Light-activated phenalen-1-one bactericides: efficacy, toxicity and mechanism compared with benzalkonium chloride

Muehler, Denise and Sommer, Kerstin and Wennige, Sara and Hiller, Karl-Anton and Cieplik, Fabian and Maisch, Tim and Spaeth, Andreas (2017) Light-activated phenalen-1-one bactericides: efficacy, toxicity and mechanism compared with benzalkonium chloride. FUTURE MICROBIOLOGY, 12 (14). pp. 1297-1310. ISSN 1746-0913, 1746-0921

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Abstract

Aim: Five photoactive compounds with variable elongated alkyl-substituents in a phenalen-1-one structure were examined in view of structural similarity to the antimicrobial agent benzalkonium chloride (BAC). Methods: All phenalen-1-ones and BAC were evaluated for their antimicrobial properties against Staphylococcus aureus, methicillin-resistant S. aureus, Escherichia coli, Pseudomonas aeruginosa and for their eukaryotic toxicity against normal human epidermal keratinocyte (NHEK) cells to narrow down the BAC-like effect and the photodynamic effect depending on the chemical structure. All compounds were investigated for effective concentration ranges, where a bacterial reduction of 5 log(10) is achieved, while an NHEK survival of 80% is ensured. Results: Effective concentration ranges were found for four out of five photoactive compounds, but not for BAC and the compound with BAC-like alkyl chain length. Conclusion: Chain length size and polar area of the respective head-groups of phenalen-1-one compounds or BAC showed an influence on the incorporation inside lipid membranes and thus, head-groups may have an impact on the toxicity of antimicrobials.

Item Type: Article
Uncontrolled Keywords: QUATERNARY AMMONIUM-COMPOUNDS; ANTIMICROBIAL PHOTODYNAMIC THERAPY; SOLID-PHASE EXTRACTION; ORAL KEY PATHOGENS; IN-VITRO; PSEUDOMONAS-AERUGINOSA; ALLERGIC REACTIONS; ESCHERICHIA-COLI; SINGLET OXYGEN; RESISTANCE; antimicrobial; benzalkonium chloride; Escherichia coli; NHEK; phenalen-1-one; photodynamic; SAPYR; singlet oxygen
Subjects: 500 Science > 540 Chemistry & allied sciences
600 Technology > 610 Medical sciences Medicine
Divisions: Medicine > Lehrstuhl für Dermatologie und Venerologie
Medicine > Lehrstuhl für Zahnerhaltung und Parodontologie > Dr. rer. nat. Karl-Anton Hiller
Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Dr. Gernot Deinzer
Date Deposited: 14 Dec 2018 13:19
Last Modified: 01 Mar 2019 08:09
URI: https://pred.uni-regensburg.de/id/eprint/1890

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