Terpene-Based Ionic Liquids from Natural Renewable Sources As Selective Agents in Antifungal Therapy,ACS Biomaterials Science & Engineering

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Terpene-Based Ionic Liquids from Natural Renewable Sources As Selective Agents in Antifungal Therapy
ACS Biomaterials Science & Engineering ( IF 5.4 ) Pub Date : 2020-06-03 , DOI: 10.1021/acsbiomaterials.0c00447
Joanna Feder-Kubis ₁ , Anita Wnętrzak ₂ , Anna Chachaj-Brekiesz ₂

Affiliation

In this study, we present a new approach toward the design of ionic liquids with biological activity. Structural analysis of bioactive compounds was performed to design—in a technological and economic manner—salts with potential antifungal properties. The length of the alkyl chain as well as the task-specific component in the cation, the type of amine core, and the type of anion were considered as having an essential impact on achieving desired biological activity. Herein, we present the synthesis and characterization of ionic liquids based on monoterpene derivatives—namely, (1R,2S,5R)-(−)-menthol or bicyclic (1R)-endo-(+)-fenchol—from renewable sources. These new salts were synthesized with high yields (>96%) in mild conditions via a two-step procedure. Physicochemical properties (i.e., melting point, thermal stability, crystal shape, specific rotation, surfactant content, solubility, and surface activity) were analyzed in detail. The obtained results suggested the influence of the steric hindrance of the discussed salts on the reactivity, solubility, thermal stability, and surface properties of the studied compounds. Their potential selectivity in antifungal therapy was studied using Langmuir monolayer mimicking fungal (ergosterol) and mammalian (cholesterol) membranes. The model study confirmed the selective destabilizing activity of terpene-based ionic liquids on the fungus membrane.

中文翻译：

天然可再生来源的萜烯离子液体作为抗真菌治疗的选择剂

在这项研究中，我们提出了一种具有生物活性的离子液体设计新方法。对生物活性化合物进行结构分析，以技术和经济的方式设计具有潜在抗真菌特性的盐。烷基链的长度以及阳离子中的特定任务组分，胺核的类型和阴离子的类型被认为对实现所需的生物活性具有重要影响。本文中，我们介绍了基于单萜衍生物的离子液体的合成和表征-即（1 R，2 S，5 R）-（-）-薄荷醇或双环（1 R）-内-（+）-苯酚-来自可再生资源。这些新的盐在温和的条件下通过两步程序以高收率（> 96％）合成。详细分析了理化性质（即熔点，热稳定性，晶体形状，比旋光度，表面活性剂含量，溶解度和表面活性）。获得的结果表明所讨论的盐的空间位阻对所研究化合物的反应性，溶解性，热稳定性和表面性质的影响。使用模仿真菌（麦角固醇）和哺乳动物（胆固醇）膜的Langmuir单层膜研究了它们在抗真菌治疗中的潜在选择性。该模型研究证实了萜烯基离子液体在真菌膜上的选择性去稳定活性。

更新日期：2020-07-13

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