Szczolko Wojciech, Kryjewski Michal, Koczorowski Tomasz, Zuchowska Eunice, Popenda Lukasz, Mlynarczyk Dariusz T
Chair and Department of Chemical Technology of Drugs, Poznan University of Medical Sciences, Rokietnicka 3, 60-806, Poznań, Poland.
Chair and Department of Inorganic and Analytical Chemistry, Poznan University of Medical Sciences, Rokietnicka 3, 60-806, Poznań, Poland.
Sci Rep. 2025 May 14;15(1):16668. doi: 10.1038/s41598-025-00428-1.
In this study, a new magnesium(II) porphyrazine derivative tetrasubstituted with dicarboxypyrrolyl moieties was synthesized. Two different approaches were used, utilizing conventional heating and microwave irradiation. The developed three-step processes were compared showing the superior performance of the microwave-assisted organic synthesis. The new macrocycle and the novel maleonitrile derivatives were characterized using spectral techniques (mass spectrometry, NMR spectroscopy, UV-Vis spectrophotometry) and the ability of the porphyrazine to generate singlet oxygen assessed using the method with 1,3-diphenylisobenzofuran. The singlet oxygen generation quantum yields were found to be moderate (Φ = 0.23 and 0.22 in DMF and DMSO, respectively) and no aggregation behavior was noted in a series of dilutions. Additionally, the acute toxicity test using Microtox was performed showing almost no toxicity at the concentration of 10 mol/L. The electrochemical studies revealed three redox processes of targeted porphyrazine with low first oxidation peak, whereas the spectroelectrochemistry showed the formation of both cationic and anionic species at proper potentials.
在本研究中，合成了一种新的用二羧基吡咯基部分四取代的镁（II）卟吩嗪衍生物。采用了两种不同的方法，即利用传统加热和微波辐射。对所开发的三步法进行了比较，结果表明微波辅助有机合成具有更优异的性能。使用光谱技术（质谱、核磁共振光谱、紫外-可见分光光度法）对新的大环化合物和新型马来腈衍生物进行了表征，并使用1,3-二苯基异苯并呋喃法评估了卟吩嗪产生单线态氧的能力。发现单线态氧产生的量子产率适中（在DMF和DMSO中分别为Φ = 0.23和0.22），并且在一系列稀释液中未观察到聚集行为。此外，使用Microtox进行的急性毒性测试表明，在10 mol/L的浓度下几乎没有毒性。电化学研究揭示了目标卟吩嗪的三个氧化还原过程，其首次氧化峰较低，而光谱电化学表明在适当的电位下形成了阳离子和阴离子物种。
