Determination of pKa values of some proton pump inhibitors in water-organic solvent mixtures: Conventional and green RPLC methods

IF 5.5 2区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Sustainable Chemistry and Pharmacy Pub Date : 2025-03-11 DOI:10.1016/j.scp.2025.101983

Y. Doğan Daldal , Ebru Çubuk Demiralay

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引用次数: 0

Abstract

In this study, the ionization/protonation constants (pK_a) of commonly used proton pump inhibitors (PPIs), omeprazole, pantoprazole, rabeprazole and lansoprazole, were determined using green reversed phase liquid chromatography (green RPLC) and conventional RPLC methods. Qualitative determination of the compounds was carried out on a Gemini NX C18 (250 × 3.0 mm I.D., 5 μm) column at 37 °C column temperature and 1 mL/min flow rate. To determine this physicochemical parameter, liquid chromatographic analyzes of PPIs were carried out in water-organic solvent binary mixtures containing 20%, 25%, 30%, and 35% (v/v) of organic solvent (acetonitrile, methanol, ethanol). The effects of substituents on the pyridine and benzimidazole rings in the structures of these compounds on the pK_a values were also investigated. The pK_a

({}_{w}^{w}{p K}_{a})

values of the compounds in water environment were calculated and compared using the

{}_{s}^{s}{p K}_{a}

values in water-organic solvent mixtures and solvent macroscopic constants. The obtained data were evaluated with AGREE and GAPI software programs that give the greenness profile, and the optimum separation condition for the green RPLC approach based on the 12 principles of green chemistry was determined.

Abstract Image

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水-有机溶剂混合物中质子泵抑制剂pKa值的测定：常规和绿色RPLC方法

本研究采用绿色反相液相色谱（green RPLC）和常规RPLC方法测定了常用质子泵抑制剂奥美拉唑、泮托拉唑、雷贝拉唑和兰索拉唑的电离/质子化常数（pKa）。色谱柱为Gemini NX C18 (250 × 3.0 mm I.D, 5 μm)，柱温为37℃，流速为1 mL/min。为了确定这一理化参数，在含有20%、25%、30%和35% （v/v）有机溶剂（乙腈、甲醇、乙醇）的水-有机溶剂二元混合物中对PPIs进行了液相色谱分析。研究了化合物结构中吡啶环和苯并咪唑环上取代基对pKa值的影响。利用水-有机溶剂混合物中的pKass值和溶剂宏观常数，计算并比较了水环境中化合物的pKa （pKaww）值。采用AGREE和GAPI软件程序对获得的数据进行评价，给出绿色度概况，并根据绿色化学的12条原则确定绿色RPLC方法的最佳分离条件。

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来源期刊

Sustainable Chemistry and Pharmacy Environmental Science-Pollution

CiteScore

8.20

自引率

6.70%

发文量

274

审稿时长

37 days

期刊介绍： Sustainable Chemistry and Pharmacy publishes research that is related to chemistry, pharmacy and sustainability science in a forward oriented manner. It provides a unique forum for the publication of innovative research on the intersection and overlap of chemistry and pharmacy on the one hand and sustainability on the other hand. This includes contributions related to increasing sustainability of chemistry and pharmaceutical science and industries itself as well as their products in relation to the contribution of these to sustainability itself. As an interdisciplinary and transdisciplinary journal it addresses all sustainability related issues along the life cycle of chemical and pharmaceutical products form resource related topics until the end of life of products. This includes not only natural science based approaches and issues but also from humanities, social science and economics as far as they are dealing with sustainability related to chemistry and pharmacy. Sustainable Chemistry and Pharmacy aims at bridging between disciplines as well as developing and developed countries.