LAQV-REQUIMTE, Chemistry Department, University of Aveiro, 3810-193 Aveiro, Portugal; Laboratory of Organic and Analytic Chemistry, Faculty of Sciences and Technics, Sultan Moulay Slimane University, BP 523, 2300 Beni-Mellal, Morocco.
CESAM and Biology Department, University of Aveiro, 3810-193 Aveiro, Portugal.
Bioorg Chem. 2020 Aug;101:103994. doi: 10.1016/j.bioorg.2020.103994. Epub 2020 Jun 3.
The synthesis of new porphyrin-indazole hybrids by a Knoevenagel condensation of 2-formyl-5,10,15,20-tetraphenylporphyrin and N-methyl-nitroindazolylacetonitrile derivatives is reported. The target compounds were isolated in moderate to good yields (32-57%) and some of the isolated porphyrin-indazole conjugates showed good performance in the generation of singlet oxygen when irradiated with visible light. Their efficiency as photosensitizers in the photoinactivation of methicillin resistant Staphylococcus aureus-MRSA was evaluated. All derivatives showed to be able to photoinactivate the MRSA bacteria. Compound 3a appears to be the most promising photosensitiser (PS) in the photoinactivation of these bacteria, despite being the least efficient in singlet oxygen generation. The addition of potassium iodide (KI) significantly potentiated the antimicrobial Photodynamic Therapy (aPDT) process mediated by all the analysed porphyrin-indazole conjugates. The combined action of nitroindazole-porphyrins with potassium iodide (KI) action appears to be promising in the photoinactivation of MRSA.
通过 2-甲酰基-5,10,15,20-四苯基卟啉和 N-甲基-硝基吲哚基乙腈衍生物的 Knoevenagel 缩合反应合成了新的卟啉-吲哚唑杂化物。目标化合物以中等至良好的收率（32-57%）分离出来，并且一些分离的卟啉-吲哚唑缀合物在可见光照射下产生单线态氧时表现出良好的性能。它们作为光解甲氧西林耐药金黄色葡萄球菌-MRSA 的光敏剂的效率进行了评估。所有衍生物均显示出能够光灭活耐甲氧西林金黄色葡萄球菌（MRSA）细菌。尽管在单线态氧生成方面效率最低，但化合物 3a 似乎是这些细菌光灭活中最有前途的光敏剂（PS）。添加碘化钾（KI）显著增强了所有分析的卟啉-吲哚唑缀合物介导的抗菌光动力疗法（aPDT）过程。硝基吲哚-卟啉与碘化钾（KI）联合作用似乎在光灭活 MRSA 方面具有广阔的前景。
