Accéder au contenu
Merck

Photosensitizing properties of compounds related to benzophenone.

Acta dermato-venereologica (2012-09-18)
Marianne Placzek, Markus Dendorfer, Bernhard Przybilla, Klaus-P Gilbertz, Bernadette Eberlein
RÉSUMÉ

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.

MATÉRIAUX
Référence du produit
Marque
Description du produit

Sigma-Aldrich
9-Fluorenone, 98%
Sigma-Aldrich
Benzophénone, ReagentPlus®, 99%
Sigma-Aldrich
Benzophénone, purified by sublimation, ≥99%
Sigma-Aldrich
1,4-Naphthoquinone, 97%
Supelco
Benzophénone, analytical standard
Sigma-Aldrich
4-Hydroxybenzophenone, 98%
Supelco
Benzophénone, traceable to primary standards (LGC)
Supelco
Benzophénone, Pharmaceutical Secondary Standard; Certified Reference Material
Supelco
Melting point standard 47-49°C, analytical standard
Sigma-Aldrich
2-Benzoylbenzoic acid, 98%
Sigma-Aldrich
Cyclohexyl phenyl ketone, 98%
Benzophénone, European Pharmacopoeia (EP) Reference Standard
Sigma-Aldrich
1,4-Naphthoquinone, purum, ≥96.5% (HPLC)