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Cationic Hypericin Derivatives as Novel Agents with Photobactericidal Activity: Synthesis and Photodynamic Inactivation of Propionibacterium acnes
Author(s) -
Hager Beate,
Strauss Wolfgang S. L.,
Falk Heinz
Publication year - 2009
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.2009.00587.x
Subject(s) - propionibacterium acnes , hypericin , cationic polymerization , pyridinium , chemistry , incubation , photosensitizer , derivative (finance) , photodynamic therapy , photochemistry , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , bacteria , biochemistry , biology , pharmacology , genetics , financial economics , economics
The present communication describes for the first time the synthesis and preliminary testing of two cationic hypericin derivatives. Uncharged hypericin derivatives with ω , ω ’‐attached C 2 ‐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 n m ) 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.