Synthesis, spectroscopic and DNA alkylating properties of malondialdehyde (MDA) bis-imine fluorescent adducts

Abstract

The synthesis of a series of malondialdehyde (MDA) fluorescent adducts that mimic the well-known pentamethine cyanine dyes is reported. This new subclass of bis-imino dyes shares some common spectroscopic properties with their polymethine analogues although absorbing at significantly shorter wavelengths. A small library of trimethine and pentamethine cyanine dye bis-imino analogues have been synthesised and characterised that cover a spectral range from blue to orange. Of particular interest is their capacity to act as mono- and bis-alkylating agents of nucleosides in general and of cytidine (and 2'-deoxycytidine) in particular.

A conceptually improved TD-DFT approach for predicting the maximum absorption wavelength of cyanine dyes

“…Compounds 1e14 were synthesized following experimental procedures previously reported by us [6,7] and others [21]. Ultraviolet absorption spectra of analytically pure samples were recorded on a V-670 UV/VIS spectrophotometer from JASCO in a 10 mm pathlength cuvette.…”

“…We used the cyanine dyes of Table 1 for which DE max has been measured under the same experimental conditions, i.e., same solvent (DMSO), counter ion, and temperature [6,7].…”

“…1) [6,7]. While the potential of polymethine cyanine dyes for labeling purposes is now wellestablished [8], the possible use of their imino analogues for either sensing malondialdehyde (MDA) or alkylating DNA/RNA nucleobases has also been recently demonstrated [7].…”