6-Aminoacridizinium bromide: a fluorescence probe which lights up in AT-rich regions of DNA

Abstract

The title compound exhibits a selective enhancement of its fluorescence intensity in the presence of AT-rich DNA.

BENA435, a new cell-permeant photoactivated green fluorescent DNA probe

“…All this suggests that BENA435 can bind to, but interacts differently with, dA/dT and dG/dC pairs of nucleotides. The observed quenching effect by dG/dC tracts could come from the low oxidation potential reported for guanine or from the electron transfer between BENA435 and guanine residues as was reported for other fluorescent intercalating molecules ( 22 , 33 , 34 ).…”

Intercalation of Organic Dye Molecules into Double‐stranded DNA. Part 2: The Annelated Quinolizinium Ion as a Structural Motif in DNA Intercalators†

“…Recently, the interactions of DNA with the benzo‐, naphtho‐, and indolo‐annelated quinolizinium derivatives 9–12 were investigated in detail (46–53). As already shown for 5 , the absorption bands of quinolizinium derivatives 9–12 are significantly redshifted upon addition of calf thymus DNA (ct DNA) or salmon testes DNA (st DNA) (Table 1).…”

“… Spectrophotometric titration of benzoquinolizinium 9b (A) and 9c (B) with ct DNA in phosphate buffer (0.01 M, pH = 7.0, T = 25°C); [ 9b ] = [ 9c ] = 10 −4 M; titration interval: 0.5 molar equivalents of DNA; arrows indicate the development of the absorption band upon addition of DNA. Figure 1A adapted from (51) with kind permission of Royal Society of Chemistry. Figure 1B adapted from (53).…”

“…Nevertheless, the fluorescence intensity increases significantly upon DNA addition (Fig. 2B) (51). Notably, the fluorescence enhancement is much more pronounced upon addition of (poly[dA–dT]‐poly[dA–dT]) than with (poly[dC–dG]–poly[dC–dG]) or ct DNA.…”

Photophysical Properties of Quinolizinium Salts and Their Interactions with DNA in Aqueous Solution

“…[1][2][3][4][5][6] This photobiological activity, photonuclease, can produce intentional DNA photodamages, for example, in tumor cells; therefore, these dyes may have applications in photochemotherapy. 7,8 Recently, investigations of DNA-binding and DNA-photodamaging properties of indolo [2,3-b]quinolizinium bromide were reported.…”