Tabenski, Isabelle and Cieplik, Fabian and Tabenski, Laura and Regensburger, Johannes and Hiller, Karl-Anton and Buchalla, Wolfgang and Maisch, Tim and Spaeth, Andreas (2016) The impact of cationic substituents in phenalen-1-one photosensitizers on antimicrobial photodynamic efficacy. PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 15 (1). pp. 57-68. ISSN 1474-905X, 1474-9092
Full text not available from this repository. (Request a copy)Abstract
Light-mediated killing of pathogens by cationic photosensitizers (PS) is a promising antimicrobial approach avoiding resistance as being present upon the use of antibiotics. In this study we focused on the impact of the substituents in phenalen-1-one PS. Photodynamic efficacy depending on positively charged moieties including a primary aliphatic, quaternary aliphatic, aromatic ammonium and a guanidinium cation was investigated against Gram-positive and Gram-negative pathogens. Considering the altered steric demand and lipophilicity of these functional groups we deduced a structure-activity relationship. SAGUA was the most potent PS in this series reaching a maximum efficacy of >= 6log(10) steps of bacteria killing at a concentration of 10 mu M upon irradiation with blue light (20 mW cm(-2)) for 60 s (1.2 J cm(-2)) without exhibiting inherent dark toxicity. Its guanidinium moiety may be able to form strong bidentate and directional hydrogen bonds to carboxylate groups of bacterial surfaces in addition to ionic charge attraction. This may supplement fast and effective antimicrobial activity.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | SINGLET OXYGEN; CROWN-ETHER; INACTIVATION; BACTERIA; RESISTANCE; THERAPY; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences 600 Technology > 610 Medical sciences Medicine |
| Divisions: | Medicine > Lehrstuhl für Dermatologie und Venerologie Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 01 Mar 2019 12:36 |
| Last Modified: | 07 Mar 2019 10:03 |
| URI: | https://pred.uni-regensburg.de/id/eprint/2230 |
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