Cationic hypericin derivatives as novel agents with photobactericidal activity: synthesis and photodynamic inactivation of Propionibacterium acnes.
The present communication describes for the first time the synthesis and preliminary testing of two cationic hypericin derivatives. Uncharged hypericin derivatives with omega,omega'-attached C2-linkers leading to a pyridyl or a 4-dimethylaminophenyl residue were prepared and subsequently quaternized by means of iodomethane. Photobactericidal activity was assessed using Propionibacterium acnes. The quaternary N,N,N-trimethyl-anilinium derivative displayed a pronounced photodynamic inactivation of the bacteria at low incubation concentrations (<100 nm) and a short incubation time (1 h) after illumination with yellow light (590 nm, 20 J cm(-2)), whereas the photobactericidal efficacy of the N-methyl-pyridinium derivative was negligible under identical experimental conditions.
Hager
Beate
B
Institute of Organic Chemistry, Johannes Kepler University, Linz, Austria.
Strauss
Wolfgang S L
WS
Falk
Heinz
H
D000873:Anthracenes; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D002412:Cations; D010569:Perylene / Q000031:analogs & derivatives* / Q000494:pharmacology; D010778:Photochemotherapy; D011425:Propionibacterium acnes / Q000187:drug effects*
D000873:Anthracenes; D000900:Anti-Bacterial Agents; D002412:Cations; D010569:Perylene; C004965:hypericin