Spaeth, Andreas and Graeler, Andre and Maisch, Tim and Plaetzer, Kristjan (2018) CureCuma-cationic curcuminoids with improved properties and enhanced antimicrobial photodynamic activity. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 159. pp. 423-440. ISSN 0223-5234, 1768-3254
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The naturally occurring photosensitizer curcumin has excellent biocompatibility, but its antimicrobial photodynamic efficacy is limited by (i) weak adherence to Gram(-) bacteria cell walls, (ii) low (photo-) stability and (iii) limited solubility in water. In this study novel curcuminoids bearing cationic substituents were prepared by different synthetic routes. The derivatives exhibit excellent water solubility, improved photostability and low aggregation. All novel curcuminoids showed antibacterial photodynamic effects (>3 log(10) reduction of CFU) against Escherichia coli and Staphylococcus aureus upon blue light illumination. In contrast to natural curcumin, effective photokilling of E. coli was possible without the addition of permeabilizing agents. Ten micro molar of the most active compound (8) achieved a 7 log(10) decrease of E. coli after light activation with a fluence of 33.8 J/cm(2), whereas S. aureus was inactivated by more than 4 log(10) at a fluence of 5.3 J/cm(2). Overall the reduction in bacterial count was at least 100-fold more effective with these new curcuminoids in comparison to natural curcumin. (C) 2017 Elsevier Masson SAS. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CURCUMA-LONGA; SINGLET OXYGEN; ANTIOXIDANT ACTIVITY; FOOD COLORANTS; FATTY-ACIDS; INACTIVATION; CYTOTOXICITY; EFFICACY; PRODUCTS; WATER; Antimicrobial; Photodynamic Inactivation; Curcumin; Diferoylmethane; Cationic photosensitizer; Escherichia coli |
| 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 > Lehrstuhl Prof. Dr. Burkhard König |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 10 Oct 2019 06:50 |
| Last Modified: | 10 Oct 2019 06:50 |
| URI: | https://pred.uni-regensburg.de/id/eprint/13555 |
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