Development of Phenalenone-Triazolium Salt Derivatives for aPDT: Synthesis and Antibacterial Screening
| Autor: | Frédérique Brégier, Nicolas Villandier, Vincent Sol, René M. Williams, Dáire Gibbons, Tan-Sothea Ouk, Stéphanie Leroy-Lhez, Jérémy Godard |
|---|---|
| Přispěvatelé: | Spectroscopy and Photonic Materials (HIMS, FNWI), PEIRENE (EA 7500), Molecular Photonics Group, Van ’t Hoff Institute for Molecular Sciences (HIMS), Universiteit van Amsterdam, van ‘t Hoff Institute for Molecular Sciences, Universiteit van Amsterdam (UvA)-Universiteit van Amsterdam (UvA), European Project: H2020 |
| Rok vydání: | 2021 |
| Předmět: |
0301 basic medicine
Microbiology (medical) triazolium salt [SDV]Life Sciences [q-bio] 030106 microbiology Quantum yield RM1-950 Alkylation 01 natural sciences Biochemistry Microbiology Article phenalenone 03 medical and health sciences chemistry.chemical_compound PDT Pharmacology (medical) Photosensitizer Ammonium General Pharmacology Toxicology and Pharmaceutics chemistry.chemical_classification Reactive oxygen species 010405 organic chemistry Singlet oxygen photosensitizers [CHIM.MATE]Chemical Sciences/Material chemistry Antimicrobial Combinatorial chemistry 0104 chemical sciences Infectious Diseases chemistry bacteria photoinactivation Therapeutics. Pharmacology Methyl iodide |
| Zdroj: | Antibiotics Antibiotics, 10(6):626. Multidisciplinary Digital Publishing Institute (MDPI) Antibiotics, MDPI, 2021, 10 (6), 13 p. ⟨10.3390/antibiotics10060626⟩ Antibiotics, Vol 10, Iss 626, p 626 (2021) Volume 10 Issue 6 |
| ISSN: | 2079-6382 0066-4758 |
| DOI: | 10.3390/antibiotics10060626 |
| Popis: | The increasing number of hospital-acquired infections demand the development of innovative antimicrobial treatments. Antimicrobial photodynamic therapy (aPDT) is a versatile technique which relies on the production of reactive oxygen species (ROS) generated by light-irradiated photosensitizers (PS) in the presence of oxygen (O2). 1H-Phenalen-1-one is a very efficient photosensitizer known for its high singlet oxygen quantum yield and its antimicrobial potential in aPDT when covalently bound to quaternary ammonium groups. Triazolium salts are stable aromatic quaternary ammonium salts that recently appeared as interesting moieties endowed with antimicrobial activities. The coupling between phenalenone and triazolium groups bearing various substituents was realized by copper-catalyzed azide-alkyne cycloaddition followed by alkylation with methyl iodide or 2-(bromomethyl)-1H-phenalen-1-one. As expected, most of the compounds retained the initial singlet oxygen quantum yield, close to unity. Minimum inhibitory concentrations (MIC) of 14 new phenalenone-triazolium salt derivatives and 2 phenalenone-triazole derivatives were determined against 6 bacterial strains (Gram-negatives and Gram-positives species). Most of these PS showed significant photoinactivation activities, the strongest effects being observed against Gram-positive strains with as low as submicromolar MIC values. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|