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Title: New nitroindazole-porphyrin conjugates: synthesis, characterization and antibacterial properties
Author: Eddahmi, Mohammed
Sousa, Vera
Moura, Nuno M. M.
Dias, Cristina J.
Bouissane, Latifa
Faustino, Maria A. F.
Cavaleiro, José A. S.
Gomes, Ana T. P. C.
Almeida, Adelaide
Neves, Maria G. P. M. S.
Mostapha Rakib, El
Keywords: Tetrapyrrolic macrocycles
Knoevenagel condensation
Antimicrobial Photodynamic Therapy (aPDT)
Potassium iodide
Issue Date: Aug-2020
Publisher: Elsevier
Abstract: 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.
Peer review: yes
DOI: 10.1016/j.bioorg.2020.103994
ISSN: 0045-2068
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