Formation and Dissociation of the Acridine Orange Dimer as a Tool for Studying Polyelectrolyte–Surfactant Interactions

Abstract

Steady-state and time-resolved fluorescence and UV-vis techniques were used to study the formation and dissociation of acridine orange dimer in order to investigate hyaluronan-acridine orange, hyaluronan-CTAB (cetyltrimethylammonium bromide), polystyrenesulfonate-acridine orange, and polystyrenesulfonate-CTAB interactions in aqueous solution. Steady-state and time-resolved fluorescence and the dimer:monomer absorbance ratio of acridine orange (AO) were used to determine dimer formation on polymer chains of polyelectrolytes. Acridine orange clearly formed dimers on polystyrensulfonate chains as well as on hyaluronan, but we show that the electrostatic interaction is much weaker in the case of hyaluronan. After the addition of surfactant, we observed an enhancement of fluorescence intensity, indicating the dissociation of AO dimers into monomers and the replacement of acridine orange on polymer chains by surfactant molecules. Importantly, we show that surfactant molecules bind to polymer chains before the critical micelle concentration is reached and form the so-called "bottle-brush" structure.

Sulfated β‐Cyclodextrin Templated Assembly and Disassembly of Acridine Orange: Unraveling Contrasting Binding Mechanisms and Light Off/On Switching

“…Inset of 4 A), we feel that the long τ 3 component in the present cases is due to the weak emission arising from dimeric dye‐SCD exo complexes. To be mentioned that very long fluorescence lifetimes similar to the present ones are in fact reported in the literature for the dimeric AOH + species bound to systems like polyelectrolytes and AOT reverse micelles ,…”

“…To be mentioned that very long fluorescence lifetimes similar to the present ones are in fact reported in the literature for the dimeric AOH + species bound to systems like polyelectrolytes and AOT reverse micelles. [70,71] As indicated from Table 2, the fluorescence decays of AOH + at 630 nm become bi-exponential again as the SCD concentration is increased further and the observed t 1 and t 2 values in these cases become very similar to the ones observed at 531 nm, representing the monomeric dye-SCD exo and inclusion complexes, respectively. The observation that at the intermediate SCD concentrations the values for the t 2 component are somewhat higher than that of the monomeric dye-SCD inclusion complexes are possibly due to small overlapping contribution arising from the longer lifetime SCD bound dimeric AOH + complexes.…”

The change in excited-state proton transfer kinetics of 1-naphthol in micelles upon the binding of polymers: The influence of hyaluronan hydration

“…In this part, we compared a synthetic polymer with a higher charge density (a "stronger polyelectrolyte") and a hyaluronan biopolymer. However, the aim of this work was not to report on the formation of hyaluronan-cationic surfactant aggregates, because we demonstrated this in our previous study with acridine orange (Mondek, Mravec, Halasová, Hnyluchová, & Pekař, 2014). Chiefly, we wanted to characterize the usefulness of the ESPT of 1-naphthol in hyaluronan-surfactant interactions.…”

A cation exchange based electrochemical sensor for cetyltrimethylammonium bromide detection using an acridine orange/polystyrene sulfonate system

“…PSS/CTAB systems show the classical behavior of oppositely charged polyelectrolyte/surfactant systems and can be well explained by electrostatic interactions and hydrophobic interactions. [26][27][28] 3,6-Bis(dimethylamino)acridine, C 17 H 19 N 3 , also known as acridine orange (AO), is a dark orange to brownish solid and exhibits a bright orange color in aqueous solution. Acridine orange is a well-known DNA intercalator and is useful for studying the photophysical processes and molecular dynamics in DNA.…”