Chajdaś Zofia, Kucharska Martyna, Wesełucha-Birczyńska Aleksandra
Faculty of Chemistry, Jagiellonian University, Kraków, Poland.
Appl Spectrosc. 2024 Sep 17:37028241279434. doi: 10.1177/00037028241279434.
Cinchonine is a quinoline alkaloid known for its antimalarial properties. Due to the advantages of using compounds of metal ions with alkaloids, a copper(II) compound with cinchonine was synthesized, and, for comparative purposes, a cadmium(II) compound with cinchonine. During the synthesis, the emerging interactions between the metal ion and cinchonine were studied. After crystallization, it was examined how the obtained compounds would interact with the model blood component, hematoporphyrin IX. Ultraviolet-visible (UV-Vis) spectroscopy, Raman spectroscopy, and attenuated total reflection Fourier transform infrared spectroscopy (ATR FT-IR) were used in the study. In the case of monitoring the synthesis, the best method turned out to be UV-Vis spectroscopy, combined with the possibility of two-dimensional correlation spectroscopy (2D-COS), which enabled the identification of peaks characteristic of the interactions of the cinchonine quinoline ring with metal ions. In turn, the obtained Raman spectra showed shifts of individual bands and changes in their intensity, and 2D-COS showed the sequence of formation of individual interactions, which confirmed the formation of cinchonine compounds with metals. ATR FT-IR also allowed us to compare the spectra of the substrates used in the synthesis with the crystallized compounds and thus confirm the formation of the expected compounds. Bands characteristic of π-π-stacking interactions between the quinoline ring and the tetrapyrrole ring of hematoporphyrin IX were also observed. Observed interaction with a model blood component may be important when designing drugs for antimalarial therapy.
辛可宁是一种以抗疟特性闻名的喹啉生物碱。由于使用金属离子与生物碱的化合物具有诸多优势,合成了一种含辛可宁的铜(II)化合物,并且,为作比较,还合成了一种含辛可宁的镉(II)化合物。在合成过程中,研究了金属离子与辛可宁之间新出现的相互作用。结晶后,研究了所得化合物与模型血液成分血卟啉IX的相互作用方式。该研究使用了紫外可见(UV-Vis)光谱、拉曼光谱和衰减全反射傅里叶变换红外光谱(ATR FT-IR)。在监测合成过程时,结果表明最佳方法是UV-Vis光谱结合二维相关光谱(2D-COS)的可能性,这使得能够识别辛可宁喹啉环与金属离子相互作用的特征峰。反过来,所得的拉曼光谱显示了各个谱带的位移及其强度变化,并且2D-COS显示了各个相互作用形成的顺序,这证实了辛可宁与金属化合物的形成。ATR FT-IR还使我们能够将合成中使用的底物光谱与结晶化合物的光谱进行比较,从而确认预期化合物的形成。还观察到了血卟啉IX的喹啉环与四吡咯环之间π-π堆积相互作用的特征谱带。在设计抗疟治疗药物时,观察到的与模型血液成分的相互作用可能很重要。