title: Photosensitizing properties of compounds related to benzophenone.
abstract: Benzophenone is a phototoxic compound with absorption maxima in the ultraviolet A (UVA) and ultraviolet B (UVB) range. Many benzophenone derivatives are known to be photosensitizing. On the other hand, 2-hydroxy-4-methoxybenzophenone is used as a photoprotective agent. The aim of the present study was to analyse a range of benzophenone derivatives and thus examine the effects of molecular changes in the benzophenone molecule on phototoxic behaviour. Phototoxicity was tested by an in vitro photohaemolysis test. The tested compounds were benzophenone itself and the derivatives 2-hydroxybenzophenone, 2-aminobenzophenone, 2-benzoylbenzoic acid, 3-hydroxybenzophenone, and 4-hydroxybenzo-phenone, as well as the structurally similar compounds 9-fluorenone, 9-fluorenone-2-carboxylic acid, cyclohexyl phenyl ketone, and 1,4-naphtho-quinone. It was shown that minor changes in molecular structure can result in highly different phototoxic characteristics.
authors.affiliation: Klinik und Poliklinik für Dermatologie und Allergologie, Ludwig-Maximilians-Universität München, München, Germany. mplaczek@gmx.net
authors.forename: Marianne
authors.initials: M
authors.lastname: Placzek
authors.forename: Markus
authors.initials: M
authors.lastname: Dendorfer
authors.forename: Bernhard
authors.initials: B
authors.lastname: Przybilla
authors.forename: Klaus-P
authors.initials: KP
authors.lastname: Gilbertz
authors.forename: Bernadette
authors.initials: B
authors.lastname: Eberlein
mesh_terms: D001577:Benzophenones / Q000494:pharmacology*; D003510:Cyclohexanes / Q000494:pharmacology; D004912:Erythrocytes / Q000187:drug effects*; D005449:Fluorenes / Q000494:pharmacology; D006461:Hemolysis / Q000187:drug effects*; D006801:Humans; D066298:In Vitro Techniques; D009285:Naphthoquinones / Q000494:pharmacology; D017319:Photosensitizing Agents / Q000494:pharmacology*; D013053:Spectrophotometry; D014466:Ultraviolet Rays
chemical_list: D001577:Benzophenones; D003510:Cyclohexanes; D005449:Fluorenes; D009285:Naphthoquinones; D017319:Photosensitizing Agents; C024292:4-hydroxybenzophenone; C007195:cyclohexylphenylketone; C047723:benzophenone; C556700:2-benzoylbenzoic acid; C028401:9-fluorenone; C562127:ortho-hydroxybenzophenone; C035342:1,4-naphthoquinone