New nitroindazole-porphyrin conjugates: Synthesis, characterization and antibacterial properties.
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.
['Eddahmi|Mohammed|M|', 'Sousa|Vera|V|', 'Moura|Nuno M M|NMM|', 'Dias|Cristina J|CJ|', 'Bouissane|Latifa|L|', 'Faustino|Maria A F|MAF|', 'Cavaleiro|José A S|JAS|', 'Gomes|Ana T P C|ATPC|', 'Almeida|Adelaide|A|', 'Neves|Maria G P M S|MGPMS|', 'Mostapha Rakib|El|E|']
D000900:Anti-Bacterial Agents D007191:Indazoles D055624:Methicillin-Resistant Staphylococcus aureus D008826:Microbial Sensitivity Tests D010778:Photochemotherapy D017319:Photosensitizing Agents D011166:Porphyrins D026082:Singlet Oxygen D013057:Spectrum Analysis
Knoevenagel condensation Photosensitizer MRSA Potassium iodide Antimicrobial Photodynamic Therapy (aPDT) Indazole Porphyrin Tetrapyrrolic macrocycles