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Meso-substituted cationic 3- and 4-N-Pyridylporphyrins and their Zn(II) derivatives for antibacterial photodynamic therapy
Journal of Innovative Optical Health Sciences ( IF 2.5 ) Pub Date : 2021-10-14 , DOI: 10.1142/s1793545821420074
Aram G. Gyulkhandanyan 1, 2 , Marina H. Paronyan 3 , Anna G. Gyulkhandanyan 1 , Karapet R. Ghazaryan 1 , Marina V. Parkhats 4 , Boris M. Dzhagarov 4 , Maria V. Korchenova 5 , Ekaterina N. Lazareva 5, 6 , Elena S. Tuchina 5 , Grigor V. Gyulkhandanyan 1 , Valery V. Tuchin 5, 6, 7
Affiliation  

Photodynamic inactivation of microorganisms known as antibacterial photodynamic therapy (APDT) is one of the most promising and innovative approaches for the destruction of pathogenic microorganisms. Among the photosensitizers (PSs), compounds based on cationic porphyrins/metalloporphyrins are most successfully used to inactivate microorganisms. Series of meso-substituted cationic pyridylporphyrins and metalloporphyrins with various peripheral groups in the third and fourth positions of the pyrrole ring have been synthesized in Armenia. The aim of this work was to determine and test the most effective cationic porphyrins and metalloporphyrins with high photoactivity against Gram negative and Gram positive microorganisms. It was shown that the synthesized cationic pyridylporphyrins/metalloporphyrins exhibit a high degree of phototoxicity towards both types of bacteria, including the methicillin-resistant S. aureus strain. Zinc complexes of porphyrins are more phototoxic than metal-free porphyrin analogs. The effectiveness of these Zn–metalloporphyrins on bacteria is consistent with the level of singlet oxygen generation. It was found that the high antibacterial activity of the studied cationic porphyrins/metalloporphyrins depends on four factors: the presence in the porphyrin macrocycle of a positive charge (+4), a central metal atom (Zn2+) and hydrophobic peripheral functional groups as well as high values of quantum yields of singlet oxygen. The results indicate that meso-substituted cationic pyridylporphyrins/metalloporphyrins can find wider application in photoinactivation of bacteria than anionic or neutral PSs usually used in APDT.

中文翻译:

用于抗菌光动力治疗的内消旋取代的阳离子 3- 和 4-N- 吡啶基卟啉及其 Zn(II) 衍生物

称为抗菌光动力疗法(APDT)的微生物的光动力灭活是破坏病原微生物的最有希望和创新的方法之一。在光敏剂 (PS) 中,基于阳离子卟啉/金属卟啉的化合物最成功地用于灭活微生物。亚美尼亚合成了一系列在吡咯环第三位和第四位具有各种外围基团的中间取代的阳离子吡啶基卟啉和金属卟啉。这项工作的目的是确定和测试对革兰氏阴性和革兰氏阳性微生物具有高光活性的最有效的阳离子卟啉和金属卟啉。金黄色葡萄球菌拉紧。卟啉的锌配合物比不含金属的卟啉类似物更具有光毒性。这些锌金属卟啉对细菌的有效性与单线态氧的产生水平一致。发现所研究的阳离子卟啉/金属卟啉的高抗菌活性取决于四个因素:卟啉大环中正电荷(+4)的存在,中心金属原子(Zn2+)和疏水性外围官能团以及单线态氧的高量子产率值。结果表明,与APDT中常用的阴离子或中性PSs相比,内消旋取代的阳离子吡啶基卟啉/金属卟啉在细菌的光灭活中具有更广泛的应用。
更新日期:2021-10-14
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