title: Spectral studies of N-nonyl acridine orange in anionic, cationic and neutral surfactants.
abstract: The spectroscopic and photophysical properties of N-nonyl acridine orange - a metachromatic dye useful as a mitochondrial probe in living cells - are reported in water and microheterogeneous media: anionic sodium dodecylsulfate (SDS), cationic cetyltrimethylammonium bromide (CTAB) and neutral octylophenylpolyoxyethylene ether (TX-100). The spectral changes of N-nonyl acridine orange were observed in the presence of varying amount of SDS, CTAB and TX-100 and indicated formation of a dye-surfactant complex. The spectral changes were also regarded to be caused by the incorporation of dye molecules to micelles. It was proved by calculated values K(b) and f in the following order: K(bTX-100)>K(bCTAB)>K(bSDS) and f(TX-100)>f(CTAB)>f(SDS). NAO binds to the micelle regardless the micellar charge. There are two types of interactions between NAO and micelles: hydrophobic and electrostatic. The hydrophobic interactions play a dominant role in binding of the dye to neutral TX-100. The unexpected fact of the binding NAO to cationic CTAB can be explained by a dominant role of hydrophobic interactions over electrostatic repulsion. Therefore, the affinity of NAO to CTAB is smaller than TX-100. Electrostatic interactions play an important role in binding of NAO to anionic micelles SDS. We observed a prolonged fluorescence lifetime after formation of the dye-surfactant complex tau(SDS)>tau(TX-100)>tau(CTAB)>tau(water), the dye being protected against water in this environment. TX-100 is found to stabilize the excited state of NAO which is more polar than the ground state. Spectroscopic and photophysical properties of NAO will be helpful for a better understanding of the nature of binding and distribution inside mammalian cells.
authors.affiliation: Institute of General Food Chemistry, Technical University of Lodz, ul. Stefanowskiego 4/10, 90-924 Lodz, Poland. awiosetek@snack.p.lodz.pl
authors.forename: Agnieszka M
authors.initials: AM
authors.lastname: Wiosetek-Reske
authors.forename: Stanisław
authors.initials: S
authors.lastname: Wysocki
mesh_terms: D000609:Aminoacridines / Q000032:analysis*; D057927:Hydrophobic and Hydrophilic Interactions; D008823:Micelles; D013056:Spectrophotometry, Ultraviolet / Q000379:methods; D013501:Surface-Active Agents / Q000032:analysis*
chemical_list: D000609:Aminoacridines; D008823:Micelles; D013501:Surface-Active Agents; C041691:10-N-nonylacridinium orange