Benzoangelicins: new monofunctional DNA photobinding agents. |
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Authors: | D Vedaldi S Caffieri G Miolo A Guiotto F Dall'Acqua G Bombieri F Benetollo |
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Affiliation: | Dipartimento di Scienze Farmaceutiche, Università di Padova, Italy. |
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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. |
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