Reversed-phase thin-layer chromatographic and computational evaluation of lipophilicity parameters of α,β-unsaturated acids

IF 1.1 4区化学 Q4 CHEMISTRY, ANALYTICAL Jpc-journal of Planar Chromatography-modern Tlc Pub Date : 2024-01-05 DOI:10.1007/s00764-023-00274-9

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Abstract

The retention behavior of 10 previously synthesized α,β-unsaturated acids that exhibited antimicrobial activity was studied using 12 reversed-phase thin-layer chromatography (RP-TLC) systems. The mobile phases consisted of three solvent combinations (methanol‒water, acetonitrile‒water, and acetone‒water) in four different ratios (50:50, 60:40, 70:30, and 80:20, V/V). The chromatographic parameters \({R}_{M}^{0}\) , a, and C₀ were calculated for each system. The lipophilicity parameters of the tested compounds were predicted using various computational methods. The acetone‒water system demonstrated the highest correlation coefficients between the chromatographic and calculated lipophilicity parameters, which makes it the most suitable for evaluating the lipophilicity of the tested compounds. This system successfully reflected the effect of the lipophilic properties of the compounds on their retention behavior. To elucidate the retention mechanisms, the molecular properties of the tested compounds were calculated and a genetic algorithm was used to identify the properties with the greatest influence on the retention behavior. The interpretation of these descriptors revealed structural and physicochemical properties crucial for the behavior of the tested compounds. In addition, the pharmacokinetic properties of the compounds were estimated using in silico methods. The observed correlation between the retention mechanism and physicochemical properties affecting membrane transport and physiological binding ability highlights the applicability of RP-TLC conditions for rapid profiling of newly synthesized α,β-unsaturated acids.

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α、β-不饱和酸亲油性参数的反相薄层色谱和计算评估

摘要利用 12 个反相薄层色谱 (RP-TLC) 系统研究了 10 种以前合成的具有抗菌活性的 α,β-不饱和酸的保留行为。流动相包括三种溶剂组合（甲醇-水、乙腈-水和丙酮-水），四种不同的比例（50:50、60:40、70:30 和 80:20，V/V）。计算了每个体系的色谱参数 \({R}_{M}^{0}/)、a 和 C0。利用各种计算方法预测了被测化合物的亲脂性参数。丙酮-水体系的色谱亲脂性参数与计算亲脂性参数之间的相关系数最高，因此最适于评价受试化合物的亲脂性。该系统成功地反映了化合物的亲脂性对其保留行为的影响。为阐明保留机制，计算了受测化合物的分子性质，并使用遗传算法确定了对保留行为影响最大的性质。对这些描述符的解释揭示了对测试化合物的行为至关重要的结构和理化性质。此外，还采用了硅学方法对化合物的药代动力学特性进行了估计。所观察到的保留机制与影响膜转运和生理结合能力的理化性质之间的相关性突出表明，RP-TLC 条件适用于快速分析新合成的 α、β-不饱和酸。

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来源期刊

Jpc-journal of Planar Chromatography-modern Tlc 化学-分析化学

CiteScore

2.20

自引率

18.80%

发文量

审稿时长

>12 weeks

期刊介绍： JPC - Journal of Planar Chromatography - Modern TLC is an international journal devoted exclusively to the publication of research papers on analytical and preparative planar chromatography. The journal covers all fields of planar chromatography, on all kinds of stationary phase (paper, layer, gel) and with various modes of migration of the mobile phase (capillary action or forced flow).