MTT assay). This study demonstrated that imidazolium ionic liquid compound exert antifungal and antibiofilm activity by affecting various cellular processes. Thus, imidazolium ionic liquids represent a promising antifungal treatment strategy in lieu of resistance development to common antifungal drugs.

Project description:BackgroundThe antibacterial activities of aqueous leaf extracts of Moringa oleifera, Vernonia amygdalina, Azadirachta indica and Acalypha wilkesiana against multidrug resistance (MDR) Staphylococcus aureus associated with skin and soft tissue infections were investigated.MethodsStaphylococcus aureus (n = 183) from the skin and soft tissue infections with evidence of purulent pus, effusions from aspirates, wounds, and otorrhea were biotyped, and evaluated for biofilm production. The phenotypic antibiotic resistance and MDR strains susceptibility to plant leaves extract were determined using disc diffusion and micro-broth dilution assays respectively. The correlation of plant extract bioactive components with inhibitory activities was determined.ResultsHigh occurrence rate of S. aureus were recorded among infant and adult age groups and 13.2% mild biofilm producers from the wound (p < 0.05). Of 60.2% MDR strains with overall significant MARI of more than 0.85 (p < 0.05), high resistant rates to linozidine (92.7%; 95% CI:7.27-10.52), ofloxacin (94.2%; 95% CI:6.09-8.15), chloramphenicol (91.2%; 95% CI:6.11-8.32), gentamicin (97.3%; 95% CI:6.20-8.22), ciprofloxacin (92.7%; 95% CI: 5.28-7.99) and vancomycin (86.6%; 95% CI:6.81-9.59) were observed. Vernonia amygdalina and Azadirachta indica showed significant antimicrobial activity at 100 mg/ml and 75 mg/ml, with low susceptibility of less than 10% to 25 mg/ml, 50 mg/ml, and 75 mg/ml Moringa oleifera. Alkaloids, saponin and terpenoids were significant in Moringa oleifera, Acalypha wilkesiana, Azadirachta indica and Vernonia amygdalina leaves extracts (p < 0.05). High inhibitory concentrations at IC50; 3.23, 3.75 and 4.80 mg/ml (p = 0.02, CI: - 0.08 - 11.52) and IC90; 12.9, 7.5, and 9.6 mg/ml (p = 0.028, CI: 2.72-23.38) were shown by Acalypha wilkesiana, Vernonia amygdalina and Moringa oleifera respectively. Comparative outcome of the plant extracts showed Acalypha wilkesiana, Vernonia amygdalina and Moringa oleifera to exhibit significant inhibition activities (p < 0.05) compared to other extracts. Significant median inhibitory concentration (15.3 mg/ml) of Azadirachta indica were observed (p < 0.01) and strong associations of phytochemical compounds of Azadirachta indica (eta = 0.527,p = 0.017), Vernonia amygdalina (eta = 0.123,p = 0.032) and Acalypha wilkesiana (eta = 0.492,p = 0.012) with their respective inhibitory values.ConclusionObserved high occurrence rate of skin and soft tissue infections caused by biofilm-producing MDR S. aureus requires alternative novel herbal formulations with rich bioactive compounds from Moringa oleifera, Acalypha wilkesiana, Azadirachta indica and Vernonia amygdalina as skin therapeutic agents.

Project description:IntroductionMeticillin-resistant staphylococcus aureus (MRSA) is an important cause of antimicrobial-resistant infections worldwide. Its prevalence remains high in the Greek hospital setting. Complicated skin and soft tissue infections (cSSTIs) due to MRSA are associated with prolonged hospitalization, additional healthcare costs and significant morbidity. The purpose of this study was to conduct a cost analysis and a budget impact analysis relative to different management scenarios for MRSA-cSSTIs from a hospital perspective.MethodsEqual efficacy was assumed for the pharmacotherapies under evaluation and resource use was elicited via an expert panel of seven local infectious disease specialists. The model was based on a previously published economic model that was adapted for the Greek hospital setting and included a decision tree for the management of hospitalized patients with MRSA-cSSTIs, which simulated costs and outcomes for the duration of hospitalization according to the therapeutic scenario. Inpatient costs consisted of hospitalization, diagnostic/laboratory testing, physician visits and antibiotic treatment.ResultsCurrent economic impact of MRSA-cSSTIs for the inpatient setting in Greek hospitals was estimated at €29,196,218. Total per patient cost according to first-line agent was €2,457, €2,762, €2,850, €3,494 and €3,094 and mean length of stay was 9.2, 12.5, 10.3, 13.0 and 14.0 days for linezolid, vancomycin, daptomycin, tigecycline, and teicoplanin, respectively. An estimated 10,287 MRSA-cSSTI patients are treated annually in Greek hospitals. Thus, increasing the use of linezolid by 11% over a 3-year period (current use 19%; 3 year projection 30%), for the management of MRSA-cSSTIs, could result in 3-year savings of €896,065.ConclusionManagement of MRSA-cSSTI requires intensive resource use; overall healthcare costs differ according to the chosen first-line treatment. In light of considerable budget constraints, development of hospital strategies which facilitate early discharge, such as the introduction of clinical criteria and guidelines for switching from intravenous to oral MRSA-cSSTI therapy, could result in substantial savings for the Greek hospital budget.

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Novel Alkylimidazolium Ionic Liquids as an Antibacterial Alternative to Pathogens of the Skin and Soft Tissue Infections.

Publications

Novel Alkylimidazolium Ionic Liquids as an Antibacterial Alternative to Pathogens of the Skin and Soft Tissue Infections.

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