New nitroindazole-porphyrin conjugates: Synthesis, characterization and antibacterial properties.
Anti-Bacterial Agents
/ chemical synthesis
Indazoles
/ chemical synthesis
Methicillin-Resistant Staphylococcus aureus
/ drug effects
Microbial Sensitivity Tests
Photochemotherapy
Photosensitizing Agents
/ chemical synthesis
Porphyrins
/ chemical synthesis
Singlet Oxygen
/ chemistry
Spectrum Analysis
/ methods
Antimicrobial Photodynamic Therapy (aPDT)
Indazole
Knoevenagel condensation
MRSA
Photosensitizer
Porphyrin
Potassium iodide
Tetrapyrrolic macrocycles
Journal
Bioorganic chemistry
ISSN: 1090-2120
Titre abrégé: Bioorg Chem
Pays: United States
ID NLM: 1303703
Informations de publication
Date de publication:
08 2020
08 2020
Historique:
received:
04
02
2020
revised:
04
05
2020
accepted:
02
06
2020
pubmed:
23
6
2020
medline:
30
3
2021
entrez:
23
6
2020
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 32569896
pii: S0045-2068(20)31291-8
doi: 10.1016/j.bioorg.2020.103994
pii:
doi:
Substances chimiques
Anti-Bacterial Agents
0
Indazoles
0
Photosensitizing Agents
0
Porphyrins
0
Singlet Oxygen
17778-80-2
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
103994Informations de copyright
Copyright © 2020 Elsevier Inc. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.