Benzoangelicins: new monofunctional DNA photobinding agents.
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.
Vedaldi
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D
Dipartimento di Scienze Farmaceutiche, Università di Padova, Italy.
Caffieri
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S
Miolo
G
G
Guiotto
A
A
Dall'Acqua
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F
Bombieri
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G
Benetollo
F
F
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
D003432:Cross-Linking Reagents; D011564:Furocoumarins; D011838:Radiation-Sensitizing Agents; C078037:4,6-dimethylbenzoangelicin; D004247:DNA