Correlation between the lipophilicity and antifungal activity of some benzoxazole derivatives

Podunavac‐Kuzmanović, Sanja O.; Velimirović, Sonja D.

doi:10.2298/apt1041177p

Cited by 8 publications

(4 citation statements)

References 20 publications

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“…A quantitative relationship between the lipophilicity and antifungal activity of some benzoxazole derivatives against Candida albicans was investigated by using quantitative structure–activity relationship (QSAR) analyses. The descriptors which describe numerically the lipophilicity, logP, were calculated using Chem-Office Software version 7.0 (PerkinElmer, Boston, MA, USA) The results of this study indicate that the lipophilicity parameter has a significant effect on antifungal activity of this class of compounds [ 19 ]. This report reassures that the monoene anacardic acid, which is more lipophilic, presents higher antifungal activity.…”

Section: Resultsmentioning

confidence: 99%

Anacardic Acid Constituents from Cashew Nut Shell Liquid: NMR Characterization and the Effect of Unsaturation on Its Biological Activities

et al. 2017

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Anacardic acids are the main constituents of natural cashew nut shell liquid (CNSL), obtained via the extraction of cashew shells with hexane at room temperature. This raw material presents high technological potential due to its various biological properties. The main components of CNSL are the anacardic acids, salicylic acid derivatives presenting a side chain of fifteen carbon atoms with different degrees of unsaturation (monoene–15:1, diene–15:2, and triene–15:3). Each constituent was isolated by column chromatography using silica gel impregnated with silver nitrate. The structures of the compounds were characterized by nuclear magnetic resonance through complete and unequivocal proton and carbon assignments. The effect of the side chain unsaturation was also evaluated in relation to antioxidant, antifungal and anticholinesterase activities, and toxicity against Artemia salina. The triene anacardic acid provided better results in antioxidant activity assessed by the inhibition of the free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH), higher cytotoxicity against A. salina, and acetylcholinesterase (AChE) inhibition. Thus, increasing the unsaturation of the side chain of anacardic acid increases its action against free radicals, AChE enzyme, and A. salina nauplii. In relation to antifungal activity, an inverse result was obtained, and the linearity of the molecule plays an important role, with monoene being the most active. In conclusion, the changes in structure of anacardic acids, which cause differences in polarity, contribute to the increase or decrease in the biological activity assessed.

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Section: Resultsmentioning

confidence: 99%

Anacardic Acid Constituents from Cashew Nut Shell Liquid: NMR Characterization and the Effect of Unsaturation on Its Biological Activities

et al. 2017

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“…The lipid solubility of SER is much higher than that of REB (log P = 5.15 vs. log P = 3.28, respectively) [32,33]. In one study, it was found that the parameter of lipophilicity, or lipid solubility, plays an important role in the antifungal activity of a class of experimental compounds [34]. The lipophilicity of the drug has a major role not only in determining the assimilation and distribution of that drug in living organisms but also in allowing the drug to penetrate the biofilm created by the fungal cell by destroying its matrix; it may also damage the plasmatic and mitochondrial membranes [22].…”

Section: Discussionmentioning

confidence: 99%

Anti-Candidal Activity of Reboxetine and Sertraline Antidepressants: Effects on Pre-Formed Biofilms

et al. 2023

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Reboxetine (REB) and sertraline (SER) are antidepressants. The antifungal potential of these drugs against planktonic Candida has been recently reported with limited data about their effects on Candidal biofilms. Biofilms are self-derived extracellular matrixes produced by the microbial population that is attached to biotic surfaces, such as vaginal and oral mucosa, or abiotic surfaces, such as biomedical devices, resulting in persistent fungal infections. The commonly prescribed antifungals, azoles, are usually less effective when biofilms are formed, and most of the prescribed antifungals are only fungistatic. Therefore, the current study investigates the antifungal potentials of REB and SER, alone and in combination with fluconazole (FLC) and itraconazole (ITR) against Candidal biofilms. Using proper controls, Candida species (Candida albicans, C. albicans; Candida krusei, C. krusei; and Candida glabrata, C. glabrata) were used to form biofilms in 96-well microplates. Serial dilutions corresponding to concentrations ranging from 2 to 4096 µg/mL of the target drugs (REB, SER, FLC, ITR) were prepared and added to the plates. Impairment of the biofilm biomass and biofilm metabolic viability was detected using the crystal violet (CV) assay and 3-(4,5-dimethyl-thiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay, respectively. In the checkerboard assay, the sessile fractional inhibitory concentration index (SFICI) was calculated to evaluate the effects of drug combinations. SER was more effective in reducing the biomass than REB for C. albicans and C. glabrata, but both were equal for C. krusei. For the reduction in metabolic activity in C. albicans and C. glabrata, SER had a slight advantage over REB. In C. krusei, REB was slightly more potent. Overall, FLC and ITR were almost equal and produced more significant reductions in metabolic activity when compared to SER and REB, except for C. glabrata, where SER was almost equal to FLC. Synergism was detected between REB + FLC and REB + ITR against biofilm cells of C. albicans. Synergism was detected between REB + ITR against biofilm cells of C. krusei. Synergism was detected between REB + FLC and REB + ITR against biofilm cells of C. albicans, C. krusei, and C. glabrata. The results of the present study support the potential of SER and REB as anti-Candidal biofilm agents that are beneficial as a new antifungal to combat Candidal resistance.

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“…Thiourea derivatives act as intermediates for the synthesis of variety of acyclic and heterocyclic compounds [7][8]. Log P is a most commonly used molecular descriptor in SAR analyses [9][10][11][12][13][14]. It is a quantitative descriptor of lipophilicity, one of the significant factors of pharmacokinetic properties.…”

Section: Introductionmentioning

confidence: 99%

DFT Calculations of Thiourea Derivatives Containing a Thiazole Moiety for the Evaluation of Antifungal Activity

Dongare

Inamdar

Tigote

2022

JASR

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We report here the correlation between the quantum chemical parameters and the reported antifungal activity of thiourea derivatives containing a thiazole moiety (1a-1d). The structure of thiourea derivatives were optimized by Density Functional Theory (DFT) using B3LYP method with 6-31G (d,p) basis set. The optimized molecular geometry, bond lengths, bond angles and band gap were investigated. Quantum chemical parameters of the compounds viz. EA, IP, Electronegativity, hardness (η) and softness (σ) showed strong correlation with the reported antifungal activity of studied compounds. Geometrical parameters have been compared with the available experimental results. The structureactivity relationship was also studied.

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Correlation between the lipophilicity and antifungal activity of some benzoxazole derivatives

Cited by 8 publications

References 20 publications

Anacardic Acid Constituents from Cashew Nut Shell Liquid: NMR Characterization and the Effect of Unsaturation on Its Biological Activities

Anacardic Acid Constituents from Cashew Nut Shell Liquid: NMR Characterization and the Effect of Unsaturation on Its Biological Activities

Anti-Candidal Activity of Reboxetine and Sertraline Antidepressants: Effects on Pre-Formed Biofilms

DFT Calculations of Thiourea Derivatives Containing a Thiazole Moiety for the Evaluation of Antifungal Activity

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