Summary
The furonaphthopyrone6, a novel DNA intercalator, was synthesized in two steps (ca. 56% overall yield) starting from naphthopyrone3. The new naphthopyrone derivatives4 and6 were fully characterized and the absorption and fluorescence spectroscopic properties of6 were determined. The dark interactions of furonaphthopyrone1 and6 with DNA have been investigated by a fluorescence quenching technique and their apparentScatchard binding constants were calculated. The crystal structure of6 was determined. The planarity of6 and the geometry of the active double bond between the α-pyrone and the furan moieties of6 suggest that furonaphthopyrones are efficient monofunctional DNA intercalators.
Zusammenfassung
Der neue DNA-Intercalator6 wurde, ausgehend vom Naphthopyron3, in zwei Stufen mit einer Gesamtausbeute vonca. 56% hergestellt. Die neuen Naphthopyronderivate4 und6 wurden vollständig charakterisiert; die Absorptions- und Fluoreszenzeigenschaften von6 wurden bestimmt. Die Dunkelwechselwirkungen von1 und6 mit DNA wurden mittels einer Fluoreszenzquenchtechnik untersucht; ihreScatchard-Bindungskonstanten wurden berechnet. Die Kristallstruktur von6 wurde bestimmt. Die Planarität von6 und die Geometrie der aktiven Doppelbindung zwischen dem α-Pyron- und dem Furanteil von6 lassen erwarten, daß Furonaphthopyrone effiziente monofunktionelle DNA-Intercalatoren sind.
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Qian, X., Tao, ZF., Wei, D. et al. Synthesis, crystal structure, and properties of 2H-4,8-dimethylfuro[2′,3′:5,6]naphtho[1,2-b]pyran-2-one, a novel DNA intercalator. Monatsh Chem 127, 569–577 (1996). https://doi.org/10.1007/BF00807082
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DOI: https://doi.org/10.1007/BF00807082