RT Journal Article
T1 Thiophene-based dyes for probing membranes
A1 López Duarte, Ismael
A1 Chairatana, Phoom
A1 Wu, Yilei
A1 Pérez-Moreno, Javier
A1 Bennett, Philip M.
A1 Reeve, James E.
A1 Boczarow, Igor
A1 Kaluza, Wojciech
A1 Hosny, Neveen A.
A1 Stranks, Samuel D.
A1 Nicholas, Robin J.
A1 Clays, Koen
A1 Kuimova, Marina K.
A1 Anderson, Harry L.
AB We report the synthesis of four new cationic dipolar push-pull dyes, together with an evaluation of their photophysical and photobiological characteristics pertinent to imaging membranes by fluorescence and second harmonic generation (SHG). All four dyes consist of an N, N-diethylaniline electron-donor conjugated to a pyridinium electron-acceptor via a thiophene bridge, with either vinylene (-CH=CH-) or ethynylene (-C=C-) linking groups, and with either singly-charged or doubly-charged pyridinium terminals. The absorption and fluorescence behavior of these dyes were compared to a commercially available fluorescent membrane stain, the styryl dye FM4-64. The hyperpolarizabilities of all dyes were compared using hyper-Rayleigh scattering at 800 nm. Cellular uptake, localization, toxicity and phototoxicity were evaluated using tissue cell cultures (HeLa, SK-OV-3 and MDA-231). Replacing the central alkene bridge of FM4-64 with a thiophene does not substantially change the absorption, fluorescence or hyperpolarizability, whereas changing the vinylene-links to ethynylenes shifts the absorption and fluorescence to shorter wavelengths, and reduces the hyperpolarizability by about a factor of two. SHG and fluorescence imaging experiments in live cells showed that the doubly-charged thiophene dyes localize in plasma membranes, and exhibit lower internalization rates compared to FM4-64, resulting in less signal from the cell cytosol. At a typical imaging concentration of 1 mu M, the doubly-charged dyes showed no significant light or dark toxicity, whereas the singly-charged dyes are phototoxic even at 0.5 mu M. The doubly-charged dyes showed phototoxicity at concentrations greater than 10 mu M, although they do not generate singlet oxygen, indicating that the phototoxicity is type I rather than type II. The doubly-charged thiophene dyes are more effective than FM4-64 as SHG dyes for live cells.
PB Royal Society of Chemistry
SN 1477-0520
SN 1477-0539
YR 2015
FD 2015
LK https://hdl.handle.net/20.500.14352/114887
UL https://hdl.handle.net/20.500.14352/114887
LA eng
NO López-Duarte I, Chairatana P, Wu Y, Pérez-Moreno J, Bennett PM, Reeve JE, et al. Thiophene-based dyes for probing membranes. Org Biomol Chem [Internet]. 2015 [citado 17 de enero de 2025];13(12):3792-802. Disponible en: https://xlink.rsc.org/?DOI=C4OB02507E
DS Docta Complutense
RD 24 abr 2025