A water-soluble near-infrared aminocyanine dye has been developed with a long triplet-state lifetime (τ = 9.16 μs in deaerated ethanol). Thereby, extremely high singlet oxygen quantum yield (ΦΔ = 0.20) and low dark cytotoxicity (IC50 = 715.4 μM) were achieved. The potential of the dye as a PDT photosensitizer was demonstrated.
Aggregation-caused quenching (ACQ)
and poor photostability in aqueous
media are two common problems for organic fluorescence dyes which
cause a dramatic loss of fluorescence imaging quality and photodynamic
therapy (PDT) failure. Herein, a local hydrophobic cage is built up
inside near-infrared (NIR) cyanine-anchored fluorescent silica nanoparticles
(FSNPs) in which a hydrophobic silane coupling agent (n-octyltriethoxysilane, OTES) is doped into FSNPs for the first time
to significantly inhibit the ACQ effect and inward diffusion of water
molecules. Therefore, the obtained optimal FSNP-C with OTES-modification
can provide hydrophobic repulsive forces to effectively inhibit the
π–π stacking interaction of cyanine dyes and simultaneously
reduce the formation of strong oxidizing species (•OH and H2O2) in reaction with H2O, resulting
in the best photostability (fluorescent intensity remained at 90.1%
of the initial value after 300 s of laser scanning) and a high PDT
efficiency on two- and three-dimensional (spheroids) HeLa cell culture
models. Moreover, through molecular engineering (including increasing
covalent anchoring sites and steric hindrance groups of cyanine dyes),
FSNP-C exhibits the highest fluorescent intensity both in water solution
(12.3-fold improvement compared to free dye) and living cells due
to the limitation of molecular motion. Thus, this study provides an
effectively strategy by combining a local hydrophobic cage and molecular
engineering for NIR FSNPs in long-term bright fluorescence imaging
and a stable PDT process.
Near-infrared (NIR) fluorescence imaging technology calls for highly bright and photostable emissive materials for long-term and real-time bioimaging and medical diagnosis.
Fluorescent silica nanoparticles which encapsulated dye DCF-BYT with thermally activated delayed fluorescence (TADF) were fabricated by a simple synthetic method.
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