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基于分子间相互作用解释含离子液体的氟康唑乳液的抗真菌活性及稳定性

Antifungal Activity and Stability of Fluconazole Emulsion Containing Ionic Liquids Explained by Intermolecular Interactions.

作者信息

Hennemann Bruno L, Bender Caroline R, Moleta Guilherme S, Carvalho Ânderson R, Bazana Luana C G, Fuentefria Alexandre M, Frizzo Clarissa P

机构信息

Department of Chemistry, Federal University of Santa Maria, Santa Maria 97105900, Brazil.

Department of Chemistry, Federal University of Pampa, São Gabriel 97307020, Brazil.

出版信息

Pharmaceutics. 2022 Mar 26;14(4):710. doi: 10.3390/pharmaceutics14040710.

DOI:10.3390/pharmaceutics14040710
PMID:35456544
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9026797/
Abstract

This research reports accelerated stability experiments, the evaluation of intermolecular interactions, and antifungal assays for fluconazole emulsions prepared using ultrasound (US) and magnetic stirring (MS) in the presence of ionic liquids derived from 1,n-(3-methylimidazolium-1-yl)alkane bromide ([CnMIM]Br; n = 12 or 16). The goals of the investigation are to quantify the stability, identify the forces that drive the formation and stability, and determine the antifungal activity of fluconazole-containing emulsions, and corroborate the data from our previous results that indicated that the emulsion based on [C16MIM]Br seemed to be more stable. In this study, accelerated stability experiments evidenced a considerable stability for the [C16MIM]Br emulsions at two temperatures (25 and 37 °C)—the instability index increased in the following order: US40% < US20% < MS. The 1H NMR data showed that the ILs interacts differently with medium-chain triglycerides (MCT). Two distinct interaction mechanisms were also observed for [C12MIM]Br and [C16MIM]Br with fluconazole, in which the latter formed more compact mixed aggregates than the former. The result was corroborated by diffusion data, which showed that ILs suffered a decrease in diffusion in the presence of fluconazole. The antifungal assay showed that emulsions containing ILs displayed superior activity compared with fluconazole alone. The emulsions also showed potent activity in inhibiting a resistant species (C. glabrata—CG34) to FLZ. All emulsions showed weak irritant potential in HET-CAM assay.

摘要

本研究报告了在由1,n-(3-甲基咪唑鎓-1-基)烷烃溴化物（[CnMIM]Br；n = 12或16）衍生的离子液体存在下，使用超声（US）和磁力搅拌（MS）制备的氟康唑乳液的加速稳定性实验、分子间相互作用评估和抗真菌测定。该研究的目的是量化稳定性、确定驱动形成和稳定性的作用力、测定含氟康唑乳液的抗真菌活性，并证实我们之前的结果数据，即基于[C16MIM]Br的乳液似乎更稳定。在本研究中，加速稳定性实验证明了[C16MIM]Br乳液在两个温度（25和37°C）下具有相当的稳定性——不稳定指数按以下顺序增加：US40% < US20% < MS。1H NMR数据表明离子液体与中链甘油三酯（MCT）的相互作用不同。对于[C12MIM]Br和[C16MIM]Br与氟康唑，还观察到两种不同的相互作用机制，其中后者形成的混合聚集体比前者更紧密。扩散数据证实了这一结果，该数据表明离子液体在氟康唑存在下扩散减少。抗真菌测定表明，含离子液体的乳液比单独的氟康唑表现出更强的活性。这些乳液在抑制对氟康唑耐药的菌株（光滑念珠菌——CG34）方面也显示出强效活性。在鸡胚绒毛尿囊膜（HET-CAM）试验中，所有乳液均显示出较弱的刺激性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/ecbae0d87dcf/pharmaceutics-14-00710-g013.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/79d3dc076c24/pharmaceutics-14-00710-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/e6d0c350fc27/pharmaceutics-14-00710-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/079c3a0ff01c/pharmaceutics-14-00710-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/3aebc6443939/pharmaceutics-14-00710-g010.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/d1bfd927ebcb/pharmaceutics-14-00710-g002.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/cec3532e65a0/pharmaceutics-14-00710-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/d8973897c0e0/pharmaceutics-14-00710-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/79d3dc076c24/pharmaceutics-14-00710-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/e6d0c350fc27/pharmaceutics-14-00710-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/079c3a0ff01c/pharmaceutics-14-00710-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/3aebc6443939/pharmaceutics-14-00710-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/a83d739801c5/pharmaceutics-14-00710-g011.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/8a99d7ba34f1/pharmaceutics-14-00710-g012.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4521/9026797/ecbae0d87dcf/pharmaceutics-14-00710-g013.jpg

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