Nitrogen onium salts have a photoactivatable Nitrogen-Oxygen bond which yields two reactive species upon photolysis. Those reactive species have been identified as effective DNA cleavers. Simple nitrogen onium salts based on quinoline, isoquinoline and phenanthridine have been shown to cleave DNA inefficiently even though the DNA cleaving intermediates are produced with high quantum yields of about 0.6. Weak ground state association presumably leads to a decay of the transient species without interaction with DNA.Combination of a known DNA binder, 1,8-naphthalimide, with N-alkoxy aromatic heterocycles has led to the synthesis of bifunctional DNA cleaving reagent. Separate synthesis of the building blocks leads to a library of compounds which then can be combined in several ways. The products undergo a full characterization as well as the analysis of their spectroscopic and photochemical properties. Several synthetic pathways are presented and discussed.

Towards the synthesis of bifunctional nitrogen onium salts used for DNA-cleaving

245th National Meeting (2013)

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