Spectral-luminescence and quantum-chemical study of the anionic forms of 5-fluorouracil

Resumo

A spectral-luminescence study of neutral (pH 7) and alkaline (pH 11 and 14) aqueous solutions of the anticancer drugs 5-fluorouracil (FU) and tegafur has been performed. The fluorescence spectra of the N3- and N1-centered anions of 5-fluorouracil, its dianion, and the tegafur monoanion with emission maxima at wavelengths (λ_em) of 358, 372, 366, and 358 nm and photoluminescence quantum yields (φ) of 11.2 × 10^–4, 35.1 × 10^–4, 26.5 × 10^–4, and 8.6 × 10^–4, respectively, have been recorded for the first time. The fluorescence characteristics of the FU anionic forms have been related to the magnetic shielding constant as one of the criteria of aromaticity.