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Prototropic Interactions of Pyrimidine Nucleic Acid Bases with Acridine: A Spectroscopic Investigation

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journal contribution
posted on 30.08.2012 by Manas Kumar Sarangi, Ankita Mitra, Samita Basu
In this article, we have investigated the interactions of three pyrimidine nucleic acid bases, cytosine (C), thymine (T), and uracil (U) with acridine (Acr), an N-heterocyclic DNA intercalator, through the changes in photophysics of Acr inside SDS micelles. Fluorescence of AcrH+* at 478 nm and its lifetime are quenched on addition of C, T, and U, while a concomitant increment of Acr* is observed only with C. However, the relative amplitude of Acr* increases with a simultaneous decrease in AcrH+* only with C. The fluorescence quenching of AcrH+* is explained by photoinduced electron transfer (PET), while changes in the relative contributions of Acr* and AcrH+* with C are due to associated excited-state proton transfer (ESPT). The rate of electron transfer (kET) is maximum for T, followed by U and C. The associated ESPT from AcrH+* is the reason behind the reduced efficiency of PET with C. The lack of proton transfer with T and U as well as the higher kET for T compared to U are explained by keto–enol tautomerization and subtle changes in the structure and geometry of the pyrimidine bases.

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