Application of chemometric methods for determination the lipophilicity of pentacyclic triterpene derivatives

IF 0.4 4区 医学 Q4 PHARMACOLOGY & PHARMACY
Katarzyna Bober-Majnusz, E. Bębenek, E. Chrobak, Monika Kadela-Tomanek
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引用次数: 1

Abstract

Chemometric analysis is often used in many fields of science. One of the most popular are cluster analysis and principal component analysis. The presented work considers those methods to evaluate the lipophilicity of groups of pentacyclic triterpene derivatives. They are newly synthesized compounds with biological activity, so they can be used in the future as drugs and lipophilicity is an essential parameter. The experimental values of lipophilicity were determined using thin-layer chromatography. The plates were precoated with silica gel, and a mixture of 1,4-dioxane and acetate buffer was applied as the mobile phase. The experimental values of lipophilicity for investigated compounds were correlated with lipophilicity taken from freely available databases (ALOGPs, KowWin, XLOGP2, XLOGP3, miLogP, AClogP, ALOGP, MLOGP, iLOGP, WLOGP and SILICOS-IT). Those experimental values were also correlated with physicochemical properties such as molecular weight, the topological polar surface of the molecule, the number of rotatable bonds, and the number of donor and acceptor sites for hydrogen bonds. Some correlation equations could be formed for the correlation obtained. The cluster and principal component analysis were done based on the data obtained. All the experimental lipophilicity data correlate well with those theoretically calculated based on the structural formula. Almost all dependencies can be described by the correlation equation, with a high correlation coefficient. Thus, it is possible to infer the lipophilicity values of triterpene derivatives without any laboratory work. The physicochemical properties turned out to be less valuable and, apart from the compounds' molar mass, not helpful.
化学计量学方法测定五环三萜衍生物的亲脂性
化学计量分析常用于许多科学领域。其中最流行的是聚类分析和主成分分析。本文考虑了这些方法来评价五环三萜衍生物基团的亲脂性。它们是新合成的具有生物活性的化合物,在未来可作为药物使用,亲脂性是一个重要的参数。采用薄层色谱法测定亲水性实验值。用硅胶预涂板,以1,4-二氧六环和乙酸酯缓冲液的混合物为流动相。所研究化合物的亲脂性实验值与可免费获取的数据库(ALOGP、KowWin、XLOGP2、XLOGP3、miLogP、AClogP、ALOGP、MLOGP、iLOGP、WLOGP和SILICOS-IT)的亲脂性相关。这些实验值还与物理化学性质相关,如分子量、分子的拓扑极性表面、可旋转键的数量以及氢键的供体和受体位点的数量。对所得到的相关关系可以形成相关方程。根据所得数据进行聚类分析和主成分分析。所有的实验亲脂性数据与基于结构式的理论计算结果吻合良好。几乎所有的依赖关系都可以用相关方程来描述,并且具有很高的相关系数。因此,不需要任何实验室工作就可以推断出三萜衍生物的亲脂性值。事实证明,除了化合物的摩尔质量外,物理化学性质的价值更低,也没有什么帮助。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
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来源期刊
CiteScore
0.80
自引率
0.00%
发文量
74
审稿时长
6-12 weeks
期刊介绍: The international journal of the Polish Pharmaceutical Society is published in 6 issues a year. The journal offers Open Access publication of original research papers, short communications and reviews written in English, in all areas of pharmaceutical sciences. The following areas of pharmaceutical sciences are covered: Analysis, Biopharmacy, Drug Biochemistry, Drug Synthesis, Natural Drugs, Pharmaceutical Technology, Pharmacology and General. A bimonthly appearing in English since 1994, which continues “Acta Poloniae Pharmaceutica”, whose first issue appeared in December 1937. The war halted the activity of the journal’s creators. Issuance of “Acta Poloniae Pharmaceutica” was resumed in 1947. From 1947 the journal appeared irregularly, initially as a quarterly, then a bimonthly. In the years 1963 – 1973 alongside the Polish version appeared the English edition of the journal. Starting from 1974 only works in English are published in the journal. Since 1995 the journal has been appearing very regularly in two-month intervals (six books a year). The journal publishes original works from all fields of pharmacy, summaries of postdoctoral dissertations and laboratory notes.
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