title: Benzoangelicins: new monofunctional DNA photobinding agents.
abstract: 4,6-Dimethylbenzoangelicin, obtained by fusing a benzene ring at the furan side of 4,6-dimethylangelicin, was studied in terms of crystal structure and interactions with DNA in both ground and excited states. 4,6-Dimethylbenzoangelicin has a planar structure and forms a molecular complex with DNA, undergoing intercalation inside the double helix. Under UVA irradiation, it photoconjugates covalently with the macromolecule, showing a DNA photobinding rate slightly lower than that of 8-methoxypsoralen, involving however only its 3,4 double bond, i.e. behaving as a pure monofunctional agent. The parameters of dark binding and photobinding were determined, and two C4 cycloadducts with thymine were isolated and characterized.
authors.affiliation: Dipartimento di Scienze Farmaceutiche, Università di Padova, Italy.
authors.forename: D
authors.initials: D
authors.lastname: Vedaldi
authors.forename: S
authors.initials: S
authors.lastname: Caffieri
authors.forename: G
authors.initials: G
authors.lastname: Miolo
authors.forename: A
authors.initials: A
authors.lastname: Guiotto
authors.forename: F
authors.initials: F
authors.lastname: Dall'Acqua
authors.forename: G
authors.initials: G
authors.lastname: Bombieri
authors.forename: F
authors.initials: F
authors.lastname: Benetollo
mesh_terms: D000818:Animals; D003432:Cross-Linking Reagents / Q000737:chemistry*; D004247:DNA / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D011564:Furocoumarins / Q000737:chemistry* / Q000378:metabolism; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D009690:Nucleic Acid Conformation; D011838:Radiation-Sensitizing Agents / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet; D014961:X-Ray Diffraction
chemical_list: D003432:Cross-Linking Reagents; D011564:Furocoumarins; D011838:Radiation-Sensitizing Agents; C078037:4,6-dimethylbenzoangelicin; D004247:DNA