Department of Bioinorganic Chemistry, Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland.
Department of Theoretical Chemistry, Faculty of Chemistry, University of Gdańsk, Wita Stwosza 63, 80-308 Gdańsk, Poland.
Molecules. 2022 Jun 9;27(12):3704. doi: 10.3390/molecules27123704.
Pyrazine and its derivatives are a large group of compounds that exhibit broad biological activity, the changes of which can be easily detected by a substituent effect or a change in the functional group. The present studies combined theoretical research with the density functional theory (DFT) approach (B3LYP/6-311+G**) and experimental (potentiometric and spectrophotometric) analysis for a thorough understanding of the structure of chlorohydrazinopyrazine, its physicochemical and cytotoxic properties, and the site and nature of interaction with DNA. The obtained results indicated that 2-chloro-3-hydrazinopyrazine (2Cl3HP) displayed the highest affinity to DNA. Cytotoxicity studies revealed that the compound did not exhibit toxicity toward human dermal keratinocytes, which supported the potential application of 2Cl3HP in clinical use. The study also attempted to establish the possible equilibria occurring in the aqueous solution and, using both theoretical and experimental methods, clearly showed the hydrophilic nature of the compound. The experimental and theoretical results of the study confirmed the quality of the compound, as well as the appropriateness of the selected set of methods for similar research.
吡嗪及其衍生物是一类具有广泛生物活性的化合物，其变化可以通过取代效应或官能团的变化来轻松检测。本研究结合理论研究和密度泛函理论（DFT）方法（B3LYP/6-311+G**）以及实验（电位和分光光度分析）来深入了解氯代肼基吡嗪的结构、理化性质和细胞毒性，以及与 DNA 的相互作用位点和性质。研究结果表明，2-氯-3-肼基吡嗪（2Cl3HP）与 DNA 的亲和力最高。细胞毒性研究表明，该化合物对人皮肤角质形成细胞没有毒性，这支持了 2Cl3HP 在临床应用中的潜在应用。该研究还试图建立在水溶液中可能发生的可能平衡，并使用理论和实验方法，清楚地表明了化合物的亲水性。研究的实验和理论结果证实了化合物的质量，以及所选方法组合用于类似研究的适当性。
