Estimation of the octanol-water distribution coefficient of basic compounds by a cationic microemulsion electrokinetic chromatography system.

IF 0.5 4区 环境科学与生态学 Q4 ENVIRONMENTAL SCIENCES International Journal of Environment and Pollution Pub Date : 2020-03-04 eCollection Date: 2020-01-01 DOI:10.5599/admet.760
Alejandro Fernández-Pumarega, Belén Martín-Sanz, Susana Amézqueta, Elisabet Fuguet, Martí Rosés
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Abstract

The octanol-water partition coefficient (Po/w), or the octanol-water distribution coefficient (Do/w) for ionized compounds, is a key parameter in the drug development process. In a previous work, this parameter was estimated through the retention factor measurements in a sodium dodecyl sulfate (SDS) - microemulsion electrokinetic chromatography (MEEKC) system for acidic compounds. Nonetheless, when ionized basic compounds were analyzed, undesirable ion pairs were formed with the anionic surfactant and avoided a good estimation of log Do/w. For this reason, an alternative MEEKC system based on a cationic surfactant has been evaluated to estimate Po/w or Do/w of neutral compounds and ionized bases. To this end, it has been characterized through the solvation parameter model (SPM) and compared to the octanol-water partition system. Results pointed out that both systems show a similar partition behavior. Hence, the log Po/w of a set of neutral compounds has been successfully correlated against the logarithm of the retention factor (log k) determined in this MEEKC system. Then, the log Do/w of 6 model bases have been estimated at different pH values and they have been compared to data from the literature, determined by the reference shake-flask and potentiometric methods. Good agreement has been observed between the literature and the estimated values when the base is neutral or partially ionized (up to 99% of ionization).

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利用阳离子微乳液电动色谱系统估算碱性化合物的辛醇-水分配系数。
辛醇-水分配系数(Po/w)或离子化化合物的辛醇-水分配系数(Do/w)是药物开发过程中的一个关键参数。在之前的研究中,该参数是通过十二烷基硫酸钠(SDS)-微乳液电动色谱(MEEKC)系统中酸性化合物的保留因子测量来估算的。然而,在分析离子化碱性化合物时,阴离子表面活性剂会形成不理想的离子对,从而无法很好地估算对数 Do/w。因此,我们对基于阳离子表面活性剂的替代 MEEKC 系统进行了评估,以估算中性化合物和离子化碱的 Po/w 或 Do/w。为此,通过溶解参数模型(SPM)对其进行了表征,并与辛醇-水分配体系进行了比较。结果表明,这两种体系表现出相似的分配行为。因此,一组中性化合物的对数 Po/w 与在该 MEEKC 系统中测定的保留因子(log k)的对数成功地建立了关联。然后,我们估算了 6 种模型碱在不同 pH 值下的 Do/w 对数值,并将其与参考摇瓶法和电位法测定的文献数据进行了比较。当碱为中性或部分电离(电离度高达 99%)时,文献数据与估算值之间具有良好的一致性。
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来源期刊
CiteScore
1.10
自引率
0.00%
发文量
3
审稿时长
4.5 months
期刊介绍: IJEP provides an international forum in the field of environment and pollution and addresses early and medium-term challenges involving scientific prediction, modelling and assessment. It focuses on ground-breaking research in the science of environmental pollution, at the early scientific stage. It is one of three key journals which together offer complete coverage of environmental issues: IJETM focuses on technical/engineering, policy and management solutions for environmental problems, and IJGEnvI focuses on future, longer-term environmental scenarios, ecological economics, climate change and biodiversity.
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